241:
166:
555:
520:
493:
31:
368:
430:, meaning that the relative concentrations of the two compounds can be used to estimate how recently crack cocaine has been smoked. Methylecgonidine has been shown to be specifically more harmful to the body than other byproducts of cocaine; for example to the heart, lungs & liver. The toxicity is due to a
880:
Basmadjian GP, Singh S, Sastrodjojo B, Smith BT, Avor KS, Chang F, et al. (November 1995). "Generation of polyclonal catalytic antibodies against cocaine using transition state analogs of cocaine conjugated to diphtheria toxoid".
787:
Fandiño AS, Toennes SW, Kauert GF (December 2002). "Studies on hydrolytic and oxidative metabolic pathways of anhydroecgonine methyl ester (methylecgonidine) using microsomal preparations from rat organs".
727:
Pharmacokinetics and
Pharmacodynamics of Methylecgonidine, a Crack Cocaine Pyrolyzate - Scheidweiler et al. 307 (3): 1179 Figure IG6 - Journal of Pharmacology and Experimental Therapeutics
381:
17:
1093:
Davies, H. M. L.; Saikali, E.; Young, W. B. (1991). "Synthesis of (.+-.)-ferruginine and (.+-.)-anhydroecgonine methyl-ester by a tandem cyclopropanation/Cope rearrangement".
473:
422:
is smoked, making this substance a useful biomarker to specifically test for use of crack cocaine, as opposed to powder cocaine which does not form methylecgonidine as a
684:
Scheidweiler KB, Plessinger MA, Shojaie J, Wood RW, Kwong TC (December 2003). "Pharmacokinetics and pharmacodynamics of methylecgonidine, a crack cocaine pyrolyzate".
1120:
Davies HM, Young WB, Smith HD (January 1989). "Novel entry to the tropane system by reaction of rhodium (II) acetate stabilized vinylcarbenoids with pyrroles".
290:
970:
Kline RH, Wright J, Fox KM, Eldefrawi ME (July 1990). "Synthesis of 3-arylecgonine analogues as inhibitors of cocaine binding and dopamine uptake".
1021:"Transition-metal-catalyzed reactions of diazo compounds. 2. Addition to aromatic molecules: Catalysis of Buchner's synthesis of cycloheptatrienes"
123:
439:
435:
527:
The scheme by Kline is based on the reaction of 2,4,6-cycloheptatriene-7-carboxylic acid with methylamine. This is a modified version of
1058:
Davies HM, Huby NJ (1992). "Enantioselective synthesis of tropanes by reaction of rhodium-stabilized vinylcarbenoids with pyrroles".
916:
De Jong AW (1937). "Some properties of the ecgonines and their esters II. The structural formulae of the ecgonines and ecgonidine".
255:
825:"M1 and M3 muscarinic receptors may play a role in the neurotoxicity of anhydroecgonine methyl ester, a cocaine pyrolysis product"
1006:"Methyl 2,4,6-cycloheptatriene-1-carboxylate - C9H10O2, density, melting point, boiling point, structural formula, synthesis"
740:"Evidence for cocaine and methylecgonidine stimulation of M(2) muscarinic receptors in cultured human embryonic lung cells"
388:
198:
219:
1153:
630:
161:
1163:
1158:
53:
43:
426:. Methylecgonidine has a relatively short half-life of 18–21 minutes, after which it is metabolised to
836:
559:
481:
403:(anhydromethylecgonine; anhydroecgonine methyl ester; AEME) is a chemical intermediate derived from
236:
89:
1005:
726:
709:
610:
582:
457:
554:
519:
492:
1075:
987:
898:
862:
805:
769:
701:
443:
143:
823:
Garcia RC, Dati LM, Torres LH, da Silva MA, Udo MS, Abdalla FM, et al. (December 2015).
1129:
1102:
1067:
1040:
1032:
979:
952:
925:
890:
852:
844:
797:
759:
751:
693:
563:
544:
313:
207:
99:
431:
240:
165:
264:
InChI=1S/C10H15NO2/c1-11-7-3-5-8(10(12)13-2)9(11)6-4-7/h5,7,9H,3-4,6H2,1-2H3/t7-,9+/m0/s1
943:
Matchett JR, Levine J (1941). "Isolation of
Ecgonidine Methyl Ester from Coca Seeds 1".
