285:
188:
34:
769:
43:
483:
649:
has been described in 2011 by Fujii and Ohno. Lysergic acid monohydrate crystallizes in very thin hexagonal leaflets when recrystallized from water. Lysergic acid monohydrate, when dried (140 °C at 2 mmHg or 270 Pa) forms anhydrous lysergic acid.
996:
Inuki, S.; Iwata, A.; Oishi, S.; Fujii, N.; Ohno, H. (2011). "Enantioselective Total
Synthesis of (+)-Lysergic Acid, (+)-Lysergol, and (+)-Isolysergol by Palladium-Catalyzed Domino Cyclization of Allenes Bearing Amino and Bromoindolyl Groups".
595:
1456:
969:
Kornfeld, Edmund C.; Fornefeld, E. J.; Kline, G. Bruce; Mann, Marjorie J.; Morrison, Dwight E.; Jones, Reuben G.; Woodward, R. B. (1956). "The Total
Synthesis of Lysergic Acid".
1451:
833:
125:
828:[Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).
1168:
855:"List of Precursors and Chemicals Frequently Used in the Illicit Manufacture of Narcotic Drugs and Psychotropic Substances Under International Control"
496:
461:
1174:
334:
1272:
308:
InChI=1S/C16H16N2O2/c1-18-8-10(16(19)20)5-12-11-3-2-4-13-15(11)9(7-17-13)6-14(12)18/h2-5,7,10,14,17H,6,8H2,1H3,(H,19,20)/t10-,14-/m1/s1
1426:
318:
InChI=1/C16H16N2O2/c1-18-8-10(16(19)20)5-12-11-3-2-4-13-15(11)9(7-17-13)6-14(12)18/h2-5,7,10,14,17H,6,8H2,1H3,(H,19,20)/t10-,14-/m1/s1
1359:
930:
Martínková, L.; Kren, V.; Cvak, L.; Ovesná, M.; Prepechalová, I. (Nov 17, 2001). "Hydrolysis of lysergamide to lysergic acid by
206:
825:
1441:
1106:
491:
1032:
Wong, Garrett; Lim, Li Rong; Tan, Yong Quan; Go, Maybelle Kho; Bell, David J.; Freemont, Paul S.; Yew, Wen Shan (2022).
821:
299:
854:
503:
1257:
446:
826:"RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial"
65:
1446:
829:
242:
183:
1436:
263:
1498:
1467:
1292:
1267:
591:
414:
20:
1687:
705:. Oxidative ring closure followed by decarboxylation, reduction, cyclization, oxidation, and allylic
667:
280:
1702:
1099:
693:
715:-(+)-lysergic acid. The biosynthetic pathway has been reconsituted in transgenic baker's yeast.
596:
United
Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances
555:
724:
634:
55:
1697:
1630:
1045:
646:
251:
165:
8:
1370:
1163:
1158:
91:
1049:
284:
187:
101:
1692:
1364:
1153:
1092:
1066:
1033:
907:
882:
145:
947:
1665:
1461:
1179:
1071:
1014:
951:
912:
544:
629:
of natural lysergamides, but can also be synthesized in the laboratory by a complex
1650:
1533:
1312:
1061:
1053:
1006:
978:
943:
902:
894:
638:
587:
560:
550:
357:
33:
1553:
1548:
1543:
1513:
630:
565:
231:
1057:
679:
583:
474:
1681:
1222:
1143:
706:
404:
176:
1586:
1563:
1538:
1528:
1523:
1508:
1316:
1297:
1205:
1200:
1075:
1018:
955:
916:
787:
728:
579:
1606:
1568:
1558:
1518:
1503:
1302:
1287:
1282:
1216:
1195:
1184:
1148:
1133:
861:
569:
982:
768:
16:
Precursor for a range of ergoline alkaloids produced by the ergot fungus
1601:
1591:
1381:
1334:
1252:
1242:
1237:
1232:
1138:
806:
Brown, H. C.; et al. (1955). Braude, E. A.; Nachod, F. C. (eds.).
