287:
198:
634:
33:
24:
430:
669:(6) is proposed to be catalyzed by TiDPAS, although it is unclear if the reduction is actually enzymatic due to a lack of a reaction trial with only NADPH. After formation of 6, the substrate is then 10-hydroxylated by ibogamine 10-hydroxylase (I10H), a
1210:
Mair CE, de
Miranda Silva C, Grienke U, Kratz JM, Carreño F, Zimmermann ES, de Araújo BV, Dalla Costa T, Rollinger JM (July 2016). "Pharmacokinetics of hERG Channel Blocking Voacangine in Wistar Rats Applying a Validated LC-ESI-MS/MS Method".
664:
on dehydrosecodine (4) to form coronaridine iminium (5). A proposed mechanism for dehydrosecodine formation from 3 involves iminium-formation/deacetylation, enamine-formation, and subsequent isomerization. Reduction of 5 to
1256:
Terada Y, Horie S, Takayama H, Uchida K, Tominaga M, Watanabe T (February 2014). "Activation and inhibition of thermosensitive TRP channels by voacangine, an alkaloid present in
Voacanga africana, an African tree".
935:
1294:
Lo MW, Matsumoto K, Iwai M, Tashima K, Kitajima M, Horie S, Takayama H (January 2011). "Inhibitory effect of Iboga-type indole alkaloids on capsaicin-induced contraction in isolated mouse rectum".
115:
1058:
Andrade MT, Lima JA, Pinto AC, Rezende CM, Carvalho MP, Epifanio RA (June 2005). "Indole alkaloids from
Tabernaemontana australis (Muell. Arg) Miers that inhibit acetylcholinesterase enzyme".
656:
Up to this point, the biosynthetic path towards the (-)-ibogamine alkaloids and (+)-ibogamine alkaloids is identical. Stereochemical divergence occurs during the cyclization step, whereby
950:
649:
precondylocarpine acetate synthases (TiPAS1/2/3), a flavin-dependent oxidase. Next, 2 is reduced to the enamine (3), dihydroprecondylocarpine acetate, by one of two NADPH-dependent
443:
1150:
310:
InChI=1S/C22H28N2O3/c1-4-14-9-13-11-22(21(25)27-3)19-16(7-8-24(12-13)20(14)22)17-10-15(26-2)5-6-18(17)23-19/h5-6,10,13-14,20,23H,4,7-9,11-12H2,1-3H3/t13-,14+,20+,22-/m1/s1
1353:
Farrow, Scott C.; Kamileen, Mohamed O.; Caputi, Lorenzo; Bussey, Kate; Munday, Julia E. A.; McAtee, Rory C.; Stephenson, Corey R. J.; O'Connor, Sarah E. (31 July 2019).
326:
1407:"Solution of the multistep pathway for assembly of corynanthean, strychnos, iboga, and aspidosperma monoterpenoid indole alkaloids from 19E-geissoschizine"
1466:"Cytochrome P450 and O-methyltransferase catalyze the final steps in the biosynthesis of the anti-addictive alkaloid ibogaine from Tabernanthe iboga"
1095:
Kim Y, Sugihara Y, Kim TY, Cho SM, Kim JY, Lee JY, Yoo JS, Song D, Han G, Rezeli M, Welinder C, Appelqvist R, Marko-Varga G, Kwon HJ (March 2020).
622:-derived biosynthetic intermediate for a wide number of plant natural products. The biosynthesis of stemmadenine acetate has been characterized in
1003:"Two fast screening methods (GC-MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures"
32:
1405:
Qu, Yang; Easson, Micahel E. A. M.; Simionescu, Razvan; Hajicek, Josef; Thamm, Antje M. K.; Salim, Vonny; De Luca, Vicenzo (March 6, 2018).
720:
See supplementary figure 15 of the Farrow et al. paper, citation 18. After initial incubation with TiCorS, no trial was run with just NADPH.
962:
1060:
513:. It has been demonstrated in animals to have similar anti-addictive properties to ibogaine itself. It also potentiates the effects of
1525:
301:
1464:
Farrow, Scott C.; Kamileen, Mohamed O.; Meades, Jessica; Ameyaw, Belinda; Xiao, Youli; O'Connor, Sarah E. (September 7, 2018).
1148:
Kim Y, Jung HJ, Kwon HJ (January 2012). "A natural small molecule voacangine inhibits angiogenesis both in vitro and in vivo".
