329:
220:
1053:
555:
38:
1116:
662:
29:
884:
785:
667:
666:
1132:
Butane-1,4-diol seems to have two types of pharmacological actions. The major psychoactive effects of 1,4-butanediol are because it is metabolized into GHB; however there is a study suggesting that 1,4-butanediol may have potential alcohol-like pharmacological effects on its own. The study arrived at
1952:
United States v. Turcotte, 405 F.3d 515 (7th Cir. 2005) "With specific regard to 1,4 Butanediol, the jury has returned a special verdict which states that 1,4-Butanediol is not a
Schedule I Narcotic Drug Controlled Substance analogue, because 1,4-Butanediol's chemical structure is not significantly
1173:
of GHB under federal law, but that decision was later overturned by the Second
Circuit. A jury in Federal District Court in Chicago found that 1,4-butanediol was not an analog of GHB under federal law, which was not disputed on the case's appeal to the Seventh Circuit Court of Appeals, however this
1152:
Like gamma-hydroxybutyric acid, butane-1,4-diol is safe only in small amounts. Adverse effects in higher doses include nausea, vomiting, dizziness, sedation, vertigo, and potentially death if ingested in large amounts. Anxiolytic effects are diminished and side effects increased when used in
665:
5592:
1133:
this conclusion based on the finding that butane-1,4-diol coadministered with ethanol led to potentiation of some of the behavioral effects of ethanol. However, potentiation of ethanol's effects may simply be caused by competition for the
1212:" ("Aqua Dots" in North America) was recalled by the distributor in November 2007 because of the presence of butane-1,4-diol. The toy consists of small beads that stick to each other by sprinkling water. Butane-1,4-diol was detected by
1099:
with 1,4-butanediol will interact considerably and has many other potential risks. This is because the same enzymes that are responsible for metabolizing alcohol also metabolize 1,4-butanediol so there is a strong chance of a dangerous
1496:
5411:
6038:
5416:
5988:
4903:
6149:
4928:
6141:
6068:
6043:
1148:
Another study found no effect following intracerebroventricular injection of butane-1,4-diol in rats. This contradicts the hypothesis of butane-1,4-diol having inherent alcohol-like pharmacological effects.
4171:
563:
4141:
5461:
6111:
1112:
initially and as the ethanol is metabolized the 1,4-butanediol is then able to better compete for the enzyme and a second period of intoxication ensues as the 1,4-butanediol is converted into GHB.
6048:
4942:
1141:
enzymes with co-administered 1,4-butanediol. The shared metabolic rate-limiting steps thus leads to slowed metabolism and clearance for both compounds including ethanol's known toxic metabolite
535:
1220:
with butane-1,4-diol. ChemNet China listed the price of butane-1,4-diol at between about US$ 1,350–2,800 per metric ton, while the price for 1,5-pentanediol is about US$ 9,700 per metric ton.
6053:
5456:
5451:
5446:
5441:
6058:
6033:
1236:, and a 30-year-old person was, for a time, in a critical state. Butane-1,4-diol had been detected in milk packages, as well as in water filters. At the location, detectives also found
3944:
5835:
1071:
in the USA have stated that 1,4-butanediol exerts effects similar to its metabolite gamma-hydroxybutyrate (GHB), but several other federal courts have ruled that it does not.
5850:
6116:
5983:
4898:
4868:
3924:
3766:
1327:
3826:
6063:
3776:
3979:
668:
6096:
1625:
875:
first synthesized in 1890 via acidic hydrolysis of N,N'-dinitro-1,4-butanediamine by Dutch chemist Pieter
Johannes Dekkers, who called it "tetramethylene glycol".
3989:
1737:
1663:
3561:
2010:
1186:
controlled substance. In
Germany, the drug is not explicitly illegal, but might also be treated as illegal if used as a drug. It is controlled as a Schedule VI
2048:
6465:
6136:
6081:
4733:
1165:, a number of states have classified 1,4-butanediol as a controlled substance. Individuals have been prosecuted for possession of 1,4-butanediol under the
1029:
2,000 (€1,600) per ton (2005). In 2013, worldwide production was claimed to be billions of pounds (consistent with approximately one million metric tons).
5346:
5930:
4652:
798:
6539:
5935:
5582:
5542:
4738:
3969:
3702:
2085:
5276:
2895:
5795:
3959:
3949:
3934:
1941:
690:
1918:"Erowid 1,4-Butanediol Vault : Law : New York Federal Court Rules Analogue Act Unconstitutionally Vague with regard to 1,4-Butanediol"
3954:
3939:
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6500:
4798:
4788:
3107:
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5366:
4111:
375:
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4309:
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6290:
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6126:
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5391:
4778:
4773:
4748:
2546:
2058:
1389:
1068:
683:
5612:
5371:
3999:
3836:
3831:
1990:
1839:
Carter, LP; Koek, W; France, CP (2006), "Lack of effects of GHB precursors GBL and 1,4-BD following i.c.v. Administration in rats",
1797:
Poldrugo, Flavio; Snead III, O. Carter (1984), "1,4-butanediol, γ-hydroxybutyric acid and ethanol: Relationships and interactions",
6420:
4029:
4024:
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621:
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2078:
2039:
1603:
5900:
793:
6581:
4618:
4477:
5965:
1633:
1169:
as substantially similar to GHB. A federal case in New York in 2002 ruled that 1,4-butanediol could not be considered an
1655:
1023:
World production of butane-1,4-diol was claimed to be about one million metric tons per year and market price is about
1228:
In August 2021, several people fell severely ill after consuming drinks at building L2.01 at the
Lichtwiese Campus of
6611:
6018:
4638:
4604:
4056:
2812:
1537:
1458:
1296:
1263:
887:
Conversion of butane to butanediol or butyrolactone via oxidation to maleic anhydride followed by hydrogenation over
343:
6226:
4684:
4136:
4039:
1497:"United States Patent: 8067214 - Compositions and methods for the biosynthesis of 1,4-butanediol and its precursors"
919:
in the Davy process, which is first converted to the methyl maleate ester, then hydrogenated. Other routes are from
6586:
3688:
2071:
2054:
805:
4421:
4398:
1258:
1002:
676:
6591:
5870:
5572:
1969:
1229:
1942:
https://scholar.google.com/scholar_case?case=13457043198797192346&q=363+F.3d+118&hl=en&as_sdt=6,39
6198:
935:
617:
6521:
4597:
4088:
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595:
286:
215:
5925:
3583:
3233:
1590:, Polymer Science and Technology Series, vol. 1, Dordrecht: Springer Netherlands, pp. 211–216,
1316:, International Chemical Safety Card 1104, Geneva: International Programme on Chemical Safety, March 1999
307:
157:
3338:
3152:
1064:
known by some users as "Bute", "One Comma Four", "Liquid
Fantasy", "One Four Bee" or "One Four B-D-O".
1017:
1711:
6606:
6561:
6315:
6305:
5731:
4675:
2989:
1356:
227:
6159:
1556:(2005), "Acceptorless, neat, ruthenium-catalyzed dehydrogenative cyclization of diols to lactones",
324:
3781:
3315:
3129:
1183:
713:
633:
554:
4434:
4244:
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3796:
6601:
6596:
6285:
5940:
4743:
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1905:
1684:
498:
6310:
3801:
5706:
5567:
5301:
4543:
3448:
3387:
3201:
2161:
1991:"US mother says her son began to stumble and vomit after eating Chinese-made toy, now recalled"
1138:
1084:
117:
177:
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3731:
3369:
3183:
1384:
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1134:
1080:
943:
577:
547:
1427:
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6270:
5790:
5426:
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3518:
3036:
1109:
1025:
295:
50:
4101:
1474:
625:
8:
6320:
6300:
5784:
5421:
5125:
4947:
4838:
3004:
2999:
2566:
2123:
1311:
1179:
1120:
975:
751:
110:
86:
76:
3791:
328:
219:
137:
6571:
5509:
5181:
5143:
4667:
4279:
4176:
4077:
3717:
3435:
2865:
2781:
2146:
2044:
1864:
1822:
1738:"Date-rape drug 'bute' increasingly linked to sexual assaults in Australia, police say"
1166:
896:
3984:
3811:
3786:
1964:
1056:
FDA warning against products containing GHB and its prodrugs, such as butane-1,4-diol.