663:
659:
626:
391:
196:
156:
1034:"Reconstituting the complete biosynthesis of D-lysergic acid in yeast"
1010:
1637:
1611:
1477:
1227:
898:
642:
473:
Except where otherwise noted, data are given for materials in their
1596:
1277:
1247:
1210:
1115:
744:
736:
671:
535:
532:
124:
78:)-7-Methyl-4,6,6a,7,8,9-hexahydroindoloquinoline-9-carboxylic acid
1656:
1482:
1431:
1421:
1416:
1391:
1329:
218:
594:(LSD). Lysergic acid is listed as a Table I precursor under the
42:
1472:
1406:
1396:
1386:
1354:
1349:
1344:
1339:
1324:
1189:
782:
732:
1401:
1376:
602:
575:
539:
136:
114:
1084:
268:
735:
with inverted configuration at carbon atom 8 close to the
601:
Lysergic acid received its name as it was a product of the
409:
238 to 240 °C (460 to 464 °F; 511 to 513 K)
968:
1411:
929:
860:. International Narcotics Control Board. Archived from
808:
Determination of
Organic Structures by Physical Methods
995:
205:
59:6-Methyl-9,10-didehydroergoline-8β-carboxylic acid
1679:
230:
100:
1100:
1031:
772:Chemical structures of lysergic acid isomers
1663:(Morning Glory, Tlitliltzin, Badoh Negro),
1107:
1093:
283:
186:
164:
1065:
906:
250:
876:
874:
767:
1025:
658:The biosynthetic route is based on the
625:Lysergic acid is generally produced by
279:
1680:
1171:(Dihydroergonovine, Dihydroergobasine)
880:
820:
177:
1088:
871:
805:
743:. Inversion at carbon 5 close to the
531:, is a precursor for a wide range of
311:Key: ZAGRKAFMISFKIO-QMTHXVAHSA-N
144:
1464:(Methylergonovine, Methylergobasine)
989:
342:CN1C(C=C21CC3=CNC4=CC=CC2=C34)C(=O)O
1442:Lysergic Acid 2,4-Dimethylazetidide
321:Key: ZAGRKAFMISFKIO-QMTHXVAHBD
221:
13:
14:
1714:
542:fungus and found in the seeds of
481:
375:
369:
41:
32:
836:from the original on 2023-08-03
810:. New York, NY: Academic Press.
653:
477:(at 25 °C , 100 kPa).
1457:Lysergic acid cyclopentylamide
962:
923:
881:Schiff, P. L. (Oct 15, 2006).
847:
814:
799:
455:
381:
363:
1:
1452:Lysergic acid cyclobutylamide
1114:
948:10.1016/s0168-1656(00)00332-1
793:
620:
615:
7:
1447:Lysergic Acid 3-Pentylamide
776:
641:total synthesis based on a
10:
1721:
1654:(Hawaiian Baby Woodrose),
1499:9-Deacetoxyfumigaclavine C
1437:Lysergic Acid 2-Butylamide
1268:Lysergic acid methyl ester
1192:(LSA; LA-111; Lysergamide)
1058:10.1038/s41467-022-28386-6
718:
592:lysergic acid diethylamide
21:Lysergic acid diethylamide
18:
1620:
1577:
1491:
1311:
1122:
883:"Ergot and its alkaloids"
682:) giving 4-dimethylallyl-
668:dimethylallyl diphosphate
538:that are produced by the
471:
350:
330:
295:
84:
64:
54:
49:
40:
31:
1669:(Coaxihuitl, Ololiúqui)
1219:(Ergonovine, Ergobasine)
832:(published 2023-04-04).