1002:
450:
1535:
594:
244:
1097:"Identification and Validation of VEGFR2 Kinase as a Target of Voacangine by a Systematic Combination of DARTS and MSI"
23:
1550:
1259:
489:
265:
645:
involves five enzymes. First, stemmadenine acetate (1) is converted to precondylocarpine acetate (2) by one of three
1001:
VIEIRA I, MEDEIROS W, MONNERAT C, SOUZA J, MATHIAS L, BRAZ-FILHO R, PINTO A, SOUSA P, REZENDE C, EPIFANIO R (2008).
495:
1296:
1520:
1339:
483:
205:
660:
coronaridine synthase (TiCorS), a catharanthine synthase (CS) homologue, catalyzes a stereoselective formal
193:
1545:
1540:
686:
538:
inhibitory activity. Docking simulation reveals that it has inhibitory effect on VEGF2 kinase and reduces
211:
155:
1530:
674:
501:
406:
55:
45:
633:
930:
1418:
661:
535:
282:
740:
607:
81:
1321:
1238:
912:
861:
814:
1497:
1446:
1384:
1313:
1276:
1230:
1167:
1130:
1077:
1033:
1025:
904:
853:
806:
767:
598:
585:
477:
471:
175:
1487:
1477:
1436:
1426:
1374:
1366:
1305:
1268:
1222:
1159:
1120:
1110:
1069:
1017:
896:
845:
798:
349:
253:
670:
60:
Methyl 17-ethyl-7-methoxy-3,13-diazapentacyclo nonadeca-2(10),4,6,8-tetraene-1-carboxylate
286:
197:
135:
91:
1422:
597:. Suspected RNA transcripts involved in (-)-voacangine biosynthesis were identified via
1492:
1465:
1441:
1406:
1379:
1354:
1125:
1096:
421:
1514:
1213:
673:, and subsequently 10-O-methylated by noribogaine-10-O-methyltransferase (N10OMT), a
619:
602:
396:
186:
1325:
1242:
1041:
1021:
916:
865:
517:. Under UV-A and UV-B light its crystals fluoresce blue-green, and it is soluble in
1101:
984:
691:
666:
615:
542:. Like ibogaine, its a potent HERG blocker in vitro. It also acts as antagonist to
539:
514:
818:
233:
900:
701:
1163:
637:
Schematic of the late-stage biosynthesis of (-)-voacangine in
Tabernanthe iboga
1309:
1073:
832:
Liu, G.; Liu, X.; Feng, X. Z. (1988). "Ervayunine: A New Indole
Alkaloid from
383:
166:
1482:
1029:
614:
Ibogamine-type alkaloids are biosynthesized from the late stage intermediate
1431:
590:
1501:
1450:
1388:
1317:
1280:
1234:
1171:
1134:
1081:
1037:
908:
810:
1226:
857:
849:
802:
785:
Fatima, T.; Ijaz, S.; Crank, G.; Wasti, S. (1987). "Indole
Alkaloids from
771:
1370:
1115:
696:
510:
506:
466:
754:
Patel, M. B.; Miet, C.; Poisson, J. (1967). "Alkaloids of some
African
518:
220:
1272:
605:, a (+)-ibogamine-type alkaloid from the taxonomically related plant
146:
933:, "Derivatives of the Ibogaine Alkaloids", issued 1957-11-19
420:
Except where otherwise noted, data are given for materials in their
1185:
632:
551:
547:
543:
126:
114:
104:
509:
which commonly serves as a precursor for the semi-synthesis of
1355:"Biosynthesis of an Anti-Addiction Agent from the Iboga Plant"
562:
The absolute bioavailability of voacangine is around 11–13%.
465:(12-methoxyibogamine-18-carboxylic acid methyl ester) is an
270:
570:
High doses of voacangine produce convulsions and asphyxia.
401:
136 to 137 °C (277 to 279 °F; 409 to 410 K)
641:
Conversion of stemmadenine acetate to (-)-voacangine in
653:
dihydroprecondylocarpine acetate synthase (TiDPAS1/2).
438:
1194:
Academic
Journal of Second Military Medical University
959:
Academic
Journal of Second Military Medical University
49:
12-Methoxyibogamine-18-carboxylic acid, methyl ester
1151:
583:The late-stage biosynthesis of (-)-voacangine in
741:"Compound Report Card CHEMBL182120 - Voacangine"
232:
1411:Proceedings of the National Academy of Sciences
1400:
1398:
1340:"Erowid Voacanga africana Vault : Info #1"
1205:
1203:
601:to previously described enzymes comprising the
90:
677:dependent enzyme, to form (-)-voacangine (7).
