788:
781:
430:
413:
887:
396:
154:
38:
855:
382:
654:
556:
165:
143:
207:
570:
331:, which are electron donating and electron withdrawing respectively. Activators are known as ortho-para directors, and deactivators are known as meta directors. Upon reacting, substituents will be added at the ortho, para or meta positions, depending on the directivity of the current substituents to make more complex benzene derivatives, often with several isomers. Electron flow leading to re-aromatization is key in ensuring the stability of such products.
542:
458:
528:
215:
514:
910:
281:
1963:
486:
472:
368:
500:
444:
60:" and "cyclically conjugated." The word "aromatic" originates from the past grouping of molecules based on odor, before their general chemical properties were understood. The current definition of aromatic compounds does not have any relation to their odor. Aromatic compounds are now defined as cyclic compounds satisfying
91:
Arenes are typically split into two categories - benzoids, that contain a benzene derivative and follow the benzene ring model, and non-benzoids that contain other aromatic cyclic derivatives. Aromatic compounds are commonly used in organic synthesis and are involved in many reaction types, following
244:
in the 19th century. Each carbon atom in the hexagonal cycle has four electrons to share. One electron forms a sigma bond with the hydrogen atom, and one is used in covalently bonding to each of the two neighboring carbons. This leaves six electrons, shared equally around the ring in delocalized pi
268:. Some argue that, in order to stay in line with Robinson's originally intended proposal, the use of the circle symbol should be limited to monocyclic 6 Ï-electron systems. In this way the circle symbol for a six-center six-electron bond can be compared to the Y symbol for a
3563:
1701:
1257:
1726:
1027:
IUPAC. Compendium of
Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). Online version (2019-) created by S. J. Chalk. ISBN 0-9678550-9-8.
1438:"Polycyclic Aromatic Hydrocarbons â Occurrence in foods, dietary exposure and health effects" (PDF). European Commission, Scientific Committee on Food. December 4, 2002. Archived (PDF) from the original on 2022-10-09.
716:. PAHs are also found in cooked foods. Studies have shown that high levels of PAHs are found, for example, in meat cooked at high temperatures such as grilling or barbecuing, and in smoked fish. They are also a good
1362:
622:, is aromatic, though strain within the structure causes a slight deviation from the precisely planar structure necessary for aromatic categorization. Another example of a non-benzylic monocyclic arene is the
1337:
1309:
260:
and his student James Armit in 1925 and popularized starting in 1959 by the
Morrison & Boyd textbook on organic chemistry. The proper use of the symbol is debated: some publications use it to
1497:
Scientific
Opinion of the Panel on Contaminants in the Food Chain on a request from the European Commission on Marine Biotoxins in Shellfish â Saxitoxin Group. The EFSA Journal (2009) 1019, 1-76.
637:
Other non-benzylic monocyclic arenes include the aforementioned heteroarenes that can replace carbon atoms with other heteroatoms such as N, O or S. Common examples of these are the six-membered
3475:
704:
deposits, and are produced as byproducts of fuel burning (whether fossil fuel or biomass). As pollutants, they are of concern because some compounds have been identified as
1546:
Thomas, Philippe J.; Newell, Emily E.; Eccles, Kristin; Holloway, Alison C.; Idowu, Ifeoluwa; Xia, Zhe; Hassan, Elizabeth; Tomy, Gregg; Quenneville, Cheryl (2021-02-01).
630:
with an n equal to 0. Note, only the cationic form of this cyclic propenyl is aromatic, given that neutrality in this compound would violate either the octet rule or
7253:
7248:
7243:
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6321:
5999:
2741:
2323:
2262:
5624:
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5143:
5629:
5123:
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6025:
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5138:
5133:
5128:
5118:
5113:
5108:
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3636:
2726:
2247:
5954:
5517:
5507:
3468:
2713:
2234:
7479:
602:
Although benzylic arenes are common, non-benzylic compounds are also exceedingly important. Any compound containing a cyclic portion that conforms to
6012:
2305:
7484:
5619:
4978:
7489:
6100:
5634:
2753:
2274:
253:. The electrons are visualized as floating above and below the ring, with the electromagnetic fields they generate acting to keep the ring flat.
236:, is the least complex aromatic hydrocarbon, and it was the first one defined as such. Its bonding nature was first recognized independently by
5984:
5522:
5055:
5045:
5035:
4883:
4510:
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2814:
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2794:
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5015:
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2631:
2621:
2506:
5684:
7891:
5974:
5838:
5396:
5070:
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4943:
4918:
4873:
4812:
4777:
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4578:
4245:
3823:
3641:
2888:
2867:
2862:
2646:
2641:
2636:
2626:
2521:
2516:
2511:
2501:
2167:
1548:"Co-exposures to trace elements and polycyclic aromatic compounds (PACs) impacts North American river otter (Lontra canadensis) baculum"
6551:
5336:
5296:
4908:
4903:
4868:
4714:
4704:
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4689:
4636:
4626:
4621:
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4606:
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757:
7871:
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7841:
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7831:
7811:
7806:
7801:
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7756:
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7651:
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7398:
7393:
7383:
7373:
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4290:
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4220:
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4180:
3995:
7308:
7303:
7293:
7273:
5380:
4354:
4160:
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4105:
323:
are devised. When reacting to form more complex benzene derivatives, the substituents on a benzene ring can be described as either
135:, a heterocyclic compound with a six-membered ring containing one nitrogen atom. Hydrocarbons without an aromatic ring are called
6156:
4125:
4015:
4005:
4000:
3697:
902:
the aromaticity of the reactant is lost. In this regard, the dearomatization is related to hydrogenation. A classic approach is
787:
5255:
5250:
5245:
5240:
5230:
2008:
308:
group. When there is more than one substituent present on the ring, their spatial relationship becomes important for which the
354:). Given that both the methyl and hydroxyl group are ortho-para directors, the ortho and para isomers are typically favoured.
5969:
1762:
1012:
245:
molecular orbitals the size of the ring itself. This represents the equivalent nature of the six carbon-carbon bonds all of
5316:
3948:
5927:
3928:
768:
749:
81:
8034:
6240:
795:
753:
85:
780:
6889:
5785:
5341:
5331:
5321:
5306:
5291:
1118:
257:
5326:
5301:
5286:
3549:
670:
8616:
5311:
3918:
3573:
2933:
665:
7068:
269:
17:
342:
because the methyl group and the hydroxyl group (both ortho para directors) can be placed next to each other (
7063:
6053:
5724:
5406:
3545:
1285:
594:
at the hydroxyl (OH), as charge on the oxygen (alkoxide âO) is partially delocalized into the benzene ring.
3838:
3663:
886:
814:
aromatic compounds undergo nucleophilic substitution. Mechanistically, this reaction differs from a common
180:
Aromatic compounds are pervasive in nature and industry. Key industrial aromatic hydrocarbons are benzene,
8891:
8411:
7161:
5766:
3833:
3690:
1002:
309:
854:
6208:
6131:
3968:
3938:
2001:
1967:
811:
673:, also known as polynuclear aromatic compounds (PAHs) are aromatic hydrocarbons that consist of fused
6938:
6472:
6341:
6250:
3495:
3484:
823:
1508:
7560:
6444:
6326:
899:
358:
has two methyl groups in addition to the hydroxyl group, and, for this structure, 6 isomers exist.
139:. Approximately half of compounds known in the year 2000 are described as aromatic to some extent.
292:
attached to the central benzene core. Examples of benzene compounds with just one substituent are
7499:
7453:
7212:
3568:
2393:
381:
8527:
7203:
6418:
6336:
6136:
6063:
5816:
5776:
5748:
3735:
3683:
3343:
2157:
1388:
952:
237:
31:
5654:
5649:
412:
8435:
6402:
6331:
5932:
5811:
5714:
5577:
3404:
3338:
1994:
947:
741:
250:
748:
on the arene ring, usually hydrogen, is replaced by another reagent. The two main types are
429:
395:
131:, a heterocyclic compound with a five-membered ring that includes a single oxygen atom, and
8554:
8317:
7283:
7188:
5497:
3577:
3541:
2922:
2721:
1600:
1216:
717:
677:
619:
555:
8605:
8:
8517:
8069:
6455:
6366:
5281:
3863:
3646:
3617:
3250:
457:
189:
3593:
1604:
1451:
Larsson, Bonny K.; Sahlberg, Greger P.; Eriksson, Anders T.; Busk, Leif A. (July 1983).
1220:
631:
627:
603:
265:
61:
8588:
7999:
6115:
5979:
5567:
3858:
3773:
3487:
3453:
3437:
3394:
2252:
2242:
1935:
1902:
1878:
1845:
1683:
1588:
1416:
623:
618:
larger than benzene, annulene and annulene are weakly aromatic compounds and annulene,
569:
328:
136:
1564:
1547:
7175:
6483:
6316:
5890:
5674:
5669:
5664:
5659:
5547:
3979:
3933:
3328:
3300:
3143:
2903:
2898:
2736:
2257:
1940:
1922:
1883:
1865:
1817:
1784:
1758:
1687:
1675:
1670:
1624:
1616:
1569:
1528:
1480:
1472:
1408:
1232:
1182:
1114:
1068:
1060:
1008:
942:
657:
1420:
606:
and is not a benzene derivative can be considered a non-benzylic aromatic compound.
527:
8814:
8484:
8323:
7098:
6738:
5964:
5761:
5457:
3714:
3522:
3511:
3292:
1930:
1914:
1873:
1857:
1665:
1655:
1608:
1587:
Ehrenfreund, Pascale; Rasmussen, Steen; Cleaves, James; Chen, Liaohai (June 2006).
1559:
1520:
1464:
1452:
1400:
1224:
1174:
1052:
870:
541:
513:
324:
53:
41:
2D model of a benzene molecule. The carbon "ring" is what makes benzene "aromatic".
241:
8819:
8431:
8423:
8419:
8274:
7939:
7123:
7018:
6933:
6893:
6715:
6515:
5080:
4983:
3763:
3720:
3442:
3399:
3308:
3182:
2147:
2137:
1524:
1204:
1138:"Benzene | Definition, Discovery, Structure, Properties, & Uses | Britannica"
903:
1812:
1779:
1757:(Second ed.). Oxford, New York: Oxford University Press. pp. 514â515.
1589:"Experimentally Tracing the Key Steps in the Origin of Life: The Aromatic World"
1163:"CCXI.âPolynuclear heterocyclic aromatic types. Part II. Some anhydronium bases"
973:
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5614:
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3581:
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3368:
3333:
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3190:
2162:
2152:
1918:
772:
463:
153:
108:
1660:
1643:
1404:
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1186:
1137:
1064:
1040:
878:
834:
807:
799:
653:
104:
37:
1973:
1039:
Balaban, Alexandru T.; Oniciu, Daniela C.; Katritzky, Alan R. (2004-05-01).
164:
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6913:
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1072:
866:
815:
761:
533:
519:
471:
387:
142:
1484:
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367:
188:
called BTX. Many biomolecules have phenyl groups including the so-called
8824:
8776:
8766:
8751:
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8736:
8701:
8641:
8636:
8626:
8469:
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5994:
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3031:
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2804:
2784:
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2703:
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2693:
2683:
2673:
2660:
2491:
2224:
2219:
2214:
2204:
2194:
2181:
2017:
1846:"Dearomatization Strategies in the Synthesis of Complex Natural Products"
1178:
1162:
998:
745:
689:
685:
575:
561:
289:
206:
201:
1468:
443:
264:
cyclic Ï system, while others use it only for those Ï systems that obey
92:
both additions and removals, as well as saturation and dearomatization.
8845:
8756:
8741:
8731:
8721:
8711:
8686:
8666:
8646:
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8583:
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6566:
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6477:
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5401:
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4827:
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4402:
4382:
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3808:
3768:
3758:
3621:
3614:
3528:
3518:
3514:
3263:
3151:
2955:
2842:
2832:
2761:
2496:
2318:
2313:
2288:
2142:
2132:
937:
862:
838:
705:
681:
435:
246:
112:
5679:
1228:
1056:
8860:
8850:
8806:
8796:
8781:
8726:
8661:
8631:
8621:
8576:
8501:
8381:
8371:
8361:
8336:
8204:
8199:
8169:
8144:
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8084:
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7964:
7959:
7924:
7899:
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7469:
7464:
7073:
7053:
6998:
6923:
6883:
6824:
6809:
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6725:
6679:
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6371:
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6276:
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6203:
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6151:
6110:
6058:
6048:
6035:
6030:
5989:
5959:
5922:
5895:
5885:
5806:
5801:
5796:
5537:
5492:
4807:
4802:
4792:
4787:
4782:
4772:
4767:
4757:
4752:
4684:
3953:
3753:
3625:
3608:
3599:
3533:
3268:
3006:
2975:
2965:
2960:
2837:
2565:
2353:
2348:
2127:
932:
713:
582:
Arene rings can stabilize charges, as seen in, for example, phenol (C
8840:
8791:
8716:
8681:
8542:
8537:
8511:
8496:
8491:
8479:
8351:
8284:
8179:
8149:
8114:
8109:
8074:
7949:
7138:
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6903:
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6789:
6556:
6500:
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4709:
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3221:
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3001:
2996:
2970:
2893:
2605:
2585:
2435:
2363:
2358:
2338:
721:
718:
candidate molecule to act as a basis for the earliest forms of life
674:
642:
615:
477:
297:
214:
158:
132:
120:
909:
775:, where a nitro group is added para to the hydroxide substituent:
280:
8786:
8559:
8547:
8415:
8279:
8259:
8254:
8189:
8184:
8119:
8089:
8079:
8039:
7944:
7881:
7876:
7866:
7851:
7846:
7826:
7821:
7816:
7791:
7786:
7776:
7771:
7761:
7751:
7736:
7726:
7721:
7716:
7706:
7701:
7696:
7691:
7681:
7676:
7671:
7666:
7661:
7656:
7646:
7641:
7636:
7631:
7626:
7621:
7616:
7611:
7606:
7601:
7596:
7591:
7586:
7581:
7576:
7571:
7443:
7433:
7423:
7413:
7408:
7403:
7388:
7378:
7368:
7363:
7358:
7353:
7348:
7048:
7043:
7038:
7033:
6779:
6652:
6391:
5756:
5704:
5639:
5436:
4988:
4558:
4538:
4533:
4270:
4235:
4225:
4215:
4210:
4205:
4195:
3958:
3923:
3913:
3898:
3878:
3803:
3538:
3389:
3363:
3213:
3058:
2991:
2590:
2580:
2570:
2460:
2450:
2440:
2328:
2294:
2282:
2096:
2086:
2076:
2066:
928:
874:
842:
709:
638:
547:
505:
373:
355:
301:
225:
219:
181:
127:. Examples of non-benzene compounds with aromatic properties are
57:
3675:
1004:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
218:
Electron flow through p orbitals showing the aromatic nature of
8706:
8671:
8608:
8532:
8464:
8439:
8299:
8289:
8234:
8154:
8019:
7974:
7969:
7929:
7914:
7550:
7545:
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7535:
7530:
7525:
7520:
7515:
7510:
7333:
7328:
7323:
7318:
7313:
7298:
7288:
7278:
7268:
7263:
7258:
7223:
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6769:
6410:
5699:
5689:
5431:
5370:
5260:
5201:
5191:
4349:
4300:
4295:
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4165:
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4145:
4140:
4115:
4080:
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3903:
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3813:
3798:
3778:
3258:
3177:
3077:
3026:
2600:
2595:
2575:
2535:
2475:
2470:
2465:
2455:
2445:
2406:
2333:
2111:
2106:
2101:
2091:
2081:
2071:
2036:
1986:
1962:
1751:
Clayden, Jonathan; Greeves, Nick; Warren, Stuart (2012-03-15).