915:
of butyne-1,4-diol gives butane-1,4-diol. It is also made on an industrial scale from
6566:
6430:
6101:
5762:
5153:
5000:
4955:
4793:
2828:
2786:
2619:
2294:
2289:
1917:
1856:
1852:
1814:
1810:
1599:
1533:
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1406:
1292:
1268:
1241:
1233:
1170:
1061:
971:
2011:"Ermittler finden nach Vergiftungen an TU Darmstadt offenbar K.-o.-Tropfen in Küche"
1868:
1826:
6255:
6008:
5666:
5466:
5396:
5231:
5129:
4961:
4842:
4387:
4337:
4211:
4106:
4004:
2969:
2579:
2015:
1848:
1806:
1591:
1565:
1525:
1446:
1398:
1217:
1216:. The production plant seems to have intended to cut costs by replacing less toxic
1178:, 1,4-butanediol was scheduled in December 2009 (along with another GHB precursor,
1101:
1087:, and differing levels of these enzymes may account for differences in effects and
1079:
Butane-1,4-diol is rapidly converted into gamma-hydroxybutyric acid by the enzymes
1006:
916:
849:
845:
511:
475:
403:
5767:
5676:
5641:
5309:
5291:
5216:
5173:
5036:
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4299:
3851:
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3554:
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3255:
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2823:
2705:
2214:
1881:
1595:
1553:
1425:
1237:
1033:
994:
983:
979:
908:
888:
841:
609:
259:
2102:
1767:
Benzer, Theodore I.; Cameron, Scott; Russi, Christopher Scott (8 January 2007),
1052:
6350:
5295:
5165:
5060:
4986:
4951:
4495:
4449:
4357:
4327:
4289:
4201:
3841:
3374:
3302:
3188:
3099:
3049:
2993:
2953:
2937:
2833:
2314:
2259:
2156:
2141:
2111:
1583:
1253:
1232:, Germany. Seven showed severe symptoms, two were transported to a hospital in
1175:
776:
763:
747:
743:
739:
601:
5157:
1768:
6555:
6260:
5950:
5757:
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5626:
5562:
5489:
5401:
5351:
5317:
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5241:
5191:
5031:
5026:
5016:
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4883:
4818:
4768:
4717:
4661:
4454:
4444:
4216:
4166:
4151:
3994:
3771:
3627:
3617:
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3576:
3496:
3361:
3320:
3175:
3134:
3069:
2974:
2927:
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2900:
2860:
2738:
2723:
2475:
2470:
2460:
2377:
2362:
2357:
2352:
2254:
2244:
2239:
2229:
2209:
2151:
2063:
1995:
1689:
1450:
1410:
1402:
998:
928:
924:
912:
767:
613:
464:
454:
208:
6217:
6188:
6182:
5993:
5780:
5743:
5739:
5661:
5557:
5245:
5220:
5196:
4918:
4723:
4630:
4556:
4439:
4332:
4294:
4249:
4239:
4191:
4131:
4121:
4116:
3742:
3711:
3669:
3571:
3566:
3476:
3379:
3330:
3265:
3193:
3144:
3089:
3084:
2890:
2807:
2776:
2771:
2766:
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2713:
2609:
2599:
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2445:
2387:
2372:
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2234:
2224:
2204:
2199:
2189:
2179:
1860:
1142:
1088:
967:
939:
904:
6225:
4322:
3680:
1818:
689:
37:
6470:
6395:
6330:
6169:
6106:
6013:
5955:
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5726:
5686:
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5010:
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3162:
3112:
3079:
3064:
3024:
2885:
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2875:
2746:
2728:
2718:
2647:
2627:
2589:
2465:
2402:
2397:
2342:
2327:
2299:
2264:
2249:
2184:
2171:
2136:
702:
5481:
1115:
675:
197:
6355:
6265:
6174:
6164:
6023:
5840:
5830:
5815:
5810:
5805:
5772:
5751:
5721:
5656:
5636:
5630:
5532:
5499:
5493:
5485:
5386:
5381:
5376:
5361:
5313:
5286:
5251:
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5074:
5021:
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4966:
4853:
4708:
4571:
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4528:
4518:
4367:
4284:
4269:
4264:
4254:
4186:
4014:
3649:
3622:
3612:
3533:
3513:
3486:
3421:
3397:
3392:
3275:
3270:
3260:
3250:
3211:
3206:
3117:
3059:
3044:
2855:
2761:
2657:
2637:
2604:
2594:
2584:
2574:
2541:
2523:
2508:
2455:
2450:
2412:
2407:
2382:
2367:
2337:
2332:
2322:
2304:
1626:"Polybutylene Terephthalate (PBT) Material Guide & Properties Info"
1529:
733:
682:
486:
431:
228:
168:
1569:
6490:
6485:
6475:
6435:
6380:
6365:
6345:
6340:
6325:
6121:
6091:
5998:
5978:
5973:
5825:
5747:
5681:
5651:
5622:
5552:
5537:
5504:
5471:
5235:
5211:
5169:
5161:
5120:
5110:
5094:
5090:
5066:
5051:
5046:
5006:
4923:
4908:
4873:
4863:
4848:
4823:
4803:
4758:
4566:
4411:
4352:
4259:
4196:
4181:
4009:
3893:
3659:
3453:
3343:
3310:
3245:
3157:
3122:
3074:
2917:
2870:
2677:
2662:
2652:
2642:
2551:
2513:
2503:
2495:
2480:
2437:
2427:
2422:
2392:
2347:
2284:
2219:
1774:
987:
920:
900:
869:
775:
Except where otherwise noted, data are given for materials in their
6480:
6410:
6400:
6360:
6335:
6275:
6178:
6086:
5960:
5890:
5845:
5776:
5716:
5701:
5616:
5577:
5476:
5356:
5265:
5205:
5185:
5177:
5070:
5056:
5040:
4990:
4888:
4878:
4858:
4828:
4812:
4703:
4576:
4533:
4310:
4274:
4227:
4161:
3906:
3888:
3643:
3634:
3528:
3280:
3009:
2979:
2905:
2840:
2695:
2672:
2667:
2632:
2485:
2417:
2279:
2194:
2098:
2094:
1223:
990:
648:
188:
641:
116:
109:
6385:
6370:
6280:
6193:
5920:
5880:
5875:
5800:
5711:
5691:
5607:
5256:
4996:
4912:
4893:
4728:
4523:
4490:
4347:
3911:
3588:
3325:
3139:
3014:
2910:
2817:
2536:
2269:
1209:
1203:
1105:
1096:
1092:
1037:
959:
955:
605:
444:
246:
28:
5436:
5431:
6250:
5201:
5104:
4808:
4381:
3821:
3639:
2791:
2687:
1441:
1191:
883:
872:
587:
148:
1906:
http://cases.justia.com/us-court-of-appeals/F3/312/926/608696/
6295:
5945:
5671:
5521:
5137:
4753:
3866:
3861:
3846:
3664:
2984:
1361:
1213:
1010:
982:
and high temperature, it dehydrates to the important solvent
963:
934:
A biological route to BD has been commercialized that uses a
270:
128:
99:
4478:
312:
6390:
6203:
5885:
5855:
5597:
5587:
5527:
5517:
5513:
5100:
4342:
4146:
2131:
1735:
1291:(62nd ed.), Boca Raton, FL: CRC Press, p. C-190,
1041:
707:(open cup) 121 °C (250 °F; 394 K)
5901:
1095:
and GHB already poses serious risks, co-administration of
5305:
1712:"Malaysia: New 1,4-butanediol plant used below capacity"
1656:"Commercial-scale production of bio-based BDO announced"
1174:
finding did not affect the outcome of the case. In the
4422:
4399:
1940:
United States v. Roberts, 363 F.3d 118 (2d Cir. 2004);
1582:
Monte, Salvatore J. (1998), Pritchard, Geoffrey (ed.),
6227:
4685:
4040:
2049:
Organisation for
Economic Co-operation and Development
3504:
2045:
4089:
1965:"Industrial Chemical Sullies Popular Children's Toy"
1197:
4315:
Tooltip Vesicular inhibitory amino acid transporter
4232:
Tooltip Sodium-coupled monocarboxylate transporters
1584:"Diluents and viscosity modifiers for epoxy resins"
1344:"1,4-Butanediol Laboratory Chemical Safety Summary"
1766:
1108:and 1,4-butanediol often present with symptoms of
986:. At about 200 °C in the presence of soluble
583:
1796:
1329:HSNO Chemical Classification Information Database
6553:
1838:
1332:, New Zealand Environmental Protection Authority
1224:2021 poisoning at Darmstadt Technical University
258:
1522:Kirk-Othmer Encyclopedia of Chemical Technology
1357:"1,4-Butanediol - Uses, Side Effects, and More"
1104:. Emergency room patients who overdose on both
664:
85:
4544:
2093:
1443:Ullmann's Encyclopedia of Industrial Chemistry
974:, 1,4-butanediol is used for the synthesis of
637:
4646:
4506:
3712:
3696:
3108:Serotonin antagonists and reuptake inhibitors
2079:
1047:
4660:
4483:Tooltip Hydroxyacid-oxoacid transhydrogenase
1016:1,4-Butanediol is used in the production of
4662:
3710:
3497:
1792:
1790:
1736:Australian Associated Press (30 May 2024).
1551:
5910:Tooltip γ-Aminobutyric acid A-rho receptor
4653:
4639:
3703:
3689:
2086:
2072:
1648:
1390:Recueil des Travaux Chimiques des Pays-Bas
1091:between users. While co-administration of
954:Butane-1,4-diol is used industrially as a
629:
459:20.1 °C (68.2 °F; 293.2 K)
327:
325:DTXSID2042307 DTXSID2024666, DTXSID2042307
218:
176:
1953:similar to the chemical structure of GHB.
1762:
1760:
1758:
1685:"Butanediol (price and demand in market)"
352:InChI=1S/C4H10O2/c5-3-1-2-4-6/h5-6H,1-4H2
294:
1882:"21 U.S. Code § 841 - Prohibited acts A"
1787:
1440:
1163:scheduled federally in the United States
1114:
1051:
958:and in the manufacture of some types of
882:
362:InChI=1/C4H10O2/c5-3-1-2-4-6/h5-6H,1-4H2
16:One of four stable isomers of butanediol
4427:Tooltip 4-Hydroxybutyrate dehydrogenase
4404:Tooltip Succinic semialdehyde reductase
2040:International Chemical Safety Card 1104
1904:USA v Washam (2002) 312 F.3d 926, 930;
1434:
1423:
1382:
1161:While butane-1,4-diol is not currently
323:
196:
6554:
6235:Tooltip γ-Aminobutyric acid B receptor
4693:Tooltip γ-Aminobutyric acid A receptor
4048:Tooltip γ-Aminobutyric acid B receptor
2057:in the Household Products Database of
1755:
1119:Metabolic pathway of butane-1,4-diol,
721:350 °C (662 °F; 623 K)
469:235 °C (455 °F; 508 K)
209:
4634:
3684:
2067:
1581:
1519:
1513:
1289:CRC Handbook of Chemistry and Physics
1286:
355:Key: WERYXYBDKMZEQL-UHFFFAOYSA-N
156:
136:
6540:GABA metabolism/transport modulators
4094:Tooltip Monocarboxylate transporters
3743:
1962:
1841:The European Journal of Neuroscience
1729:
1666:from the original on 4 February 2015
1588:Plastics Additives: An A-Z reference
1475:"1,4-Butanediol Production And Uses"
4936:Positive modulators (abridged; see
1999:, Associated Press, 8 November 2007
1304:
1127:
1074:
1032:Almost half of it is dehydrated to
249:
13:
1520:Karas, L.; Piel, W. J., "Ethers",
1383:Dekkers, M. P. J. (January 1890).
1060:Butane-1,4-diol is also used as a
660:
14:
6623:
6471:Homotaurine (tramiprosate, 3-APS)
5969:-Chloroacetylcytosine arabinoside
4764:Homotaurine (tramiprosate, 3-APS)
2813:Acetylglycinamide chloral hydrate
2033:
1886:LII / Legal Information Institute
1424:Dekkers, Pieter Johannes (1890).
1264:2-Methyl-2-propyl-1,3-propanediol
1198:2007 contamination of Bindeez toy
949:
1853:10.1111/j.1460-9568.2006.05146.x
1123:and γ-hydroxybutyric acid (GHB).
1018:polybutylene terephthalate (PBT)
783:
553:
415:
36:
27:
5763:Pentylenetetrazol (pentetrazol)
3886:Positive allosteric modulators:
2003:
1983:
1970:Chemical & Engineering News
1963:Wang, Linda (9 November 2007),
1956:
1946:
1934:
1910:
1898:
1874:
1832:
1770:Toxicity, Gamma-Hydroxybutyrate
1704:
1677:
1618:
1575:
1545:
1489:
1430:(in Dutch). L. van Nifterik Hz.
1259:1,4-Butanediol diglycidyl ether
1003:1,4-Butanediol diglycidyl ether
903:reacts with two equivalents of
779:(at 25 °C , 100 kPa).
4549:Tooltip Aldehyde dehydrogenase
1467:
1417:
1376:
1349:
1336:
1320:
1287:Weast, Robert C., ed. (1981),
1280:
1230:Darmstadt Technical University
421:
409:
1:
6522:Receptor/signaling modulators
5677:Isopregnanolone (sepranolone)
4612:Glutamate receptor modulators
4598:Receptor/signaling modulators
4529:Fomepizole (4-methylpyrazole)
4511:Tooltip Alcohol dehydrogenase
1385:"Le glycol tétraméthylénique"
1274:
936:genetically modified organism
6533:receptor positive modulators
5041:ergoloid (dihydroergotoxine)
1811:10.1016/0028-3908(84)90226-0
1596:10.1007/978-94-011-5862-6_24
878:
7:
6582:Neurotransmitter precursors
4619:Glycine receptor modulators
3772:Aceburic acid (GHB acetate)
3339:Tetracyclic antidepressants
3153:Tetracyclic antidepressants
1247:
1156:
1001:. It is used to synthesize
10:
6628:
5732:Nonsteroidal antiandrogens
1201:
1153:combination with alcohol.
