1289:
385:
236:
1216:
1275:
1247:
1147:
49:
1180:
1111:
1075:
1013:
40:
1044:
501:
958:
1430:β-carbolines also occur in many foodstuffs, however in lower concentrations. The highest amounts have been detected in brewed coffee, raisins, well-done fish and meats. Smoking is another source of fully aromatic β-carbolines, with levels up to thousands of μg per smoker each day.
2769:
Hemmateenejad B, Abbaspour A, Maghami H, Miri R, Panjehshahin MR (August 2006). "Partial least squares-based multivariate spectral calibration method for simultaneous determination of beta-carboline derivatives in
Peganum harmala seed extracts".
4191:
4010:
1718:
Glennon RA, Dukat M, Grella B, Hong S, Costantino L, Teitler M, et al. (August 2000). "Binding of beta-carbolines and related agents at serotonin (5-HT(2) and 5-HT(1A)), dopamine (D(2)) and benzodiazepine receptors".
1809:
Fortunato JJ, Réus GZ, Kirsch TR, Stringari RB, Fries GR, Kapczinski F, et al. (October 2010). "Chronic administration of harmine elicits antidepressant-like effects and increases BDNF levels in rat hippocampus".
4637:
4015:
4587:
3502:
4748:
3527:
2027:
Hamann J, Wernicke C, Lehmann J, Reichmann H, Rommelspacher H, Gille G (March 2008). "9-Methyl-beta-carboline up-regulates the appearance of differentiated dopaminergic neurones in primary mesencephalic culture".
4740:
4667:
4642:
724:
but can promote anxiety and convulsions at high doses. With modification in position 9 similar positive effects have been observed for learning and memory without promotion of anxiety or convulsion.
4060:
4710:
4647:
3541:
4652:
4055:
4050:
906:(NMDA) receptors, some researchers speculatively attributed the rapid improvement in patients with Parkinson's disease to these antiglutamatergic effects. However, the advent of synthetic
4045:
4040:
1932:
Wernicke C, Hellmann J, Zieba B, Kuter K, Ossowska K, Frenzel M, et al. (January 2010). "9-Methyl-beta-carboline has restorative effects in an animal model of
Parkinson's disease".
4657:
4632:
2887:
Badre A, Boulanger A, Abou-Mansour E, Banaigs B, Combaut G, Francisco C (April 1994). "Eudistomin U and isoeudistomin U, new alkaloids from the
Caribbean ascidian Lissoclinum fragile".
3124:"Novel cytocidal compounds, oxopropalines from Streptomyces sp. G324 producing lavendamycin. I. Taxonomy of the producing organism, fermentation, isolation and biological activities"
6010:
4434:
2569:"Banisteriopsis caapi, a unique combination of MAO inhibitory and antioxidative constituents for the activities relevant to neurodegenerative disorders and Parkinson's disease"
6647:
6544:
4449:
2813:
Herraiz T, González D, Ancín-Azpilicueta C, Arán VJ, Guillén H (March 2010). "beta-Carboline alkaloids in
Peganum harmala and inhibition of human monoamine oxidase (MAO)".
4715:
4582:
3497:
3467:
2168:
Mendelson WB, Cain M, Cook JM, Paul SM, Skolnick P (January 1983). "A benzodiazepine receptor antagonist decreases sleep and reverses the hypnotic actions of flurazepam".
720:
in rodents and – by itself – can decrease sleep in a dose-dependent manner. Another derivative, methyl-β-carboline-3-carboxylate, stimulates learning and memory at low
4662:
2071:
Polanski W, Reichmann H, Gille G (June 2011). "Stimulation, protection and regeneration of dopaminergic neurons by 9-methyl-β-carboline: a new anti-Parkinson drug?".
4695:
6171:
6753:
6050:
5792:
946:
atom, to produce a three-ringed structure. The biosynthesis of β-carbolines is believed to follow this route from analogous tryptamines. Different levels of
6042:
5064:
4735:
4680:
3332:
2957:
Becher PG, Beuchat J, Gademann K, Jüttner F (December 2005). "Nostocarboline: isolation and synthesis of a new cholinesterase inhibitor from Nostoc 78-12A".
1622:"Harmine treatment enhances short-term memory in old rats: Dissociation of cognition and the ability to perform the procedural requirements of maze testing"
6005:
5985:
5583:
2481:
Schwarz MJ, Houghton PJ, Rose S, Jenner P, Lees AD (June 2003). "Activities of extract and constituents of
Banisteriopsis caapi relevant to parkinsonism".
5995:
5990:
5980:
3945:
863:, mood, and sometimes rigidity improved by treatment with harmine. Altogether, 25 studies had been published in the 1920s and 1930s about patients with
6549:
6534:
6126:
5230:
4529:
3251:
970:
Some of the more important β-carbolines are tabulated by structure below. Their structures may contain the aforementioned bonds marked by red or blue.
514:
6529:
5138:
4534:
4181:
4141:
3337:
1980:"9-Methyl-β-carboline-induced cognitive enhancement is associated with elevated hippocampal dopamine levels and dendritic and synaptic proliferation"
3875:
6524:
5475:
4394:
1853:
López-Muñoz F, Alamo C (2009-05-01). "Monoaminergic neurotransmission: the history of the discovery of antidepressants from 1950s until today".
6146:
6669:
6584:
5954:
5929:
5837:
5588:
5099:
3397:
3387:
2722:"Manganese dioxide mediated one-pot synthesis of methyl 9H-pyrido[3,4-b]indole-1-carboxylate: Concise synthesis of alangiobussinine"
5673:
5380:
5260:
4201:
3965:
434:
5355:
5290:
5255:
5250:
5127:
5059:
5054:
5049:
5044:
5039:
5004:
4675:
4419:
5014:
4889:
4730:
4725:
4459:
4295:
3990:
3377:
3372:
3347:
4211:
3970:
2922:
Davis RA, Carroll AR, Quinn RJ (July 1998). "Eudistomin V, a new beta-carboline from the
Australian ascidian Pseudodistoma aureum".
6663:
5019:
3193:
Farzin D, Mansouri N (July 2006). "Antidepressant-like effect of harmane and other beta-carbolines in the mouse forced swim test".
2665:
Du W, Aloyo VJ, Harvey JA (October 1997). "Harmaline competitively inhibits MK-801 binding to the NMDA receptor in rabbit brain".
5663:
1343:
Altogether, eight plant families are known to express 64 different kinds of β-carboline alkaloids. For example, the β-carbolines
843:
as the active substance. This discovery stimulated the interest to further investigate its potential as a medicine. For example,
3244:
2524:
Brierley DI, Davidson C (January 2013). "Harmine augments electrically evoked dopamine efflux in the nucleus accumbens shell".
2339:"A small molecule produced by Lactobacillus species blocks Candida albicans filamentation by inhibiting a DYRK1-family kinase"
6748:
5285:
5172:
3013:
1905:
272:
4499:
509:
957:
5508:
5480:
4564:
947:
2280:"β-carboline chemical signals induce reveromycin production through a LuxR family regulator in Streptomyces sp. SN-593"
4617:
3237:
1288:
867:
and postencephalitic
Parkinsonism. The pharmacological effects of harmine have been attributed mainly to its central
623:
619:
399:
4825:
3283:
1759:"Acute harmine administration induces antidepressive-like effects and increases BDNF levels in the rat hippocampus"
749:
141:
2618:"DYRK1A promotes dopaminergic neuron survival in the developing brain and in a mouse model of Parkinson's disease"
521:
1323:. Some β-carbolines, notably tetrahydro-β-carbolines, may be formed naturally in plants and the human body with
6655:
4469:
4171:
1498:
Francik R, Kazek G, Cegła M, Stepniewski M (March 2011). "Antioxidant activity of beta-carboline derivatives".
17:
847:, a prominent pharmacologist, demonstrated a dramatic benefit in neurological impairments after injections of
4797:
852:
6161:
6096:
716:
and memory enhancing effects. Moreover, 3-hydroxymethyl-beta-carboline blocks the sleep-promoting effect of
5212:
5120:
2454:
Foley P (2003). "Beans, roots and leaves: a brief history of the pharmacological therapy of parkinsonism".
342:
231:
6189:
6539:
4524:
635:
363:
193:
1215:
309:
6348:
5812:
6758:
6335:
6245:
5890:
5827:
5165:
4914:
4904:
4330:
3274:
1757:
Fortunato JJ, Réus GZ, Kirsch TR, Stringari RB, Stertz L, Kapczinski F, et al. (November 2009).
243:
6081:
4758:
6738:
5747:
3176:
3170:
900:
380:
303:
5847:
5712:
5623:
5618:
5420:
4884:
4539:
3342:
2567:
Samoylenko V, Rahman MM, Tekwani BL, Tripathi LM, Wang YH, Khan SI, et al. (February 2010).
1577:
Aaghaz S, Sharma K, Jain R, Kamal A (April 2021). "β-Carbolines as potential anticancer agents".
776:
6374:
4909:
1223:
654:
6643:
5593:
5280:
5189:
5181:
4305:
4166:
3900:
864:
745:
690:
650:
564:
5817:
5757:
5722:
5410:
4146:
1978:
Gruss M, Appenroth D, Flubacher A, Enzensperger C, Bock J, Fleck C, et al. (June 2012).
1336:
1246:
615:
6220:
767:
growth form (yeast-to-filament transition). Thereby, β-carboline reverses imbalances in the
6763:
6733:
6728:
5158:
4869:
4389:
4025:
3536:
3166:
2779:
2350:
2291:
2232:
2177:
1357:
822:
666:
351:
213:
61:
6215:
6166:
6073:
3036:"β-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO)"
2337:
MacAlpine J, Daniel-Ivad M, Liu Z, Yano J, Revie NM, Todd RT, et al. (October 2021).
2278:
Panthee S, Kito N, Hayashi T, Shimizu T, Ishikawa J, Hamamoto H, et al. (June 2020).
839:
in the middle of the 19th century. In early 20th century, European pharmacists identified
8:
6743:
6412:
5875:
5852:
5573:
5465:
4919:
4899:
4383:
4020:
3724:
3546:
3437:
1405:
721:
173:
117:
107:
2783:
2354:
2295:
2236:
2181:
1146:
384:
235:
6589:
6034:
6000:
5964:
5865:
5732:
5727:
4108:
3780:
3742:
3266:
3218:
2746:
2721:
2690:
2642:
2617:
2616:
Barallobre MJ, Perier C, Bové J, Laguna A, Delabar JM, Vila M, Arbonés ML (June 2014).