1586:
846:
803:
591:
491:
449:
418:
401:
339:
335:
305:
293:
185:
124:
116:
810:. Aromatic rings usually nucleophilic, but in the presence of
8566:
8249:
8244:
8239:
8214:
8209:
8164:
8159:
8049:
7228:
6869:
6854:
6774:
6520:
6414:
6406:
6396:
5734:
5729:
5441:
5391:
5365:
5360:
5186:
5181:
4320:
4305:
4130:
4095:
4035:
4020:
3893:
3868:
2942:
2908:
2824:
996:
732:
Aromatic ring systems participate in many organic reactions.
169:
147:
128:
77:
Burn with a strong sooty yellow flame, due to high C:H ratio
64:. Aromatic compounds have the following general properties:
8676:
8229:
8224:
8219:
8194:
7193:
6642:
6608:
6591:
5853:
5421:
5416:
5411:
5235:
5225:
5206:
5196:
4310:
4135:
4120:
4110:
4100:
4090:
4085:
4045:
4040:
4030:
4025:
4010:
3990:
1450:
924:
697:
1545:
1509:"The Source of U.S. EPA's Sixteen PAH Priority Pollutants"
8356:
5270:
3908:
701:
693:
4593:
3483:
1642:
Wang, Xiao-Ye; Yao, Xuelin; MĂŒllen, Klaus (2019-09-01).
1041:"Aromaticity as a Cornerstone of Heterocyclic Chemistry"
27:
Compound containing rings with delocalized pi electrons
6222:
1644:"Polycyclic aromatic hydrocarbons in the graphene era"
1038:
913:
Dearomatization of benzene through the Birch reduction
4447:
4369:
275:
146:
Electron flow through p orbitals for the heterocycle
1750:
955:, a catalyst used to hydrogenate aromatic compounds.
256:
The circle symbol for aromaticity was introduced by
648:
6185:
4744:
1903:"Advances in Catalytic Asymmetric Dearomatization"
1453:"Polycyclic aromatic hydrocarbons in grilled food"
822:, because it occurs at a trigonal carbon atom (sp
752:, when the active reagent is an electrophile, and
5909:
4666:
3496:
1844:Roche, Stéphane P.; Porco, John A. (2011-04-26).
1205:"The Origin of the Circle Symbol for Aromaticity"
8883:
692:is the simplest example of a PAH. PAHs occur in
4525:
2035:
1777:
837:of arenes create saturated rings. The compound
6092:
5946:
1161:Armit, James Wilson; Robinson, Robert (1925).
1007:(6th ed.), New York: Wiley-Interscience,
724:the PAH motif is extended to large 2D sheets.
5867:
5830:
3691:
3469:
2002:
1978:
1641:
1286:"Cresol - an overview | ScienceDirect Topics"
1258:"16.5: An Explanation of Substituent Effects"
1160:
350:), or two positions removed from each other (
645:, both of which have a substituted nitrogen
249:1.5. This equivalency can also explained by
30:"Arene" redirects here. For other uses, see
1702:"22.4: Electrophilic Aromatic Substitution"
660:is a large polycyclic aromatic hydrocarbon.
103:are aromatic compounds, where at least one
3698:
3684:
3476:
3462:
2009:
1995:
1843:
1778:Meyers, A. I.; Beverung, W. N.; Gault, R.
1727:"16.7: Nucleophilic Aromatic Substitution"
1457:Journal of Agricultural and Food Chemistry
1389:"THE CHEMISTRY AND ANALYSIS OF LARGE PAHs"
758:radical-nucleophilic aromatic substitution
1934:
1877:
1669:
1659:
1563:
626:(cyclopropenium cation), which satisfies
346:), one position removed from each other (
288:Benzene derivatives have from one to six
1900:
908:
906:. The methodology is used in synthesis.
756:, when the reagent is a nucleophile. In
652:
279:
213:
205:
163:
152:
141:
111:(-C= or -CH=CH-) group is replaced by a
36:
1901:Zheng, Chao; You, Shu-Li (2021-03-24).
1850:Angewandte Chemie International Edition
1811:Noland, Wayland E.; Baude, Frederic J.
1810:
1113:(3rd ed.). John Wiley & Sons.
168:Line bond structure of the heterocycle
157:Line bond structure of the heterocycle
14:
8884:
1386:
1280:
1278:
1202:
1104:
1102:
841:is completely reduced to a mixture of
597:
3679:
3457:
1990:
1977:
1506:
1446:
1444:
1434:
1432:
1430:
1332:
1330:
1252:
1250:
1248:
1246:
1108:
1100:
1098:
1096:
1094:
1092:
1090:
1088:
1086:
1084:
1082:
195:
4341:
1198:
1196:
1132:
1130:
609:
284:Substitution nomenclature of benzene
82:electrophilic substitution reactions
3978:
1338:"What does "aromatic" really mean?"
1310:"What does "aromatic" really mean?"
1275:
769:electrophilic aromatic substitution
750:electrophilic aromatic substitution
86:nucleophilic aromatic substitutions
24:
1719:
1441:
1427:
1327:
1243:
1079:
893:
796:Nucleophilic aromatic substitution
791:Aromatic nucleophilic substitution
786:
754:nucleophilic aromatic substitution
276:Benzene and derivatives of benzene
25:
8903:
3705:
3569:Modified low-density lipoproteins
3501:Tooltip Aryl hydrocarbon receptor
1955:
1565:10.1016/j.chemosphere.2020.128920
1507:Keith, Lawrence H. (2015-03-15).
1203:Jensen, William B. (April 2009).
1193:
1127:
1028:https://doi.org/10.1351/goldbook.
881:to 2-methyl-1,3-cyclohexandione:
3574:Polycyclic aromatic hydrocarbons
2016:
1961:
885:
853:
829:
779:
671:Polycyclic aromatic hydrocarbons
649:Polycyclic aromatic hydrocarbons
568:
554:
540:
526:
512:
498:
484:
470:
456:
442:
428:
411:
394:
380:
366:
1894:
1837:
1804:
1771:
1744:
1694:
1635:
1580:
1539:
1500:
1491:
1380:
1355:
1302:
735:
666:Polycyclic aromatic hydrocarbon
175:
95:
71:Often non polar and hydrophobic
3546:polychlorinated dibenzodioxins
1387:Fetzer, John C. (2007-04-16).
1154:
1032:
1020:
990:
966:
362:Representative arene compounds
270:three-center two-electron bond
210:Line bond structure of benzene
56:"with a chemistry typified by
13:
1:
3664:Receptor/signaling modulators
1513:Polycyclic Aromatic Compounds
1393:Polycyclic Aromatic Compounds
1209:Journal of Chemical Education
959:
8412:dopamine reuptake inhibitors
1813:"Ethyl Indole-2-carboxylate"
1525:10.1080/10406638.2014.892886
727:
7:
7892:Misc. designer cannabinoids
917:
812:electron-withdrawing groups
798:involves displacement of a
310:arene substitution patterns
10:
8908:
1919:10.1021/acscentsci.0c01651
760:, the active reagent is a
663:
199:
74:High carbon-hydrogen ratio
29:
8833:
8805:
8604:
8510:
8450:
8316:
7890:
7559:
7498:
7452:
7211:
7202:
7174:
7154:
7147:
6882:
6762:
6724:
6693:
6665:
6635:
6539:
6473:2-Fluorodeschloroketamine
6465:
6454:
6433:
6354:
6259:
6217:
6180:
6124:
6087:
5941:
5904:
5862:
5825:
5784:
5775:
5747:
5607:
5576:
5450:
5379:
5350:
5269:
5215:
5171:
5079:
5001:
4841:
4738:
4660:
4587:
4519:
4441:
4363:
4335:
4319:
3967:
3787:
3734:
3713:
3655:
3494:
3485:Aryl hydrocarbon receptor
3420:
3382:
3356:
3321:
3277:
3249:
3212:
3203:
3170:
3142:
3133:
3113:
3076:
3067:
3049:
2984:
2941:
2932:
2921:
2876:
2823:
2770:
2752:
2712:
2659:
2614:
2558:
2534:
2484:
2428:
2405:
2392:
2372:
2304:
2273:
2233:
2180:
2120:
2059:
2024:
1984:
1979:Links to related articles
1671:21.11116/0000-0004-B547-0
1661:10.1007/s11426-019-9491-2
1405:10.1080/10406630701268255
900:dearomatization reactions
1109:Klein, David R. (2017).
877:which is alkylated with
6419:substituted benzofurans
6231:(Mipracetin) 4-AcO-MiPT
5844:(Daltacetin) 4-AcO-DALT
1648:Science China Chemistry
923:Aromatic substituents:
869:in presence of aqueous
8528:Aliphatic hydrocarbons
6101:(Depracetin) 4-AcO-DPT
5918:(Ipracetin) 4-AcO-DiPT
3600:Tapinarof (benvitimod)
3344:1,3,5-Triheptylbenzene
1862:10.1002/anie.201006017
1613:10.1089/ast.2006.6.490
953:Rhodium-platinum oxide
914:
792:
661:
285:
222:
211:
172:
161:
150:
42:
32:Arene (disambiguation)
8555:Aromatic hydrocarbons
6282:(Lucigenol) 4-HO-MPMI
6199:(Metocetin) 4-AcO-MET
6079:(Psilocybin) 4-PO-DMT
5876:(Ethacetin) 4-AcO-DET
3542:aromatic hydrocarbons
3339:1,3,5-Triethylbenzene
1363:"4.2: Covalent Bonds"
1290:www.sciencedirect.com
948:Simple aromatic rings
912:
790:
656:
283:
217:
209:
167:
156:
145:
40:
6491:(N-Ethylnorketamine)
6236:(Miprocin) 4-HO-MiPT
6059:(Bufotenin) 5-HO-DMT
5896:(Ethocybin) 4-PO-DET
5839:(Daltocin) 4-HO-DALT
5498:Cyclopropylmescaline
3578:3-methylcholanthrene
2742:Isopropylcyclohexene
2324:Perhydrophenanthrene
2263:Isopropylcyclohexane
1970:at Wikimedia Commons
1731:Chemistry LibreTexts
1706:Chemistry LibreTexts
1367:Chemistry LibreTexts
1342:Chemistry LibreTexts
1314:Chemistry LibreTexts
1262:Chemistry LibreTexts
1179:10.1039/CT9252701604
1167:J. Chem. Soc., Trans
865:, hydrogenated with
771:is the nitration of
620:Cyclooctadecanonaene
190:aromatic amino acids
68:Typically unreactive
8589:Chlorofluorocarbons
6405:in general (e. g.:
6287:(Meprocin) 4-HO-MPT
6106:(Deprocin) 4-HO-DPT
6074:(Psilocin) 4-HO-DMT
5923:(Iprocin) 4-HO-DiPT
5625:2C-B-DragonFLY-NBOH
5159:N-(2C-TFM) fentanyl
5154:N-(2C-T-7) fentanyl
5149:N-(2C-T-4) fentanyl
5144:N-(2C-T-2) fentanyl
4842:Atypical structures
3864:Dimethyllysergamide
3839:3-Pentyllysergamide
3647:Cyproterone acetate
3529:Dietary carotenoids
3438:Alicyclic compounds
3251:Tetramethylbenzenes
1907:ACS Central Science
1605:2006AsBio...6..490E
1469:10.1021/jf00118a049
1221:2009JChEd..86..423J
997:Smith, Michael B.;
680:and do not contain
598:Non-benzylic arenes
334:For example, three
258:Sir Robert Robinson
8892:Aromatic compounds
8815:Calea zacatechichi
8410:agonists, such as
8000:ADAMANTYL-THPINACA
6194:(Metocin) 4-HO-MET
5980:4-Propionyloxy-DMT
5881:(Ethocin) 4-HO-DET
5630:2C-B-FLY-NB2EtO5Cl
5568:Trifluoromescaline
5451:Mescaline (subst.)