1048:Use as a recreational drug
1040:. The largest producer is
978:(GBL). In the presence of
6513:
6216:
5899:
4683:
4674:
4589:
4542:
4504:
4476:
4420:
4397:
4380:
4308:
4225:
4087:
4070:
4038:
3741:
3724:
3542:
3495:
3467:
3434:
3414:
3360:
3316:Tricyclic antidepressants
3301:
3289:
3232:
3174:
3130:Tricyclic antidepressants
3098:
3035:
3023:
2952:
2800:
2737:
2704:
2686:
2618:
2565:
2522:
2494:
2436:
2313:
2170:
2122:
2110:
773:
725:
534:
529:
396:
371:
339:
69:
61:
49:
44:
35:
26:
6612:1,4-Butanediyl compounds
5281:sulfonmethane (sulfonal)
4605:GABA receptor modulators
2901:Sulfonmethane (sulfonal)
1524:, New York: John Wiley,
1451:10.1002/14356007.a13_487
1403:10.1002/recl.18900090403
1005:which is then used as a
596:Precautionary statements
6587:GABAB receptor agonists
3388:Atypical antipsychotics
3202:Atypical antipsychotics
1630:omnexus.specialchem.com
1036:to make fibers such as
499:Magnetic susceptibility
6160:5α-Dihydroprogesterone
5707:Morphine-3-glucuronide
5367:Hyenachin (mellitoxin)
5252:Retigabine (ezogabine)
3562:Chlorophenylalkyldiols
3370:Typical antipsychotics
3184:Typical antipsychotics
1716:Asian Textile Business
1139:aldehyde dehydrogenase
1124:
1085:aldehyde dehydrogenase
1057:
892:
868:OH. It is a colorless
671:
6592:GHB receptor agonists
5548:Chlorophenylsilatrane
4435:α-Ketoisocaproic acid
1135:alcohol dehydrogenase
1118:
1081:alcohol dehydrogenase
1055:
993:, the diol undergoes
886:
824:(other names include
670:
64:Tetramethylene glycol
6498:Negative modulators:
6378:Positive modulators:
6271:Arbaclofen placarbil
6157:Negative modulators:
6006:Positive modulators:
5791:Pregnenolone sulfate
5427:17-Phenylandrostenol
5409:Negative modulators:
5294:constituents (e.g.,
5264:constituents (e.g.,
5126:Neuroactive steroids
5103:constituents (e.g.,
4839:Neuroactive steroids
3748:Tooltip GHB receptor
3519:Gabapentin enacarbil
2567:Neuroactive steroids
2537:Apronal (apronalide)
1660:Chemical Engineering
1110:alcohol intoxication
653:(fire diamond)
449:1.0171 g/cm (20 °C)
51:Preferred IUPAC name
6087:Gabazine (SR-95531)
6077:CGP-36742 (SGS-742)
5785:dihydropicrotoxinin
5510:Bicyclic phosphates
5422:11-Ketoprogesterone
5357:Gabazine (SR-95531)
5182:pyrazolopyrimidines
3907:Gabazine (SR-95531)
1636:on 24 November 2023
1180:gamma-butyrolactone
752:cis-Butene-1,4-diol
476:Solubility in water
439: g·mol
23:
5608:FG-7142 (ZK-31906)
5154:Nonbenzodiazepines
4270:Mesalazine (5-ASA)
4177:Phenylpyruvic acid
3807:GHV (4-methyl-GHB)
3584:Diethylpropanediol
2866:Dichloralphenazone
2782:Methylmethaqualone
2620:Nonbenzodiazepines
2147:Diethylpropanediol
1530:10.1002/0471238961
1167:Federal Analog Act
1125:
1058:
897:chemical synthesis
895:In one industrial
893:
806:Infobox references
726:Related compounds
672:
21:
6549:
6548:
6509:
6508:
6431:2-Hydroxysaclofen
6212:
6211:
6102:Isonipecotic acid
5467:Anabolic steroids
5437:α5IA (LS-193,268)
5347:Dihydrosecurinine
5232:Pyrazolopyridines
5001:potassium bromide
4999:compounds (e.g.,
4962:Anabolic steroids
4940:for a full list):
4794:Isonipecotic acid
4628:
4627:
4585:
4584:
4467:
4391:
4376:
4375:
4102:α-Ketoisocaproate
4081:
4066:
4065:
3919:Unknown/unsorted:
3735:
3678:
3677:
3430:
3429:
3228:
3227:
2948:
2947:
2829:Potassium bromide
2787:Nitromethaqualone
2295:Thiotetrabarbital
2142:Ethanol (alcohol)
1799:Neuropharmacology
1662:, February 2013,
1605:978-94-011-5862-6
1570:10.1021/om048983m
1269:4-Amino-1-butanol
1242:dicyclohexylamine
1234:Frankfurt am Main
1062:recreational drug
972:organic chemistry
944:4-hydroxybutyrate
814:Chemical compound
812:
811:
759:Related compounds
578:Hazard statements
308:CompTox Dashboard
118:Interactive image
111:Interactive image
6619:
6607:Primary alcohols
6562:Alcohol solvents
6256:4-Fluorophenibut
6236:
6232:
6223:
6222:
6092:Gaboxadol (THIP)
6009:Allopregnanolone
5911:
5907:
5642:Fluoroquinolones
5397:Thiocolchicoside
5217:Piperidinediones
5174:imidazopyridines
5130:allopregnanolone
5037:Dihydroergolines
4952:drinking alcohol
4843:allopregnanolone
4759:Gaboxadol (THIP)
4694:
4690:
4681:
4680:
4664:
4655:
4648:
4641:
4632:
4631:
4550:
4546:
4512:
4508:
4484:
4480:
4468:-Glucuronic acid
4465:
4428:
4424:
4405:
4401:
4395:
4394:
4385:
4316:
4312:
4233:
4229:
4212:Sodium valproate
4107:Acetoacetic acid
4095:
4091:
4085:
4084:
4075:
4049:
4045:
4005:Prochlorperazine
3749:
3745:
3739:
3738:
3729:
3714:
3705:
3698:
3691:
3682:
3681:
3603:muscle relaxants
3506:
3503:
3299:
3298:
3033:
3032:
2970:4-Fluorophenibut
2706:Piperidinediones
2580:Allopregnanolone
2162:Trichloroethanol
2120:
2119:
2088:
2081:
2074:
2065:
2064:
2028:
2027:
2026:
2024:
2019:, 27 August 2021
2007:
2001:
2000:
1987:
1981:
1980:
1979:
1977:
1960:
1954:
1950:
1944:
1938:
1932:
1931:
1930:
1928:
1914:
1908:
1902:
1896:
1895:
1894:
1892:
1878:
1872:
1871:
1836:
1830:
1829:
1794:
1785:
1784:
1783:
1781:
1764:
1753:
1752:
1750:
1748:
1733:
1727:
1726:
1725:
1723:
1708:
1702:
1701:
1700:
1698:
1681:
1675:
1674:
1673:
1671:
1652:
1646:
1645:
1643:
1641:
1632:. Archived from
1622:
1616:
1615:
1614:
1612:
1579:
1573:
1572:
1554:Hartwig, John F.
1549:
1543:
1542:
1517:
1511:
1510:
1509:
1507:
1493:
1487:
1486:
1484:
1482:
1471:
1465:
1464:
1438:
1432:
1431:
1421:
1415:
1414:
1380:
1374:
1373:
1371:
1369:
1353:
1347:
1346:
1340:
1334:
1333:
1324:
1318:
1317:
1308:
1302:
1301:
1284:
1218:pentane-1,5-diol
1128:Pharmacodynamics
1102:drug interaction
1075:Pharmacokinetics
1028:
1007:reactive diluent
917:maleic anhydride
846:organic compound
796:
790:
787:
786:
692:
685:
678:
663:
643:
639:
635:
631:
627:
623:
619:
615:
611:
607:
603:
589:
585:
557:
512:Refractive index
505:-61.5·10 cm/mol
438:
423:
417:
411:
404:Chemical formula
332:
331:
316:
314:
298:
262:
251:
230:
222:
211:
200:
180:
160:
140:
120:
113:
89:
40:
31:
24:
20:
6627:
6626:
6622:
6621:
6620:
6618:
6617:
6616:
6552:
6551:
6550:
6545:
6532:
6505:
6234:
6231:
6208:
5936:Homohypotaurine
5909:
5905:
5895:
5768:Phenylsilatrane
5310:chloral hydrate
5277:Sulfonylalkanes
5166:cyclopyrrolones
4987:Benzodiazepines
4739:Dihydromuscimol
4692:
4689:
4670:
4659:
4629:
4624:
4581:
4548:
4538:
4510:
4500:
4482:
4472:
4426:
4416:
4403:
4384:
4372:
4314:
4304:
4300:Salicyclic acid
4231:
4221:
4093:
4074:
4062:
4047:
4044:
4034:
3970:azido-BnOPh-GHB
3747:
3728:
3720:
3709:
3679:
3674:
3538:
3501:
3491:
3463:
3426:
3410:
3356:
3303:Antidepressants
3294:
3285:
3256:Dexmedetomidine
3237:
3224:
3170:
3100:Antidepressants
3094:
3055:Diphenhydramine
3028:
3019:
2957:
2944:
2933:Isovaleric acid
2896:Sulfonylalkanes
2851:Chloral hydrate
2846:Chloral betaine
2824:Lithium bromide
2796:
2733:
2700:
2682:
2614:
2561:
2518:
2490:
2432:
2315:Benzodiazepines
2309:
2215:Ethallobarbital
2166:
2115:
2106:
2092:
2036:
2031:
2022:
2020:
2009:
2008:
2004:
1989:
1988:
1984:
1975:
1973:
1961:
1957:
1951:
1947:
1939:
1935:
1926:
1924:
1916:
1915:
1911:
1903:
1899:
1890:
1888:
1880:
1879:
1875:
1847:(9): 2595–600,
1837:
1833:
1795:
1788:
1779:
1777:
1765:
1756:
1746:
1744:
1734:
1730:
1721:
1719:
1710:
1709:
1705:
1696:
1694:
1693:, 12 April 2006
1683:
1682:
1678:
1669:
1667:
1654:
1653:
1649:
1639:
1637:
1624:
1623:
1619:
1610:
1608:
1606:
1580:
1576:
1564:(10): 2441–46,
1558:Organometallics
1550:
1546:
1540:
1518:
1514:
1505:
1503:
1495:
1494:
1490:
1480:
1478:
1473:
1472:
1468:
1461:
1439:
1435:
1422:
1418:
1381:
1377:
1367:
1365:
1355:
1354:
1350:
1342:
1341:
1337:
1326:
1325:
1321:
1310:
1309:
1305:
1299:
1285:
1281:
1277:
1250:
1226:
1206:
1200:
1159:
1130:
1121:γ-butyrolactone
1077:
1050:
1034:tetrahydrofuran
1024:
995:dehydrogenation
984:tetrahydrofuran
980:phosphoric acid
976:γ-butyrolactone
952:
909:butyne-1,4-diol
889:copper chromite
881:
867:
863:
859:
855:
842:primary alcohol
822:Butane-1,4-diol
815:
808:
803:
802:
801: ?)