2593:
2568:
2549:
2506:
2431:
2402:
2371:
2338:
2314:
2279:
2255:
2220:
2201:
2145:
2118:
2096:
2053:
2009:
1957:
1911:
1835:
1788:
1700:
1646:
1621:
1602:
1556:
951:
674:
634:
in humans. The antidepressant effect of harmine might also be due to its function as a
153:
3099:
3082:
2678:
2494:
2119:"From the behavioral pharmacology of beta-carbolines to seizures, anxiety, and memory"
1945:
1732:
1179:
6402:
6025:
5860:
5717:
5707:
5029:
4700:
4361:
3752:
3599:
3554:
3392:
3210:
3145:
3104:
3063:
3055:
3009:
2974:
2939:
2904:
2838:
2795:
2751:
2682:
2647:
2598:
2541:
2498:
2463:
2436:
2376:
2319:
2260:
2193:
2150:
2088:
2045:
2001:
1996:
1979:
1949:
1901:
1870:
1827:
1792:
1780:
1736:
1692:
1687:
1670:
1651:
1606:
1594:
1560:
1548:
1543:
1526:
1507:
1352:
1187:
1012:
897:
868:
828:
694:
670:
631:
3222:
3206:
3181:
2694:
2553:
2510:
2205:
2100:
2057:
1961:
1915:
1839:
1704:
1110:
1074:
551:
and synthetic compounds. The effects of these substances depend on their respective
6359:
5692:
5197:
4854:
4607:
4265:
4065:
3995:
3830:
3728:
3560:
3441:
3202:
3135:
3094:
3047:
3001:
2966:
2931:
2896:
2869:
2830:
2822:
2787:
2741:
2733:
2674:
2637:
2629:
2588:
2580:
2533:
2490:
2426:
2418:
2366:
2358:
2309:
2299:
2250:
2240:
2221:"β-carboline biomediators induce reveromycin production in Streptomyces sp. SN-593"
2185:
2140:
2130:
2080:
2037:
2013:
1991:
1941:
1893:
1862:
1819:
1770:
1728:
1682:
1641:
1633:
1586:
1538:
1468:
1362:
919:
760:
607:
596:
572:
457:
1637:
331:
6317:
5975:
4366:
4275:
4240:
3908:
3890:
3815:
3772:
3635:
2993:
2041:
1590:
1463:
1375:
1370:
1274:
907:
881:
662:
658:
568:
556:
6106:
3187:
3140:
3123:
3005:
2720:
Baiget J, Llona-Minguez S, Lang S, Mackay SP, Suckling CJ, Sutcliffe OB (2011).
1775:
1758:
813:
6435:
5832:
5275:
5245:
4949:
4844:
3894:
3764:
3659:
3585:
3550:
3035:
2856:
Lake RJ, Blunt JW, Munro MH (1989). "Eudistomins from the New
Zealand ascidian
2708:
The
Encyclopedia of Psychoactive Plants: Ethnopharmacology and its Applications
2362:
2304:
2245:
1866:
1420:
1416:
892:
release. Furthermore, harmine supports the survival of dopaminergic neurons in
759:
secretes a β-carboline (1-acetyl-β-carboline) preventing the pathogenic fungus
705:
701:
611:
603:
492:
6378:
6366:
3756:
3122:
Abe N, Nakakita Y, Nakamura T, Enoki N, Uchida H, Takeo S, Munekata M (1993).
3051:
2826:
2791:
2584:
1897:
1823:
6722:
6439:
6202:
5870:
5563:
5265:
5240:
4859:
4549:
4356:
4244:
4225:
4161:
4088:
4000:
3950:
3916:
3879:
3840:
3790:
3630:
3625:
3615:
3579:
3482:
3417:
3367:
3316:
3260:
3059:
2537:
1170:
756:
643:
224:
3034:
Herraiz T, González D, Ancín-Azpilicueta C, Arán V, Guillén H (March 2010).
2189:
1043:
587:
The pharmacological effects of specific β-carbolines are dependent on their
6594:
6507:
6491:
6445:
6307:
6287:
6156:
6151:
6121:
6116:
6111:
6058:
5787:
5682:
5643:
5628:
5613:
5603:
5598:
5558:
5455:
5450:
5445:
5440:
5430:
5425:
5405:
4816:
4787:
4781:
4592:
4379:
4342:
4338:
4260:
4156:
3844:
3819:
3795:
3517:
3322:
3229:
3214:
3108:
3067:
2978:
2842:
2799:
2755:
2651:
2633:
2602:
2545:
2502:
2467:
2440:
2380:
2323:
2264:
2154:
2092:
2049:
2005:
1953:
1874:
1831:
1784:
1740:
1696:
1655:
1598:
1552:
1511:
1473:
1442:
1297:
1293:
836:
738:
733:
700:
However, β-carbolines with substituents in position 3 reduce the effect of
678:
4824:
3149:
2943:
2908:
2686:
2197:
689:
proliferation. It also exhibited therapeutic effects in animal models for
6691:
6503:
6483:
6431:
6344:
6302:
6297:
6277:
6272:
6254:
6176:
5807:
5638:
5608:
5553:
5470:
5435:
5415:
5400:
5069:
4994:
4929:
4768:
4705:
4612:
4554:
4464:
4334:
4325:
4285:
3940:
3935:
3924:
3920:
3870:
3860:
3747:
3732:
3714:
3609:
3575:
3432:
3382:
3362:
3312:
1450:
1446:
1427:
856:
844:
627:
588:
560:
552:
6101:
6086:
4080:
2900:
2135:
6683:
6674:
6651:
6633:
6604:
6599:
6579:
6495:
6487:
6465:
6406:
6354:
6330:
6325:
6282:
6141:
5949:
5944:
5939:
5909:
5895:
5885:
5797:
5697:
5668:
5543:
5533:
5523:
5493:
5390:
5375:
5340:
5235:
4954:
4864:
4773:
4763:
4622:
4439:
4429:
4414:
4409:
4404:
4371:
4350:
4320:
4255:
4235:
4229:
4131:
4098:
4092:
4084:
3985:
3980:
3975:
3960:
3912:
3885:
3850:
3825:
3684:
3679:
3673:
3620:
3569:
3565:
3452:
3307:
2834:
2737:
2422:
1765:. Bed nucleus of the stria terminalis: anatomy, physiology, functions.
1478:
1395:
1382:
1378:) contain between 0.16% and 5.9% β-carboline alkaloids (by dry weight).
1332:
1324:
1312:
1301:
935:
931:
810:/BRCP1, etc.), they are also discussed as potential anticancer agents.
768:
728:
717:
713:
709:
480:
262:
244:
204:
2970:
2935:
2873:
2400:
1973:
1971:
1620:
Mennenga SE, Gerson JE, Dunckley T, Bimonte-Nelson HA (January 2015).
595:
has substituents on position 7 and 1. Thereby, it acts as a selective
6702:
6687:
6659:
6628:
6623:
6618:
6569:
6564:
6554:
6499:
6479:
6460:
6455:
6427:
6382:
6370:
6240:
6235:
6225:
6136:
6131:
6091:
6020:
6015:
5924:
5822:
5802:
5762:
5687:
5633:
5578:
5568:
5548:
5538:
5528:
5518:
5513:
5503:
5498:
5460:
5395:
5385:
5370:
5360:
5345:
5335:
5325:
5315:
5305:
5270:
5217:
5089:
5084:
5074:
5034:
4979:
4964:
4944:
4939:
4924:
4720:
4690:
4597:
4577:
4572:
4424:
4346:
4280:
4250:
4221:
4151:
4136:
4103:
4070:
3834:
3810:
3768:
3760:
3719:
3709:
3693:
3689:
3665:
3650:
3645:
3605:
3522:
3507:
3472:
3462:
3447:
3422:
3402:
3357:
2998:
Isoquinolines And Beta-Carbolines As
Neurotoxins And Neuroprotectants
2084:
1890:
Isoquinolines And Beta-Carbolines As Neurotoxins And Neuroprotectants
1572:
1570:
1390:
1365:
1348:
1328:
1118:
832:
772:
764:
639:
3033:
2812:
2219:
Panthee S, Takahashi S, Hayashi T, Shimizu T, Osada H (April 2019).
1619:
547:) represents the basic chemical structure for more than one hundred
491:
Except where otherwise noted, data are given for materials in their
6697:
6574:
6559:
6475:
6470:
6423:
6398:
6386:
6340:
6292:
5919:
5904:
5772:
5767:
5365:
5350:
5330:
5320:
5310:
5300:
5295:
5207:
5202:
5079:
5009:
4999:
4959:
4934:
4874:
4777:
4685:
4559:
4489:
4444:
4375:
4315:
4300:
4215:
4176:
4075:
3955:
3864:
3804:
3784:
3776:
3669:
3655:
3639:
3589:
3487:
3477:
3457:
3427:
3411:
3302:
1977:
1968:
1438:
1386:
1308:
1154:
1020:
923:
889:
886:
860:
686:
548:
541:
292:
48:
1567:
140:
6679:
6394:
6390:
6264:
6230:
6063:
5934:
5653:
5648:
4984:
4969:
4879:
4792:
4519:
4479:
4474:
4399:
4310:
4290:
4206:
3855:
3595:
3511:
3492:
3327:
2886:
2768:
1434:
1344:
1203:
1134:
1098:
1082:
1051:
1028:
872:
840:
803:
682:
592:
318:
39:
4035:
4030:
1887:
1763:
Progress in Neuro-Psychopharmacology & Biological Psychiatry
6707:
6609:
6419:
5880:
5842:
5777:
5742:
5737:
5658:
4849:
3800:
3703:
3407:
2566:
1320:
1237:
1192:
1159:
1123:
1087:
1056:
943:
939:
927:
799:
791:
783:
600:
576:
544:
408:
InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H
184:
5150:
2401:
Djamshidian A, Bernschneider-Reif S, Poewe W, Lees AJ (2016).
2218:
2026:
1361:
and play a pivotal role in the pharmacology of the indigenous
950:
are possible in the third ring which is indicated here in the
418:
InChI=1/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H
6638:
6450:
5914:
4894:
4544:
4270:
4120:
3736:
3352:
2719:
1316:
930:
skeleton. The structure of β-carboline is similar to that of
819:
814:
Explorative human studies for the medical use of β-carbolines
807:
164:
130:
2956:
1808:
1756:
1497:
910:
drugs at that time led to the total abandonment of harmine.
368:
5782:
5752:
5702:
4989:
4802:
4484:
4454:
4196:
4186:
4126:
4116:
4112:
3699:
3080:
2336:
893:
795:
741:
727:β-carboline derivatives also enhance the production of the
283:
4500:
2615:
1931:
3904:
2480:
2407:, a Forgotten Potential Therapy for Parkinson's Disease?"
2277:
787:
673:
activity. This derivative has also been shown to enhance
3121:
3081:
Stachel SJ, Stockwell SA, Van Vranken DL (August 1999).
744:
is facilitated by binding of the β-carboline to a large
630:. A decreased BDNF level has been associated with major
4826:
3284:
2070:
1717:
954:
by coloring the optionally double bonds red and blue:
2167:
1888:
Antkiewicz-Michaluk L, Rommelspacher H, eds. (2012).
1576:
3083:"The fluorescence of scorpions and cataractogenesis"
1381:
A specific group of β-carboline derivatives, termed
271:
2116:
1671:"Activation, regulation, and inhibition of DYRK1A"
2921:
6720:
2523:
1852:
961:Substituted beta-carbolines (structural formula)
330:
2710:. Ratsch, Christian. Park Street Press c. 2005
875:and rodent studies have shown that extracts of
116:
3192:
2855:
782:Since β-carbolines also interact with various
6754:GABAA receptor negative allosteric modulators
5166:
3245:
2664:
1524:
3259:
3000:, Boston, MA: Springer US, pp. 77–103,
563:effects. Synthetically designed β-carboline
3261:
1668:
965:
555:. Natural β-carbolines primarily influence
5173:
5159:
4509:Tooltip γ-Aminobutyric acid A-rho receptor
3252:
3238:
2456:Wurzburger Medizinhistorische Mitteilungen
2117:Venault P, Chapouthier G (February 2007).