5124:N-(2C-IP) fentanyl
3859:Diallyllysergamide
3834:2-Butyllysergamide
3395:Cyclopropenylidene
2732:Methylcyclopentene
2722:Methylcyclopropene
2253:Methylcyclopentane
2243:Methylcyclopropane
1968:aromatic compounds
1142:www.britannica.com
915:
793:
662:
641:and five-membered
296:, which carries a
286:
223:
212:
196:Benzene ring model
173:
162:
151:
52:usually refers to
46:Aromatic compounds
43:
8879:
8878:
8873:
8872:
8869:
8868:
8521:
8443:
8312:
8311:
8308:
8307:
7168:
6897:
6878:
6877:
6694:Diarylethylamines
6661:
6660:
6484:Deschloroketamine
6448:
6429:
6428:
6422:
6350:
6349:
6246:(Moxy) 5-MeO-MiPT
5789:-alkyltryptamines
5743:
5742:
5563:Trifluoroescaline
5548:Methallylescaline
5503:Difluoromescaline
5167:
5166:
5139:N-(2C-T) fentanyl
5134:N-(2C-P) fentanyl
5129:N-(2C-N) fentanyl
5119:N-(2C-I) fentanyl
5114:N-(2C-H) fentanyl
5109:N-(2C-G) fentanyl
5104:N-(2C-E) fentanyl
5099:N-(2C-D) fentanyl
5094:N-(2C-C) fentanyl
5089:N-(2C-B) fentanyl
4997:
4996:
3934:Methylergometrine
3728:
3673:
3672:
3637:7-Ketocholesterol
3451:
3450:
3416:
3415:
3352:
3351:
3329:Hexamethylbenzene
3317:
3316:
3199:
3198:
3144:Trimethylbenzenes
3129:
3128:
3045:
3044:
2917:
2916:
2904:Cyclododecatriene
2899:Cyclooctatetraene
2737:Methylcyclohexene
2727:Methylcyclobutene
2714:Alkylcycloalkenes
2655:
2654:
2530:
2529:
2388:
2387:
2258:Methylcyclohexane
2248:Methylcyclobutane
2235:Alkylcycloalkanes
2176:
2175:
1966:Media related to
1856:(18): 4068â4093.
1830:Collected Volumes
1818:Organic Syntheses
1797:Collected Volumes
1785:Organic Syntheses
1764:978-0-19-927029-3
1754:Organic Chemistry
1229:10.1021/ed086p423
1111:Organic Chemistry
1057:10.1021/cr0306790
1014:978-0-471-72091-1
943:Hydrodealkylation
658:Hexabenzocoronene
610:Monocyclic arenes
54:organic compounds
16:(Redirected from
8899:
8515:
8485:Amanita muscaria
8424:releasing agents
8405:
7209:
7208:
7189:THC (Dronabinol)
7172:
7171:
7159:
7152:
7151:
7099:Phenyltoloxamine
6887:
6739:Dextromethorphan
6466:Ketamine-related
6463:
6462:
6452:
6451:
6438:
6400:
6224:
6187:
6125:Ibogaine-related
6094:
5948:
5911:
5869:
5832:
5782:
5781:
5518:Fluoroproscaline
5508:Difluoroescaline
5458:2-Bromomescaline
4746:
4668:
4595:
4527:
4449:
4371:
4343:
4333:
4332:
4317:
4316:
3976:
3975:
3732:
3731:
3718:
3700:
3693:
3686:
3677:
3676:
3594:ÎČ-naphthoflavone
3523:prostaglandin G2
3512:Arachidonic acid
3502:
3498:
3478:
3471:
3464:
3455:
3454:
3408:-Propenylbenzene
3210:
3209:
3140:
3139:
3074:
3073:
3065:
3064:
2939:
2938:
2930:
2929:
2615:Branched alkynes
2556:
2555:
2485:Branched alkenes
2426:
2425:
2403:
2402:
2306:Polycycloalkanes
2291:(bicycloheptane)
2285:(bicyclopentane)
2121:Branched alkanes
2057:
2056:
2033:
2032:
2011:
2004:
1997:
1988:
1987:
1975:
1974:
1965:
1949:
1948:
1938:
1898:
1892:
1891:
1881:
1841:
1835:
1833:
1826:
1808:
1802:
1800:
1793:
1775:
1769:
1768:
1748:
1742:
1741:
1739:
1738:
1723:
1717:
1716:
1714:
1713:
1698:
1692:
1691:
1673:
1663:
1654:(9): 1099â1144.
1639:
1633:
1632:
1584:
1578:
1577:
1567:
1543:
1537:
1536:
1519:(2â4): 147â160.
1504:
1498:
1495:
1489:
1488:
1448:
1439:
1436:
1425:
1424:
1384:
1378:
1377:
1375:
1374:
1359:
1353:
1352:
1350:
1349:
1334:
1325:
1324:
1322:
1321:
1306:
1300:
1299:
1297:
1296:
1282:
1273:
1272:
1270:
1269:
1254:
1241:
1240:
1200:
1191:
1190:
1158:
1152:
1151:
1149:
1148:
1134:
1125:
1124:
1106:
1077:
1076:
1051:(5): 2777â2812.
1045:Chemical Reviews
1036:
1030:
1024:
1018:
1017:
994:
988:
987:
985:
984:
970:
889:
871:sodium hydroxide
857:
783:
572:
558:
544:
530:
516:
502:
488:
474:
460:
446:
432:
415:
398:
384:
370:
238:Joseph Loschmidt
21:
8907:
8906:
8902:
8901:
8900:
8898:
8897:
8896:
8882:
8881:
8880:
8875:
8874:
8865:
8829:
8820:Silene capensis
8801:
8600:
8514:
8506:
8457:
8455:
8446:
8432:methamphetamine
8420:methylphenidate
8409:
8406:Also indirect D
8404:
8321:
8304:
8275:THC-O-phosphate
7940:5F-CUMYL-PINACA
7886:
7555:
7494:
7448:
7198:
7165:
7158:
7143:
7124:Trihexyphenidyl
7019:Diphenhydramine
6934:Brompheniramine
6892:
6886:
6874:
6758:
6720:
6716:Methoxphenidine
6689:
6657:
6631:
6535:
6516:Methoxyketamine
6457:
6443:
6437:
6425:
6399:
6346:
6255:
6213:
6176:
6120:
6116:(The Light) DPT
6083:
6026:5-MeO-α,N,N-TMT
5937:
5900:
5858:
5821:
5771:
5739:
5603:
5572:
5446:
5375:
5346:
5265:
5211:
5163:
5081:N-(2C)-fentanyl
5075:
4993:
4984:NBOMe-mescaline
4837:
4734:
4656:
4583:
4515:
4437:
4359:
4315:
3970:
3963:
3790:
3783:
3764:Bromo-DragonFLY
3726:
3724:
3717:
3709:
3704:
3674:
3669:
3651:
3586:benzanthracenes
3500:
3490:
3482:
3452:
3447:
3443:Petroleum jelly
3412:
3400:Phenylacetylene
3378:
3348:
3313:
3309:Isobutylbenzene
3273:
3245:
3195:
3166:
3125:
3109:
3063:
3041:
2980:
2924:
2913:
2872:
2819:
2766:
2748:
2708:
2651:
2610:
2552:
2544:
2538:
2526:
2480:
2422:
2415:
2409:
2398:
2396:
2384:
2368:
2300:
2297:(bicyclodecane)
2269:
2229:
2172:
2138:3-Methylpentane
2116:
2053:
2045:
2039:
2028:
2026:
2020:
2015:
1980:
1958:
1953:
1952:
1899:
1895:
1842:
1838:
1828:
1809:
1805:
1795:
1776:
1772:
1765:
1749:
1745:
1736:
1734:
1725:
1724:
1720:
1711:
1709:
1700:
1699:
1695:
1640:
1636:
1585:
1581:
1544:
1540:
1505:
1501:
1496:
1492:
1449:
1442:
1437:
1428:
1385:
1381:
1372:
1370:
1361:
1360:
1356:
1347:
1345:
1336:
1335:
1328:
1319:
1317:
1308:
1307:
1303:
1294:
1292:
1284:
1283:
1276:
1267:
1265:
1256:
1255:
1244:
1201:
1194:
1159:
1155:
1146:
1144:
1136:
1135:
1128:
1121:
1107:
1080:
1037:
1033:
1025:
1021:
1015:
995:
991:
982:
980:
972:
971:
967:
962:
920:
904:Birch reduction
896:
894:Dearomatization
832:
819:
738:
730:
668:
651:
612:
600:
590:âOH), which is
589:
585:
578:
573:
564:
559:
550:
545:
536:
531:
522:
517:
508:
503:
494:
489:
480:
475:
466:
461:
452:
447:
438:
433:
424:
416:
407:
399:
390:
385:
376:
371:
278:
251:resonance forms
235:
231:
204:
198:
178:
98:
35:
28:
23:
22:
15:
12:
11:
5:
8905:
8895:
8894:
8877:
8876:
8871:
8870:
8867:
8866:
8864:
8863:
8858:
8853:
8848:
8843:
8837:
8835:
8831:
8830:
8828:
8827:
8822:
8817:
8811:
8809:
8803:
8802:
8800:
8799:
8794:
8789:
8784:
8779:
8774:
8769:
8764:
8762:Racemethorphan
8759:
8754:
8749:
8744:
8739:
8734:
8729:
8724:
8719:
8714:
8709:
8704:
8699:
8697:Levomethorphan
8694:
8689:
8684:
8679:
8674:
8669:
8664:
8659:
8654:
8649:
8644:
8639:
8634:
8629:
8624:
8619:
8613:
8611:
8602:
8601:
8599:
8598:
8597:
8596:
8591:
8581:
8580:
8579:
8574:
8564:
8563:
8562:
8552:
8551:
8550:
8545:
8540:
8535:
8524:
8522:
8508:
8507:
8505:
8504:
8499:
8494:
8489:
8477:
8472:
8467:
8461:
8459:
8453:
8448:
8447:
8445:
8444:
8407:
8399:
8394:
8389:
8384:
8379:
8377:Phenethylamine
8374:
8369:
8364:
8359:
8354:
8349:
8344:
8339:
8334:
8328:
8326:
8319:
8314:
8313:
8310:
8309:
8306:
8305:
8303:
8302:
8297:
8292:
8287:
8282:
8277:
8272:
8267:
8262:
8257:
8252:
8247:
8242:
8237:
8232:
8227:
8222:
8217:
8212:
8207:
8202:
8197:
8192:
8187:
8182:
8177:
8172:
8167:
8162:
8157:
8152:
8147:
8142:
8137:
8132:
8127:
8122:
8117:
8112:
8107:
8102:
8097:
8092:
8087:
8082:
8077:
8072:
8067:
8065:CUMYL-THPINACA
8062:
8057:
8052:
8047:
8042:
8037:
8032:
8027:
8022:
8017:
8012:
8007:
8002:
7997:
7992:
7987:
7982:
7977:
7972:
7967:
7962:
7957:
7952:
7947:
7942:
7937:
7932:
7927:
7922:
7917:
7912:
7907:
7902:
7896:
7894:
7888:
7887:
7885:
7884:
7879:
7874:
7869:
7864:
7859:
7854:
7849:
7844:
7839:
7834:
7829:
7824:
7819:
7814:
7809:
7804:
7799:
7794:
7789:
7784:
7779:
7774:
7769:
7764:
7759:
7754:
7749:
7744:
7739:
7734:
7729:
7724:
7719:
7714:
7709:
7704:
7699:
7694:
7689:
7684:
7679:
7674:
7669:
7664:
7659:
7654:
7649:
7644:
7639:
7634:
7629:
7624:
7619:
7614:
7609:
7604:
7599:
7594:
7589:
7584:
7579:
7574:
7568:
7566:
7557:
7556:
7554:
7553:
7548:
7543:
7538:
7533:
7528:
7523:
7518:
7513:
7507:
7505:
7496:
7495:
7493:
7492:
7487:
7482:
7477:
7472:
7467:
7461:
7459:
7450:
7449:
7447:
7446:
7441:
7436:
7431:
7426:
7421:
7416:
7411:
7406:
7401:
7396:
7391:
7386:
7381:
7376:
7371:
7366:
7361:
7356:
7351:
7346:
7341:
7336:
7331:
7326:
7321:
7316:
7311:
7306:
7301:
7296:
7291:
7286:
7281:
7276:
7271:
7266:
7261:
7256:
7251:
7246:
7241:
7236:
7231:
7226:
7220:
7218:
7206:
7200:
7199:
7197:
7196:
7191:
7186:
7180:
7178:
7169:
7163:
7149:
7145:
7144:
7142:
7141:
7136:
7131:
7129:Tripelennamine
7126:
7121:
7116:
7111:
7106:
7101:
7096:
7091:
7086:
7081:
7076:
7071:
7066:
7061:
7056:
7051:
7046:
7041:
7036:
7031:
7026:
7021:
7016:
7014:Dimenhydrinate
7011:
7006:
7004:Cyproheptadine
7001:
6996:
6991:
6986:
6984:Chlorphenamine
6981:
6979:Chloropyramine
6976:
6971:
6966:
6961:
6956:
6951:
6946:
6941:
6936:
6931:
6926:
6921:
6916:
6911:
6906:
6900:
6898:
6880:
6879:
6876:
6875:
6873:
6872:
6867:
6862:
6857:
6852:
6847:
6842:
6837:
6832:
6827:
6822:
6817:
6812:
6807:
6802:
6797:
6792:
6787:
6782:
6777:
6772:
6766:
6764:
6760:
6759:
6757:
6756:
6751:
6749:Racemethorphan
6746:
6741:
6736:
6734:Dextrallorphan
6730:
6728:
6722:
6721:
6719:
6718:
6713:
6708:
6703:
6697:
6695:
6691:
6690:
6688:
6687:
6682:
6677:
6671:
6669:
6663:
6662:
6659:
6658:
6656:
6655:
6650:
6645:
6639:
6637:
6633:
6632:
6630:
6629:
6623:
6617:
6611:
6606:
6600:
6597:Dieticyclidine
6594:
6589:
6584:
6579:
6574:
6569:
6564:
6559:
6554:
6549:
6543:
6541:
6537:
6536:
6534:
6533:
6528:
6523:
6518:
6513:
6511:Methoxmetamine
6508:
6503:
6498:
6497:((S)-ketamine)
6492:
6486:
6481:
6480:((R)-ketamine)
6475:
6469:
6467:
6460:
6449:
6431:
6430:
6427:
6426:
6424:
6423:
6394:
6389:
6384:
6379:
6374:
6369:
6364:
6358:
6356:
6352:
6351:
6348:
6347:
6345:
6344:
6339:
6334:
6329:
6324:
6319:
6314:
6309:
6304:
6299:
6294:
6289:
6284:
6279:
6274:
6269:
6263:
6261:
6257:
6256:
6254:
6253:
6248:
6243:
6238:
6233:
6227:
6225:
6215:
6214:
6212:
6211:
6206:
6201:
6196:
6190:
6188:
6178:
6177:
6175:
6174:
6169:
6164:
6159:
6154:
6149:
6144:
6139:
6134:
6128:
6126:
6122:
6121:
6119:
6118:
6113:
6108:
6103:
6097:
6095:
6085:
6084:
6082:
6081:
6076:
6071:
6066:
6061:
6056:
6051:
6046:
6033:
6028:
6023:
6010:
5997:
5992:
5987:
5982:
5977:
5972:
5970:4-HO-5-MeO-DMT
5967:
5962:
5957:
5951:
5949:
5939:
5938:
5936:
5935:
5930:
5925:
5920:
5914:
5912:
5902:
5901:
5899:
5898:
5893:
5888:
5883:
5878:
5872:
5870:
5860:
5859:
5857:
5856:
5851:
5846:
5841:
5835:
5833:
5823:
5822:
5820:
5819:
5814:
5809:
5804:
5799:
5793:
5791:
5779:
5773:
5772:
5770:
5769:
5764:
5759:
5753:
5751:
5745:
5744:
5741:
5740:
5738:
5737:
5732:
5727:
5722:
5717:
5712:
5707:
5702:
5697:
5692:
5687:
5682:
5677:
5672:
5667:
5662:
5657:
5652:
5647:
5642:
5637:
5632:
5627:
5622:
5620:2C-B-DragonFLY
5617:
5615:2C-B-BUTTERFLY
5611:
5609:
5605:
5604:
5602:
5601:
5598:
5595:
5592:
5589:
5586:
5582:
5580:
5574:
5573:
5571:
5570:
5565:
5560:
5558:Thioproscaline
5555:
5550:
5545:
5540:
5535:
5530:
5525:
5520:
5515:
5510:
5505:
5500:
5495:
5490:
5485:
5480:
5475:
5470:
5465:
5460:
5454:
5452:
5448:
5447:
5445:
5444:
5439:
5434:
5429:
5424:
5419:
5414:
5409:
5404:
5399:
5394:
5388:
5386:
5384:
5377:
5376:
5374:
5373:
5368:
5363:
5357:
5355:
5348:
5347:
5345:
5344:
5339:
5334:
5329:
5324:
5319:
5314:
5309:
5304:
5299:
5294:
5289:
5284:
5278:
5276:
5267:
5266:
5264:
5263:
5258:
5253:
5248:
5243:
5238:
5233:
5228:
5222:
5220:
5213:
5212:
5210:
5209:
5204:
5199:
5194:
5189:
5184:
5178:
5176:
5169:
5168:
5165:
5164:
5162:
5161:
5156:
5151:
5146:
5141:
5136:
5131:
5126:
5121:
5116:
5111:
5106:
5101:
5096:
5091:
5085:
5083:
5077:
5076:
5074:
5073:
5068:
5063:
5058:
5053:
5048:
5043:
5038:
5033:
5028:
5023:
5018:
5012:
5010:
4999:
4998:
4995:
4994:
4992:
4991:
4986:
4981:
4979:NBOMe-escaline
4976:
4971:
4966:
4961:
4956:
4951:
4946:
4941:
4936:
4931:
4926:
4921:
4916:
4911:
4906:
4901:
4896:
4891:
4886:
4881:
4876:
4871:
4866:
4861:
4856:
4851:
4845:
4843:
4839:
4838:
4836:
4835:
4830:
4825:
4820:
4815:
4810:
4805:
4800:
4795:
4790:
4785:
4780:
4775:
4770:
4765:
4760:
4755:
4749:
4747:
4736:
4735:
4733:
4732:
4727:
4722:
4717:
4712:
4707:
4702:
4697:
4692:
4687:
4682:
4677:
4671:
4669:
4658:
4657:
4655:
4654:
4649:
4644:
4639:
4634:
4629:
4624:
4619:
4614:
4609:
4604:
4598:
4596:
4585:
4584:
4582:
4581:
4576:
4571:
4566:
4561:
4556:
4551:
4546:
4541:
4536:
4530:
4528:
4517:
4516:
4514:
4513:
4508:
4503:
4498:
4493:
4488:
4483:
4478:
4473:
4468:
4463:
4458:
4452:
4450:
4439:
4438:
4436:
4435:
4430:
4425:
4420:
4415:
4410:
4405:
4400:
4395:
4390:
4385:
4380:
4374:
4372:
4361:
4360:
4358:
4357:
4352:
4346:
4344:
4330:
4314:
4313:
4308:
4303:
4298:
4293:
4288:
4283:
4278:
4273:
4268:
4263:
4258:
4253:
4248:
4243:
4238:
4233:
4228:
4223:
4218:
4213:
4208:
4203:
4198:
4193:
4188:
4183:
4178:
4173:
4168:
4163:
4158:
4153:
4148:
4143:
4138:
4133:
4128:
4123:
4118:
4113:
4108:
4103:
4098:
4093:
4088:
4083:
4078:
4073:
4068:
4063:
4058:
4053:
4048:
4043:
4038:
4033:
4028:
4023:
4018:
4013:
4008:
4003:
3998:
3993:
3987:
3985:
3973:
3965:
3964:
3962:
3961:
3956:
3951:
3946:
3941:
3936:
3931:
3926:
3921:
3916:
3911:
3906:
3901:
3896:
3891:
3886:
3881:
3876:
3871:
3866:
3861:
3856:
3851:
3846:
3841:
3836:
3831:
3826:
3821:
3816:
3811:
3806:
3801:
3795:
3793:
3785:
3784:
3782:
3781:
3776:
3771:
3766:
3761:
3756:
3751:
3746:
3740:
3738:
3729:
3722:
3711:
3710:
3703:
3702:
3695:
3688:
3680:
3671:
3670:
3668:
3667:
3660:
3656:
3653:
3652:
3650:
3649:
3644:
3639:
3630:
3629:
3612:
3602:
3597:
3571:
3566:
3561:
3536:
3531:
3526:
3505:
3503:
3492:
3491:
3481:
3480:
3473:
3466:
3458:
3449:
3448:
3446:
3445:
3440:
3435:
3430:
3424:
3422:
3418:
3417:
3414:
3413:
3411:
3410:
3402:
3397:
3392:
3386:
3384:
3380:
3379:
3377:
3376:
3374:4-Vinyltoluene
3371:
3369:Divinylbenzene
3366:
3360:
3358:
3354:
3353:
3350:
3349:
3347:
3346:
3341:
3336:
3334:2-Phenylhexane
3331:
3325:
3323:
3319:
3318:
3315:
3314:
3312:
3311:
3306:
3298:
3290:
3281:
3279:
3275:
3274:
3272:
3271:
3266:
3261:
3255:
3253:
3247:
3246:
3244:
3243:
3235:
3227:
3218:
3216:
3207:
3201:
3200:
3197:
3196:
3194:
3193:
3191:4-Ethyltoluene
3188:
3186:-Propylbenzene
3180:
3174:
3172:
3168:
3167:
3165:
3164:
3159:
3154:
3148:
3146:
3137:
3131:
3130:
3127:
3126:
3124:
3123:
3117:
3115:
3111:
3110:
3108:
3107:
3099:
3091:
3082:
3080:
3071:
3062:
3061:
3055:
3053:
3047:
3046:
3043:
3042:
3040:
3039:
3034:
3029:
3024:
3019:
3014:
3009:
3004:
2999:
2994:
2988:
2986:
2982:
2981:
2979:
2978:
2973:
2968:
2963:
2958:
2953:
2947:
2945:
2936:
2927:
2919:
2918:
2915:
2914:
2912:
2911:
2906:
2901:
2896:
2891:
2886:
2880:
2878:
2874:
2873:
2871:
2870:
2865:
2860:
2855:
2850:
2845:
2840:
2835:
2829:
2827:
2821:
2820:
2818:
2817:
2812:
2807:
2802:
2797:
2792:
2787:
2782:
2776:
2774:
2768:
2767:
2765:
2764:
2758:
2756:
2754:Bicycloalkenes
2750:
2749:
2747:
2746:
2744:
2739:
2734:
2729:
2724:
2718:
2716:
2710:
2709:
2707:
2706:
2701:
2696:
2691:
2686:
2681:
2676:
2671:
2665:
2663:
2657:
2656:
2653:
2652:
2650:
2649:
2644:
2639:
2634:
2629:
2624:
2618:
2616:
2612:
2611:
2609:
2608:
2603:
2598:
2593:
2588:
2583:
2578:
2573:
2568:
2562:
2560:
2559:Linear alkynes
2553:
2546:
2540:
2532:
2531:
2528:
2527:
2525:
2524:
2519:
2514:
2509:
2504:
2499:
2494:
2488:
2486:
2482:
2481:
2479:
2478:
2473:
2468:
2463:
2458:
2453:
2448:
2443:
2438:
2432:
2430:
2429:Linear alkenes
2423:
2417:
2411:
2400:
2390:
2389:
2386:
2385:
2383:
2382:
2376:
2374:
2370:
2369:
2367:
2366:
2361:
2356:
2351:
2346:
2341:
2336:
2331:
2326:
2321:
2316:
2310:
2308:
2302:
2301:
2299:
2298:
2292:
2286:
2279:
2277:
2275:Bicycloalkanes
2271:
2270:
2268:
2267:
2265:
2260:
2255:
2250:
2245:
2239:
2237:
2231:
2230:
2228:
2227:
2222:
2217:
2212:
2207:
2202:
2197:
2192:
2186:
2184:
2178:
2177:
2174:
2173:
2171:
2170:
2165:
2160:
2155:
2150:
2145:
2140:
2135:
2130:
2124:
2122:
2118:
2117:
2115:
2114:
2109:
2104:
2099:
2094:
2089:
2084:
2079:
2074:
2069:
2063:
2061:
2060:Linear alkanes
2054:
2047:
2041:
2030:
2022:
2021:
2014:
2013:
2006:
1999:
1991:
1985:
1982:
1981:
1972:
1971:
1957:
1956:External links
1954:
1951:
1950:
1913:(3): 432â444.
1893:
1836:
1803:
1770:
1763:
1743:
1718:
1693:
1634:
1599:(3): 490â520.
1579:
1538:
1499:
1490:
1463:(4): 867â873.
1440:
1426:
1399:(2): 143â162.