792:
788:
784:
780:
766:
760:
750:
746:
742:
736:
718:
715:
697:
696:
695:
694:
687:
680:
673:
669:
661:
598:
580:
566:
550:
525:1.4460 (20 °C)
522:
520:
502:
478:
436:
426:
420:
414:
406:
392:
389:
384:
379:
378:
367:
364:
363:
357:
356:
353:
347:
346:
335:
317:
310:
301:
281:
265:
252:
240:
203:
183:
163:
143:
123:
103:
92:
79:
65:
57:
56:
55:Butane-1,4-diol
22:1,4-Butanediol
17:
12:
11:
5:
6625:
6615:
6614:
6609:
6604:
6602:GABA analogues
6599:
6597:Designer drugs
6594:
6589:
6584:
6579:
6574:
6569:
6564:
6547:
6546:
6544:
6543:
6536:
6530:
6525:
6518:
6514:
6511:
6510:
6507:
6506:
6504:
6503:
6494:
6493:
6488:
6483:
6478:
6473:
6468:
6463:
6458:
6453:
6448:
6443:
6438:
6433:
6424:
6423:
6418:
6413:
6408:
6403:
6398:
6393:
6388:
6383:
6374:
6373:
6368:
6363:
6358:
6353:
6351:Sodium oxybate
6348:
6343:
6338:
6333:
6328:
6323:
6318:
6313:
6308:
6303:
6298:
6293:
6288:
6283:
6278:
6273:
6268:
6263:
6258:
6253:
6248:
6246:1,4-Butanediol
6239:
6237:
6229:
6220:
6214:
6213:
6210:
6209:
6207:
6206:
6201:
6196:
6191:
6186:
6172:
6167:
6162:
6153:
6152:
6147:
6139:
6134:
6129:
6124:
6119:
6114:
6109:
6104:
6099:
6094:
6089:
6084:
6079:
6074:
6066:
6061:
6056:
6051:
6046:
6041:
6036:
6027:
6026:
6021:
6016:
6011:
6002:
6001:
5996:
5991:
5986:
5981:
5976:
5971:
5963:
5958:
5953:
5948:
5943:
5938:
5933:
5928:
5923:
5914:
5912:
5903:
5897:
5896:
5894:
5893:
5888:
5883:
5878:
5873:
5868:
5863:
5858:
5853:
5848:
5843:
5838:
5833:
5828:
5823:
5818:
5813:
5808:
5803:
5798:
5793:
5788:
5770:
5765:
5760:
5755:
5729:
5724:
5719:
5714:
5709:
5704:
5699:
5694:
5689:
5684:
5679:
5674:
5669:
5664:
5659:
5654:
5649:
5639:
5634:
5620:
5610:
5605:
5600:
5595:
5590:
5585:
5580:
5575:
5570:
5565:
5560:
5555:
5550:
5545:
5540:
5535:
5530:
5525:
5507:
5502:
5497:
5490:cephalosporins
5479:
5474:
5469:
5464:
5459:
5454:
5449:
5444:
5439:
5434:
5429:
5424:
5419:
5414:
5405:
5404:
5399:
5394:
5389:
5384:
5379:
5374:
5369:
5364:
5359:
5354:
5349:
5344:
5339:
5330:
5329:
5299:
5296:valerenic acid
5289:
5284:
5274:
5269:
5259:
5254:
5249:
5242:Quinazolinones
5239:
5229:
5224:
5214:
5209:
5199:
5194:
5189:
5151:
5146:
5141:
5123:
5118:
5113:
5108:
5098:
5088:
5083:
5078:
5064:
5061:mefenamic acid
5054:
5049:
5044:
5034:
5029:
5024:
5019:
5014:
5004:
4994:
4984:
4974:
4964:
4959:
4945:
4932:
4931:
4926:
4921:
4916:
4906:
4901:
4896:
4891:
4886:
4881:
4876:
4871:
4866:
4861:
4856:
4851:
4846:
4836:
4831:
4826:
4821:
4816:
4806:
4801:
4796:
4791:
4786:
4781:
4776:
4771:
4766:
4761:
4756:
4751:
4746:
4741:
4736:
4731:
4726:
4721:
4711:
4706:
4697:
4695:
4687:
4678:
4672:
4671:
4658:
4657:
4650:
4643:
4635:
4626:
4625:
4623:
4622:
4615:
4608:
4601:
4594:
4590:
4587:
4586:
4583:
4582:
4580:
4579:
4574:
4569:
4564:
4559:
4553:
4551:
4540:
4539:
4537:
4536:
4531:
4526:
4521:
4515:
4513:
4502:
4501:
4499:
4498:
4496:Phenanthroline
4493:
4487:
4485:
4474:
4473:
4471:
4470:
4458:
4457:
4452:
4450:Salicylic acid
4447:
4442:
4437:
4431:
4429:
4418:
4417:
4415:
4414:
4408:
4406:
4392:
4378:
4377:
4374:
4373:
4371:
4370:
4365:
4360:
4358:Nipecotic acid
4355:
4350:
4345:
4340:
4335:
4330:
4328:Bafilomycin A1
4325:
4319:
4317:
4306:
4305:
4303:
4302:
4297:
4292:
4290:Propionic acid
4287:
4282:
4280:Nicotinic acid
4277:
4272:
4267:
4262:
4257:
4252:
4247:
4242:
4236:
4234:
4223:
4222:
4220:
4219:
4214:
4209:
4204:
4202:Salicylic acid
4199:
4194:
4189:
4184:
4179:
4174:
4169:
4164:
4159:
4154:
4149:
4144:
4139:
4134:
4129:
4124:
4119:
4114:
4109:
4104:
4098:
4096:
4082:
4068:
4067:
4064:
4063:
4061:
4060:
4052:
4050:
4042:
4036:
4035:
4033:
4032:
4027:
4022:
4017:
4012:
4007:
4002:
3997:
3992:
3987:
3982:
3977:
3972:
3967:
3962:
3957:
3952:
3947:
3942:
3937:
3932:
3927:
3915:
3914:
3909:
3897:
3896:
3891:
3879:
3874:
3869:
3864:
3859:
3854:
3849:
3844:
3842:Sodium oxybate
3839:
3834:
3829:
3824:
3819:
3814:
3809:
3804:
3799:
3794:
3789:
3784:
3779:
3774:
3769:
3764:
3752:
3750:
3736:
3722:
3721:
3708:
3707:
3700:
3693:
3685:
3676:
3675:
3673:
3672:
3667:
3662:
3657:
3652:
3650:Passion flower
3647:
3637:
3632:
3631:
3630:
3625:
3620:
3615:
3610:
3596:
3591:
3586:
3581:
3580:
3579:
3574:
3569:
3559:
3558:
3557:
3546:
3544:
3540:
3539:
3537:
3536:
3531:
3526:
3521:
3516:
3510:
3508:
3499:
3493:
3492:
3490:
3489:
3484:
3479:
3473:
3471:
3465:
3464:
3462:
3461:
3456:
3451:
3446:
3440:
3438:
3432:
3431:
3428:
3427:
3425:
3424:
3418:
3416:
3412:
3411:
3409:
3408:
3407:
3406:
3400:
3395:
3385:
3384:
3383:
3377:
3375:Chlorpromazine
3366:
3364:
3362:Antipsychotics
3358:
3357:
3355:
3354:
3353:
3352:
3346:
3336:
3335:
3334:
3328:
3323:
3313:
3307:
3305:
3296:
3292:
3287:
3286:
3284:
3283:
3278:
3273:
3268:
3263:
3258:
3253:
3248:
3242:
3240:
3235:
3230:
3229:
3226:
3225:
3223:
3222:
3221:
3220:
3214:
3209:
3199:
3198:
3197:
3191:
3189:Chlorpromazine
3180:
3178:
3176:Antipsychotics
3172:
3171:
3169:
3168:
3167:
3166:
3160:
3150:
3149:
3148:
3142:
3137:
3127:
3126:
3125:
3120:
3115:
3104:
3102:
3096:
3095:
3093:
3092:
3087:
3082:
3077:
3072:
3067:
3062:
3057:
3052:
3050:Cyproheptadine
3047:
3041:
3039:
3037:Antihistamines
3030:
3026:
3021:
3020:
3018:
3017:
3012:
3007:
3002:
2997:
2994:sodium oxybate
2987:
2982:
2977:
2972:
2967:
2965:1,4-Butanediol
2961:
2959:
2955:
2950:
2949:
2946:
2945:
2943:
2942:
2941:
2940:
2938:Valerenic acid
2935:
2930:
2920:
2915:
2914:
2913:
2908:
2903:
2893:
2888:
2883:
2878:
2873:
2868:
2863:
2858:
2853:
2848:
2843:
2838:
2837:
2836:
2834:Sodium bromide
2831:
2826:
2815:
2810:
2804:
2802:
2798:
2797:
2795:
2794:
2789:
2784:
2779:
2774:
2769:
2764:
2759:
2754:
2749:
2743:
2741:
2739:Quinazolinones
2735:
2734:
2732:
2731:
2726:
2721:
2716:
2710:
2708:
2702:
2701:
2699:
2698:
2692:
2690:
2684:
2683:
2681:
2680:
2675:
2670:
2665:
2660:
2655:
2650:
2645:
2640:
2635:
2630:
2624:
2622:
2616:
2615:
2613:
2612:
2607:
2602:
2597:
2592:
2587:
2582:
2577:
2571:
2569:
2563:
2562:
2560:
2559:
2554:
2549:
2544:
2539:
2534:
2528:
2526:
2520:
2519:
2517:
2516:
2511:
2506:
2500:
2498:
2492:
2491:
2489:
2488:
2483:
2478:
2473:
2468:
2463:
2458:
2453:
2448:
2442:
2440:
2434:
2433:
2431:
2430:
2425:
2420:
2415:
2410:
2405:
2400:
2395:
2390:
2385:
2380:
2375:
2370:
2365:
2360:
2355:
2350:
2345:
2340:
2335:
2330:
2325:
2319:
2317:
2311:
2310:
2308:
2307:
2302:
2297:
2292:
2287:
2282:
2277:
2272:
2267:
2262:
2260:Propylbarbital
2257:
2252:
2247:
2242:
2237:
2232:
2227:
2222:
2217:
2212:
2207:
2202:
2197:
2192:
2187:
2182:
2176:
2174:
2168:
2167:
2165:
2164:
2159:
2157:Methylpentynol
2154:
2149:
2144:
2139:
2134:
2128:
2126:
2117:
2113:
2108:
2107:
2091:
2090:
2083:
2076:
2068:
2062:
2061:
2052:
2042:
2035:
2034:External links
2032:
2030:
2029:
2002:
1982:
1955:
1945:
1933:
1922:www.erowid.org
1909:
1897:
1873:
1831:
1786:
1754:
1728:
1703:
1676:
1647:
1617:
1604:
1574:
1544:
1538:
1512:
1488:
1477:. 30 July 2023
1466:
1459:
1433:
1416:
1375:
1348:
1335:
1319:
1313:1,4-Butanediol
1303:
1297:
1278:
1276:
1273:
1272:
1271:
1266:
1261:
1256:
1254:1,3-Butanediol
1249:
1246:
1225:
1222:
1208:A toy called "
1199:
1196:
1176:United Kingdom
1158:
1155:
1129:
1126:
1076:
1073:
1069:federal courts
1049:
1046:
951:
950:Industrial use
948:
880:
877:
865:
861:
857:
853:
820:, also called
818:1,4-Butanediol
813:
810:
809:
804:
782:
781:
777:standard state
774:
771:
770:
764:Succinaldehyde
761:
758:
755:
754:
748:2,3-Butanediol
744:1,3-Butanediol
740:1,2-Butanediol
737:
731:
728:
727:
723:
722:
719:
712:
709:
708:
705:
699:
698:
688:
681:
674:
659:
658:
657:
656:
654:
645:
644:
599:
594:
591:
590:
581:
576:
573:
572:
567:
562:
559:
558:
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546:
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531:
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523:
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510:
507:
506:
503:
497:
494:
493:
490:
483:
482:
479:
474:
471:
470:
467:
461:
460:
457:
451:
450:
447:
441:
440:
434:
428:
427:
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418:
412:
407:
402:
399:
398:
394:
393:
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387:
385:
382:
374:
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372:
369:
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350:
342:
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334:
333:
320:
318:
306:
303:
302:
300:
299:
291:
289:
283:
282:
280:
279:
275:
273:
267:
266:
264:
263:
255:
253:
245:
242:
241:
239:
238:
234:
232:
224:
223:
213:
205:
204:
202:
201:
193:
191:
185:
184:
182:
181:
173:
171:
165:
164:
162:
161:
153:
151:
145:
144:
142:
141:
133:
131:
125:
124:
122:
121:
114:
106:
104:
97:
94:
93:
91:
90:
82:
80:
75:
72:
71:
67:
66:
63:
59:
58:
54:
53:
47:
46:
42:
41:
33:
32:
15:
9:
6:
4:
3:
2:
6624:
6613:
6610:
6608:
6605:
6603:
6600:
6598:
6595:
6593:
6590:
6588:
6585:
6583:
6580:
6578:
6575:
6573:
6570:
6568:
6565:
6563:
6560:
6559:
6557:
6542:
6541:
6537:
6535:
6534:
6526:
6524:
6523:
6519:
6516:
6515:
6512:
6502:
6499:
6496:
6495:
6492:
6489:
6487:
6484:
6482:
6479:
6477:
6474:
6472:
6469:
6467:
6464:
6462:
6459:
6457:
6454:
6452:
6449:
6447:
6444:
6442:
6439:
6437:
6434:
6432:
6429:
6426:
6425:
6422:
6419:
6417:
6414:
6412:
6409:
6407:
6404:
6402:
6399:
6397:
6394:
6392:
6389:
6387:
6384:
6382:
6379:
6376:
6375:
6372:
6369:
6367:
6364:
6362:
6359:
6357:
6354:
6352:
6349:
6347:
6344:
6342:
6339:
6337:
6334:
6332:
6329:
6327:
6324:
6322:
6319:
6317:
6314:
6312:
6309:
6307:
6304:
6302:
6299:
6297:
6294:
6292:
6289:
6287:
6284:
6282:
6279:
6277:
6274:
6272:
6269:
6267:
6264:
6262:
6261:Aceburic acid
6259:
6257:
6254:
6252:
6249:
6247:
6244:
6241:
6240:
6238:
6233:
6224:
6221:
6219:
6215:
6205:
6202:
6200:
6197:
6195:
6192:
6190:
6187:
6184:
6180:
6176:
6173:
6171:
6168:
6166:
6163:
6161:
6158:
6155:
6154:
6151:
6148:
6146:
6144:
6140:
6138:
6135:
6133:
6130:
6128:
6125:
6123:
6120:
6118:
6115:
6113:
6110:
6108:
6105:
6103:
6100:
6098:
6095:
6093:
6090:
6088:
6085:
6083:
6080:
6078:
6075:
6073:
6071:
6067:
6065:
6062:
6060:
6057:
6055:
6052:
6050:
6047:
6045:
6042:
6040:
6037:
6035:
6032:
6029:
6028:
6025:
6022:
6020:
6017:
6015:
6012:
6010:
6007:
6004:
6003:
6000:
5997:
5995:
5992:
5990:
5987:
5985:
5982:
5980:
5977:
5975:
5972:
5970:
5968:
5964:
5962:
5959:
5957:
5954:
5952:
5951:Ibotenic acid
5949:
5947:
5944:
5942:
5939:
5937:
5934:
5932:
5929:
5927:
5924:
5922:
5919:
5916:
5915:
5913:
5908:
5898:
5892:
5889:
5887:
5884:
5882:
5879:
5877:
5874:
5872:
5869:
5867:
5864:
5862:
5859:
5857:
5854:
5852:
5849:
5847:
5844:
5842:
5839:
5837:
5834:
5832:
5829:
5827:
5824:
5822:
5819:
5817:
5814:
5812:
5809:
5807:
5804:
5802:
5799:
5797:
5796:Propybicyphat
5794:
5792:
5789:
5786:
5782:
5778:
5774:
5771:
5769:
5766:
5764:
5761:
5759:
5758:Oenanthotoxin
5756:
5753:
5749:
5745:
5741:
5737:
5733:
5730:
5728:
5725:
5723:
5720:
5718:
5715:
5713:
5710:
5708:
5705:
5703:
5700:
5698:
5695:
5693:
5690:
5688:
5685:
5683:
5680:
5678:
5675:
5673:
5670:
5668:
5667:Iomazenil (I)
5665:
5663:
5660:
5658:
5655:
5653:
5650:
5647:
5646:ciprofloxacin
5643:
5640:
5638:
5635:
5632:
5628:
5627:amentoflavone
5624:
5621:
5618:
5614:
5611:
5609:
5606:
5604:
5601:
5599:
5596:
5594:
5591:
5589:
5586:
5584:
5581:
5579:
5576:
5574:
5571:
5569:
5566:
5564:
5563:Cyclothiazide
5561:
5559:
5556:
5554:
5551:
5549:
5546:
5544:
5541:
5539:
5536:
5534:
5531:
5529:
5526:
5523:
5519:
5515:
5511:
5508:
5506:
5503:
5501:
5498:
5495:
5491:
5487:
5483:
5480:
5478:
5475:
5473:
5470:
5468:
5465:
5463:
5460:
5458:
5455:
5453:
5450:
5448:
5445:
5443:
5440:
5438:
5435:
5433:
5430:
5428:
5425:
5423:
5420:
5418:
5415:
5413:
5410:
5407:
5406:
5403:
5400:
5398:
5395:
5393:
5390:
5388:
5385:
5383:
5380:
5378:
5375:
5373:
5370:
5368:
5365:
5363:
5360:
5358:
5355:
5353:
5352:Famiraprinium
5350:
5348:
5345:
5343:
5340:
5338:
5335:
5332:
5331:
5327:
5323:
5319:
5318:diethyl ether
5315:
5311:
5307:
5303:
5300:
5297:
5293:
5290:
5288:
5285:
5282:
5278:
5275:
5273:
5270:
5267:
5263:
5260:
5258:
5255:
5253:
5250:
5247:
5243:
5240:
5237:
5233:
5230:
5228:
5225:
5222:
5218:
5215:
5213:
5210:
5207:
5203:
5200:
5198:
5195:
5193:
5192:Norfluoxetine
5190:
5187:
5183:
5179:
5175:
5171:
5167:
5163:
5159:
5155:
5152:
5150:
5147:
5145:
5142:
5139:
5135:
5131:
5127:
5124:
5122:
5119:
5117:
5114:
5112:
5109:
5106:
5102:
5099:
5096:
5092:
5089:
5087:
5084:
5082:
5079:
5076:
5072:
5068:
5065:
5062:
5058:
5055:
5053:
5050:
5048:
5045:
5042:
5038:
5035:
5033:
5032:Clomethiazole
5030:
5028:
5027:Chlormezanone
5025:
5023:
5020:
5018:
5017:Carbamazepine
5015:
5012:
5008:
5005:
5002:
4998:
4995:
4992:
4988:
4985:
4982:
4981:phenobarbital
4978:
4975:
4972:
4968:
4965:
4963:
4960:
4957:
4953:
4949:
4946:
4944:
4941:
4939:
4934:
4933:
4930:
4927:
4925:
4922:
4920:
4917:
4914:
4910:
4907:
4905:
4902:
4900:
4897:
4895:
4892:
4890:
4887:
4885:
4884:Quisqualamine
4882:
4880:
4877:
4875:
4872:
4870:
4867:
4865:
4862:
4860:
4857:
4855:
4852:
4850:
4847:
4844:
4840:
4837:
4835:
4832:
4830:
4827:
4825:
4822:
4820:
4819:Methylglyoxal
4817:
4814:
4810:
4807:
4805:
4802:
4800:
4797:
4795:
4792:
4790:
4787:
4785:
4782:
4780:
4777:
4775:
4772:
4770:
4769:Ibotenic acid
4767:
4765:
4762:
4760:
4757:
4755:
4752:
4750:
4747:
4745:
4742:
4740:
4737:
4735:
4732:
4730:
4727:
4725:
4722:
4719:
4718:phenobarbital
4715:
4712:
4710:
4707:
4705:
4702:
4699:
4698:
4696:
4691:
4682:
4679:
4677:
4673:
4669:
4666:
4656:
4651:
4649:
4644:
4642:
4637:
4636:
4633:
4621:
4620:
4616:
4614:
4613:
4609:
4607:
4606:
4602:
4600:
4599:
4595:
4592:
4591:
4588:
4578:
4575:
4573:
4570:
4568:
4565:
4563:
4560:
4558:
4555:
4554:
4552:
4547:
4541:
4535:
4532:
4530:
4527:
4525:
4522:
4520:
4517:
4516:
4514:
4509:
4503:
4497:
4494:
4492:
4489:
4488:
4486:
4481:
4475:
4469:
4463:
4460:
4459:
4456:
4455:Valproic acid
4453:
4451:
4448:
4446:
4445:Phenylacetate
4443:
4441:
4438:
4436:
4433:
4432:
4430:
4425:
4419:
4413:
4410:
4409:
4407:
4402:
4396:
4393:
4389:
4383:
4379:
4369:
4366:
4364:
4361:
4359:
4356:
4354:
4351:
4349:
4346:
4344:
4341:
4339:
4336:
4334:
4331:
4329:
4326:
4324:
4321:
4320:
4318:
4313:
4307:
4301:
4298:
4296:
4293:
4291:
4288:
4286:
4283:
4281:
4278:
4276:
4273:
4271:
4268:
4266:
4263:
4261:
4258:
4256:
4253:
4251:
4248:
4246:
4243:
4241:
4238:
4237:
4235:
4230:
4224:
4218:
4217:Valproic acid
4215:
4213:
4210:
4208:
4205:
4203:
4200:
4198:
4195:
4193:
4190:
4188:
4185:
4183:
4180:
4178:
4175:
4173:
4170:
4168:
4167:Niflumic acid
4165:
4163:
4160:
4158:
4155:
4153:
4152:Hexanoic acid
4150:
4148:
4145:
4143:
4140:
4138:
4135:
4133:
4130:
4128:
4125:
4123:
4120:
4118:
4115:
4113:
4110:
4108:
4105:
4103:
4100:
4099:
4097:
4092:
4086:
4083:
4079:
4073:
4069:
4058:
4054:
4053:
4051:
4046:
4037:
4031:
4028:
4026:
4023:
4021:
4018:
4016:
4013:
4011:
4008:
4006:
4003:
4001:
3998:
3996:
3995:Levosulpiride
3993:
3991:
3988:
3986:
3983:
3981:
3978:
3976:
3973:
3971:
3968:
3966:
3963:
3961:
3960:4-Phenyl-THCA
3958:
3956:
3953:
3951:
3950:4-Methyl-THCA
3948:
3946:
3943:
3941:
3938:
3936:
3935:3-Methyl-THCA
3933:
3931:
3928:
3926:
3923:
3920:
3917:
3916:
3913:
3910:
3908:
3905:
3902:
3899:
3898:
3895:
3892:
3890:
3887:
3883:
3880:
3878:
3875:
3873:
3870:
3868:
3865:
3863:
3860:
3858:
3855:
3853:
3850:
3848:
3845:
3843:
3840:
3838:
3835:
3833:
3830:
3828:
3825:
3823:
3820:
3818:
3815:
3813:
3810:
3808:
3805:
3803:
3800:
3798:
3795:
3793:
3790:
3788:
3785:
3783:
3780:
3778:
3775:
3773:
3770:
3768:
3765:
3763:
3760:
3757:
3754:
3753:
3751:
3746:
3740:
3737:
3733:
3727:
3723:
3719:
3716:
3706:
3701:
3699:
3694:
3692:
3687:
3686:
3683:
3671:
3668:
3666:
3663:
3661:
3658:
3656:
3653:
3651:
3648:
3645:
3641:
3638:
3636:
3633:
3629:
3628:Methocarbamol
3626:
3624:
3621:
3619:
3618:Mephenoxalone
3616:
3614:
3611:
3609:
3608:Chlorphenesin
3606:
3605:
3604:
3600:
3597:
3595:
3592:
3590:
3587:
3585:
3582:
3578:
3577:Phenaglycodol
3575:
3573:
3570:
3568:
3565:
3564:
3563:
3560:
3556:
3553:
3552:
3551:
3548:
3547:
3545:
3541:
3535:
3532:
3530:
3527:
3525:
3522:
3520:
3517:
3515:
3512:
3511:
3509:
3507:
3494:
3488:
3485:
3483:
3480:
3478:
3475:
3474:
3472:
3470:
3466:
3460:
3457:
3455:
3452:
3450:
3447:
3445:
3442:
3441:
3439:
3437:
3433:
3423:
3420:
3419:
3417:
3413:
3404:
3401:
3399:
3396:
3394:
3391:
3390:
3389:
3386:
3381:
3378:
3376:
3373:
3372:
3371:
3368:
3367:
3365:
3363:
3359:
3350:
3347:
3345:
3342:
3341:
3340:
3337:
3332:
3329:
3327:
3324:
3322:
3321:Amitriptyline
3319:
3318:
3317:
3314:
3312:
3309:
3308:
3306:
3304:
3300:
3297:
3295:
3288:
3282:
3279:
3277:
3274:
3272:
3269:
3267:
3264:
3262:
3259:
3257:
3254:
3252:
3249:
3247:
3244:
3243:
3241:
3239:
3231:
3218:
3215:
3213:
3210:
3208:
3205:
3204:
3203:
3200:
3195:
3192:
3190:
3187:
3186:
3185:
3182:
3181:
3179:
3177:
3173:
3164:
3161:
3159:
3156:
3155:
3154:
3151:
3146:
3143:
3141:
3138:
3136:
3135:Amitriptyline
3133:
3132:
3131:
3128:
3124:
3121:
3119:
3116:
3114:
3111:
3110:
3109:
3106:
3105:
3103:
3101:
3097:
3091:
3088:
3086:
3083:
3081:
3078:
3076:
3073:
3071:
3070:Methapyrilene
3068:
3066:
3063:
3061:
3058:
3056:
3053:
3051:
3048:
3046:
3043:
3042:
3040:
3038:
3034:
3031:
3029:
3022:
3016:
3013:
3011:
3008:
3006:
3003:
3001:
2998:
2995:
2991:
2988:
2986:
2983:
2981:
2978:
2976:
2975:Aceburic acid
2973:
2971:
2968:
2966:
2963:
2962:
2960:
2958:
2951:
2939:
2936:
2934:
2931:
2929:
2928:Isovaleramide
2926:
2925:
2924:
2923:Sesquiterpene
2921:
2919:
2916:
2912:
2909:
2907:
2904:
2902:
2899:
2898:
2897:
2894:
2892:
2889:
2887:
2884:
2882:
2879:
2877:
2874:
2872:
2869:
2867:
2864:
2862:
2861:Clomethiazole
2859:
2857:
2854:
2852:
2849:
2847:
2844:
2842:
2839:
2835:
2832:
2830:
2827:
2825:
2822:
2821:
2819:
2816:
2814:
2811:
2809:
2806:
2805:
2803:
2799:
2793:
2790:
2788:
2785:
2783:
2780:
2778:
2775:
2773:
2770:
2768:
2765:
2763:
2760:
2758:
2755:
2753:
2750:
2748:
2745:
2744:
2742:
2740:
2736:
2730:
2727:
2725:
2724:Pyrithyldione
2722:
2720:
2717:
2715:
2712:
2711:
2709:
2707:
2703:
2697:
2694:
2693:
2691:
2689:
2685:
2679:
2676:
2674:
2671:
2669:
2666:
2664:
2661:
2659:
2656:
2654:
2651:
2649:
2646:
2644:
2641:
2639:
2636:
2634:
2631:
2629:
2626:
2625:
2623:
2621:
2617:
2611:
2608:
2606:
2603:
2601:
2598:
2596:
2593:
2591:
2588:
2586:
2583:
2581:
2578:
2576:
2573:
2572:
2570:
2568:
2564:
2558:
2555:
2553:
2550:
2548:
2545:
2543:
2540:
2538:
2535:
2533:
2530:
2529:
2527:
2525:
2521:
2515:
2512:
2510:
2507:
2505:
2502:
2501:
2499:
2497:
2493:
2487:
2484:
2482:
2479:
2477:
2476:Phenprobamate
2474:
2472:
2471:Methocarbamol
2469:
2467:
2464:
2462:
2461:Hexapropymate
2459:
2457:
2454:
2452:
2449:
2447:
2444:
2443:
2441:
2439:
2435:
2429:
2426:
2424:
2421:
2419:
2416:
2414:
2411:
2409:
2406:
2404:
2401:
2399:
2396:
2394:
2391:
2389:
2386:
2384:
2381:
2379:
2378:Flutoprazepam
2376:
2374:
2371:
2369:
2366:
2364:
2363:Flunitrazepam
2361:
2359:
2358:Flunitrazolam
2356:
2354:
2353:Flubromazolam
2351:
2349:
2346:
2344:
2341:
2339:
2336:
2334:
2331:
2329:
2326:
2324:
2321:
2320:
2318:
2316:
2312:
2306:
2303:
2301:
2298:
2296:
2293:
2291:
2288:
2286:
2283:
2281:
2278:
2276:
2273:
2271:
2268:
2266:
2263:
2261:
2258:
2256:
2255:Phenobarbital
2253:
2251:
2248:
2246:
2245:Pentobarbital
2243:
2241:
2240:Narcobarbital
2238:
2236:
2233:
2231:
2230:Mephobarbital
2228:
2226:
2223:
2221:
2218:
2216:
2213:
2211:
2210:Cyclobarbital
2208:
2206:
2203:
2201:
2198:
2196:
2193:
2191:
2188:
2186:
2183:
2181:
2178:
2177:
2175:
2173:
2169:
2163:
2160:
2158:
2155:
2153:
2152:Ethchlorvynol
2150:
2148:
2145:
2143:
2140:
2138:
2135:
2133:
2130:
2129:
2127:
2125:
2121:
2118:
2116:
2109:
2104:
2100:
2096:
2089:
2084:
2082:
2077:
2075:
2070:
2069:
2066:
2060:
2056:
2053:
2050:
2046:
2043:
2041:
2038:
2037:
2018:
2017:
2012:
2006:
1998:
1997:
1996:Boston Herald
1992:
1986:
1972:
1971:
1966:
1959:
1949:
1943:
1937:
1923:
1919:
1913:
1907:
1901:
1887:
1883:
1877:
1870:
1866:
1862:
1858:
1854:
1850:
1846:
1842:
1835:
1828:
1824:
1820:
1816:
1812:
1808:
1805:(1): 109–13,
1804:
1800:
1793:
1791:
1776:
1772:
1771:
1763:
1761:
1759:
1743:
1739:
1732:
1717:
1713:
1707:
1692:
1691:
1690:Chemical Week
1686:
1680:
1665:
1661:
1657:
1651:
1635:
1631:
1627:
1621:
1607:
1601:
1597:
1593:
1589:
1585:
1578:
1571:
1567:
1563:
1559:
1555:
1548:
1541:
1539:9780471238966
1535:
1531:
1527:
1523:
1516:
1502:
1498:
1492:
1476:
1470:
1462:
1460:3-527-30673-0
1456:
1452:
1448:
1444:
1437:
1429:
1428:
1420:
1412:
1408:
1404:
1400:
1397:(4): 92–102.