618:. Furthermore, it increases levels of the
614:-like effects in rats by interacting with
383:
234:
212:
27:Chemical compound also known as norharmane
3169:at the U.S. National Library of Medicine
3139:
3098:
2745:
2641:
2592:
2430:
2370:
2313:
2303:
2254:
2244:
2144:
2134:
1995:
1774:
1686:
1645:
1542:
1433:β-Carbolines have also been found in the
350:
2483:Pharmacology, Biochemistry, and Behavior
1287:
855:. By 1930, it was generally agreed that
2991:
1579:European Journal of Medicinal Chemistry
591:. For example, the natural β-carboline
379:
308:
14:
6721:
4834:Tooltip γ-Aminobutyric acid B receptor
3292:Tooltip γ-Aminobutyric acid A receptor
2726:Beilstein Journal of Organic Chemistry
225:
5154:
3233:
2453:
2396:
2394:
2392:
2390:
2112:
2110:
1927:
1925:
1283:
737:species. Specifically, expression of
411:Key: AIFRHYZBTHREPW-UHFFFAOYSA-N
192:
172:
5574:5-Methoxytryptamine (5-MT; mexamine)
5139:GABA metabolism/transport modulators
2411:Movement Disorders Clinical Practice
1804:
1802:
1752:
1750:
918:β-Carbolines belong to the group of
3535:Positive modulators (abridged; see
1449:light at certain wavelengths (e.g.
827:has been used by the tribes of the
421:Key: AIFRHYZBTHREPW-UHFFFAOYAG
321:
291:
24:
2387:
2161:
2107:
2073:Expert Review of Neurotherapeutics
1922:
1669:Becker W, Sippl W (January 2011).
956:
896:-treated mice. Since harmine also
25:
6775:
5070:Homotaurine (tramiprosate, 3-APS)
4568:-Chloroacetylcytosine arabinoside
3363:Homotaurine (tramiprosate, 3-APS)
3160:
1799:
1747:
1525:Gulyaeva N, Aniol V (June 2012).
620:brain-derived neurotrophic factor
567:have recently been shown to have
3195:European Neuropsychopharmacology
1997:10.1111/j.1471-4159.2012.07713.x
1688:10.1111/j.1742-4658.2010.07956.x
1544:10.1111/j.1471-4159.2012.07708.x
1273:
1245:
1214:
1178:
1145:
1109:
1073:
1042:
1011:
499:
47:
38:
5856:-Feruloylserotonin (moschamine)
5180:
4362:Pentylenetetrazol (pentetrazol)
3207:10.1016/j.euroneuro.2005.08.005
3115:
3074:
3027:
2985:
2950:
2915:
2880:
2849:
2806:
2762:
2713:
2701:
2658:
2609:
2560:
2517:
2474:
2447:
2330:
2271:
2212:
2064:
2020:
1881:
1527:"Good guys from a shady family"
731:reveromycin A in soil-dwelling
582:
495:(at 25 °C , 100 kPa).
6011:6,7-Dichloro-2-methylmelatonin
1846:
1812:Journal of Neural Transmission
1711:
1662:
1613:
1518:
1491:
1254:3-Carboxy-Tetrahydrononharman
13:
1:
5121:Receptor/signaling modulators
4276:Isopregnanolone (sepranolone)
3100:10.1016/S1074-5521(99)80085-4
2994:"β-Carbolines as Neurotoxins"
2679:10.1016/s0006-8993(97)00606-9
2526:Journal of Psychopharmacology
2495:10.1016/s0091-3057(03)00129-1
1946:10.1016/s1734-1140(10)70241-3
1855:Current Pharmaceutical Design
1733:10.1016/s0376-8716(99)00148-9
1638:10.1016/j.physbeh.2014.09.001
1484:
1419:was isolated from freshwater
871:(MAO) inhibitory properties.
853:postencephalitic Parkinsonism
638:by reducing the breakdown of
6749:Monoamine oxidase inhibitors
6167:α-Methylserotonin (5-HO-αMT)
5674:Benzotript (4-chlorobenzoyl-
5132:receptor positive modulators
3640:ergoloid (dihydroergotoxine)
3040:Food and Chemical Toxicology
2815:Food and Chemical Toxicology
2573:Journal of Ethnopharmacology
2042:10.1016/j.neuint.2007.08.018
2030:Neurochemistry International
1591:10.1016/j.ejmech.2021.113321
1355:are components of the liana
913:
681:neuron count and facilitate
661:effects including increased
7:
5900:-acetylpsilocin; 4-AcO-DMT)
3141:10.7164/antibiotics.46.1672
3006:10.1007/978-1-4614-1542-8_5
2959:Journal of Natural Products
2924:Journal of Natural Products
2889:Journal of Natural Products
1776:10.1016/j.pnpbp.2009.07.021
1721:Drug and Alcohol Dependence
1500:Acta Poloniae Pharmaceutica
1457:
786:-related molecules such as
610:. It also exhibits various
606:, a molecule necessary for
10:
6780:
4331:Nonsteroidal antiandrogens
2363:10.1038/s41467-021-26390-w
2305:10.1038/s41598-020-66974-y
2246:10.1038/s41598-019-42268-w
1867:10.2174/138161209788168001
938:chain re-connected to the
748:-binding regulator of the
485:168.20 g/mol
6517:
6316:
6263:
6172:α-Methyltryptophan (αMTP)
6072:
5963:
5188:
5112:
4815:
4498:
3282:
3273:
3188:Beta-carbolines in coffee
3052:10.1016/j.fct.2009.12.019
2827:10.1016/j.fct.2009.12.019
2792:10.1016/j.aca.2006.05.093
2585:10.1016/j.jep.2009.10.030
2123:TheScientificWorldJournal
1984:Journal of Neurochemistry
1898:10.1007/978-1-4614-1542-8
1824:10.1007/s00702-010-0451-2
1626:Physiology & Behavior
1531:Journal of Neurochemistry
1368:. Moreover, the seeds of
990:
987:
984:
981:
978:
975:
926:ring that is fused to an
489:
450:
430:
395:
100:
76:
60:
55:
46:
37:
3880:sulfonmethane (sulfonal)
3171:Medical Subject Headings
2992:Herraiz T (2011-11-10),
2858:Ritterella sigillinoides
2622:Cell Death & Disease
2538:10.1177/0269881112463125
1441:, causing their skin to
1401:Ritterella sigillinoides
966:Examples of β-carbolines
6644:Substituted benzofurans
6379:β-carboline (norharman)
6226:AL-37350A (4,5-DHP-αMT)
5713:Desformylflustrabromine
5644:Aeruginascin (4-PO-TMT)
3087:Chemistry & Biology
2190:10.1126/science.6294835
1934:Pharmacological Reports
835:and was described as a
708:and can therefore have
6030:-acetylserotonin; NAS)
5871:Norbaeocystin (4-PO-T)
5594:5-(Nonyloxy)tryptamine
4759:5α-Dihydroprogesterone
4306:Morphine-3-glucuronide
3966:Hyenachin (mellitoxin)
3851:Retigabine (ezogabine)
2772:Analytica Chimica Acta
2634:10.1038/cddis.2014.253
1385:, were extracted from
1304:
962:
6420:DM-506 (ibogaminalog)
6092:4-HO-MPMI (lucigenol)
5910:Psilocybin (4-PO-DMT)
5818:Methylbutyltryptamine
5669:Baeocystin (4-PO-NMT)
4147:Chlorophenylsilatrane
2343:Nature Communications
1291:
960:
616:serotonin receptor 2A
559:but can also exhibit
6318:Cyclized tryptamines
5823:Miprocin (4-HO-MiPT)
5793:Indolylethylfentanyl
5763:Ethocybin (4-PO-DET)
5688:Bufotenin (5-HO-DMT)
5683:Bufotenidine (5-HTQ)
5097:Negative modulators:
4977:Positive modulators:
4870:Arbaclofen placarbil
4756:Negative modulators:
4605:Positive modulators:
4390:Pregnenolone sulfate
4026:17-Phenylandrostenol
4008:Negative modulators:
3893:constituents (e.g.,
3863:constituents (e.g.,
3725:Neuroactive steroids
3702:constituents (e.g.,
3438:Neuroactive steroids
2405:Banisteriopsis caapi
1411:Pseudodistoma aureum
1358:Banisteriopsis caapi
1224:9-Methyl-β-carboline
877:Banisteriopsis caapi
824:Banisteriopsis caapi
771:composition causing
763:to change to a more
667:neurotrophic factors
655:9-methyl-β-carboline
442:c1ccc3c(c1)c2cnccc23
62:Preferred IUPAC name
6418:and related (e.g.,
6054:-Propionylmelatonin
5905:Psilocin (4-HO-DMT)
5803:Iprocin (4-HO-DiPT)
4686:Gabazine (SR-95531)
4676:CGP-36742 (SGS-742)
4384:dihydropicrotoxinin
4109:Bicyclic phosphates
4021:11-Ketoprogesterone
3956:Gabazine (SR-95531)
3781:pyrazolopyrimidines
2901:10.1021/np50106a016
2784:2006AcAC..575..290H
2355:2021NatCo..12.6151M
2296:2020NatSR..1010230P
2237:2019NatSR...9.5802P
2182:1983Sci...219..414M
2136:10.1100/tsw.2007.48
1406:Lissoclinum fragile
904:-methyl-d-aspartate
865:Parkinson's disease
818:The extract of the
777:vaginal candidiasis
691:Parkinson's disease
573:cognitive enhancing
154:Beilstein Reference
34:
6074:α-Alkyltryptamines
6046:-Butanoylmelatonin
6006:6-Methoxymelatonin
6001:6-Hydroxymelatonin
5986:5-Methoxyluzindole
5968:-Acetyltryptamines
5639:Acetryptine (5-AT)
5584:5-Methyltryptamine
5466:5-HTP (oxitriptan)
4207:FG-7142 (ZK-31906)
3753:Nonbenzodiazepines
2738:10.3762/bjoc.7.164
2423:10.1002/mdc3.12242
2284:Scientific Reports
2225:Scientific Reports
1311:are widespread in
1305:
1284:Natural occurrence
963:
952:structural formula
942:ring via an extra
779:to fungal sepsis.
757:Lactobacillus spp.
675:cognitive function
522:Infobox references
32:
6716:
6715:
6518:Related compounds
6403:tetrahydroharmine
6216:αET (etryptamine)
6038:-Acetyltryptamine
5996:6-Fluoromelatonin
5991:6-Chloromelatonin
5981:2-Phenylmelatonin
5677:
5148:
5147:
5108:
5107:
5030:2-Hydroxysaclofen
4811:
4810:
4701:Isonipecotic acid
4066:Anabolic steroids
4036:α5IA (LS-193,268)
3946:Dihydrosecurinine
3831:Pyrazolopyridines
3600:potassium bromide
3598:compounds (e.g.,
3561:Anabolic steroids
3539:for a full list):
3393:Isonipecotic acid
3134:(11): 1672–1677.
3015:978-1-4614-1541-1
2971:10.1021/np050312l
2965:(12): 1793–1795.
2936:10.1021/np9800452
2874:10.1071/CH9891201
2176:(4583): 414–416.
1907:978-1-4614-1541-1
1861:(14): 1563–1586.
1818:(10): 1131–1137.
1353:tetrahydroharmine
1281:
1280:
1188:Tetrahydroharmine
869:monoamine oxidase
851:in patients with
695:neurodegenerative
671:respiratory chain
530:Chemical compound
528:
527:
364:CompTox Dashboard
142:Interactive image
16:(Redirected from
6771:
6759:Indole alkaloids
6550:7-Aza-5-MeO-DiPT
6535:5-Aza-4-MeO-DiPT
5925:Serotonin (5-HT)
5693:Convolutindole A
5675:
5198:1-Methylpsilocin
5175:
5168:
5161:
5152:
5151:
4855:4-Fluorophenibut
4835:
4831:
4822:
4821:
4691:Gaboxadol (THIP)
4608:Allopregnanolone
4510:
4506:
4241:Fluoroquinolones
3996:Thiocolchicoside
3816:Piperidinediones
3773:imidazopyridines
3729:allopregnanolone
3636:Dihydroergolines
3551:drinking alcohol
3442:allopregnanolone
3358:Gaboxadol (THIP)
3293:
3289:
3280:
3279:
3263:
3254:
3247:
3240:
3231:
3230:
3226:
3154:
3153:
3143:
3119:
3113:
3112:
3102:
3078:
3072:
3071:
3031:
3025:
3024:
3023:
3022:
2989:
2983:
2982:
2954:
2948:
2947:
2919:
2913:
2912:
2884:
2878:
2877:
2868:(7): 1201–1206.