19:Not to be confused with
830:Diário Oficial da União
773:
556:Hawaiian baby woodrose
1134:2-Bromo-LSD (BOL-148)
1038:Nature Communications
771:
688:-tryptophan which is
635:Robert Burns Woodward
582:, are widely used as
66:Systematic IUPAC name
1631:Achnatherum robustum
647:cyclization reaction
637:'s team in 1956. An
1371:Dimethyllysergamide
1213:(Dihydroergotoxine)
1164:Dihydroergocryptine
1159:Dihydroergocristine
1050:2022NatCo..13..712W
983:10.1021/ja01594a039
723:Lysergic acid is a
399: g·mol
28:
1365:Diallyllysergamide
1169:Dihydroergometrine
1154:Dihydroergocornine
887:Am. J. Pharm. Educ
774:
727:compound with two
662:of the amino acid
645:-catalyzed domino
578:of lysergic acid,
504:Infobox references
26:
1675:
1674:
1462:Methylergometrine
1180:Dihydroergotamine
1011:10.1021/jo102388e
977:(13): 3087–3114.
763:-isolysergic acid
692:-methylated with
633:, for example by
588:psychedelic drugs
545:Turbina corymbosa
529:(+)-lysergic acid
512:Chemical compound
510:
509:
464:(Drug precursors)
459:
264:CompTox Dashboard
126:Interactive image
1710:
1688:Beta-Amino acids
1651:Argyreia nervosa
1534:Epoxyagroclavine
1109:
1102:
1095:
1086:
1085:
1080:
1079:
1069:
1029:
1023:
1022:
1005:(7): 2072–2083.
993:
987:
986:
971:J. Am. Chem. Soc
966:
960:
959:
932:Rhodococcus equi
927:
921:
920:
910:
899:10.5688/aj700598
878:
869:
868:
866:
859:
851:
845:
844:
842:
841:
818:
812:
811:
803:
765:, respectively.
762:
761:
753:
752:
741:isolysergic acid
739:group is called
714:
713:
702:
701:
687:
686:
639:enantioselective
561:Ipomoea tricolor
551:Argyreia nervosa
524:
523:
518:, also known as
494:
488:
485:
484:
457:
454:
398:
383:
377:
371:
365:
358:Chemical formula
288:
287:
272:
270:
254:
234:
223:
209:
190:
179:
168:
148:
128:
104:
45:
36:
29:
25:
1720:
1719:
1713:
1712:
1711:
1709:
1708:
1707:
1703:Total synthesis
1678:
1677:
1676:
1671:
1666:Rivea corymbosa
1648:Morning glory:
1644:
1622:
1616:
1579:
1573:
1554:Fumigaclavine C
1549:Fumigaclavine B
1544:Fumigaclavine A
1514:Chanoclavine II
1487:
1315:
1307:
1175:Dihydroergosine
1126:
1118:
1113:
1083:
1030:
1026:
994:
990:
967:
963:
928:
924:
879:
872:
864:
857:
853:
852:
848:
839:
837:
819:
815:
804:
800:
796:
779:
759:
758:
750:
749:
721:
711:
710:
699:
698:
684:
683:
656:
631:total synthesis
623:
618:
584:pharmaceuticals
566:morning glories
521:
520:
513:
506:
501:
500:
499: ?)
490:
486:
482:
478:
467:
440:
433:
423:
396:
386:
380:
374:
368:
360:
346:
343:
338:
337:
326:
323:
322:
319:
313:
312:
309:
303:
302:
291:
273:
266:
257:
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199:
171:
151:
131:
118:
107:
94:
80:
79:
60:
24:
17:
12:
11:
5:
1718:
1717:
1706:
1705:
1700:
1695:
1690:
1673:
1672:
1646:
1645:
1635:
1634:(Sleepy Grass)
1626:
1624:
1618:
1617:
1615:
1614:
1609:
1604:
1599:
1594:
1589:
1583:
1581:
1575:
1574:
1572:
1571:
1566:
1561:
1556:
1551:
1546:
1541:
1536:
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1526:
1521:
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1511:
1506:
1501:
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1485:
1480:
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1404:
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1235:
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1136:
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1128:
1120:
1119:
1112:
1111:
1104:
1097:
1089:
1082:
1081:
1024:
988:
961:
922:
870:
867:on 2008-02-27.
846:
824:(2023-03-31).
813:
797:
795:
792:
791:
790:
785:
778:
775:
754:-lysergic acid
747:atom leads to
720:
717:
680:mevalonic acid
674:derived from 3
655:
652:
622:
619:
617:
614:
612:ot alkaloids.