1396:
1392:
1391:
1386:
1379:
1364:
1363:
1358:
1352:
1345:
1339:
1331:
1330:
1323:
1315:
1314:
1307:
1300:
1298:0-8493-0462-8
1294:
1290:
1283:
1279:
1270:
1267:
1265:
1262:
1260:
1257:
1255:
1252:
1251:
1245:
1243:
1239:
1235:
1231:
1221:
1219:
1215:
1211:
1205:
1195:
1193:
1189:
1185:
1181:
1177:
1172:
1168:
1164:
1154:
1150:
1146:
1144:
1140:
1136:
1122:
1117:
1113:
1111:
1107:
1103:
1098:
1094:
1090:
1086:
1082:
1072:
1070:
1065:
1063:
1054:
1045:
1043:
1039:
1035:
1030:
1027:
1021:
1019:
1014:
1012:
1008:
1004:
1000:
999:butyrolactone
996:
992:
989:
985:
981:
977:
973:
969:
968:polyurethanes
965:
961:
957:
947:
945:
942:proceeds via
941:
937:
932:
930:
929:succinic acid
926:
925:allyl acetate
922:
918:
914:
913:Hydrogenation
910:
906:
902:
898:
890:
885:
876:
874:
871:
851:
847:
843:
839:
835:
831:
827:
823:
819:
807:
800:
795:
778:
772:
769:
768:Succinic acid
765:
762:
757:
756:
753:
749:
745:
741:
738:
735:
730:
729:
724:
720:
717:
711:
710:
706:
704:
701:
700:
693:
686:
679:
655:
652:
651:
647:
646:
600:
597:
593:
592:
582:
579:
575:
574:
571:
568:
565:
561:
560:
556:
552:
549:
545:
544:
540:
538:
533:
528:
524:
517:
513:
509:
508:
504:
500:
496:
495:
491:
488:
485:
484:
480:
477:
473:
472:
468:
466:
465:Boiling point
463:
462:
458:
456:
455:Melting point
453:
452:
448:
446:
443:
442:
435:
433:
430:
429:
408:
405:
401:
400:
395:
386:
381:
380:
377:
370:
359:
349:
348:
345:
338:
330:
326:
322:
321:
319:
309:
305:
304:
297:
293:
292:
290:
288:
285:
284:
277:
276:
274:
272:
269:
268:
261:
257:
256:
254:
248:
244:
243:
236:
235:
233:
231:
226:
225:
221:
217:
214:
212:
210:ECHA InfoCard
207:
206:
199:
195:
194:
192:
190:
187:
186:
179:
175:
174:
172:
170:
167:
166:
159:
155:
154:
152:
150:
147:
146:
139:
135:
134:
132:
130:
127:
126:
119:
115:
112:
108:
107:
105:
101:
96:
95:
88:
84:
83:
81:
78:
74:
73:
68:
60:
52:
48:
43:
39:
34:
30:
25:
19:
6538:
6527:
6520:
6497:
6428:Antagonists:
6427:
6377:
6245:
6242:
6218:Metabotropic
6189:Pregnanolone
6183:picrotoxinin
6156:
6142:
6069:
6039:(S)-4-ACPBPA
6034:(S)-2-MeGABA
6031:Antagonists:
6030:
6005:
5994:Thiomuscimol
5966:
5917:
5781:picrotoxinin
5744:enzalutamide
5740:bicalutamide
5662:Golexanolone
5558:Cloflubicyne
5408:
5334:Antagonists:
5333:
5246:methaqualone
5221:glutethimide
5197:Petrichloral
5158:β-carbolines
4977:Barbiturates
4935:
4919:Thiomuscimol
4724:Beta-Alanine
4714:Barbiturates
4704:(+)-Catechin
4700:
4617:
4610:
4603:
4596:
4557:Acetaldehyde
4461:
4440:Ethosuximide
4333:Butyric acid
4295:Pyruvic acid
4250:Butyric acid
4240:Benzoic acid
4192:Pyruvic acid
4132:Butyric acid
4122:Benzoic acid
4117:Atorvastatin
3955:4-Phenyl-GHB
3940:4-Benzyl-GHB
3930:3-Methyl-GHB
3921:
3918:
3903:
3901:Antagonists:
3900:
3889:(+)-Catechin
3885:
3761:
3758:
3755:
3670:Valnoctamide
3572:Metaglycodol
3567:Fenpentadiol
3477:Daridorexant
3380:Thioridazine
3331:Trimipramine
3266:Medetomidine
3194:Thioridazine
3145:Trimipramine
3090:Propiomazine
3085:Promethazine
2964:
2891:Petrichloral
2876:Kavalactones
2808:Acetophenone
2777:Methaqualone
2772:Mecloqualone
2767:Mebroqualone
2757:Diproqualone
2752:Cloroqualone
2714:Glutethimide
2610:Progesterone
2600:Hydroxydione
2532:Acecarbromal
2446:Carisoprodol
2388:Lormetazepam
2373:Flutemazepam
2275:Secobarbital
2235:Methohexital
2225:Hexobarbital
2205:Butobarbital
2200:Butabarbital
2190:Aprobarbital
2180:Allobarbital
2172:Barbiturates
2021:, retrieved
2014:
2005:
1994:
1985:
1974:, retrieved
1968:
1958:
1948:
1936:
1925:, retrieved
1921:
1912:
1900:
1889:, retrieved
1885:
1876:
1844:
1840:
1834:
1802:
1798:
1778:, retrieved
1769:
1745:. Retrieved
1742:the Guardian
1741:
1731:
1720:, retrieved
1718:, April 2004
1715:
1706:
1695:, retrieved
1688:
1679:
1668:, retrieved
1659:
1650:
1638:. Retrieved
1634:the original
1629:
1620:
1609:, retrieved
1587:
1577:
1561:
1557:
1552:Zhao, Jing;
1547:
1521:
1515:
1504:, retrieved
1500:
1491:
1479:. Retrieved
1469:
1442:
1436:
1426:
1419:
1394:
1388:
1378:
1366:. Retrieved
1360:
1351:
1338:
1328:
1322:
1312:
1306:
1288:
1282:
1238:bromophenols
1227:
1207:
1160:
1151:
1147:
1143:acetaldehyde
1131:
1089:side effects
1078:
1066:
1059:
1031:
1022:
1015:
953:
940:biosynthesis
933:
905:formaldehyde
894:
837:
833:
829:
825:
821:
817:
816:
714:Autoignition
649:
569:
536:
515:
271:RTECS number
158:ChEMBL171623
70:Identifiers
62:Other names
18:
6577:Alkanediols
6501:Compound 14
6331:Lesogaberan
6170:Loreclezole
6107:Loreclezole
6044:(S)-4-ACPCA
6024:Lanthanides
6014:Alphaxolone
5956:Isoguvacine
5866:Terbequinil
5736:apalutamide
5727:Nicardipine
5687:Laudanosine
5494:carbapenems
5486:penicillins
5342:Coriamyrtin
5337:Bicuculline
5326:sevoflurane
5322:paraldehyde
5272:Stiripentol
5149:Niacinamide
5134:cholesterol
5116:Loreclezole
5011:meprobamate
4967:Avermectins
4834:Nefiracetam
4799:Kojic amine
4789:Isomuscimol
4784:Isoguvacine
4363:Valinomycin
4207:Simvastatin
4157:Lactic acid
4072:Transporter
3965:Amisulpride
3847:T-HCA (GHC)
3777:BDDA (DABD)
3655:Scopolamine
3599:Guaifenesin
3594:Fenadiazole
3550:Cannabidiol
3524:Mirogabalin
3482:Lemborexant
3459:Tasimelteon
3444:Agomelatine
3403:Risperidone
3349:Mirtazapine
3238:-Adrenergic
3217:Risperidone
3163:Mirtazapine
3113:Etoperidone
3080:Pheniramine
3065:Hydroxyzine
2886:Paraldehyde
2881:Loreclezole
2747:Afloqualone
2729:Piperidione
2719:Methyprylon
2648:Pazinaclone
2628:Eszopiclone
2590:Alphaxolone
2585:Alphadolone
2524:Monoureides
2466:Meprobamate
2403:Nitemazepam
2398:Nimetazepam
2343:Doxefazepam
2328:Cinolazepam
2300:Vinbarbital
2265:Proxibarbal
2250:Phenallymal
2185:Amobarbital
2137:Chloralodol
2023:1 September
1722:21 November
1697:21 November
1670:21 February
1640:24 November
734:butanediols
716:temperature
703:Flash point
564:Signal word
489:in ethanol
397:Properties
216:100.003.443
138:CHEBI:41189
6556:Categories
6356:SKF-97,541
6266:Arbaclofen
6175:Picrotoxin
6165:Bilobalide
5841:Suritozole
5831:Sarmazenil
5816:Ro 19-4603
5811:Ro 15-4513
5806:Radequinil
5773:Picrotoxin
5752:nilutamide
5722:Naltrexone
5657:Furosemide
5637:Flumazenil
5631:oroxylin A
5623:Flavonoids
5603:Etbicyphat
5533:Bilobalide
5500:Basmisanil
5387:Sinomenine
5382:Securinine
5377:Pitrazepin
5362:Hydrastine
5314:chloroform
5287:Topiramate
5227:Propanidid
5091:Imidazoles
5086:Flupirtine
5081:Fluoxetine
5075:hispidulin
5067:Flavonoids
5022:Chloralose
5007:Carbamates
4971:ivermectin
4909:Terpenoids
4854:PF-6372865
4709:Bamaluzole
4676:Ionotropic
4668:modulators
4572:Disulfiram
4562:Cimetidine
4519:Cimetidine
4462:Enhancers:
4388:inhibitors
4368:Vigabatrin
4338:Evans blue
4285:Probenecid
4265:Ketoprofen
4255:Fenoprofen
4187:Probenecid
4112:AR-C155858
4015:Sultopride
3922:Main site:
3904:Main site:
3759:Main site:
3718:modulators
3623:Metaxalone
3613:Mephenesin
3534:Pregabalin
3514:Gabapentin
3487:Suvorexant
3422:Niaprazine
3398:Quetiapine
3393:Olanzapine
3276:Tizanidine
3271:Romifidine
3261:Lofexidine
3251:Detomidine
3212:Quetiapine
3207:Olanzapine
3118:Nefazodone
3060:Doxylamine
3045:Captodiame
2856:Chloralose
2820:compounds
2762:Etaqualone
2658:Suproclone
2638:Lirequinil
2605:Minaxolone
2595:Eltanolone
2575:Acebrochol
2542:Bromisoval
2509:Metomidate
2496:Imidazoles
2456:Ethinamate
2451:Emylcamate
2438:Carbamates
2413:Nitrazolam
2408:Nitrazepam
2383:Loprazolam
2368:Flurazepam
2338:Clonazolam
2333:Climazolam
2323:Brotizolam
2305:Vinylbital
2290:Thiopental
1275:References
1202:See also:
962:, elastic
548:Pictograms
487:Solubility
432:Molar mass
296:7XOO2LE6G3
169:ChemSpider
98:3D model (
77:CAS Number
6572:Sedatives
6491:SKF-97541
6486:SCH-50911
6476:Phaclofen
6461:CGP-64213
6456:CGP-55845
6451:CGP-54626
6446:CGP-52432
6441:CGP-46381
6436:CGP-35348
6406:CGP-13501
6381:ADX-71441
6366:Tolgabide
6346:Progabide
6341:Picamilon
6326:Isovaline
6243:Agonists:
6145:-3-ACPBPA
6122:SKF-97541
6072:-3-ACPBPA
5999:Tolgabide
5979:Progabide
5974:Picamilon
5918:Agonists:
5826:RO4938581
5821:RO4882224
5748:flutamide
5682:L-655,708
5652:Flurothyl
5553:Cicutoxin
5538:Bupropion
5505:Bemegride
5482:β-Lactams
5472:Amiloride
5302:Volatiles
5236:etazolate
5212:Phenytoin
5170:zopiclone
5162:abecarnil
5121:Monastrol
5111:Lanthanum
5095:etomidate
5057:Fenamates
5052:Etifoxine
5047:Etazepine
4924:Tolgabide
4874:Progabide
4864:Picamilon
4849:Org 20599
4824:Monastrol
4804:L-838,417
4701:Agonists:
4567:Cyanamide
4412:Quercetin
4353:Nigericin
4323:β-Alanine
4260:Ibuprofen
4197:Quercetin
4182:Phloretin
4010:Sulpiride
3975:BnOPh-GHB
3894:Monastrol
3756:Agonists:
3660:Trazodone
3601:-related
3454:Ramelteon
3449:Melatonin
3436:Melatonin
3344:Mianserin
3311:Trazodone
3246:Clonidine
3158:Mianserin
3123:Trazodone
3075:Perlapine
2918:Triclofos
2871:Gaboxadol
2678:Zopiclone
2663:Suriclone
2653:Saripidem
2643:Necopidem
2557:Ectylurea
2552:Carbromal
2514:Propoxate
2504:Etomidate
2481:Procymate
2428:Triazolam
2423:Temazepam
2393:Midazolam
2348:Estazolam
2285:Thiamylal
2220:Heptabarb
2099:sedatives
2095:Hypnotics
2047:from the
1976:11 August
1780:29 August
1775:eMedicine
1501:uspto.gov
1411:0165-0513
1188:precursor
1020:plastic.