2853:
2847:
2846:
2810:
2804:
2803:
2766:
2760:
2759:
2749:
2717:
2711:
2705:
2699:
2698:
2662:
2656:
2655:
2645:
2613:
2607:
2606:
2596:
2564:
2558:
2557:
2521:
2515:
2514:
2478:
2472:
2471:
2451:
2445:
2444:
2434:
2398:
2385:
2384:
2374:
2334:
2328:
2327:
2317:
2307:
2275:
2269:
2268:
2258:
2248:
2216:
2210:
2209:
2165:
2159:
2158:
2148:
2138:
2114:
2105:
2104:
2085:10.1586/ern.11.1
2068:
2062:
2061:
2036:(4–5): 688–700.
2024:
2018:
2017:
1999:
1975:
1966:
1965:
1929:
1920:
1919:
1885:
1879:
1878:
1850:
1844:
1843:
1806:
1797:
1796:
1778:
1769:(8): 1425–1430.
1754:
1745:
1744:
1715:
1709:
1708:
1690:
1675:The FEBS Journal
1666:
1660:
1659:
1649:
1617:
1611:
1610:
1574:
1565:
1564:
1546:
1522:
1516:
1515:
1495:
1469:Harmala alkaloid
1445:upon exposed to
1363:psychedelic drug
1277:
1249:
1218:
1182:
1149:
1113:
1077:
1046:
1015:
973:
972:
920:indole alkaloids
761:Candida albicans
706:GABA-A receptors
608:neurodevelopment
512:
506:
503:
502:
458:Chemical formula
388:
387:
372:
370:
354:
334:
323:
312:
295:
275:
246:
238:
227:
216:
196:
176:
144:
120:
51:
42:
35:
31:
21:
6779:
6778:
6774:
6773:
6772:
6770:
6769:
6768:
6739:Beta-Carbolines
6719:
6718:
6717:
6712:
6530:4-Aza-5-MeO-DPT
6513:
6312:
6259:
6068:
5976:2-Iodomelatonin
5959:
5184:
5179:
5149:
5144:
5131:
5104:
4833:
4830:
4807:
4535:Homohypotaurine
4508:
4504:
4494:
4367:Phenylsilatrane
3909:chloral hydrate
3876:Sulfonylalkanes
3765:cyclopyrrolones
3586:Benzodiazepines
3338:Dihydromuscimol
3291:
3288:
3269:
3258:
3167:Beta-Carbolines
3163:
3158:
3157:
3120:
3116:
3079:
3075:
3032:
3028:
3020:
3018:
3016:
2990:
2986:
2955:
2951:
2920:
2916:
2885:
2881:
2854:
2850:
2811:
2807:
2767:
2763:
2718:
2714:
2706:
2702:
2663:
2659:
2614:
2610:
2565:
2561:
2522:
2518:
2479:
2475:
2452:
2448:
2399:
2388:
2335:
2331:
2276:
2272:
2217:
2213:
2166:
2162:
2115:
2108:
2069:
2065:
2025:
2021:
1976:
1969:
1930:
1923:
1908:
1886:
1882:
1851:
1847:
1807:
1800:
1755:
1748:
1716:
1712:
1667:
1663:
1618:
1614:
1575:
1568:
1523:
1519:
1496:
1492:
1487:
1464:Gamma-carboline
1460:
1371:Peganum harmala
1286:
1260:
1241:
1207:
1196:
1163:
1138:
1127:
1102:
1091:
1060:
1032:
968:
922:and consist of
916:
908:anticholinergic
882:Peganum harmala
816:
659:neuroprotective
636:MAO-A inhibitor
585:
569:neuroprotective
557:brain functions
531:
524:
519:
518:
517: ?)
508:
504:
500:
496:
474:
470:
466:
460:
446:
443:
438:
437:
426:
423:
422:
419:
413:
412:
409:
403:
402:
391:
373:
366:
357:
337:
324:
298:
278:
265:
256:
219:
199:
179:
156:
147:
134:
123:
110:
96:
95:
72:
71:
28:
23:
22:
15:
12:
11:
5:
6777:
6767:
6766:
6761:
6756:
6751:
6746:
6741:
6736:
6731:
6714:
6713:
6711:
6710:
6705:
6700:
6695:
6677:
6672:
6667:
6641:
6636:
6631:
6626:
6621:
6616:
6607:
6602:
6597:
6592:
6587:
6582:
6577:
6572:
6567:
6562:
6557:
6552:
6547:
6542:
6537:
6532:
6527:
6521:
6519:
6515:
6514:
6512:
6511:
6473:
6468:
6463:
6458:
6453:
6448:
6443:
6436:tabernanthalog
6410:
6357:
6352:
6338:
6333:
6328:
6322:
6320:
6314:
6313:
6311:
6310:
6305:
6300:
6295:
6290:
6285:
6280:
6275:
6269:
6267:
6261:
6260:
6258:
6257:
6252:
6243:
6238:
6233:
6228:
6223:
6218:
6213:
6200:
6187:
6174:
6169:
6164:
6159:
6154:
6149:
6144:
6139:
6134:
6129:
6124:
6119:
6114:
6109:
6104:
6099:
6094:
6089:
6084:
6078:
6076:
6070:
6069:
6067:
6066:
6061:
6056:
6048:
6040:
6032:
6026:Normelatonin (
6023:
6018:
6013:
6008:
6003:
5998:
5993:
5988:
5983:
5978:
5972:
5970:
5961:
5960:
5958:
5957:
5952:
5947:
5942:
5937:
5932:
5927:
5922:
5917:
5912:
5907:
5902:
5893:
5888:
5883:
5878:
5873:
5868:
5863:
5858:
5850:
5845:
5840:
5835:
5830:
5825:
5820:
5815:
5810:
5805:
5800:
5795:
5790:
5785:
5780:
5775:
5770:
5765:
5760:
5755:
5750:
5745:
5740:
5735:
5730:
5725:
5720:
5715:
5710:
5705:
5700:
5695:
5690:
5685:
5680:
5671:
5666:
5661:
5656:
5651:
5646:
5641:
5636:
5631:
5626:
5621:
5616:
5611:
5606:
5601:
5596:
5591:
5586:
5581:
5576:
5571:
5566:
5561:
5556:
5551:
5546:
5541:
5536:
5531:
5526:
5521:
5516:
5511:
5506:
5501:
5496:
5491:
5478:
5473:
5468:
5463:
5458:
5453:
5448:
5443:
5438:
5433:
5428:
5423:
5418:
5413:
5408:
5403:
5398:
5393:
5388:
5383:
5378:
5373:
5368:
5363:
5358:
5353:
5348:
5343:
5338:
5333:
5328:
5323:
5318:
5313:
5308:
5303:
5298:
5293:
5288:
5286:4-HO-5-MeO-DMT
5283:
5278:
5273:
5268:
5263:
5258:
5253:
5248:
5243:
5238:
5233:
5228:
5215:
5210:
5205:
5200:
5194:
5192:
5186:
5185:
5178:
5177:
5170:
5163:
5155:
5146:
5145:
5143:
5142:
5135:
5129:
5124:
5117:
5113:
5110:
5109:
5106:
5105:
5103:
5102:
5093:
5092:
5087:
5082:
5077:
5072:
5067:
5062:
5057:
5052:
5047:
5042:
5037:
5032:
5023:
5022:
5017:
5012:
5007:
5002:
4997:
4992:
4987:
4982:
4973:
4972:
4967:
4962:
4957:
4952:
4950:Sodium oxybate
4947:
4942:
4937:
4932:
4927:
4922:
4917:
4912:
4907:
4902:
4897:
4892:
4887:
4882:
4877:
4872:
4867:
4862:
4857:
4852:
4847:
4845:1,4-Butanediol
4838:
4836:
4828:
4819:
4813:
4812:
4809:
4808:
4806:
4805:
4800:
4795:
4790:
4785:
4771:
4766:
4761:
4752:
4751:
4746:
4738:
4733:
4728:
4723:
4718:
4713:
4708:
4703:
4698:
4693:
4688:
4683:
4678:
4673:
4665:
4660:
4655:
4650:
4645:
4640:
4635:
4626:
4625:
4620:
4615:
4610:
4601:
4600:
4595:
4590:
4585:
4580:
4575:
4570:
4562:
4557:
4552:
4547:
4542:
4537:
4532:
4527:
4522:
4513:
4511:
4502:
4496:
4495:
4493:
4492:
4487:
4482:
4477:
4472:
4467:
4462:
4457:
4452:
4447:
4442:
4437:
4432:
4427:
4422:
4417:
4412:
4407:
4402:
4397:
4392:
4387:
4369:
4364:
4359:
4354:
4328:
4323:
4318:
4313:
4308:
4303:
4298:
4293:
4288:
4283:
4278:
4273:
4268:
4263:
4258:
4253:
4248:
4238:
4233:
4219:
4209:
4204:
4199:
4194:
4189:
4184:
4179:
4174:
4169:
4164:
4159:
4154:
4149:
4144:
4139:
4134:
4129:
4124:
4106:
4101:
4096:
4089:cephalosporins
4078:
4073:
4068:
4063:
4058:
4053:
4048:
4043:
4038:
4033:
4028:
4023:
4018:
4013:
4004:
4003:
3998:
3993:
3988:
3983:
3978:
3973:
3968:
3963:
3958:
3953:
3948:
3943:
3938:
3929:
3928:
3898:
3895:valerenic acid
3888:
3883:
3873:
3868:
3858:
3853:
3848:
3841:Quinazolinones
3838:
3828:
3823:
3813:
3808:
3798:
3793:
3788:
3750:
3745:
3740:
3722:
3717:
3712:
3707:
3697:
3687:
3682:
3677:
3663:
3660:mefenamic acid
3653:
3648:
3643:
3633:
3628:
3623:
3618:
3613:
3603:
3593:
3583:
3573:
3563:
3558:
3544:
3531:
3530:
3525:
3520:
3515:
3505:
3500:
3495:
3490:
3485:
3480:
3475:
3470:
3465:
3460:
3455:
3450:
3445:
3435:
3430:
3425:
3420:
3415:
3405:
3400:
3395:
3390:
3385:
3380:
3375:
3370:
3365:
3360:
3355:
3350:
3345:
3340:
3335:
3330:
3325:
3320:
3310:
3305:
3296:
3294:
3286:
3277:
3271:
3270:
3257:
3256:
3249:
3242:
3234:
3228:
3227:
3201:(5): 324–328.
3190:
3185:
3179:
3174:
3162:
3161:External links
3159:
3156:
3155:
3114:
3093:(8): 531–539.
3073:
3046:(3): 839–845.
3026:
3014:
2984:
2949:
2930:(7): 959–960.
2914:
2895:(4): 528–533.
2879:
2848:
2821:(3): 839–845.
2805:
2778:(2): 290–299.
2761:
2712:
2700:
2673:(1–2): 26–29.
2667:Brain Research
2657:
2608:
2579:(2): 357–367.
2559:
2516:
2489:(3): 627–633.
2473:
2446:
2386:
2329:
2270:
2211:
2160:
2106:
2079:(6): 845–860.