1379:
1354:
1326:
1301:
1274:
1242:
1192:
1153:
1126:
1119:
1078:
1031:
1019:
1013:
989:
978:IUPAC GoldBook
964:
963:
961:
958:
957:
956:
950:
945:
940:
935:
919:
916:
895:
892:
891:
890:
859:
858:
831:
828:
817:
785:
784:
773:salicylic acid
767:An example of
737:
734:
729:
726:
664:Main article:
650:
647:
611:
608:
599:
596:
587:
583:
580:
579:
574:
567:
565:
560:
553:
551:
546:
539:
537:
532:
525:
523:
518:
511:
509:
504:
497:
495:
490:
483:
481:
476:
469:
467:
464:2-Phenylhexane
462:
455:
453:
448:
441:
439:
434:
427:
425:
417:
410:
408:
400:
393:
391:
386:
379:
377:
372:
365:
363:
277:
274:
233:
229:
200:Main article:
197:
194:
177:
174:
97:
94:
89:
88:
78:
75:
72:
69:
26:
18:Arene compound
9:
6:
4:
3:
2:
8904:
8893:
8890:
8889:
8887:
8862:
8859:
8857:
8856:Prenoxdiazine
8854:
8852:
8849:
8847:
8844:
8842:
8839:
8838:
8836:
8832:
8826:
8823:
8821:
8818:
8816:
8813:
8812:
8810:
8808:
8804:
8798:
8795:
8793:
8790:
8788:
8785:
8783:
8780:
8778:
8775:
8773:
8770:
8768:
8765:
8763:
8760:
8758:
8755:
8753:
8750:
8748:
8745:
8743:
8740:
8738:
8735:
8733:
8730:
8728:
8725:
8723:
8720:
8718:
8715:
8713:
8710:
8708:
8705:
8703:
8700:
8698:
8695:
8693:
8690:
8688:
8685:
8683:
8680:
8678:
8675:
8673:
8670:
8668:
8665:
8663:
8660:
8658:
8657:Diprenorphine
8655:
8653:
8652:Cyprenorphine
8650:
8648:
8645:
8643:
8640:
8638:
8635:
8633:
8630:
8628:
8625:
8623:
8620:
8618:
8615:
8614:
8612:
8610:
8607:
8603:
8595:
8592:
8590:
8587:
8586:
8585:
8582:
8578:
8575:
8573:
8572:Diethyl ether
8570:
8569:
8568:
8565:
8561:
8558:
8557:
8556:
8553:
8549:
8546:
8544:
8541:
8539:
8536:
8534:
8531:
8530:
8529:
8526:
8525:
8523:
8519:
8513:
8509:
8503:
8500:
8498:
8495:
8493:
8490:
8487:
8486:
8481:
8478:
8476:
8475:Ibotenic acid
8473:
8471:
8468:
8466:
8463:
8462:
8460:
8456:
8449:
8441:
8437:
8433:
8429:
8425:
8421:
8417:
8413:
8403:
8400:
8398:
8395:
8393:
8390:
8388:
8385:
8383:
8380:
8378:
8375:
8373:
8370:
8368:
8365:
8363:
8360:
8358:
8355:
8353:
8350:
8348:
8345:
8343:
8342:Bromocriptine
8340:
8338:
8335:
8333:
8330:
8329:
8327:
8325:
8322:
8315:
8301:
8298:
8296:
8293:
8291:
8288:
8286:
8283:
8281:
8278:
8276:
8273:
8271:
8270:THC-O-acetate
8268:
8266:
8263:
8261:
8258:
8256:
8253:
8251:
8248:
8246:
8243:
8241:
8238:
8236:
8233:
8231:
8228:
8226:
8223:
8221:
8218:
8216:
8213:
8211:
8208:
8206:
8203:
8201:
8198:
8196:
8193:
8191:
8188:
8186:
8183:
8181:
8178:
8176:
8173:
8171:
8168:
8166:
8163:
8161:
8158:
8156:
8153:
8151:
8148:
8146:
8143:
8141:
8140:MDMB-FUBINACA
8138:
8136:
8135:MDMB-CHMINACA
8133:
8131:
8128:
8126:
8125:Levonantradol
8123:
8121:
8118:
8116:
8113:
8111:
8108:
8106:
8103:
8101:
8098:
8096:
8093:
8091:
8088:
8086:
8083:
8081:
8078:
8076:
8073:
8071:
8068:
8066:
8063:
8061:
8058:
8056:
8053:
8051:
8048:
8046:
8043:
8041:
8038:
8036:
8033:
8031:
8028:
8026:
8023:
8021:
8018:
8016:
8013:
8011:
8008:
8006:
8003:
8001:
7998:
7996:
7993:
7991:
7988:
7986:
7983:
7981:
7978:
7976:
7973:
7971:
7968:
7966:
7963:
7961:
7958:
7956:
7953:
7951:
7948:
7946:
7943:
7941:
7938:
7936:
7933:
7931:
7928:
7926:
7923:
7921:
7920:5F-ADB-PINACA
7918:
7916:
7913:
7911:
7908:
7906:
7905:5F-AB-FUPPYCA
7903:
7901:
7898:
7897:
7895:
7893:
7889:
7883:
7880:
7878:
7875:
7873:
7870:
7868:
7865:
7863:
7860:
7858:
7855:
7853:
7850:
7848:
7845:
7843:
7840:
7838:
7835:
7833:
7830:
7828:
7825:
7823:
7820:
7818:
7815:
7813:
7810:
7808:
7805:
7803:
7800:
7798:
7795:
7793:
7790:
7788:
7785:
7783:
7780:
7778:
7775:
7773:
7770:
7768:
7765:
7763:
7760:
7758:
7755:
7753:
7750:
7748:
7745:
7743:
7740:
7738:
7735:
7733:
7730:
7728:
7725:
7723:
7720:
7718:
7715:
7713:
7710:
7708:
7705:
7703:
7700:
7698:
7695:
7693:
7690:
7688:
7685:
7683:
7680:
7678:
7675:
7673:
7670:
7668:
7665:
7663:
7660:
7658:
7655:
7653:
7650:
7648:
7645:
7643:
7640:
7638:
7635:
7633:
7630:
7628:
7625:
7623:
7620:
7618:
7615:
7613:
7610:
7608:
7605:
7603:
7600:
7598:
7595:
7593:
7590:
7588:
7585:
7583:
7580:
7578:
7575:
7573:
7570:
7569:
7567:
7565:
7564:
7558:
7552:
7549:
7547:
7544:
7542:
7539:
7537:
7534:
7532:
7529:
7527:
7524:
7522:
7519:
7517:
7514:
7512:
7509:
7508:
7506:
7504:
7503:
7497:
7491:
7490:(-)-CP 55,940
7488:
7486:
7485:(+)-CP 55,940
7483:
7481:
7480:(±)-CP 55,940
7478:
7476:
7473:
7471:
7468:
7466:
7463:
7462:
7460:
7458:
7457:
7451:
7445:
7442:
7440:
7437:
7435:
7432:
7430:
7427:
7425:
7422:
7420:
7417:
7415:
7412:
7410:
7407:
7405:
7402:
7400:
7397:
7395:
7392:
7390:
7387:
7385:
7382:
7380:
7377:
7375:
7372:
7370:
7367:
7365:
7362:
7360:
7357:
7355:
7352:
7350:
7347:
7345:
7342:
7340:
7337:
7335:
7332:
7330:
7327:
7325:
7322:
7320:
7317:
7315:
7312:
7310:
7307:
7305:
7302:
7300:
7297:
7295:
7292:
7290:
7287:
7285:
7282:
7280:
7277:
7275:
7272:
7270:
7267:
7265:
7262:
7260:
7257:
7255:
7252:
7250:
7247:
7245:
7242:
7240:
7237:
7235:
7232:
7230:
7227:
7225:
7222:
7221:
7219:
7217:
7216:
7210:
7207:
7205:
7201:
7195:
7192:
7190:
7187:
7185:
7182:
7181:
7179:
7177:
7173:
7170:
7166:
7157:
7153:
7150:
7146:
7140:
7137:
7135:
7132:
7130:
7127:
7125:
7122:
7120:
7117:
7115:
7112:
7110:
7107:
7105:
7102:
7100:
7097:
7095:
7092:
7090:
7087:
7085:
7082:
7080:
7077:
7075:
7072:
7070:
7067:
7065:
7062:
7060:
7057:
7055:
7052:
7050:
7047:
7045:
7042:
7040:
7037:
7035:
7032:
7030:
7027:
7025:
7022:
7020:
7017:
7015:
7012:
7010:
7009:Dicycloverine
7007:
7005:
7002:
7000:
6997:
6995:
6992:
6990:
6987:
6985:
6982:
6980:
6977:
6975:
6972:
6970:
6967:
6965:
6962:
6960:
6957:
6955:
6952:
6950:
6947:
6945:
6942:
6940:
6937:
6935:
6932:
6930:
6927:
6925:
6922:
6920:
6917:
6915:
6912:
6910:
6907:
6905:
6902:
6901:
6899:
6895:
6891:
6885:
6881:
6871:
6868:
6866:
6863:
6861:
6858:
6856:
6853:
6851:
6848:
6846:
6843:
6841:
6840:Nitrous oxide
6838:
6836:
6833:
6831:
6828:
6826:
6823:
6821:
6818:
6816:
6813:
6811:
6808:
6806:
6803:
6801:
6798:
6796:
6793:
6791:
6788:
6786:
6783:
6781:
6778:
6776:
6773:
6771:
6768:
6767:
6765:
6761:
6755:
6752:
6750:
6747:
6745:
6742:
6740:
6737:
6735:
6732:
6731:
6729:
6727:
6723:
6717:
6714:
6712:
6711:Fluorolintane
6709:
6707:
6704:
6702:
6699:
6698:
6696:
6692:
6686:
6683:
6681:
6678:
6676:
6673:
6672:
6670:
6668:
6664:
6654:
6651:
6649:
6646:
6644:
6641:
6640:
6638:
6634:
6627:
6626:Tenocyclidine
6624:
6621:
6620:Rolicyclidine
6618:
6615:
6614:Phencyclidine
6612:
6610:
6607:
6604:
6601:
6598:
6595:
6593:
6590:
6588:
6585:
6583:
6580:
6578:
6575:
6573:
6570:
6568:
6565:
6563:
6560:
6558:
6555:
6553:
6550:
6548:
6545:
6544:
6542:
6538:
6532:
6529:
6527:
6524:
6522:
6519:
6517:
6514:
6512:
6509:
6507:
6506:Methoxetamine
6504:
6502:
6499:
6496:
6493:
6490:
6487:
6485:
6482:
6479:
6476:
6474:
6471:
6470:
6468:
6464:
6461:
6459:
6453:
6450:
6446:
6442:
6436:
6435:Dissociatives
6432:
6420:
6416:
6412:
6408:
6404:
6398:
6395:
6393:
6390:
6388:
6385:
6383:
6380:
6378:
6375:
6373:
6370:
6368:
6365:
6363:
6360:
6359:
6357:
6353:
6343:
6340:
6338:
6335:
6333:
6330:
6328:
6325:
6323:
6320:
6318:
6315:
6313:
6310:
6308:
6305:
6303:
6300:
6298:
6295:
6293:
6290:
6288:
6285:
6283:
6280:
6278:
6275:
6273:
6270:
6268:
6265:
6264:
6262:
6258:
6252:
6249:
6247:
6244:
6242:
6239:
6237:
6234:
6232:
6229:
6228:
6226:
6220:
6216:
6210:
6207:
6205:
6202:
6200:
6197:
6195:
6192:
6191:
6189:
6183:
6179:
6173:
6170:
6168:
6167:Tabernanthine
6165:
6163:
6160:
6158:
6155:
6153:
6150:
6148:
6145:
6143:
6140:
6138:
6135:
6133:
6130:
6129:
6127:
6123:
6117:
6114:
6112:
6109:
6107:
6104:
6102:
6099:
6098:
6096:
6090:
6086:
6080:
6077:
6075:
6072:
6070:
6069:Norbaeocystin
6067:
6065:
6062:
6060:
6057:
6055:
6052:
6050:
6047:
6045:
6043:
6039:
6034:
6032:
6029:
6027:
6024:
6022:
6020:
6016:
6011:
6009:
6007:
6003:
5998:
5996:
5993:
5991:
5988:
5986:
5983:
5981:
5978:
5976:
5973:
5971:
5968:
5966:
5963:
5961:
5958:
5956:
5953:
5952:
5950:
5944:
5940:
5934:
5931:
5929:
5926:
5924:
5921:
5919:
5916:
5915:
5913:
5907:
5903:
5897:
5894:
5892:
5889:
5887:
5884:
5882:
5879:
5877:
5874:
5873:
5871:
5865:
5861:
5855:
5852:
5850:
5847:
5845:
5842:
5840:
5837:
5836:
5834:
5828:
5824:
5818:
5815:
5813:
5810:
5808:
5805:
5803:
5800:
5798:
5795:
5794:
5792:
5790:
5788:
5783:
5780:
5778:
5774:
5768:
5765:
5763:
5760:
5758:
5755:
5754:
5752:
5750:
5746:
5736:
5733:
5731:
5728:
5726:
5723:
5721:
5718:
5716:
5713:
5711:
5708:
5706:
5703:
5701:
5698:
5696:
5693:
5691:
5688:
5686:
5683:
5681:
5678:
5676:
5673:
5671:
5668:
5666:
5663:
5661:
5658:
5656:
5653:
5651:
5648:
5646:
5643:
5641:
5638:
5636:
5635:2CB-5-hemifly
5633:
5631:
5628:
5626:
5623:
5621:
5618:
5616:
5613:
5612:
5610:
5606:
5599:
5596:
5593:
5590:
5587:
5584:
5583:
5581:
5579:
5575:
5569:
5566:
5564:
5561:
5559:
5556:
5554:
5551:
5549:
5546:
5544:
5541:
5539:
5536:
5534:
5531:
5529:
5528:Isoproscaline
5526:
5524:
5521:
5519:
5516:
5514:
5511:
5509:
5506:
5504:
5501:
5499:
5496:
5494:
5491:
5489:
5488:Asymbescaline
5486:
5484:
5483:Allylescaline
5481:
5479:
5476:
5474:
5471:
5469:
5466:
5464:
5461:
5459:
5456:
5455:
5453:
5449:
5443:
5440:
5438:
5435:
5433:
5430:
5428:
5425:
5423:
5420:
5418:
5415:
5413:
5410:
5408:
5405:
5403:
5400:
5398:
5395:
5393:
5390:
5389:
5387:
5385:
5382:
5378:
5372:
5369:
5367:
5364:
5362:
5359:
5358:
5356:
5354:
5349:
5343:
5340:
5338:
5335:
5333:
5330:
5328:
5325:
5323:
5320:
5318:
5315:
5313:
5310:
5308:
5305:
5303:
5300:
5298:
5295:
5293:
5290:
5288:
5285:
5283:
5280:
5279:
5277:
5275:
5274:
5268:
5262:
5259:
5257:
5254:
5252:
5249:
5247:
5244:
5242:
5239:
5237:
5234:
5232:
5229:
5227:
5224:
5223:
5221:
5219:
5214:
5208:
5205:
5203:
5200:
5198:
5195:
5193:
5190:
5188:
5185:
5183:
5180:
5179:
5177:
5175:
5170:
5160:
5157:
5155:
5152:
5150:
5147:
5145:
5142:
5140:
5137:
5135:
5132:
5130:
5127:
5125:
5122:
5120:
5117:
5115:
5112:
5110:
5107:
5105:
5102:
5100:
5097:
5095:
5092:
5090:
5087:
5086:
5084:
5082:
5078:
5072:
5069:
5067:
5064:
5062:
5059:
5057:
5054:
5052:
5049:
5047:
5044:
5042:
5039:
5037:
5034:
5032:
5029:
5027:
5024:
5022:
5019:
5017:
5014:
5013:
5011:
5009:
5005:
5000:
4990:
4987:
4985:
4982:
4980:
4977:
4975:
4972:
4970:
4967:
4965:
4962:
4960:
4957:
4955:
4952:
4950:
4947:
4945:
4942:
4940:
4937:
4935:
4932:
4930:
4927:
4925:
4922:
4920:
4917:
4915:
4912:
4910:
4907:
4905:
4902:
4900:
4897:
4895:
4892:
4890:
4887:
4885:
4882:
4880:
4877:
4875:
4872:
4870:
4867:
4865:
4862:
4860:
4857:
4855:
4852:
4850:
4847:
4846:
4844:
4840:
4834:
4831:
4829:
4826:
4824:
4821:
4819:
4816:
4814:
4811:
4809:
4806:
4804:
4801:
4799:
4796:
4794:
4791:
4789:
4786:
4784:
4781:
4779:
4776:
4774:
4771:
4769:
4766:
4764:
4761:
4759:
4756:
4754:
4751:
4750:
4748:
4742:
4737:
4731:
4728:
4726:
4723:
4721:
4718:
4716:
4713:
4711:
4708:
4706:
4703:
4701:
4698:
4696:
4693:
4691:
4688:
4686:
4683:
4681:
4678:
4676:
4673:
4672:
4670:
4664:
4659:
4653:
4650:
4648:
4645:
4643:
4640:
4638:
4635:
4633:
4630:
4628:
4625:
4623:
4620:
4618:
4615:
4613:
4610:
4608:
4605:
4603:
4600:
4599:
4597:
4591:
4586:
4580:
4577:
4575:
4572:
4570:
4567:
4565:
4562:
4560:
4557:
4555:
4552:
4550:
4547:
4545:
4542:
4540:
4537:
4535:
4532:
4531:
4529:
4523:
4518:
4512:
4509:
4507:
4504:
4502:
4499:
4497:
4494:
4492:
4489:
4487:
4484:
4482:
4479:
4477:
4474:
4472:
4469:
4467:
4464:
4462:
4459:
4457:
4454:
4453:
4451:
4445:
4440:
4434:
4431:
4429:
4426:
4424:
4421:
4419:
4416:
4414:
4411:
4409:
4406:
4404:
4401:
4399:
4396:
4394:
4391:
4389:
4386:
4384:
4381:
4379:
4376:
4375:
4373:
4367:
4362:
4356:
4353:
4351:
4348:
4347:
4345:
4339:
4334:
4331:
4329:
4328:
4324:
4318:
4312:
4309:
4307:
4304:
4302:
4299:
4297:
4294:
4292:
4289:
4287:
4284:
4282:
4279:
4277:
4274:
4272:
4269:
4267:
4264:
4262:
4259:
4257:
4254:
4252:
4249:
4247:
4244:
4242:
4239:
4237:
4234:
4232:
4229:
4227:
4224:
4222:
4219:
4217:
4214:
4212:
4209:
4207:
4204:
4202:
4199:
4197:
4194:
4192:
4189:
4187:
4184:
4182:
4179:
4177:
4174:
4172:
4169:
4167:
4164:
4162:
4159:
4157:
4154:
4152:
4149:
4147:
4144:
4142:
4139:
4137:
4134:
4132:
4129:
4127:
4124:
4122:
4119:
4117:
4114:
4112:
4109:
4107:
4104:
4102:
4099:
4097:
4094:
4092:
4089:
4087:
4084:
4082:
4079:
4077:
4074:
4072:
4069:
4067:
4064:
4062:
4059:
4057:
4054:
4052:
4049:
4047:
4044:
4042:
4039:
4037:
4034:
4032:
4029:
4027:
4024:
4022:
4019:
4017:
4014:
4012:
4009:
4007:
4004:
4002:
3999:
3997:
3994:
3992:
3989:
3988:
3986:
3984:
3983:
3977:
3974:
3972:
3966:
3960:
3957:
3955:
3952:
3950:
3947:
3945:
3942:
3940:
3937:
3935:
3932:
3930:
3927:
3925:
3922:
3920:
3917:
3915:
3912:
3910:
3907:
3905:
3902:
3900:
3897:
3895:
3892:
3890:
3887:
3885:
3882:
3880:
3877:
3875:
3872:
3870:
3867:
3865:
3862:
3860:
3857:
3855:
3852:
3850:
3847:
3845:
3842:
3840:
3837:
3835:
3832:
3830:
3827:
3825:
3822:
3820:
3817:
3815:
3812:
3810:
3807:
3805:
3802:
3800:
3797:
3796:
3794:
3792:
3786:
3780:
3777:
3775:
3772:
3770:
3767:
3765:
3762:
3760:
3757:
3755:
3752:
3750:
3747:
3745:
3742:
3741:
3739:
3737:
3733:
3730:
3725:
3716:
3712:
3708:
3707:Hallucinogens
3701:
3696:
3694:
3689:
3687:
3682:
3681:
3678:
3666:
3665:
3661:
3658:
3657:
3654:
3648:
3645:
3643:
3640:
3638:
3635:
3632:
3631:
3627:
3623:
3619:
3616:
3613:
3610:
3606:
3603:
3601:
3598:
3595:
3591:
3590:benzoflavones
3587:
3583:
3579:
3575:
3572:
3570:
3567:
3565:
3562:
3559:
3555:
3554:dibenzofurans
3551:
3547:
3543:
3540:
3537:
3535:
3532:
3530:
3527:
3524:
3520:
3516:
3513:
3510:
3507:
3506:
3504:
3499:
3493:
3489:
3486:
3479:
3474:
3472:
3467:
3465:
3460:
3459:
3456:
3444:
3441:
3439:
3436:
3434:
3431:
3429:
3426:
3425:
3423:
3419:
3409:
3407:
3403:
3401:
3398:
3396:
3393:
3391:
3388:
3387:
3385:
3381:
3375:
3372:
3370:
3367:
3365:
3362:
3361:
3359:
3357:Vinylbenzenes
3355:
3345:
3342:
3340:
3337:
3335:
3332:
3330:
3327:
3326:
3324:
3320:
3310:
3307:
3305:
3304:-Butylbenzene
3303:
3299:
3297:
3296:-Butylbenzene
3295:
3291:
3289:
3288:-Butylbenzene
3287:
3283:
3282:
3280:
3276:
3270:
3267:
3265:
3262:
3260:
3257:
3256:
3254:
3252:
3248:
3242:
3240:
3236:
3234:
3232:
3228:
3226:
3224:
3220:
3219:
3217:
3215:
3211:
3208:
3206:
3202:
3192:
3189:
3187:
3185:
3181:
3179:
3176:
3175:
3173:
3169:
3163:
3160:
3158:
3155:
3153:
3150:
3149:
3147:
3145:
3141:
3138:
3136:
3132:
3122:
3119:
3118:
3116:
3112:
3106:
3104:
3100:
3098:
3096:
3092:
3090:
3088:
3084:
3083:
3081:
3079:
3075:
3072:
3070:
3066:
3060:
3057:
3056:
3054:
3052:
3051:Alkylbenzenes
3048:
3038:
3035:
3033:
3030:
3028:
3025:
3023:
3020:
3018:
3015:
3013:
3010:
3008:
3005:
3003:
3000:
2998:
2995:
2993:
2990:
2989:
2987:
2983:
2977:
2974:
2972:
2969:
2967:
2964:
2962:
2959:
2957:
2954:
2952:
2949:
2948:
2946:
2944:
2940:
2937:
2935:
2931:
2928:
2926:
2920:
2910:
2907:
2905:
2902:
2900:
2897:
2895:
2892:
2890:
2887:
2885:
2882:
2881:
2879:
2875:
2869:
2866:
2864:
2861:
2859:
2856:
2854:
2851:
2849:
2846:
2844:
2841:
2839:
2836:
2834:
2831:
2830:
2828:
2826:
2822:
2816:
2813:
2811:
2808:
2806:
2803:
2801:
2798:
2796:
2793:
2791:
2788:
2786:
2783:
2781:
2778:
2777:
2775:
2773:
2769:
2763:
2760:
2759:
2757:
2755:
2751:
2745:
2743:
2740:
2738:
2735:
2733:
2730:
2728:
2725:
2723:
2720:
2719:
2717:
2715:
2711:
2705:
2702:
2700:
2697:
2695:
2692:
2690:
2687:
2685:
2682:
2680:
2677:
2675:
2672:
2670:
2667:
2666:
2664:
2662:
2658:
2648:
2645:
2643:
2640:
2638:
2635:
2633:
2630:
2628:
2625:
2623:
2620:
2619:
2617:
2613:
2607:
2604:
2602:
2599:
2597:
2594:
2592:
2589:
2587:
2584:
2582:
2579:
2577:
2574:
2572:
2569:
2567:
2564:
2563:
2561:
2557:
2554:
2550:
2543:
2537:
2533:
2523:
2520:
2518:
2515:
2513:
2510:
2508:
2505:
2503:
2500:
2498:
2495:
2493:
2490:
2489:
2487:
2483:
2477:
2474:
2472:
2469:
2467:
2464:
2462:
2459:
2457:
2454:
2452:
2449:
2447:
2444:
2442:
2439:
2437:
2434:
2433:
2431:
2427:
2424:
2421:
2414:
2408:
2404:
2401:
2395:
2391:
2381:
2378:
2377:
2375:
2371:
2365:
2362:
2360:
2357:
2355:
2352:
2350:
2347:
2345:
2344:Dodecahedrane
2342:
2340:
2337:
2335:
2332:
2330:
2327:
2325:
2322:
2320:
2317:
2315:
2312:
2311:
2309:
2307:
2303:
2296:
2293:
2290:
2287:
2284:
2281:
2280:
2278:
2276:
2272:
2266:
2264:
2261:
2259:
2256:
2254:
2251:
2249:
2246:
2244:
2241:
2240:
2238:
2236:
2232:
2226:
2223:
2221:
2218:
2216:
2213:
2211:
2208:
2206:
2203:
2201:
2198:
2196:
2193:
2191:
2188:
2187:
2185:
2183:
2179:
2169:
2166:
2164:
2161:
2159:
2156:
2154:
2151:
2149:
2146:
2144:
2141:
2139:
2136:
2134:
2131:
2129:
2126:
2125:
2123:
2119:
2113:
2110:
2108:
2105:
2103:
2100:
2098:
2095:
2093:
2090:
2088:
2085:
2083:
2080:
2078:
2075:
2073:
2070:
2068:
2065:
2064:
2062:
2058:
2055:
2051:
2044:
2038:
2034:
2031:
2023:
2019:
2012:
2007:
2005:
2000:
1998:
1993:
1992:
1989:
1983:
1976:
1969:
1964:
1960:
1959:
1946:
1942:
1937:
1932:
1928:
1924:
1920:
1916:
1912:
1908:
1904:
1897:
1889:
1885:
1880:
1875:
1871:
1867:
1863:
1859:
1855:
1851:
1847:
1840:
1832:, vol. 5
1831:
1824:
1820:
1819:
1814:
1807:
1799:, vol. 6
1798:
1791:
1787:
1786:
1781:
1774:
1766:
1760:
1756:
1755:
1747:
1732:
1728:
1722:
1707:
1703:
1697:
1689:
1685:
1681:
1677:
1672:
1667:
1662:
1657:
1653:
1649:
1645:
1638:
1630:
1626:
1622:
1618:
1614:
1610:
1606:
1602:
1598:
1594:
1590:
1583:
1575:
1571:
1566:
1561:
1557:
1553:
1549:
1542:
1534:
1530:
1526:
1522:
1518:
1514:
1510:
1503:
1494:
1486:
1482:
1478:
1474:
1470:
1466:
1462:
1458:
1454:
1447:
1445:
1435:
1433:
1431:
1422:
1418:
1414:
1410:
1406:
1402:
1398:
1394:
1390:
1383:
1368:
1364:
1358:
1343:
1339:
1333:
1331:
1315:
1311:
1305:
1291:
1287:
1281:
1279:
1263:
1259:
1253:
1251:
1249:
1247:
1238:
1234:
1230:
1226:
1222:
1218:
1214:
1210:
1206:
1199:
1197:
1188:
1184:
1180:
1176:
1173:: 1604â1618.