8:
879:Jenks, C. W. (2002). "Extraction Studies of
469:found predominantly in the root bark of the
1010:Annals of the Brazilian Academy of Sciences
285:
196:
174:
15:
1491:
1481:
1440:
1430:
1378:
1124:
1114:
475:tree, as well as in other plants such as
334:O=C(OC)43c2c1ccc(OC)cc1c2CCN53(C(C4)C5)CC
252:
69:Methyl 12-methoxyibogamine-18-carboxylate
1359:Journal of the American Chemical Society
732:
713:
331:
306:
281:
210:
187:
313:Key: MMAYTCMMKJYIAM-PHKAQXKASA-N
154:
134:
7:
1061:Bioorganic & Medicinal Chemistry
595:homology-guided transcriptome mining
1186:"Antiaddictive Indole Alkaloids in
951:"Antiaddictive Indole Alkaloids in
223:
760:Annales Pharmaceutiques Françaises
14:
428:
367:
361:
31:
22:
1022:10.1590/s0001-37652008000300003
626:but remains uncharacterized in
424:(at 25 °C , 100 kPa).
949:Tsing Hua (January 28, 2006).
603:(+)-catharanthine biosynthesis
373:
355:
1:
1297:Journal of Natural Medicines
1260:Journal of Natural Products
787:Trachelospermum jasminoides
591:(-)-ibogamine-type alkaloid
490:Trachelospermum jasminoides
1567:
1164:10.1016/j.bbrc.2011.11.109
901:10.1080/1057563029001/4881
593:, has been elucidated via
496:Tabernaemontana divaricata
1310:10.1007/s11418-010-0478-6
1074:10.1016/j.bmc.2005.03.045
550:receptor, but agonist of
418:
342:
322:
297:
74:
66:
54:
44:
39:
30:
21:
1526:Alkaloids found in Iboga
1483:10.1074/jbc.RA118.004060
484:Tabernaemontana africana
1432:10.1073/pnas.1719979115
889:Natural Product Letters
1190:and their Bioactivity"
955:and their Bioactivity"
687:18-Methoxycoronaridine
638:
1227:10.1055/s-0042-107800
1188:Ervatamia yunnanensis
953:Ervatamia yunnanensis
931:US patent 2813873
850:10.1055/s-2006-962535
834:Ervatamia yunnanensis
803:10.1055/s-2006-962620
636:
502:Ervatamia yunnanensis
56:Systematic IUPAC name
1371:10.1021/jacs.9b05999
1116:10.3390/biom10040508
965:on February 13, 2012
662:Diels-Alder reaction
534:Voacangine exhibits
1536:Drug rehabilitation
1476:(36): 13821–13833.
1423:2018PNAS..115.3180Q
1365:(33): 12979–12983.
1196:. January 28, 2006.
608:Catharanthus roseus
391: g·mol
18:
1551:Carboxylate esters
639:
451:Infobox references
16:
1417:(12): 3180–3185.
1273:10.1021/np400885u
1221:(11–12): 1030–8.
885:Voacanga africana
881:Tabernanthe iboga
599:sequence homology
586:Tabernanthe iboga
505:. It is an iboga
478:Tabernanthe iboga
472:Voacanga africana
459:Chemical compound
457:
456:
266:CompTox Dashboard
116:Interactive image
1558:
1521:Indole alkaloids
1506:
1505:
1495:
1485:
1461:
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1444:
1434:
1402:
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1392:
1382:
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1330:
1329:
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1284:
1253:
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1246:
1207:
1198:
1197:
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1176:
1175:
1145:
1139:
1138:
1128:
1118:
1092:
1086:
1085:
1055:
1049:
1048:
1046:
1040:. Archived from
1007:
998:
992:
991:
989:
981:
975:
974:
972:
970:
961:. Archived from
946:
940:
939:
938:
934:
927:
921:
920:
876:
870:
869:
829:
823:
822:
782:
776:
775:
751:
745:
744:
737:
721:
718:
667:(-)-coronaridine
558:Pharmacokinetics
530:Pharmacodynamics
441:
435:
432:
431:
390:
375:
369:
363:
357:
350:Chemical formula
290:
289:
274:
272:
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118:
94:
35:
26:
19:
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1201:
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1044:
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987:
983:
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978:
968:
966:
948:
947:
943:
936:
929:
928:
924:
878:
877:
873:
831:
830:
826:
784:
783:
779:
756:Tabernaemontana
753:
752:
748:
739:
738:
734:
730:
725:
724:
719:
715:
710:
683:
581:
576:
568:
560:
532:
527:
460:
453:
448:
447:
446: ?)