2063:
2019:
1990:(6): 924–931.
1967:
1921:
1906:
1880:
1845:
1798:
1746:
1727:(2): 121–132.
1710:
1681:(2): 246–256.
1661:
1612:
1566:
1537:(6): 841–842.
1517:
1506:(2): 185–189.
1489:
1488:
1486:
1483:
1482:
1481:
1476:
1471:
1466:
1459:
1456:
1455:
1454:
1431:
1424:
1421:cyanobacterium
1417:Nostocarboline
1414:
1393:of the family
1379:
1285:
1282:
1279:
1278:
1271:
1268:
1265:
1262:
1258:
1255:
1251:
1250:
1243:
1239:
1235:
1232:
1229:
1226:
1220:
1219:
1212:
1209:
1205:
1201:
1198:
1194:
1190:
1184:
1183:
1176:
1173:
1168:
1165:
1161:
1157:
1151:
1150:
1143:
1140:
1136:
1132:
1129:
1125:
1121:
1115:
1114:
1107:
1104:
1100:
1096:
1093:
1089:
1085:
1079:
1078:
1071:
1068:
1065:
1062:
1058:
1054:
1048:
1047:
1040:
1037:
1034:
1030:
1026:
1023:
1017:
1016:
1009:
1006:
1003:
1000:
997:
993:
992:
989:
986:
983:
980:
977:
967:
964:
915:
912:
815:
812:
702:benzodiazepine
612:antidepressant
604:protein kinase
584:
581:
529:
526:
525:
520:
498:
497:
493:standard state
490:
487:
486:
483:
477:
476:
472:
468:
464:
461:
456:
453:
452:
448:
447:
445:
444:
441:
433:
432:
431:
428:
427:
425:
424:
420:
417:
416:
414:
410:
407:
406:
398:
397:
396:
393:
392:
390:
389:
376:
374:
362:
359:
358:
356:
355:
347:
345:
339:
338:
336:
335:
327:
325:
317:
314:
313:
306:
300:
299:
297:
296:
288:
286:
280:
279:
277:
276:
268:
266:
261:
258:
257:
255:
254:
250:
248:
240:
239:
229:
221:
220:
218:
217:
209:
207:
201:
200:
198:
197:
189:
187:
181:
180:
178:
177:
169:
167:
161:
160:
157:
152:
149:
148:
146:
145:
137:
135:
128:
125:
124:
122:
121:
113:
111:
106:
103:
102:
98:
97:
94:
93:
86:
83:
79:
78:
74:
73:
65:
64:
58:
57:
53:
52:
44:
43:
26:
18:Beta-carboline
9:
6:
4:
3:
2:
6776:
6765:
6762:
6760:
6757:
6755:
6752:
6750:
6747:
6745:
6742:
6740:
6737:
6735:
6732:
6730:
6727:
6726:
6724:
6709:
6706:
6704:
6701:
6699:
6696:
6693:
6689:
6685:
6681:
6678:
6676:
6673:
6671:
6668:
6665:
6661:
6657:
6653:
6649:
6645:
6642:
6640:
6637:
6635:
6632:
6630:
6627:
6625:
6622:
6620:
6617:
6615:
6613:
6608:
6606:
6603:
6601:
6598:
6596:
6593:
6591:
6588:
6586:
6583:
6581:
6578:
6576:
6573:
6571:
6568:
6566:
6563:
6561:
6558:
6556:
6553:
6551:
6548:
6546:
6543:
6541:
6538:
6536:
6533:
6531:
6528:
6526:
6525:2-Azapsilocin
6523:
6522:
6520:
6516:
6509:
6505:
6501:
6497:
6493:
6489:
6485:
6481:
6477:
6474:
6472:
6469:
6467:
6464:
6462:
6459:
6457:
6454:
6452:
6449:
6447:
6444:
6441:
6440:tabernanthine
6437:
6433:
6429:
6425:
6421:
6417:
6415:
6411:
6408:
6404:
6400:
6396:
6392:
6388:
6384:
6380:
6376:
6372:
6368:
6364:
6362:
6358:
6356:
6353:
6350:
6346:
6342:
6339:
6337:
6334:
6332:
6329:
6327:
6324:
6323:
6321:
6319:
6315:
6309:
6306:
6304:
6301:
6299:
6296:
6294:
6291:
6289:
6286:
6284:
6281:
6279:
6276:
6274:
6271:
6270:
6268:
6266:
6262:
6256:
6253:
6251:
6249:
6244:
6242:
6239:
6237:
6234:
6232:
6229:
6227:
6224:
6222:
6219:
6217:
6214:
6212:
6210:
6206:
6201:
6199:
6197:
6193:
6188:
6186:
6184:
6180:
6175:
6173:
6170:
6168:
6165:
6163:
6160:
6158:
6155:
6153:
6150:
6148:
6145:
6143:
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:
6079:
6077:
6075:
6071:
6065:
6062:
6060:
6057:
6055:
6053:
6049:
6047:
6045:
6041:
6039:
6037:
6033:
6031:
6029:
6024:
6022:
6019:
6017:
6014:
6012:
6009:
6007:
6004:
6002:
5999:
5997:
5994:
5992:
5989:
5987:
5984:
5982:
5979:
5977:
5974:
5973:
5971:
5969:
5967:
5962:
5956:
5953:
5951:
5948:
5946:
5943:
5941:
5938:
5936:
5933:
5931:
5928:
5926:
5923:
5921:
5918:
5916:
5913:
5911:
5908:
5906:
5903:
5901:
5899:
5894:
5892:
5889:
5887:
5884:
5882:
5879:
5877:
5874:
5872:
5869:
5867:
5864:
5862:
5859:
5857:
5855:
5851:
5849:
5846:
5844:
5841:
5839:
5836:
5834:
5831:
5829:
5826:
5824:
5821:
5819:
5816:
5814:
5811:
5809:
5806:
5804:
5801:
5799:
5796:
5794:
5791:
5789:
5786:
5784:
5781:
5779:
5776:
5774:
5771:
5769:
5766:
5764:
5761:
5759:
5756:
5754:
5751:
5749:
5746:
5744:
5741:
5739:
5736:
5734:
5731:
5729:
5726:
5724:
5721:
5719:
5716:
5714:
5711:
5709:
5706:
5704:
5701:
5699:
5696:
5694:
5691:
5689:
5686:
5684:
5681:
5679:
5672:
5670:
5667:
5665:
5662:
5660:
5657:
5655:
5652:
5650:
5647:
5645:
5642:
5640:
5637:
5635:
5632:
5630:
5627:
5625:
5622:
5620:
5617:
5615:
5612:
5610:
5607:
5605:
5602:
5600:
5597:
5595:
5592:
5590:
5587:
5585:
5582:
5580:
5577:
5575:
5572:
5570:
5567:
5565:
5564:5-MeO-T-NBOMe
5562:
5560:
5557:
5555:
5552:
5550:
5547:
5545:
5542:
5540:
5537:
5535:
5532:
5530:
5527:
5525:
5522:
5520:
5517:
5515:
5512:
5510:
5507:
5505:
5502:
5500:
5497:
5495:
5492:
5490:
5488:
5484:
5479:
5477:
5476:5-MeO-34MPEMT
5474:
5472:
5469:
5467:
5464:
5462:
5459:
5457:
5454:
5452:
5449:
5447:
5444:
5442:
5439:
5437:
5434:
5432:
5429:
5427:
5424:
5422:
5419:
5417:
5414:
5412:
5409:
5407:
5404:
5402:
5399:
5397:
5394:
5392:
5389:
5387:
5384:
5382:
5379:
5377:
5374:
5372:
5369:
5367:
5364:
5362:
5359:
5357:
5354:
5352:
5349:
5347:
5344:
5342:
5339:
5337:
5334:
5332:
5329:
5327:
5324:
5322:
5319:
5317:
5314:
5312:
5309:
5307:
5304:
5302:
5299:
5297:
5294:
5292:
5289:
5287:
5284:
5282:
5281:4-F-5-MeO-DMT
5279:
5277:
5274:
5272:
5269:
5267:
5264:
5262:
5259:
5257:
5254:
5252:
5249:
5247:
5244:
5242:
5239:
5237:
5234:
5232:
5229:
5227:
5225:
5221:
5216:
5214:
5213:2-Methyl-5-HT
5211:
5209:
5206:
5204:
5201:
5199:
5196:
5195:
5193:
5191:
5187:
5183:
5176:
5171:
5169:
5164:
5162:
5157:
5156:
5153:
5141:
5140:
5136:
5134:
5133:
5125:
5123:
5122:
5118:
5115:
5114:
5111:
5101:
5098:
5095:
5094:
5091:
5088:
5086:
5083:
5081:
5078:
5076:
5073:
5071:
5068:
5066:
5063:
5061:
5058:
5056:
5053:
5051:
5048:
5046:
5043:
5041:
5038:
5036:
5033:
5031:
5028:
5025:
5024:
5021:
5018:
5016:
5013:
5011:
5008:
5006:
5003:
5001:
4998:
4996:
4993:
4991:
4988:
4986:
4983:
4981:
4978:
4975:
4974:
4971:
4968:
4966:
4963:
4961:
4958:
4956:
4953:
4951:
4948:
4946:
4943:
4941:
4938:
4936:
4933:
4931:
4928:
4926:
4923:
4921:
4918:
4916:
4913:
4911:
4908:
4906:
4903:
4901:
4898:
4896:
4893:
4891:
4888:
4886:
4883:
4881:
4878:
4876:
4873:
4871:
4868:
4866:
4863:
4861:
4860:Aceburic acid
4858:
4856:
4853:
4851:
4848:
4846:
4843:
4840:
4839:
4837:
4832:
4823:
4820:
4818:
4814:
4804:
4801:
4799:
4796:
4794:
4791:
4789:
4786:
4783:
4779:
4775:
4772:
4770:
4767:
4765:
4762:
4760:
4757:
4754:
4753:
4750:
4747:
4745:
4743:
4739:
4737:
4734:
4732:
4729:
4727:
4724:
4722:
4719:
4717:
4714:
4712:
4709:
4707:
4704:
4702:
4699:
4697:
4694:
4692:
4689:
4687:
4684:
4682:
4679:
4677:
4674:
4672:
4670:
4666:
4664:
4661:
4659:
4656:
4654:
4651:
4649:
4646:
4644:
4641:
4639:
4636:
4634:
4631:
4628:
4627:
4624:
4621:
4619:
4616:
4614:
4611:
4609:
4606:
4603:
4602:
4599:
4596:
4594:
4591:
4589:
4586:
4584:
4581:
4579:
4576:
4574:
4571:
4569:
4567:
4563:
4561:
4558:
4556:
4553:
4551:
4550:Ibotenic acid
4548:
4546:
4543:
4541:
4538:
4536:
4533:
4531:
4528:
4526:
4523:
4521:
4518:
4515:
4514:
4512:
4507:
4497:
4491:
4488:
4486:
4483:
4481:
4478:
4476:
4473:
4471:
4468:
4466:
4463:
4461:
4458:
4456:
4453:
4451:
4448:
4446:
4443:
4441:
4438:
4436:
4433:
4431:
4428:
4426:
4423:
4421:
4418:
4416:
4413:
4411:
4408:
4406:
4403:
4401:
4398:
4396:
4395:Propybicyphat
4393:
4391:
4388:
4385:
4381:
4377:
4373:
4370:
4368:
4365:
4363:
4360:
4358:
4357:Oenanthotoxin
4355:
4352:
4348:
4344:
4340:
4336:
4332:
4329:
4327:
4324:
4322:
4319:
4317:
4314:
4312:
4309:
4307:
4304:
4302:
4299:
4297:
4294:
4292:
4289:
4287:
4284:
4282:
4279:
4277:
4274:
4272:
4269:
4267:
4266:Iomazenil (I)
4264:
4262:
4259:
4257:
4254:
4252:
4249:
4246:
4245:ciprofloxacin
4242:
4239:
4237:
4234:
4231:
4227:
4226:amentoflavone
4223:
4220:
4217:
4213:
4210:
4208:
4205:
4203:
4200:
4198:
4195:
4193:
4190:
4188:
4185:
4183:
4180:
4178:
4175:
4173:
4170:
4168:
4165:
4163:
4162:Cyclothiazide
4160:
4158:
4155:
4153:
4150:
4148:
4145:
4143:
4140:
4138:
4135:
4133:
4130:
4128:
4125:
4122:
4118:
4114:
4110:
4107:
4105:
4102:
4100:
4097:
4094:
4090:
4086:
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:
4006:
4005:
4002:
3999:
3997:
3994:
3992:
3989:
3987:
3984:
3982:
3979:
3977:
3974:
3972:
3969:
3967:
3964:
3962:
3959:
3957:
3954:
3952:
3951:Famiraprinium
3949:
3947:
3944:
3942:
3939:
3937:
3934:
3931:
3930:
3926:
3922:
3918:
3917:diethyl ether
3914:
3910:
3906:
3902:
3899:
3896:
3892:
3889:
3887:
3884:
3881:
3877:
3874:
3872:
3869:
3866:
3862:
3859:
3857:
3854:
3852:
3849:
3846:
3842:
3839:
3836:
3832:
3829:
3827:
3824:
3821:
3817:
3814:
3812:
3809:
3806:
3802:
3799:
3797:
3794:
3792:
3791:Norfluoxetine
3789:
3786:
3782:
3778:
3774:
3770:
3766:
3762:
3758:
3754:
3751:
3749:
3746:
3744:
3741:
3738:
3734:
3730:
3726:
3723:
3721:
3718:
3716:
3713:
3711:
3708:
3705:
3701:
3698:
3695:
3691:
3688:
3686:
3683:
3681:
3678:
3675:
3671:
3667:
3664:
3661:
3657:
3654:
3652:
3649:
3647:
3644:
3641:
3637:
3634:
3632:
3631:Clomethiazole
3629:
3627:
3626:Chlormezanone
3624:
3622:
3619:
3617:
3616:Carbamazepine
3614:
3611:
3607:
3604:
3601:
3597:
3594:
3591:
3587:
3584:
3581:
3580:phenobarbital
3577:
3574:
3571:
3567:
3564:
3562:
3559:
3556:
3552:
3548:
3545:
3543:
3540:
3538:
3533:
3532:
3529:
3526:
3524:
3521:
3519:
3516:
3513:
3509:
3506:
3504:
3501:
3499:
3496:
3494:
3491:
3489:
3486:
3484:
3483:Quisqualamine
3481:
3479:
3476:
3474:
3471:
3469:
3466:
3464:
3461:
3459:
3456:
3454:
3451:
3449:
3446:
3443:
3439:
3436:
3434:
3431:
3429:
3426:
3424:
3421:
3419:
3418:Methylglyoxal
3416:
3413:
3409:
3406:
3404:
3401:
3399:
3396:
3394:
3391:
3389:
3386:
3384:
3381:
3379:
3376:
3374:
3371:
3369:
3368:Ibotenic acid
3366:
3364:
3361:
3359:
3356:
3354:
3351:
3349:
3346:
3344:
3341:
3339:
3336:
3334:
3331:
3329:
3326:
3324:
3321:
3318:
3317:phenobarbital
3314:
3311:
3309:
3306:
3304:
3301:
3298:
3297:
3295:
3290:
3281:
3278:
3276:
3272:
3268:
3265:
3255:
3250:
3248:
3243:
3241:
3236:
3235:
3232:
3224:
3220:
3216:
3212:
3208:
3204:
3200:
3196:
3191:
3189:
3186:
3183:
3180:
3178:
3175:
3172:
3168:
3165:
3164:
3151:
3147:
3142:
3137:
3133:
3129:
3125:
3118:
3110:
3106:
3101:
3096:
3092:
3088:
3084:
3077:
3069:
3065:
3061:
3057:
3053:
3049:
3045:
3041:
3037:
3030:
3017:
3011:
3007:
3003:
2999:
2995:
2988:
2980:
2976:
2972:
2968:
2964:
2960:
2953:
2945:
2941:
2937:
2933:
2929:
2925:
2918:
2910:
2906:
2902:
2898:
2894:
2890:
2883:
2875:
2871:
2867:
2863:
2862:Aust. J. Chem
2859:
2852:
2844:
2840:
2836:
2832:
2828:
2824:
2820:
2816:
2809:
2801:
2797:
2793:
2789:
2785:
2781:
2777:
2773:
2765:
2757:
2753:
2748:
2743:
2739:
2735:
2732:: 1407–1411.
2731:
2727:
2723:
2716:
2709:
2704:
2696:
2692:
2688:
2684:
2680:
2676:
2672:
2668:
2661:
2653:
2649:
2644:
2639:
2635:
2631:
2627:
2623:
2619:
2612:
2604:
2600:
2595:
2590:
2586:
2582:
2578:
2574:
2570:
2563:
2555:
2551:
2547:
2543:
2539:
2535:
2532:(1): 98–108.
2531:
2527:
2520:
2512:
2508:
2504:
2500:
2496:
2492:
2488:
2484:
2477:
2469:
2465:
2461:
2457:
2450:
2442:
2438:
2433:
2428:
2424:
2420:
2416:
2412:
2408:
2406:
2397:
2395:
2393:
2391:
2382:
2378:
2373:
2368:
2364:
2360:
2356:
2352:
2348:
2344:
2340:
2333:
2325:
2321:
2316:
2311:
2306:
2301:
2297:
2293:
2289:
2285:
2281:
2274:
2266:
2262:
2257:
2252:
2247:
2242:
2238:
2234:
2230:
2226:
2222:
2215:
2207:
2203:
2199:
2195:
2191:
2187:
2183:
2179:
2175:
2171:
2164:
2156:
2152:
2147:
2142:
2137:
2132:
2128:
2124:
2120:
2113:
2111:
2102:
2098:
2094:
2090:
2086:
2082:
2078:
2074:
2067:
2059:
2055:
2051:
2047:
2043:
2039:
2035:
2031:
2023:
2015:
2011:
2007:
2003:
1998:
1993:
1989:
1985:
1981:
1974:
1972:
1963:
1959:
1955:
1951:
1947:
1943:
1939:
1935:
1928:
1926:
1917:
1913:
1909:
1903:
1899:
1895:
1891:
1884:
1876:
1872:
1868:
1864:
1860:
1856:
1849:
1841:
1837:
1833:
1829:
1825:
1821:
1817:
1813:
1805:
1803:
1794:
1790:
1786:
1782:
1777:
1772:
1768:
1764:
1760:
1753:
1751:
1742:
1738:
1734:
1730:
1726:
1722:
1714:
1706:
1702:
1698:
1694:
1689:
1684:
1680:
1676:
1672:
1665:
1657:
1653:
1648:
1643:
1639:
1635:
1631:
1627:
1623:
1616:
1608:
1604:
1600:
1596:
1592:
1588:
1584:
1580:
1573:
1571:
1562:
1558:
1554:
1550:
1545:
1540:
1536:
1532:
1528:
1521:
1513:
1509:
1505:
1501:
1494:
1490:
1480:
1477:
1475:
1472:
1470:
1467:
1465:
1462:
1461:
1452:
1448:
1444:
1440:
1436:
1432:
1429:
1425:
1422:
1418:
1415:
1412:
1408:
1407:
1402:
1398:
1397:
1392:
1388:
1384:
1380:
1377:
1373:
1372:
1367:
1364:
1360:
1359:
1354:
1350:
1346:
1342:
1341:
1340:
1338:
1334:
1330:
1326:
1322:
1318:
1314:
1310:
1303:
1299:
1295:
1290:
1276:
1272:
1269:
1266:
1263:
1256:
1253:
1252:
1248:
1244:
1242:
1236:
1233:
1230:
1227:
1225:
1222:
1221:
1217:
1213:
1210:
1208:
1202:
1199:
1197:
1191:
1189:
1186:
1185:
1181:
1177:
1174:
1172:
1169:
1166:
1164:
1158:
1156:
1153:
1152:
1148:
1144:
1141:
1139:
1133:
1130:
1128:
1122:
1120:
1117:
1116:
1112:
1108:
1105:
1103:
1097:
1094:
1092:
1086:
1084:
1081:
1080:
1076:
1072:
1069:
1066:
1063:
1061:
1055:
1053:
1050:
1049:
1045:
1041:
1038:
1035:
1033:
1027:
1024:
1022:
1019:
1018:
1014:
1010:
1007:
1004:
1001:
998:
995:
994:
974:
971:
959:
955:
953:
949:
945:
941:
937:
933:
929:
925:
921:
911:
909:
905:
903:
899:
895:
891:
888:
884:
883:
878:
874:
870:
866:
862:
858:
854:
850:
846:
842:
838:
834:
830:
826:
825:
821:
811:
809:
805:
801:
797:
793:
789:
785:
780:
778:
775:ranging from
774:
770:
766:
762:
758:
753:
751:
747:
743:
740:
736:
735:
730:
725:
723:
719:
715:
711:
707:
703:
698:
696:
692:
688:
684:
680:
676:
672:
669:and enhanced
668:
664:
660:
656:
652:
647:
645:
644:noradrenaline
641:
637:
633:
629:
625:
621:
617:
613:
609:
605:
602:
598:
594:
590:
580:
578:
574:
570:
566:
562:
558:
554:
550:
546:
543:
539:
535:
523:
516:
511:
494:
488:
484:
482:
479:
478:
462:
459:
455:
454:
449:
440:
439:
436:
429:
415:
405:
404:
401:
394:
386:
382:
381:DTXSID2021070
378:
377:
375:
365:
361:
360:
353:
349:
348:
346:
344:
341:
340:
333:
329:
328:
326:
320:
316:
315:
311:
307:
305:
302:
301:
294:
290:
289:
287:
285:
282:
281:
274:
270:
269:
267:
264:
260:
259:
252:
251:
249:
247:
242:
241:
237:
233:
230:
228:
226:ECHA InfoCard
223:
222:
215:
211:
210:
208:
206:
203:
202:
195:
191:
190:
188:
186:
183:
182:
175:
171:
170:
168:
166:
163:
162:
158:
155:
151:
150:
143:
139:
138:
136:
132:
127:
126:
119:
115:
114:
112:
109:
105:
104:
99:
91:
87:
84:
81:
80:
75:
70:-Pyridoindole
69:
63:
59:
54:
50:
45:
41:
36:
30:
19:
6611:
6595:Latrepirdine
6508:rescinnamine
6492:corynanthine
6446:Metralindole
6413:
6367:β-carbolines
6360:
6345:lysergamides
6336:Cyclic 3-OHM
6308:Zolmitriptan
6288:Frovatriptan
6247:
6208:
6204:
6195:
6191:
6185:-methyl-αMT)
6182:
6178:
6162:7-Methyl-αET
6157:7-Chloro-αMT
6152:6-Fluoro-αMT
6147:5-Methyl-αET
6122:5-Fluoro-αMT
6117:5-Fluoro-αET
6112:5-Ethoxy-αMT
6107:5-Chloro-αMT
6059:Piromelatine
6051:
6043:
6035:
6027:
5965:
5897:
5896:Psilacetin (
5853:
5788:Idalopirdine
5678:-tryptophan)
5634:7-Methyl-DMT
5629:6-Fluoro-DMT
5614:5,6-MDO-MiPT
5604:5,6-MDO-DiPT
5599:5,6-MeO-MiPT
5579:5-Methyl-DMT
5559:5-MeO-NBpBrT
5486:
5482:
5456:5-Fluoro-MET
5451:5-Fluoro-EPT
5446:5-Fluoro-DMT
5441:5-Fluoro-DET
5431:5-Ethoxy-DMT
5426:5-Chloro-DMT
5406:4,5-MDO-DiPT
5223:
5219:
5137:
5126:
5119:
5096:
5027:Antagonists:
5026:
4976:
4841:
4817:Metabotropic
4788:Pregnanolone
4782:picrotoxinin
4755:
4741:
4668:
4638:(S)-4-ACPBPA
4633:(S)-2-MeGABA
4630:Antagonists:
4629:
4604:
4593:Thiomuscimol
4565:
4516:
4380:picrotoxinin
4343:enzalutamide
4339:bicalutamide
4261:Golexanolone
4157:Cloflubicyne
4007:
3933:Antagonists:
3932:
3845:methaqualone
3820:glutethimide
3796:Petrichloral
3757:β-carbolines
3576:Barbiturates
3534:
3518:Thiomuscimol
3323:Beta-Alanine
3313:Barbiturates
3303:(+)-Catechin
3299:
3198:
3194:
3131:
3127:
3117:
3090:
3086:
3076:
3043:
3039:
3029:
3019:, retrieved
2997:
2987:
2962:
2958:
2952:
2927:
2923:
2917:
2892:
2888:
2882:
2865:
2861:
2857:
2851:
2818:
2814:
2808:
2775:
2771:
2764:
2729:
2725:
2715:
2707:
2703:
2670:
2666:
2660:
2628:(6): e1289.