548:(ololiuhqui),
525:-lysergic acid
511:
508:
507:
502:
480:
479:
475:standard state
472:
469:
468:
466:
465:
451:
449:
443:
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281:DTXSID60904515
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81:
69:
68:
62:
61:
58:
52:
51:
47:
46:
38:
37:
27:Lysergic acid
15:
9:
6:
4:
3:
2:
1716:
1715:
1704:
1701:
1699:
1696:
1694:
1691:
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1512:
1510:
1507:
1505:
1502:
1500:
1497:
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1494:
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1471:
1469:
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1423:
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1400:
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1361:
1358:
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1351:
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1341:
1338:
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1333:
1331:
1328:
1326:
1323:
1322:
1320:
1318:
1314:
1310:
1304:
1301:
1299:
1296:
1294:
1291:
1289:
1286:
1284:
1281:
1279:
1276:
1274:
1271:
1269:
1266:
1264:
1263:Lysergic acid
1261:
1259:
1256:
1254:
1251:
1249:
1246:
1244:
1241:
1239:
1236:
1234:
1231:
1229:
1226:
1224:
1223:Ergometrinine
1221:
1218:
1215:
1212:
1209:
1207:
1204:
1202:
1199:
1197:
1194:
1191:
1188:
1186:
1183:
1181:
1178:
1176:
1173:
1170:
1167:
1165:
1162:
1160:
1157:
1155:
1152:
1150:
1147:
1145:
1144:Bromocriptine
1142:
1140:
1137:
1135:
1132:
1131:
1129:
1125:
1124:Lysergic acid
1121:
1117:
1110:
1105:
1103:
1098:
1096:
1091:
1090:
1087:
1077:
1073:
1068:
1063:
1059:
1055:
1051:
1047:
1043:
1039:
1035:
1028:
1020:
1016:
1012:
1008:
1004:
1000:
992:
984:
980:
976:
972:
965:
957:
953:
949:
945:
941:
937:
936:J. Biotechnol
933:
926:
918:
914:
909:
904:
900:
896:
892:
888:
884:
877:
875:
863:
856:
850:
835:
831:
827:
823:
817:
809:
802:
798:
789:
786:
784:
781:
780:
770:
766:
764:
755:
746:
742:
738:
734:
730:
729:stereocenters
726:
716:
708:
707:isomerization
704:
696:
691:
681:
677:
673:
669:
665:
661:
651:
648:
644:
640:
636:
632:
628:
613:
611:
607:
605:
599:
597:
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585:
581:
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571:
567:
563:
562:
557:
553:
552:
547:
546:
541:
537:
534:
530:
526:
517:
516:Lysergic acid
505:
498:
493:
476:
470:
463:
453:
452:
450:
448:
445:
444:
437:
430:
426:
420:
416:
413:
412:
408:
406:
405:Melting point
403:
402:
395:
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390:
389:
362:
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208:
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185:
182:
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178:ECHA InfoCard
175:
174:
167:
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162:
160:
158:
155:
154:
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140:
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93:
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88:
83:
77:
73:
67:
63:
57:
53:
48:
44:
39:
35:
30:
22:
1664:
1657:
1655:
1649:
1647:
1638:
1629:
1587:Acetergamine
1564:Penniclavine
1539:Festuclavine
1529:Elymoclavine
1524:Cycloclavine
1509:Chanoclavine
1317:lysergamides
1298:Methysergide
1262:
1206:Ergocryptine
1201:Ergocristine
1123:
1041:
1037:
1027:
1002:
999:J. Org. Chem
998:
991:
974:
970:
964:
939:
935:
931:
925:
890:
886:
862:the original
849:
838:. Retrieved
816:
807:
801:
788:Lysergamides
757:
748:
740:
722:
694:
689:
675:
657:
654:Biosynthesis
624:
609:
603:
600:
580:lysergamides
574:
559:
549:
543:
528:
519:
515:
514:
447:Legal status
435:
428:
418:
85:Identifiers
75:
71:
1698:Tryptamines
1607:Nicergoline
1569:Setoclavine
1559:Paliclavine
1519:Costaclavin
1504:Agroclavine
1313:Psychedelic
1303:Sergolexole
1288:Metergoline
1283:Mesulergine
1217:Ergometrine
1196:Ergocornine
1185:Epicriptine
1149:Cabergoline
1127:derivatives
942:(1): 63–6.