1172:
1168:
1164:
1157:
1143:
1139:
1133:
1131:
1122:
1120:9781119444251
1116:
1112:
1105:
1103:
1101:
1099:
1097:
1095:
1093:
1091:
1089:
1087:
1085:
1083:
1074:
1070:
1066:
1062:
1058:
1054:
1050:
1046:
1042:
1035:
1029:
1023:
1016:
1010:
1006:
1005:
1000:
993:
979:
975:
969:
965:
954:
951:
949:
946:
944:
941:
939:
936:
934:
930:
926:
922:
921:
911:
907:
905:
901:
888:
884:
883:
882:
880:
879:methyl iodide
876:
872:
868:
864:
861:The compound
856:
852:
851:
850:
848:
844:
840:
836:
835:Hydrogenation
830:Hydrogenation
827:
825:
824:hybridization
821:
813:
809:
808:aromatic ring
805:
801:
800:leaving group
797:
789:
782:
778:
777:
776:
774:
770:
765:
763:
759:
755:
751:
747:
743:
733:
725:
723:
719:
715:
711:
707:
703:
699:
695:
691:
687:
683:
679:
676:
672:
667:
659:
655:
646:
644:
640:
635:
633:
632:HĂŒckel's rule
629:
628:HĂŒckel's rule
625:
624:cyclopropenyl
621:
617:
607:
605:
604:HĂŒckel's rule
595:
593:
577:
571:
566:
563:
557:
552:
549:
543:
538:
535:
529:
524:
521:
515:
510:
507:
501:
496:
493:
487:
482:
479:
473:
468:
465:
459:
454:
451:
445:
440:
437:
431:
426:
423:
421:
414:
409:
406:
404:
397:
392:
389:
383:
378:
375:
369:
364:
361:
360:
359:
357:
353:
349:
345:
341:
337:
332:
330:
326:
322:
318:
314:
311:
307:
303:
299:
295:
291:
282:
273:
271:
267:
266:HĂŒckel's rule
263:
259:
254:
252:
248:
243:
242:August Kekulé
239:
227:
221:
216:
208:
203:
193:
191:
187:
183:
171:
166:
160:
155:
149:
144:
140:
138:
134:
130:
126:
122:
118:
114:
110:
106:
102:
93:
87:
83:
79:
76:
73:
70:
67:
66:
65:
63:
62:HĂŒckel's Rule
59:
55:
51:
47:
39:
33:
19:
8772:Salvinorin A
8692:Levallorphan
8483:
8402:Salvinorin A
8295:WIN 55,212-2
8060:CUMYL-PINACA
8045:APP-FUBINACA
8030:AMB-FUBINACA
8025:ADSB-FUB-187
8010:ADB-FUBINACA
8005:ADB-CHMINACA
7910:5F-AB-PINACA
7562:
7501:
7455:
7214:
7184:Salvinorin A
7156:Cannabinoids
7134:Triprolidine
7109:Promethazine
7104:Procyclidine
7084:Orphenadrine
6914:Benzatropine
6603:Eticyclidine
6307:Aeruginascin
6218:
6181:
6142:Coronaridine
6088:
6041:
6037:
6018:
6014:
6005:
6001:
5985:5,6-diBr-DMT
5942:
5905:
5863:
5826:
5797:4,5-DHP-α-MT
5786:
5710:Fenfluramine
5543:Metaescaline
5523:Isobuscaline
5352:
5272:
5217:
5173:
5056:25I-NMe7DHBF
5046:25B-NMe7Indz
5036:25B-NMe7DHBF
5007:
5003:
4974:N-Ethyl-2C-B
4929:2CBFly-NBOMe
4884:25I-N2Nap1OH
4740:
4662:
4589:
4521:
4511:25TFM-NB4OMe
4443:
4433:25TFM-NB3OMe
4365:
4337:
4326:
4322:
3981:
3944:Methysergide
3749:2CBFly-NBOMe
3715:Psychedelics
3662:
3634:Antagonists:
3633:
3605:Tetrapyroles
3508:
3405:
3301:
3293:
3285:
3238:
3230:
3222:
3183:
3157:Pseudocumene
3121:Ethylbenzene
3102:
3094:
3086:
3017:Phenanthrene
2925:hydrocarbons
2800:Cycloheptyne
2790:Cyclopentyne
2780:Cyclopropyne
2772:Cycloalkynes
2689:Cycloheptene
2679:Cyclopentene
2669:Cyclopropene
2661:Cycloalkenes
2548:
2541:
2419:
2412:
2399:hydrocarbons
2380:Spiroalkanes
2210:Cycloheptane
2200:Cyclopentane
2190:Cyclopropane
2182:Cycloalkanes
2049:
2042:
2029:hydrocarbons
2018:Hydrocarbons
1910:
1906:
1896:
1853:
1849:
1839:
1829:
1822:
1816:
1806:
1796:
1789:
1783:
1780:"1-Naphthol"
1773:
1753:
1746:
1735:. Retrieved
1733:. 2015-05-03
1730:
1721:
1710:. Retrieved
1708:. 2014-11-26
1705:
1696:
1651:
1647:
1637:
1596:
1593:Astrobiology
1592:
1582:
1555:
1551:
1541:
1516:
1512:
1502:
1493:
1460:
1456:
1396:
1392:
1382:
1371:. Retrieved
1369:. 2020-07-30
1366:
1357:
1346:. Retrieved
1344:. 2013-10-02
1341:
1318:. Retrieved
1316:. 2013-10-02
1313:
1304:
1293:. Retrieved
1289:
1266:. Retrieved
1264:. 2015-05-03
1261:
1212:
1208:
1170:
1166:
1156:
1145:. Retrieved
1141:
1110:
1048:
1044:
1034:
1026:
1022:
1003:
999:March, Jerry
992:
981:. Retrieved
977:
968:
897:
867:Raney nickel
860:
833:
802:, such as a
794:
766:
742:substitution
740:In aromatic
739:
736:Substitution
731:
706:carcinogenic
686:substituents
669:
636:
613:
601:
581:
534:Benzoic acid
520:Nitrobenzene
419:
402:
388:Ethylbenzene
351:
347:
343:
333:
320:
316:
312:
290:substituents
287:
261:
255:
224:
179:
176:Applications
101:Heteroarenes
100:
99:
96:Heteroarenes
90:
49:
45:
44:
8825:Galantamine
8777:Spiradoline
8767:Racemorphan
8752:Phenazocine
8747:Pentazocine
8737:Noribogaine
8702:Levorphanol
8642:Cyclazocine
8637:Butorphanol
8627:Bremazocine
8584:Haloalkanes
8470:Eszopiclone
8428:amphetamine
8387:Pramipexole
8347:Cabergoline
8332:Apomorphine
8130:MDMB-CHMICA
8100:FUB-JWH-018
8095:FUB-APINACA
7990:AB-FUBINACA
7985:AB-CHMINACA
7980:AB-CHFUPYCA
7119:Tolterodine
7114:Scopolamine
7094:Pheniramine
7059:Hyoscyamine
6974:CAR-302,668
6969:CAR-302,537
6964:CAR-302,368
6959:CAR-302,282
6954:CAR-302,196
6949:CAR-301,060
6944:CAR-226,086
6929:BRN-1484501
6919:Benzydamine
6909:Benactyzine
6894:antagonists
6850:Perzinfotel
6845:Noribogaine
6805:Dizocilpine
6754:Racemorphan
6744:Dextrorphan
6701:Diphenidine
6685:Rimantadine
6667:Adamantanes
6648:Gacyclidine
6540:PCP-related
6526:Norketamine
6489:Ethketamine
6458:hexylamines
6445:antagonists
6403:empathogens
6162:Noribogaine
5995:5-Bromo-DMT
5955:4,5-DHP-DMT
5777:Tryptamines
5749:Piperazines
5720:Macromerine
5041:25B-NMe7Ind
5031:25B-NMe7Box
5026:25B-NMe7Bim
4969:MDPEA-NBOMe
4939:5-APB-NBOMe
4924:2CBCB-NBOMe
4833:25TFM-NBOMe
4506:25T7-NB4OMe
4501:25T4-NB4OMe
4496:25T2-NB4OMe
4428:25T7-NB3OMe
4423:25T4-NB3OMe
4418:25T2-NB3OMe
3874:Ergometrine
3736:Benzofurans
3618:derivatives
3582:benzopyrene
3539:Halogenated
3515:metabolites
3205:C4-Benzenes
3162:Hemellitene
3135:C3-Benzenes
3069:C2-Benzenes
3032:Corannulene
2951:Naphthalene
2815:Cyclodecyne
2810:Cyclononyne
2805:Cyclooctyne
2795:Cyclohexyne
2785:Cyclobutyne
2704:Cyclodecene
2699:Cyclononene
2694:Cyclooctene
2684:Cyclohexene
2674:Cyclobutene
2394:Unsaturated
2225:Cyclodecane
2220:Cyclononane
2215:Cyclooctane
2205:Cyclohexane
2195:Cyclobutane
1552:Chemosphere
746:substituent
714:teratogenic
690:Naphthalene
682:heteroatoms
576:Picric acid
562:Paracetamol
329:deactivated
300:group, and
202:Aromaticity
8846:Isoaminile
8807:Oneirogens
8757:Proxorphan
8742:Oxilorphan
8732:Nalorphine
8722:Nalbuphine
8712:Metazocine
8687:Ketazocine
8667:Herkinorin
8647:Cyclorphan
8594:Chloroform
8436:precursors
8397:Rotigotine
8392:Ropinirole
8367:Nuciferine
8175:NESS-040C5
8055:CUMYL-PICA
8015:ADB-PINACA
7955:5F-SDB-006
7935:5F-APINACA
7089:Oxybutynin
7079:Mepyramine
7029:Doxylamine
6989:Clemastine
6884:Deliriants
6860:Remacemide
6835:Neramexane
6815:Herkinorin
6800:Dexoxadrol
6795:Delucemine
6726:Morphinans
6706:Ephenidine
6675:Amantadine
6582:3-MeO-PCPy
6577:3-MeO-PCPr
6567:3-MeO-PCMo
6547:2'-Oxo-PCE
6531:Tiletamine
6495:Esketamine
6478:Arketamine
6456:Arylcycloâ
6417:and other
6387:Lorcaserin
6312:Baeocystin
6302:5-MeO-MPMI
6297:5-MeO-MALT
6292:5-MeO-EiPT
6172:Voacangine
5928:5-MeO-DiPT
5849:5-MeO-DALT
5807:5-MeO-α-MT
5802:5-MeO-α-ET
5553:Proscaline
5533:Jimscaline
5402:Lophophine
5066:25I-NMeTHF
5061:25I-NMeFur
5051:25B-NMePyr
5021:25B-NMe7BT
5016:25B-NMe7BF
4964:FECIMBI-36
4934:4-EA-NBOMe
4914:25I-NBMeOH
4899:25I-NB34MD
4894:25I-N4MT3M
4889:25I-N3MT2M
4879:25C-NBOiPr
4864:25B-NB25DM
4859:25B-NB23DM
4854:25B-NAcPip
4849:25B-N1POMe
4828:25T7-NBOMe
4823:25T4-NBOMe
4818:25T2-NBOMe
4798:25iP-NBOMe
4763:25CN-NBOMe
4730:25TFM-NBOH
4652:25TFM-NBMD
4491:25P-NB4OMe
4486:25N-NB4OMe
4481:25I-NB4OMe
4476:25H-NB4OMe
4471:25E-NB4OMe
4466:25D-NB4OMe
4461:25C-NB4OMe
4456:25B-NB4OMe
4413:25P-NB3OMe
4408:25N-NB3OMe
4403:25I-NB3OMe
4398:25H-NB3OMe
4393:25E-NB3OMe
4388:25D-NB3OMe
4383:25C-NB3OMe
4378:25B-NB3OMe
3969:Phenethylâ
3819:1cP-AL-LAD
3809:1P-ETH-LAD
3759:5-MeO-DiBF
3622:indigo dye
3615:Tryptophan
3519:lipoxin A4
3488:modulators
3264:Prehnitene
3152:Mesitylene
3007:Circulenes
2956:Anthracene
2884:Alkatriene
2853:Heptadiene
2843:Pentadiene
2833:Propadiene
2762:Norbornene
2632:Isoheptyne
2622:Isopentyne
2507:Isoheptene
2497:Isopentene
2319:Diamondoid
2314:Adamantane
2289:Norbornane
2153:Isoheptane
2143:Neopentane
2133:Isopentane
1737:2023-11-29
1712:2023-11-29
1558:: 128920.
1373:2023-11-06
1348:2023-11-29
1320:2023-11-06
1295:2023-12-03
1268:2023-12-03
1215:(4): 423.
1147:2023-11-06
983:2023-11-06
974:"Aromatic"
960:References
938:Asphaltene
863:resorcinol
839:1-naphthol
820:2 reaction
436:Mesitylene
338:exist for
247:bond order
113:heteroatom
8861:Pukateine
8851:Noscapine
8797:Xorphanol
8782:Tifluadom
8727:Nalmefene
8662:Enadoline
8632:Butorphan
8622:Alazocine
8577:Enflurane
8512:Inhalants
8502:Zopiclone
8458:enhancers
8382:Piribedil
8372:Pergolide
8362:Memantine
8337:Aporphine
8205:Parahexyl
8200:Org 28611
8170:NESS-0327
8145:MEPIRAPIM
8105:FUB-PB-22
8085:FDU-PB-22
7995:AB-PINACA
7965:A-836,339
7960:A-796,260
7925:5F-ADBICA
7900:4-HTMPIPO
7475:CP 55,940
7470:CP 55,244
7465:CP 47,497
7204:Synthetic
7167:agonists)
7074:Meclozine
7054:Flavoxate
6999:Cyclizine
6924:Biperiden
6825:Midafotel
6810:Etoxadrol
6785:Aptiganel
6680:Memantine
6587:4-MeO-PCP
6572:3-MeO-PCP
6562:3-MeO-PCE
6377:Efavirenz
6372:Dimemebfe
6362:AL-38022A
6277:4-HO-McPT
6241:5-Me-MiPT
6204:5-MeO-MET
6152:Ibogamine
6111:5-MeO-DPT
6054:α,N,N-TMT
6049:7,N,N-TMT
6031:5-MeO-DMT
5990:5-AcO-DMT
5975:4,N,N-TMT
5965:4-AcO-DMT
5960:2,N,N-TMT
5891:(T-9) DET
5886:5-MeO-DET
5538:Mescaline
5493:Buscaline
5071:25I-NMeTh
4959:DOI-NBOMe
4954:DOB-NBOMe
4949:C30-NBOMe
4944:5MT-NBOMe
4919:25I-NBTFM
4874:25C-NBOEt
4813:25T-NBOMe
4808:25P-NBOMe
4803:25N-NBOMe
4793:25I-NBOMe
4788:25H-NBOMe
4783:25G-NBOMe
4778:25F-NBOMe
4773:25E-NBOMe
4768:25D-NBOMe
4758:25C-NBOMe
4753:25B-NBOMe
4725:25T7-NBOH
4720:25T2-NBOH
4685:25CN-NBOH
4647:25T7-NBMD
4642:25T2-NBMD
4579:25TFM-NBF
4246:2C-T-22.5
3954:PARGY-LAD
3824:1cP-MiPLA
3754:5-MeO-BFE
3727:agonists)
3642:CH-223191
3626:indirubin
3609:bilirubin
3558:biphenyls
3534:Flutamide
3509:Agonists:
3433:Annulynes
3428:Annulenes
3269:Isodurene
3002:Helicenes
2976:Heptacene
2966:Pentacene
2961:Tetracene
2889:Alkadiyne
2868:Decadiene
2863:Nonadiene