2625:
2621:
2611:
2576:
2572:
2562:
2529:
2525:
2519:
2486:
2482:
2476:
2459:
2455:
2449:
2417:(1): 19–26.
2414:
2410:
2404:
2346:
2342:
2332:
2290:(1): 10230.
2287:
2283:
2273:
2228:
2224:
2214:
2173:
2169:
2163:
2126:
2122:
2076:
2072:
2066:
2033:
2029:
2022:
1987:
1983:
1940:(1): 35–53.
1937:
1933:
1889:
1883:
1858:
1854:
1848:
1815:
1811:
1766:
1762:
1724:
1720:
1713:
1678:
1674:
1664:
1629:
1625:
1615:
1582:
1578:
1534:
1530:
1520:
1503:
1499:
1493:
1474:Oxopropaline
1410:
1404:
1400:
1394:
1369:
1356:
1307:β-Carboline
1306:
1294:Paruroctonus
969:
917:
901:
880:
876:
848:
837:hallucinogen
823:
817:
802:, etc.) and
781:
754:
739:biosynthetic
734:Streptomyces
732:
726:
699:
679:dopaminergic
657:, has shown
649:A synthetic
648:
589:substituents
586:
583:Pharmacology
579:properties.
537:
533:
532:
194:ChEMBL275224
174:CHEBI:109895
101:Identifiers
92:-β-Carboline
89:
77:Other names
67:
33:β-Carboline
29:
6764:Tryptamines
6734:Convulsants
6729:Anxiolytics
6692:naratriptan
6670:Tepirindole
6504:deserpidine
6484:rauwolscine
6432:noribogaine
6303:Sumatriptan
6298:Rizatriptan
6278:Donitriptan
6273:Almotriptan
5955:Z2876442907
5930:Solypertine
5838:Milipertine
5808:Lespedamine
5609:5,6-MDO-DMT
5589:5-MT-NB3OMe
5554:5-MeO-pyr-T
5471:5-MeO-2-TMT
5436:5-Ethyl-DMT
5416:5-Bromo-DMT
5401:4,5-MDO-DMT
5231:4,5-DHP-DMT
5190:Tryptamines
5182:Tryptamines
5100:Compound 14
4930:Lesogaberan
4769:Loreclezole
4706:Loreclezole
4643:(S)-4-ACPCA
4623:Lanthanides
4613:Alphaxolone
4555:Isoguvacine
4465:Terbequinil
4335:apalutamide
4326:Nicardipine
4286:Laudanosine
4093:carbapenems
4085:penicillins
3941:Coriamyrtin
3936:Bicuculline
3925:sevoflurane
3921:paraldehyde
3871:Stiripentol
3748:Niacinamide
3733:cholesterol
3715:Loreclezole
3610:meprobamate
3566:Avermectins
3433:Nefiracetam
3398:Kojic amine
3388:Isomuscimol
3383:Isoguvacine
3128:J. Antibiot
2835:10261/77694
2462:: 215–234.
2349:(1): 6151.
2231:(1): 5802.
2129:: 204–223.
1632:: 260–265.
1447:ultraviolet
1383:eudistomins
1313:prokaryotes
1298:fluorescing
996:β-Carboline
976:Short name
934:, with the
898:antagonizes
857:hypokinesia
845:Louis Lewin
773:pathologies
697:processes.
677:, increase
628:hippocampus
565:derivatives
561:antioxidant
553:substituent
534:β-Carboline
451:Properties
232:100.005.418
6744:Entheogens
6723:Categories
6684:avitriptan
6675:Tetrindole
6652:5-MeO-DiBF
6634:Sertindole
6614:)-69 (3IQ)
6605:Pirlindole
6580:EMD-386088
6496:ajmalicine
6488:spegatrine
6466:PNU-181731
6407:tryptoline
6355:Flucindole
6331:Ciclindole
6326:Bay R 1531
6283:Eletriptan
6142:5-MeO-MPMI
6132:5-MeO-αET
6127:5-iPrO-αMT
5950:Yuremamine
5945:Tryptophan
5940:Tryptamine
5886:Oxypertine
5798:Indorenate
5698:CP-132,484
5544:5-MeO-MiPT
5534:5-MeO-MALT
5524:5-MeO-EiPT
5509:5-MeO-DiPT
5494:5-MeO-DALT
5391:4-MeO-MiPT
5381:4-MeO-DiPT
5376:4-HO-pyr-T
5341:4-HO-McPeT
5276:4-AcO-MiPT
5261:4-AcO-MALT
5246:4-AcO-DiPT
5236:4-AcO-DALT
4955:SKF-97,541
4865:Arbaclofen
4774:Picrotoxin
4764:Bilobalide
4440:Suritozole
4430:Sarmazenil
4415:Ro 19-4603
4410:Ro 15-4513
4405:Radequinil
4372:Picrotoxin
4351:nilutamide
4321:Naltrexone
4256:Furosemide
4236:Flumazenil
4230:oroxylin A
4222:Flavonoids
4202:Etbicyphat
4132:Bilobalide
4099:Basmisanil
3986:Sinomenine
3981:Securinine
3976:Pitrazepin
3961:Hydrastine
3913:chloroform
3886:Topiramate
3826:Propanidid
3690:Imidazoles
3685:Flupirtine
3680:Fluoxetine
3674:hispidulin
3666:Flavonoids
3621:Chloralose
3606:Carbamates
3570:ivermectin
3508:Terpenoids
3453:PF-6372865
3308:Bamaluzole
3275:Ionotropic
3267:modulators
3184:in general
3177:TiHKAL #44
3021:2021-11-16
1585:: 113321.
1485:References
1479:Tryptamine
1451:blacklight
1426:The fully
1399:) such as
1396:Ascidiacea
1376:Syrian Rue
1337:precursors
1333:tryptamine
1325:tryptophan
1302:blacklight
991:Structure
948:saturation
936:ethylamine
932:tryptamine
924:a pyridine
769:microbiome
729:antibiotic
718:flurazepam
714:anxiogenic
710:convulsive
693:and other
663:expression
651:derivative
632:depression
481:Molar mass
352:94HMA1I78O
263:IUPHAR/BPS
205:ChemSpider
129:3D model (
108:CAS Number
82:Norharmane
6703:VU6067416
6688:LY-334370
6660:dimemebfe
6629:RU-24,969
6624:Ro60-0213
6619:Ro60-0175
6600:LY-367265
6570:BRL-54443
6565:AL-38022A
6555:AAZ-A-154
6500:reserpine
6480:yohimbine
6476:Yohimbans
6461:PNU-22394
6456:PHA-57378
6428:ibogamine
6416:alkaloids
6383:harmaline
6371:6-MeO-THH
6363:alkaloids
6341:Ergolines
6241:CP-135807
6236:BW-723C86
6137:5-MeO-αMT
6021:Melatonin
6016:Luzindole
5569:5-MeS-DMT
5549:5-MeO-NMT
5539:5-MeO-MET
5529:5-MeO-EPT
5519:5-MeO-DPT
5514:5-MeO-DMT
5504:5-MeO-DET
5499:5-MeO-DBT
5461:5-HO-DiPT
5396:4-PrO-DMT
5386:4-MeO-DMT
5371:4-HO-PiPT
5361:4-HO-NALT
5356:4-HO-MsBT
5346:4-HO-MiPT
5336:4-HO-McPT
5326:4-HO-MALT
5316:4-HO-DSBT
5306:4-HO-DiPT
5291:4-HO-DALT
5271:4-AcO-DPT
5266:4-AcO-MET
5256:4-AcO-NMT
5251:4-AcO-EPT
5241:4-AcO-DET
5090:SKF-97541
5085:SCH-50911
5075:Phaclofen
5060:CGP-64213
5055:CGP-55845
5050:CGP-54626
5045:CGP-52432
5040:CGP-46381
5035:CGP-35348
5005:CGP-13501
4980:ADX-71441
4965:Tolgabide
4945:Progabide
4940:Picamilon
4925:Isovaline
4842:Agonists:
4744:-3-ACPBPA
4721:SKF-97541
4671:-3-ACPBPA
4598:Tolgabide
4578:Progabide
4573:Picamilon
4517:Agonists:
4425:RO4938581
4420:RO4882224
4347:flutamide
4281:L-655,708
4251:Flurothyl
4152:Cicutoxin
4137:Bupropion
4104:Bemegride
4081:β-Lactams
4071:Amiloride
3901:Volatiles
3835:etazolate
3811:Phenytoin
3769:zopiclone
3761:abecarnil
3720:Monastrol
3710:Lanthanum
3694:etomidate
3656:Fenamates
3651:Etifoxine
3646:Etazepine
3523:Tolgabide
3473:Progabide
3463:Picamilon
3448:Org 20599
3423:Monastrol
3403:L-838,417
3300:Agonists:
3060:0278-6915
1793:207408868
1607:232159513
1561:205624339
1443:fluoresce
1439:scorpions
1391:tunicates
1387:ascidians
1366:ayahuasca
1349:harmaline
1329:serotonin
1309:alkaloids
1296:scorpion
1119:Harmaline
914:Structure
879:and also
833:entheogen
687:dendritic
640:serotonin
626:) in rat
597:inhibitor
575:and anti-
549:alkaloids
310:norharman
253:205-959-0
245:EC Number
85:Norharman
6698:VER-3323
6680:Triptans
6575:CP-94253
6560:AL-34662
6471:RU-28306
6424:ibogaine
6399:pinoline
6387:harmalol
6293:L-694247
6265:Triptans
6246:IPAP (α,
6102:4-Me-αMT
6097:4-Me-αET
6087:4-HO-αMT
5920:RS134-49
5773:FGIN-143
5768:FGIN-127
5481:5-MeO-7,
5366:4-HO-NMT
5351:4-HO-MPT
5331:4-HO-MET
5321:4-HO-EPT
5311:4-HO-DPT
5301:4-HO-DET
5296:4-HO-DBT
5208:2-Me-DET
5203:2-HO-NMT
5116:See also
5080:Saclofen
5015:rac-BHFF
5010:GS-39783
5000:CGP-7930
4960:SL 75102
4935:Phenibut
4890:Gabamide
4875:Baclofen
4778:picrotin
4731:SR-95813
4726:SR-95318
4648:2-MeTACA
4560:Muscimol
4490:ZK-93426
4460:TCS-1105
4445:TB-21007
4376:picrotin
4316:Naloxone
4301:Morphine
4296:MaxiPost
4216:fipronil
4212:Fiproles
4182:(+)-DMBB
4177:Dieldrin
4076:Anisatin
3991:SR-42641
3891:Valerian
3865:baicalin
3861:Skullcap
3805:propofol
3785:zaleplon
3777:zolpidem
3670:apigenin
3590:diazepam
3547:Alcohols
3488:SL-75102
3478:Propofol
3458:Phenibut
3428:Muscimol
3412:honokiol
3378:iso-THIP
3373:iso-THAZ
3348:Gabamide
3264:receptor
3223:54410407
3215:16183262
3109:10421760
3068:20036304
2979:16378379
2843:20036304
2800:17723604
2756:22043251
2695:10309111
2652:24922073
2603:19879939
2554:40115950
2546:23076833
2511:28243440
2503:12895680
2468:15641199
2441:30713897
2381:34686660
2324:32576869
2265:30967594
2206:43038332
2155:17334612
2101:24899640
2093:21651332
2058:24226033
2050:17913302
2006:22380576
1962:16729205
1954:20360614
1916:28551023
1875:19442174
1840:21595062
1832:20686906
1785:19632287
1741:10940539
1705:27837814
1697:21126318
1656:25250831
1599:33684825
1553:22372749
1512:21485291
1458:See also
1428:aromatic
1389:(marine
1300:under a
1155:Harmalol
1021:Pinoline
890:dopamine
887:striatal
885:lead to
861:drooling
849:B. caapi
804:proteins
765:virulent
752:family.