703:-methionine
608:of various
570:tlitliltzin
351:Properties
184:100.001.302
1682:Categories
1602:Lergotrile
1592:CY-208,243
1382:Ergonovine
1335:1P-ETH-LAD
1253:LY-215,840
1243:Ergovaline
1238:Ergotoxine
1233:Ergotamine
1139:Amesergide
1044:(1): 712.
840:2023-08-15
794:References
697:-adenosyl-
664:tryptophan
660:alkylation
627:hydrolysis
621:Laboratory
392:Molar mass
252:ITO20DAO7J
197:IUPHAR/BPS
157:ChemSpider
146:CHEBI:6604
113:3D model (
92:CAS Number
56:IUPAC name
1693:Ergolines
1639:Claviceps
1612:Pergolide
1580:ergolines
1478:PARGY-LAD
1273:Lysergine
1228:Ergostine
1116:Ergolines
893:(5): 98.
643:palladium
616:Synthesis
536:alkaloids
434:= 7.80, p
1597:Ergoline
1492:Clavines
1373:(DAM-57)
1278:Lysergol
1248:Lisuride
1211:Ergoloid
1076:35132076
1019:21361331
956:11035188
917:17149427
834:Archived
777:See also
745:nitrogen
737:carboxyl
672:isoprene
533:ergoline
462:Class D1
441:= 3.30
1658:Ipomoea
1643:(Ergot)
1623:sources
1621:Natural
1483:PRO-LAD
1432:LSD-Pip
1422:LSM-775
1417:LPD-824
1392:ETH-LAD
1360:CYP-LAD
1330:1cP-LSD
1067:8821704
1046:Bibcode
908:1637017
719:Isomers
709:yields
590:, e.g.
586:and as
558:), and
497:what is
495: (
415:Acidity
397:268.316
219:PubChem
102:82-58-6
1473:MLD-41
1407:LAE-32
1397:IP-LAD
1387:ETFELA
1355:BU-LAD
1350:ALD-52
1345:AL-LAD
1340:1P-LSD
1325:1B-LSD
1190:Ergine
1074:
1064:
1017:
954:
915:
905:
822:Anvisa
783:Ergine
733:isomer
731:. The
725:chiral
576:Amides
492:verify
489:
460:
335:SMILES
50:Names
1578:Other
1468:MIPLA
1402:LAMPA
1377:ECPLA
1367:(DAL)
1293:MIPLA
934:A4".
865:(PDF)
858:(PDF)
666:with
540:ergot
300:InChI
137:ChEBI
115:JSmol
1660:spp.
1641:spp.
1072:PMID
1015:PMID
952:PMID
913:PMID
756:and
527:and
243:UNII
232:6717
166:6461
1427:LSH
1412:LSD
1258:LSH
1062:PMC
1054:doi
1007:doi
979:doi
944:doi
903:PMC
895:doi
610:erg
604:lys
572:).
269:EPA
222:CID
207:139
1684::
1070:.
1060:.
1052:.
1042:13
1040:.
1036:.
1013:.
1003:76
1001:.
975:78
973:.
950:.
940:84
938:.
911:.
901:.
891:70
889:.
885:.
873:^
606:is
598:.
568:,
456:BR
439:a2
432:a1
424:)
417:(p
373:16
367:16
74:,8
70:(5
1108:e
1101:t
1094:v
1078:.
1056::
1048::
1021:.
1009::
985:.
981::
958:.
946::
919:.
897::
843:.
760:L
751:L
712:D
700:L
695:S
690:N
685:L
678:-
676:R
670:(
564:(
554:(
522:D
487:N
458::
436:K
429:K
427:p
422:a
419:K
385:2
382:O
379:2
376:N
370:H
364:C
271:)
267:(
117:)
76:R
72:R
23:.
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