437:
433:
429:
425:
388:
378:
372:
366:
360:
352:
338:
335:
330:
329:
318:
315:
314:
311:
305:
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293:
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226:
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121:
108:
97:
84:
70:
62:
61:
50:
12:
11:
5:
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1553:
1548:
1543:
1538:
1533:
1528:
1523:
1513:
1512:
1508:
1507:
1456:
1394:
1345:
1331:
1286:
1248:
1199:
1177:
1140:
1087:
1068:(12): 4092–5.
1050:
1047:on 2020-02-19.
1016:(3): 419–426.
993:
976:
941:
922:
871:
844:(6): 519–521.
824:
777:
766:(5): 379–384.
746:
731:
729:
726:
723:
722:
712:
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531:
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427:
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422:standard state
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283:DTXSID50965276
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28:
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13:
10:
9:
6:
4:
3:
2:
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1546:Phenol ethers
1544:
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1541:Methyl esters
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1349:
1346:
1341:
1335:
1332:
1327:
1323:
1319:
1315:
1311:
1307:
1304:(1): 157–65.
1303:
1299:
1298:
1290:
1287:
1282:
1278:
1274:
1270:
1267:(2): 285–97.
1266:
1262:
1261:
1252:
1249:
1244:
1240:
1236:
1232:
1228:
1224:
1220:
1216:
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1214:Planta Medica
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838:Planta Medica
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791:Planta Medica
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707:
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672:
671:CYP450 enzyme
668:
663:
659:
654:
652:
648:
644:
635:
631:
629:
625:
621:
620:strictosidine
617:
612:
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405:
404:
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397:Melting point
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188:ECHA InfoCard
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83:
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65:
57:
53:
47:
43:
38:
34:
29:
25:
20:
1531:HERG blocker
1473:
1469:
1459:
1414:
1410:
1362:
1358:
1348:
1334:
1301:
1295:
1289:
1264:
1258:
1251:
1218:
1212:
1193:
1187:
1180:
1158:(1): 330–4.
1155:
1149:
1143:
1106:
1102:Biomolecules
1100:
1090:
1065:
1059:
1053:
1042:the original
1013:
1009:
996:
979:
967:. Retrieved
963:the original
958:
952:
944:
925:
895:(1): 71–76.
892:
888:
884:
880:
874:
841:
837:
833:
827:
797:(1): 57–59.
794:
790:
786:
780:
763:
759:
755:
749:
735:
716:
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525:Pharmacology
515:barbiturates
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156:ChEMBL182120
136:CHEBI:141966
75:Identifiers
67:Other names
1470:J Biol Chem
702:Noribogaine
618:acetate, a
343:Properties
194:100.214.137
17:Voacangine
1515:Categories
1109:(4): 508.
728:References
463:Voacangine
384:Molar mass
254:9SY76D3YUK
212:Voacangine
167:ChemSpider
103:3D model (
82:CAS Number
46:IUPAC name
1030:0001-3765
985:"Unknown"
969:August 9,
743:. ChEMBL.
624:C. roseus
574:Chemistry
1502:30030374
1451:29511102
1389:31364847
1326:25706616
1318:21042867
1281:24484240
1243:24504763
1235:27257769
1172:22155252
1135:32230857
1082:15911323
1038:18797794
917:23390825
909:11942686
866:84629414
811:17268963
697:Ibogaine
681:See also
658:T. iboga
651:T. iboga
647:T. iboga
643:T. iboga
628:T. iboga
511:ibogaine
507:alkaloid
467:alkaloid
92:510-22-5
1493:6130943
1442:5866588
1419:Bibcode
1380:6706869
1126:7226133
858:3212080
772:5611538
519:ethanol
444:what is
442: (
389:368.477
221:PubChem
176:8537141
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439:verify
436:
414:3.748
327:SMILES
147:ChEMBL
40:Names
1322:S2CID
1239:S2CID
1045:(PDF)
1006:(PDF)
988:(PDF)
913:S2CID
862:S2CID
815:S2CID
708:Notes
552:TRPA1
548:TRPV1
544:TRPM8
302:InChI
234:73255
127:ChEBI
105:JSmol
1498:PMID
1447:PMID
1385:PMID
1314:PMID
1277:PMID
1231:PMID
1168:PMID
1131:PMID
1078:PMID
1034:PMID
1026:ISSN
971:2008
905:PMID
883:and
854:PMID
807:PMID
768:PMID
589:, a
546:and
536:AChE
499:and
407:log
245:UNII
206:MeSH
1488:PMC
1478:doi
1474:293
1437:PMC
1427:doi
1415:115
1375:PMC
1367:doi
1363:141
1306:doi
1269:doi
1223:doi
1160:doi
1156:417
1121:PMC
1111:doi
1070:doi
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897:doi
887:".
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675:SAM
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