683:synaptic
118:244-63-3
6682:(e.g.,
6646:(e.g.,
6478:(e.g.,
6395:harmine
6391:harmane
6375:9-Me-BC
6369:(e.g.,
6361:Harmala
6347:(e.g.,
6231:BNC-210
6082:2,α-DMT
6064:TIK-301
5935:ST-1936
5654:AGH-192
5649:AGH-107
5624:5,7-DHT
5619:5,6-DHT
4985:BHF-177
4970:Tolibut
4880:BL-1020
4793:ROD-188
4658:4-ACPAM
4653:3-APMPA
4520:BL-1020
4480:U-93631
4475:Thujone
4400:PWZ-029
4374:(i.e.,
4333:(e.g.,
4311:MRK-016
4291:Lindane
4243:(e.g.,
4224:(e.g.,
4214:(e.g.,
4083:(e.g.,
4061:β-EMGBL
3971:PHP-501
3907:(e.g.,
3878:(e.g.,
3856:ROD-188
3843:(e.g.,
3833:(e.g.,
3818:(e.g.,
3803:(e.g.,
3801:Phenols
3783:(e.g.,
3775:(e.g.,
3767:(e.g.,
3759:(e.g.,
3755:(e.g.,
3727:(e.g.,
3692:(e.g.,
3668:(e.g.,
3658:(e.g.,
3638:(e.g.,
3608:(e.g.,
3596:Bromide
3588:(e.g.,
3578:(e.g.,
3568:(e.g.,
3549:(e.g.,
3542:α-EMTBL
3512:borneol
3510:(e.g.,
3493:Taurine
3440:(e.g.,
3410:(e.g.,
3408:Lignans
3328:BL-1020
3315:(e.g.,
3150:8270488
2944:9677285
2909:8021654
2780:Bibcode
2747:3201054
2687:9372198
2643:4611726
2594:2828149
2432:6353393
2372:8536679
2351:Bibcode
2315:7311520
2292:Bibcode
2256:6456619
2233:Bibcode
2198:6294835
2178:Bibcode
2170:Science
2146:5901106
2014:8832937
1647:4406242
1435:cuticle
1345:harmine
1321:animals
1261:/ COOH
1083:Harmine
1052:Harmane
873:In-vivo
841:harmine
800:kinases
792:enzymes
599:of the
593:harmine
515:what is
513: (
475:
319:PubChem
159:128414
6708:YM-348
6664:mebfap
6545:5-MIAL
6540:5-HIAL
6181:-DMT (
5881:O-4310
5843:MS-245
5778:FT-104
5743:E-6837
5738:E-6801
5659:AH-494
5020:KK-92A
4850:3-APPA
4618:ATHDOC
4172:DHEA-S
4011:1,3M1B
3743:Niacin
3704:kavain
3221:
3213:
3182:TiHKAL
3173:(MeSH)
3148:
3107:
3066:
3058:
3012:
2977:
2942:
2907:
2841:
2798:
2754:
2744:
2693:
2685:
2650:
2640:
2601:
2591:
2552:
2544:
2509:
2501:
2466:
2439:
2429:
2379:
2369:
2322:
2312:
2263:
2253:
2204:
2196:
2153:
2143:
2099:
2091:
2056:
2048:
2012:
2004:
1960:
1952:
1914:
1904:
1873:
1838:
1830:
1791:
1783:
1739:
1703:
1695:
1654:
1644:
1605:
1597:
1559:
1551:
1510:
1351:, and
1317:plants
1257:H / CH
944:carbon
940:indole
928:indole
831:as an
829:Amazon
784:cancer
601:DYRK1A
577:cancer
545:indole
542:pyrido
510:verify
507:
435:SMILES
293:C20157
185:ChEMBL
56:Names
6648:3-APB
6639:SN-22
6451:NDTDI
6414:Iboga
6250:-DPT)
5915:Pyr-T
5664:ALiPT
4910:GHBAL
4895:GABOB
4798:THDOC
4742:trans
4736:TPMPA
4711:P4MPA
4663:4-GBA
4545:GABOB
4271:IPTBO
4121:IPTBO
4056:β-CCP
4051:β-CCM
4046:β-CCE
4041:β-CCB
4001:Tutin
3905:gases
3737:THDOC
3353:GABOB
3219:S2CID
2691:S2CID
2550:S2CID
2507:S2CID
2202:S2CID
2097:S2CID
2054:S2CID
2010:S2CID
1958:S2CID
1912:S2CID
1836:S2CID
1789:S2CID
1701:S2CID
1603:S2CID
1557:S2CID
820:liana
808:ABCG2
755:Also
742:genes
722:doses
400:InChI
332:64961
214:58486
165:ChEBI
131:JSmol
6656:BPAP
6585:I-32
6365:and
6343:and
6255:MPMI
6211:-TMS
6198:-TMT
5891:PiPT
5876:NTBT
5848:MSBT
5828:MiPT
5783:HIOC
5753:EMDT
5748:EiPT
5723:DiPT
5703:DALT
5489:-TMT
5421:5-CT
5411:5-BT
5226:-TMT
5128:GABA
5065:DAVA
4995:BSPP
4990:BHFF
4885:GABA
4827:GABA
4803:Zinc
4749:ZAPA
4696:I4AA
4681:DAVA
4588:TAMP
4583:TACA
4540:GABA
4530:CAMP
4525:CACA
4501:GABA
4485:Zinc
4470:TETS
4455:TBPS
4450:TBOB
4382:and
4197:EBOB
4192:DMPC
4187:DMCM
4167:DHEA
4142:CHEB
4127:BIDN
4117:TBPO
4113:TBPS
4031:α3IA
4016:3M2B
3700:Kava
3555:2M2B
3537:here
3528:ZAPA
3503:TAMP
3498:TACA
3343:GABA
3333:DAVA
3285:GABA
3262:GABA
3211:PMID
3146:PMID
3105:PMID
3064:PMID
3056:ISSN
3010:ISBN
2975:PMID
2940:PMID
2905:PMID
2839:PMID
2796:PMID
2752:PMID
2683:PMID
2648:PMID
2599:PMID
2542:PMID
2499:PMID
2464:PMID
2437:PMID
2377:PMID
2320:PMID
2261:PMID
2194:PMID
2151:PMID
2089:PMID
2046:PMID
2002:PMID
1950:PMID
1902:ISBN
1871:PMID
1828:PMID
1781:PMID
1737:PMID
1693:PMID
1652:PMID
1595:PMID
1549:PMID
1508:PMID
1331:and
1319:and
894:MPTP
796:GPX4
750:LuxR
685:and
642:and
624:BDNF
343:UNII
304:MeSH
284:KEGG
273:8222
6590:IAL
6349:LSD
6221:αMT
5866:NMT
5861:NET
5833:MPT
5813:MET
5758:EPT
5733:DPT
5728:DMT
5718:DET
5708:DBT
4920:GVL
4915:GHV
4905:GHB
4900:GBL
4716:P4S
4669:cis
4435:SCS
3779:),
3771:),
3763:),
3468:P4S
3203:doi
3136:doi
3095:doi
3048:doi
3002:doi
2967:doi
2932:doi
2897:doi
2870:doi
2860:".
2831:hdl
2823:doi
2788:doi
2776:575
2742:PMC
2734:doi
2675:doi
2671:770
2638:PMC
2630:doi
2589:PMC
2581:doi
2577:127
2534:doi
2491:doi
2427:PMC
2419:doi
2367:PMC
2359:doi
2310:PMC
2300:doi
2251:PMC
2241:doi
2186:doi
2174:219
2141:PMC
2131:doi
2081:doi
2038:doi
1992:doi
1988:121
1942:doi
1894:doi
1863:doi
1820:doi
1816:117
1771:doi
1729:doi
1683:doi
1679:278
1642:PMC
1634:doi
1630:138
1587:doi
1583:216
1539:doi
1535:121
1437:of
1409:or
1335:as
1204:OCH
1135:OCH
1099:OCH
1029:OCH
988:R9
985:R7
982:R6
979:R1
788:DNA
746:ATP
704:on
665:of
369:EPA
322:CID
6725::
6690:,
6686:,
6662:,
6658:,
6654:,
6650:,
6506:,
6502:,
6498:,
6494:,
6490:,
6486:,
6482:,
6438:,
6434:,
6430:,
6426:,
6422:,
6405:,
6401:,
6397:,
6393:,
6389:,
6385:,
6381:,
6377:,
6373:,
6203:α,
6190:α,
6177:α,
5218:2,
4780:,
4505:-ρ
4378:,
4349:,
4345:,
4341:,
4337:,
4228:,
4119:,
4115:,
4091:,
4087:,
3923:,
3919:,
3915:,
3911:,
3787:))
3735:,
3731:,
3672:,
3553:,
3217:.
3209:.
3199:16
3197:.
3144:.
3132:46
3130:.
3126:.
3103:.
3089:.
3085:.
3062:.
3054:.
3044:48
3042:.
3038:.
3008:,
2996:,
2973:.
2963:68
2961:.
2938:.
2928:61
2926:.
2903:.
2893:57
2891:.
2866:42
2864:.
2837:.
2829:.
2819:48
2817:.
2794:.
2786:.
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2646:.
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2530:27
2528:.
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2497:.
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2044:.
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2032:.
2008:.
2000:.
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1970:^
1956:.
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1938:62
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1327:,
1315:,
1292:A
1270:H
1267:H
1264:H
1238:CH
1193:CH
1171:OH
1160:CH
1124:CH
1088:CH
1057:CH
859:,
798:,
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