2858:Octadiene
2848:Hexadiene
2838:Butadiene
2647:Isodecyne
2642:Isononyne
2637:Isooctyne
2627:Isohexyne
2522:Isodecene
2517:Isononene
2512:Isooctene
2502:Isohexene
2492:Isobutene
2397:aliphatic
2354:Churchane
2349:Basketane
2168:Isodecane
2163:Isononane
2158:Isooctane
2148:Isohexane
2128:Isobutane
2027:aliphatic
2025:Saturated
1927:2374-7943
1870:1433-7851
1688:198333072
1680:1869-1870
1621:1531-1074
1574:0045-6535
1533:1040-6638
1477:0021-8561
1413:1040-6638
1237:0021-9584
1187:0368-1645
1065:0009-2665
933:Arenediyl
873:forms an
728:Reactions
710:mutagenic
684:or carry
616:annulenes
325:activated
137:aliphatic
8886:Category
8841:Glaucine
8792:U-69,593
8717:Morphine
8682:Ibogaine
8609:agonists
8543:Kerosene
8538:Gasoline
8497:Zolpidem
8492:Zaleplon
8480:Muscimol
8440:levodopa
8352:Lisuride
8324:agonists
8285:THJ-2201
8180:Nabilone
8150:MAM-2201
8115:JTE 7-31
8110:FUBIMINA
8075:EAM-2201
7950:5F-PB-22
7139:WIN-2299
6994:CS-27349
6904:Atropine
6865:Selfotel
6820:Ibogaine
6790:Budipine
6557:3-HO-PCP
6552:3-HO-PCE
6501:Ketamine
6382:Glaucine
6272:4-HO-EPT
6267:4-HO-DBT
6157:ME-18-MC
6147:Ibogaine
6013:5-MeO-4,
6000:5-MeO-2,
5645:2CD-5EtO
5513:Escaline
4909:25I-NBBr
4904:25I-NBAm
4869:25C-NBCl
4715:25P-NBOH
4710:25I-NBOH
4705:25H-NBOH
4700:25F-NBOH
4695:25E-NBOH
4690:25D-NBOH
4680:25C-NBOH
4675:25B-NBOH
4637:25P-NBMD
4632:25I-NBMD
4627:25H-NBMD
4622:25F-NBMD
4617:25E-NBMD
4612:25D-NBMD
4607:25C-NBMD
4602:25B-NBMD
4574:25T7-NBF
4569:25T2-NBF
3744:2C-B-FLY
3659:See also
3037:Kekulene
3022:Chrysene
3012:Butalene
2997:Fluorene
2971:Hexacene
2923:Aromatic
2894:Cumulene
2364:Twistane
2359:Pagodane
2339:Prismane
1945:33791426
1888:21506209
1629:16805704
1421:97930473
1073:15137807
1001:(2007),
918:See also
806:, on an
722:graphene
675:aromatic
643:pyridine
478:Biphenyl
298:hydroxyl
159:pyridine
133:pyridine
121:nitrogen
109:vinylene
80:Undergo
8787:U-50488
8560:Toluene
8548:Propane
8516:(Mixed
8434:), and
8416:cocaine
8280:THJ-018
8265:STS-135
8260:SDB-006
8255:SDB-005
8190:NM-2201
8185:Nabitan
8120:JTE-907
8090:FUB-144
8080:FAB-144
8040:APINACA
7945:5F-NNE1
7882:JWH-424
7877:JWH-398
7872:JWH-387
7867:JWH-359
7862:JWH-350
7857:JWH-336
7852:JWH-307
7847:JWH-302
7842:JWH-300
7837:JWH-258
7832:JWH-253
7827:JWH-251
7822:JWH-250
7817:JWH-249
7812:JWH-234
7807:JWH-229
7802:JWH-220
7797:JWH-213
7792:JWH-210
7787:JWH-210
7782:JWH-205
7777:JWH-203
7772:JWH-200
7767:JWH-199
7762:JWH-198
7757:JWH-197
7752:JWH-196
7747:JWH-195
7742:JWH-194
7737:JWH-193
7732:JWH-192
7727:JWH-185
7722:JWH-184
7717:JWH-182
7712:JWH-181
7707:JWH-176
7702:JWH-175
7697:JWH-171
7692:JWH-167
7687:JWH-166
7682:JWH-164
7677:JWH-161
7672:JWH-149
7667:JWH-149
7662:JWH-148
7657:JWH-147
7652:JWH-139
7647:JWH-133
7642:JWH-122
7637:JWH-120
7632:JWH-116
7627:JWH-098
7622:JWH-081
7617:JWH-073
7612:JWH-057
7607:JWH-051
7602:JWH-048
7597:JWH-047
7592:JWH-030
7587:JWH-019
7582:JWH-018
7577:JWH-015
7572:JWH-007
7444:AM-6545
7439:AM-4113
7434:AM-4056
7429:AM-4054
7424:AM-4030
7419:AM-3102
7414:AM-2389
7409:AM-2233
7404:AM-2232
7399:AM-2213
7394:AM-2212
7389:AM-2201
7384:AM-1902
7379:AM-1714
7374:AM-1710
7369:AM-1248
7364:AM-1241
7359:AM-1235
7354:AM-1221
7349:AM-1220
7344:AM-1172
7339:AM-1116
7176:Natural
7049:EA-3834
7044:EA-3580
7039:EA-3443
7034:EA-3167
6780:8A-PDHQ
6653:PRE-084
6392:M-ALPHA
5757:2C-B-PP
5715:Ganesha
5705:DOB-FLY
5685:ÎČk-2C-I
5680:ÎČk-2C-B
5640:2CB-Ind
5437:MMDA-3a
5397:DMMDA-2
4989:ZDCM-04
4564:25P-NBF
4559:25I-NBF
4554:25H-NBF
4549:25E-NBF
4544:25D-NBF
4539:25C-NBF
4534:25B-NBF
4291:2C-T-33
4286:2C-T-32
4281:2C-T-31
4276:2C-T-30
4271:2C-T-28
4266:2C-T-27
4261:2C-T-25
4256:2C-T-24
4251:2C-T-23
4241:2C-T-22
4236:2C-T-21
4231:2C-T-20
4226:2C-T-19
4221:2C-T-18
4216:2C-T-17
4211:2C-T-16
4206:2C-T-15
4201:2C-T-14
4196:2C-T-13
4191:2C-T-12
4186:2C-T-11
4181:2C-T-10
3996:2C-B-AN
3959:PRO-LAD
3924:LSM-775
3914:LSD-Pip
3899:LPD-824
3879:ETH-LAD
3804:1cP-LSD
3789:Lysergâ
3620:(e.g.,
3607:(e.g.,
3592:(e.g.,
3576:(e.g.,
3548:(e.g.,
3544:(e.g.,
3517:(e.g.,
3390:Benzene
3364:Styrene
3241:-Cymene
3233:-Cymene
3225:-Cymene
3214:Cymenes
3105:-Xylene
3097:-Xylene
3089:-Xylene
3078:Xylenes
3059:Toluene
2992:Azulene
2591:Heptyne
2581:Pentyne
2571:Propyne
2536:Alkynes
2461:Heptene
2451:Pentene
2441:Propene
2407:Alkenes
2329:Sterane
2295:Decalin
2283:Housane
2097:Heptane
2087:Pentane
2077:Propane
2067:Methane
2037:Alkanes
1936:8006174
1879:4136767
1601:Bibcode
1485:6352775
1217:Bibcode
929:Aryloxy
875:enolate
847:isomers
843:decalin
762:radical
639:pyrrole
548:Aspirin
506:Aniline
422:-Xylene
405:-Xylene
374:Toluene
356:Xylenol
336:isomers
304:with a
302:toluene
226:Benzene
220:benzene
182:toluene
105:methine
58:benzene
8834:Others
8707:LPK-26
8672:Heroin
8617:2-EMSB
8567:Ethers
8533:Butane
8465:CI-966
8300:XLR-11
8290:UR-144
8235:QUCHIC
8155:MDA-19
8020:ADBICA
7975:AB-005
7970:AB-001
7930:5F-AMB
7915:5F-ADB
7551:HU-345
7546:HU-336
7541:HU-331
7536:HU-320
7531:HU-308
7526:HU-243
7521:HU-239
7516:HU-211
7511:HU-210
7334:AM-938
7329:AM-926
7324:AM-919
7319:AM-906
7314:AM-905
7309:AM-883
7304:AM-881
7299:AM-855
7294:AM-735
7289:AM-694
7284:AM-679
7279:AM-678
7274:AM-661
7269:AM-630
7264:AM-411
7259:AM-404
7254:AM-381
7249:AM-374
7244:AM-356
7239:AM-281
7234:AM-279
7229:AM-251
7224:AM-087
7148:Others
7069:JB-336
7064:JB-318
7024:Ditran
6770:2-EMSB
6763:Others
6636:Others
6622:(PCPy)
6599:(PCDE)
6411:5-MAPB
6355:Others
6260:Others
6132:18-MAC
5700:DMBMPP
5690:DESOXY
5655:5-TOET
5650:2-TOET
5608:Others
5432:MMDA-2
5371:HOT-17
5261:4C-T-2
5202:3C-MAL
5192:3C-DFE
4448:NB4OMe
4370:NB3OMe
4355:25C-NB
4350:25B-NB
4301:2C-TFM
4296:2C-TFE
4176:2C-T-9
4171:2C-T-8
4166:2C-T-7
4161:2C-T-6
4156:2C-T-5
4151:2C-T-4
4146:2C-T-3
4141:2C-T-2
4116:2C-O-4
4106:2C-NH2
4081:2C-G-N
4076:2C-G-6
4071:2C-G-5
4066:2C-G-4
4061:2C-G-3
4056:2C-G-2
4051:2C-G-1
3971:amines
3949:MLD-41
3889:LAE-32
3884:IP-LAD
3854:BU-LAD
3849:ALD-52
3844:AL-LAD
3829:1V-LSD
3814:1P-LSD
3799:1B-LSD
3791:amides
3779:TFMFly
3259:Durene
3178:Cumene
3027:Pyrene
2943:Acenes
2825:Dienes
2606:Decyne
2601:Nonyne
2596:Octyne
2586:Hexyne
2576:Butyne
2566:Ethyne
2476:Decene
2471:Nonene
2466:Octene
2456:Hexene
2446:Butene
2436:Ethene
2334:Cubane
2112:Decane
2107:Nonane
2102:Octane
2092:Hexane
2082:Butane
2072:Ethane
1943:
1933:
1925:
1886:
1876:
1868:
1761:
1686:
1678:
1627:
1619:
1572:
1531:
1483:
1475:
1419:
1411:
1235:
1185:
1117:
1071:
1063:
1011:
804:halide
744:, one
712:, and
700:, and
592:acidic
492:Phenol
450:Durene
340:cresol
319:, and
306:methyl
294:phenol
186:Xylene
125:sulfur
117:oxygen
50:arenes
8250:RCS-8
8245:RCS-4
8240:QUPIC
8215:PTI-2
8210:PTI-1
8165:MN-25
8160:MN-18
8050:CB-13
8035:APICA
6890:mAChR
6870:Xenon
6855:RB-64
6775:2-MDP
6628:(TCP)
6616:(PCP)
6605:(PCE)
6521:MXiPr
6441:NMDAR
6415:6-APB
6407:5-APB
6401:Also
6397:RH-34
6367:ALPHA
6137:18-MC
5787:alpha
5735:TOMSO
5730:TCB-2
5695:DMCPA
5665:5-TOM
5660:2-TOM
5600:TMA-6
5597:TMA-5
5594:TMA-4
5591:TMA-3
5588:TMA-2
5442:MMDMA
5392:DMMDA
5366:HOT-7
5361:HOT-2
5337:DOTFM
5317:DOiPR
5187:3C-BZ
5182:3C-AL
4745:NBOMe
4306:2C-YN
4131:2C-SE
4126:2C-Ph
4096:2C-iP
4036:2C-EF
4021:2C-CP
4016:2C-CN
4006:2C-Bu
4001:2C-Bn
3939:MIPLA
3894:LAMPA
3869:ECPLA
3421:Other
3406:trans
3383:Other
3322:Other
3278:Other
3171:Other
3114:Other
2985:Other
2909:Enyne
2877:Other
2373:Other
1792:: 103
1684:S2CID
1417:S2CID
720:. In
678:rings
344:ortho
313:ortho
170:furan
148:furan
129:furan
123:, or
8677:HZ-2
8452:GABA
8230:PX-3
8225:PX-2
8220:PX-1
8195:NNE1
8070:DMHP
7561:JWH-
7194:THCV
6830:NEFA
6643:BTCP
6609:PCPr
6592:BDPC
6342:PiPT
6327:EiPT
6322:DCPT
6251:MiPT
6223:MiPT
6044:-TMT
6021:-TMT
6008:-TMT
5933:DiPT
5910:DiPT
5854:DALT
5831:DALT
5817:α-MT
5812:α-ET
5767:pFPP
5578:TMAs
5478:4-TM
5473:3-TM
5468:4-TE
5463:3-TE
5427:MMDA
5422:MDMA
5417:MDBZ
5412:MDAI
5351:HOT-
5332:DOPR
5302:DOET
5297:DOEF
5256:4C-P
5251:4C-N
5246:4C-I
5241:4C-E
5236:4C-D
5231:4C-C
5226:4C-B
5207:3C-P
5197:3C-E
4667:NBOH
4594:NBMD
4311:2C-V
4136:2C-T
4121:2C-P
4111:2C-O
4101:2C-N
4091:2C-I
4086:2C-H
4046:2C-G
4041:2C-F
4031:2C-E
4026:2C-D
4011:2C-C
3991:2C-B
3774:F-22
3721:5-HT
3550:TCDD
3302:tert
2934:PAHs
1941:PMID
1923:ISSN
1884:PMID
1866:ISSN
1825:: 56
1759:ISBN
1676:ISSN
1625:PMID
1617:ISSN
1570:ISSN
1529:ISSN
1481:PMID
1473:ISSN
1409:ISSN
1233:ISSN
1183:ISSN
1115:ISBN
1069:PMID
1061:ISSN
1009:ISBN
931:and
925:Aryl
845:-ol
698:coal
352:para
348:meta
321:para
317:meta
240:and
84:and
8606:ÎșOR
8518:MOA
8422:),
8357:LSD
7500:HU-
7454:CP
7213:AM-
6337:MPT
6332:EPT
6317:DBT
6209:MET
6186:MET
6093:DPT
6064:DMT
5947:DMT
5868:DET
5762:BZP
5725:MMA
5675:BOD
5670:BOB
5585:TMA
5407:MDA
5342:MEM
5327:DON
5322:DOM
5312:DOI
5307:DOF
5292:DOC
5287:DOB
5282:DOT
5216:4C-
5172:3C-
5006:-NM
4526:NBF
4325:-NB
3980:2C-
3929:LSZ
3919:LSH
3909:LSD
3904:LSA
3769:F-2
3564:Î΀Î
3552:),
3497:AhR
3294:sec
2551:â 2
2052:+ 2
1931:PMC
1915:doi
1874:PMC
1858:doi
1666:hdl
1656:doi
1609:doi
1560:doi
1556:265
1521:doi
1465:doi
1401:doi
1225:doi
1175:doi
1171:127
1053:doi
1049:104
898:In
826:).
702:tar
694:oil
614:Of
327:or
262:any
228:, C
107:or
48:or
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8430:,
8418:,
7162:CB
6939:BZ
6421:).
6413:,
6409:,
6036:5-
5383:xx
5381:MD
5271:DO
5002:25
4739:25
4661:25
4588:25
4520:25
4442:25
4364:25
4342:NB
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4321:25
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6015:N
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6002:N
5945:-
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5906:x
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5218:x
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3231:m
3223:o
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3087:o
2549:n
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2539:C
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