991:catalysts
988:ruthenium
921:butadiene
901:acetylene
879:Synthesis
848:with the
634:P403+P233
622:P304+P340
618:P301+P312
539:labelling
481:Miscible
278:EK0525000
237:203-786-5
229:EC Number
6567:Prodrugs
6517:See also
6481:Saclofen
6416:rac-BHFF
6411:GS-39783
6401:CGP-7930
6361:SL 75102
6336:Phenibut
6291:Gabamide
6276:Baclofen
6179:picrotin
6132:SR-95813
6127:SR-95318
6049:2-MeTACA
5961:Muscimol
5891:ZK-93426
5861:TCS-1105
5846:TB-21007
5777:picrotin
5717:Naloxone
5702:Morphine
5697:MaxiPost
5617:fipronil
5613:Fiproles
5583:(+)-DMBB
5578:Dieldrin
5477:Anisatin
5392:SR-42641
5292:Valerian
5266:baicalin
5262:Skullcap
5206:propofol
5186:zaleplon
5178:zolpidem
5071:apigenin
4991:diazepam
4948:Alcohols
4889:SL-75102
4879:Propofol
4859:Phenibut
4829:Muscimol
4813:honokiol
4779:iso-THIP
4774:iso-THAZ
4749:Gabamide
4665:receptor
4593:See also
4577:Prunetin
4534:Pyrazole
4275:Naproxen
4162:Luteolin
4078:blockers
4059:instead.
3726:Receptor
3715:receptor
3644:morphine
3635:Midaflur
3555:Cannabis
3529:Phenibut
3281:Xylazine
3010:Phenibut
2980:Baclofen
2906:Tetronal
2841:Centalun
2696:Propofol
2673:Zolpidem
2668:Zaleplon
2633:Indiplon
2547:Capuride
2486:Tybamate
2418:Quazepam
2280:Talbutal
2195:Barbital
2124:Alcohols
1891:2 August
1869:24609982
1861:17100847
1827:54415695
1664:archived
1611:29 March
1368:31 March
1248:See also
1157:Legality
1013:resins.
997:to form
960:plastics
907:to form
840:), is a
732:Related
650:NFPA 704
530:Hazards
501:(χ)
492:Soluble
388:C(CCO)CO
189:DrugBank
178:13835209
87:110-63-4
6386:BHF-177
6371:Tolibut
6281:BL-1020
6194:ROD-188
6059:4-ACPAM
6054:3-APMPA
5921:BL-1020
5881:U-93631
5876:Thujone
5801:PWZ-029
5775:(i.e.,
5734:(e.g.,
5712:MRK-016
5692:Lindane
5644:(e.g.,
5625:(e.g.,
5615:(e.g.,
5484:(e.g.,
5462:β-EMGBL
5372:PHP-501
5308:(e.g.,
5279:(e.g.,
5257:ROD-188
5244:(e.g.,
5234:(e.g.,
5219:(e.g.,
5204:(e.g.,
5202:Phenols
5184:(e.g.,
5176:(e.g.,
5168:(e.g.,
5160:(e.g.,
5156:(e.g.,
5128:(e.g.,
5093:(e.g.,
5069:(e.g.,
5059:(e.g.,
5039:(e.g.,
5009:(e.g.,
4997:Bromide
4989:(e.g.,
4979:(e.g.,
4969:(e.g.,
4950:(e.g.,
4943:α-EMTBL
4913:borneol
4911:(e.g.,
4894:Taurine
4841:(e.g.,
4811:(e.g.,
4809:Lignans
4729:BL-1020
4716:(e.g.,
4524:Ethanol
4491:Cyanide
4348:Glycine
4000:NCS-400
3912:NCS-382
3837:NCS-435
3832:NCS-356
3732:ligands
3642:(e.g.,
3640:Opioids
3589:Evoxine
3326:Doxepin
3140:Doxepin
3015:Tolibut
2911:Trional
2818:Bromide
2688:Phenols
2270:Reposal
1927:1 April
1819:6717752
1506:1 April
1481:30 July
1210:Bindeez
1204:Bindeez
1184:Class C
1182:) as a
1106:ethanol
1097:ethanol
1093:ethanol
1038:Spandex
956:solvent
938:. The
870:viscous
850:formula
844:and an
799:what is
797: (
570:Warning
445:Density
247:PubChem
198:DB01955
6421:KK-92A
6251:3-APPA
6019:ATHDOC
5573:DHEA-S
5412:1,3M1B
5144:Niacin
5105:kavain
4382:Enzyme
4030:UMB119
4025:UMB109
4020:UMB108
3945:4-HPBA
3822:HOCPCA
3817:HOCHCA
3762:1,4-BD
3543:Others
3469:Orexin
3415:Others
3405:, etc.
3382:, etc.
3351:, etc.
3333:, etc.
3219:, etc.
3196:, etc.
3165:, etc.
3147:, etc.
2801:Others
2792:SL-164
2055:Record
2051:(OECD)
1867:
1859:
1825:
1817:
1747:30 May
1602:
1536:
1457:
1409:
1295:
1192:Canada
1171:analog
970:. In
964:fibers
873:liquid
838:1,4-BD
794:verify
791:
437:90.122
383:OCCCCO
376:SMILES
149:ChEMBL
45:Names
6311:GHBAL
6296:GABOB
6199:THDOC
6143:trans
6137:TPMPA
6112:P4MPA
6064:4-GBA
5946:GABOB
5672:IPTBO
5522:IPTBO
5457:β-CCP
5452:β-CCM
5447:β-CCE
5442:β-CCB
5402:Tutin
5306:gases
5138:THDOC
4754:GABOB
4423:GHBDH
4311:VIATT
4228:SMCTs
3925:2-HPA
3882:UMB86
3877:UMB73
3872:UMB72
3867:UMB68
3862:UMB66
3857:UMB58
3802:GHBAL
3767:3-HPA
3665:UMB68
2985:GABOB
2016:Stern
1865:S2CID
1823:S2CID
1362:WebMD
1214:GC-MS
1067:Some
1011:epoxy
826:1,4-B
344:InChI
129:ChEBI
100:JSmol
6529:GABA
6466:DAVA
6396:BSPP
6391:BHFF
6286:GABA
6228:GABA
6204:Zinc
6150:ZAPA
6097:I4AA
6082:DAVA
5989:TAMP
5984:TACA
5941:GABA
5931:CAMP
5926:CACA
5902:GABA
5886:Zinc
5871:TETS
5856:TBPS
5851:TBOB
5783:and
5598:EBOB
5593:DMPC
5588:DMCM
5568:DHEA
5543:CHEB
5528:BIDN
5518:TBPO
5514:TBPS
5432:α3IA
5417:3M2B
5101:Kava
4956:2M2B
4938:here
4929:ZAPA
4904:TAMP
4899:TACA
4744:GABA
4734:DAVA
4686:GABA
4663:GABA
4545:ALDH
4343:GABA
4172:NPPB
4147:DIDS
4142:DBDS
4137:CHCA
4090:MCTs
4057:here
4055:See
4041:GABA
3990:GTBL
3744:GHBR
3505:VDCC
3291:5-HT
2954:GABA
2132:2M2B
2112:GABA
2103:N05C
2025:2021
1978:2009
1929:2018
1893:2016
1857:PMID
1815:PMID
1782:2009
1749:2024
1724:2008
1699:2008
1672:2013
1642:2023
1613:2022
1600:ISBN
1534:ISBN
1508:2018
1483:2023
1455:ISBN
1407:ISSN
1370:2024
1293:ISBN
1240:and
1137:and
1083:and
1042:BASF
1026:US$
1009:for
966:and
927:and
852:HOCH
836:and
642:P501
638:P405
630:P330
626:P312
614:P271
610:P270
606:P264
602:P261
588:H336
584:H302
287:UNII
260:8064
6321:GVL
6316:GHV
6306:GHB
6301:GBL
6117:P4S
6070:cis
5836:SCS
5180:),
5172:),
5164:),
4869:P4S
4507:ADH
4479:HOT
4400:SSR
4245:BHB
4127:BHB
3985:DVL
3980:DHV
3852:THF
3827:MAB
3812:GVL
3797:GHB
3792:GCL
3787:GBL
3782:EAB
3713:GHB
3005:GVL
3000:GBL
2990:GHB
2059:NLM
1849:doi
1807:doi
1592:doi
1566:doi
1526:doi
1447:doi
1399:doi
1190:in
834:BDO
537:GHS
313:EPA
250:CID
6558::
6181:,
5906:-ρ
5779:,
5750:,
5746:,
5742:,
5738:,
5629:,
5520:,
5516:,
5492:,
5488:,
5324:,
5320:,
5316:,
5312:,
5188:))
5136:,
5132:,
5073:,
4954:,
3884:;
3293:2A
2013:,
1993:,
1967:,
1920:,
1884:,
1863:,
1855:,
1845:24
1843:,
1821:,
1813:,
1803:23
1801:,
1789:^
1773:,
1757:^
1740:.
1714:,
1687:,
1658:,
1628:.
1598:,
1586:,
1562:24
1560:,
1532:,
1499:,
1453:.
1445:.
1405:.
1393:.
1387:.
1359:.
1244:.
1194:.
1145:.
1044:.
946:.
931:.
923:,
911:.
899:,
891:.
864:CH
860:CH
856:CH
832:,
830:BD
828:,
640:,
636:,
632:,
628:,
624:,
620:,
616:,
612:,
608:,
604:,
586:,
541::
419:10
6531:A
6230:B
6185:)
6177:(
5967:N
5904:A
5787:)
5754:)
5648:)
5633:)
5619:)
5524:)
5512:(
5496:)
5328:)
5304:/
5298:)
5283:)
5268:)
5248:)
5238:)
5223:)
5208:)
5140:)
5107:)
5097:)
5077:)
5063:)
5043:)
5013:)
5003:)
4993:)
4983:)
4973:)
4958:)
4915:)
4845:)
4815:)
4720:)
4688:A
4654:e
4647:t
4640:v
4466:D
4390:)
4386:(
4080:)
4076:(
4043:B
3734:)
3730:(
3704:e
3697:t
3690:v
3646:)
3502:δ
3500:2
3498:α
3236:2
3234:α
3027:1
3025:H
2996:)
2992:(
2956:B
2114:A
2105:)
2101:(
2097:/
2087:e
2080:t
2073:v
1851::
1809::
1751:.
1644:.
1594::
1568::
1528::
1485:.
1463:.
1449::
1413:.
1401::
1395:9
1372:.
866:2
862:2
858:2
854:2
789:Y
691:0
684:1
677:1
521:)
519:D
516:n
514:(
425:2
422:O
416:H
413:4
410:C
315:)
311:(
102:)
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