840:
274:
InChI=1/C10H15NO2/c1-11-7-3-5-8(10(12)13-2)9(11)6-4-7/h5,7,9H,3-4,6H2,1-2H3/t7-,9+/m0/s1
857:
824:
764:
739:
513:
359:
1133:
1071:
1147:
540:
454:
419:
154:
713:
664:
465:
187:
597:) in the presence of rhodium(II) hexanoate/hexane gave the -azabicyclic system (
509:
30:
659:
535:
529:
505:
469:
427:
423:
344:
134:
1079:
929:
551:. The methyl 2,4,6-cycloheptatriene-1-carboxylate can be made synthetically.
1020:
697:
654:
501:
447:
415:
866:
809:
773:
755:
705:
991:
902:
609:
in 62% yield. The unsubstituted double bond was selectively reduced using
543:
to form a tertiary alcohol by "hard" addition to the ester and not "soft"
1019:
Anciaux AJ, Demonceau A, Noels AF, Hubert AJ, Warin R, Teyssie P (1981).
548:
461:
404:
1106:
1036:
983:
956:
894:
539:
these same authors react their methylecgonidine with two equivalents of
1044:
477:
408:
174:
848:
801:
358:
Except where otherwise noted, data are given for materials in their
553:
518:
491:
122:
112:
626:
453:
AEME is also used in scientific research for the manufacture of
476:. Methylecgonidine could also theoretically be used to produce
224:
16:"AEME" redirects here. For the Australian Army corps, see
686:
The
Journal of Pharmacology and Experimental Therapeutics
738:
Yang Y, Ke Q, Cai J, Xiao YF, Morgan JP (January 2001).
547:. However, the product is only one tenth the potency of
376:
613:
to provide N-protected anhydroecgonine methyl ester ((
533:
by
Grundmann and Ottmann. In the accompanying patent
18:
Royal
Australian Electrical and Mechanical Engineers
629:and reductive methylation with formaldehyde and
581:)-methylecgonidine by a tandem cyclopropanation/
186:
98:
625:). Following deprotection of N8 nitrogen with
66:)-8-methyl-8-azabicyclooct-2-ene-2-carboxylate
8:
918:Recueil des Travaux Chimiques des Pays-Bas
585:. Thus, reaction of methyldiazobutenoate (
239:
164:
142:
22:
856:
763:
206:
500:Methylecgonidine can be synthesized non
676:
496:Methylecgonidine synthesis from cocaine
295:
260:
235:
883:Chemical & Pharmaceutical Bulletin
155:
267:Key: MPSNEAHFGOEKBI-IONNQARKSA-N
7:
645:was obtained in overall good yield.
593:-((2-(TMS)ethoxy)carbonyl)pyrrole (
523:Methylecgonidine synthesis by Kline
277:Key: MPSNEAHFGOEKBI-IONNQARKBC
177:
14:
1025:The Journal of Organic Chemistry
366:
331:
325:
47:Methyl trop-2-ene-2β-carboxylate
29:
790:Chemical Research in Toxicology
744:British Journal of Pharmacology
362:(at 25 °C , 100 kPa).
972:Journal of Medicinal Chemistry
558:Methylecgonidine synthesis by
334:
319:
1:
1134:10.1016/S0040-4039(01)80766-8
1072:10.1016/S0040-4039(00)60899-7
77:Anhydroecgonine methyl ester
1180:
15:
356:
306:
286:
251:
82:
72:
52:
42:
37:
28:
930:10.1002/recl.19370560215
698:10.1124/jpet.103.055434
631:sodium cyanoborohydride
440:M3 muscarinic receptors
924:(2): 186–97, 198–201.
756:10.1038/sj.bjp.0703819
566:
524:
497:
446:and neuronal death by
414:Methylecgonidine is a
298:CN2/1CC2C\C=C\1C(=O)OC
557:
536:U.S. patent 2,783,236
530:U.S. patent 2,783,235
522:
495:
75:Anhydromethylecgonine
54:Systematic IUPAC name
482:controlled substance
418:product formed when
1122:Tetrahedron Letters
1107:10.1021/jo00019a044
1060:Tetrahedron Letters
1037:10.1021/jo00318a010
984:10.1021/jm00169a036
957:10.1021/ja01854a038
895:10.1021/ja01502a049
841:2015NatSR...517555G
484:in some countries.
352: g·mol
25:
829:Scientific Reports
611:Wilkinson catalyst
589:) with 5 equiv of
583:Cope rearrangement
567:
525:
498:
389:Infobox references
23:
1154:Tropane alkaloids
1101:(19): 5696–5700.
1066:(46): 6935–6938.
849:10.1038/srep17555
802:10.1021/tx0255828
504:from cocaine via
444:DNA fragmentation
397:Chemical compound
395:
394:
220:CompTox Dashboard
124:Interactive image
24:Methylecgonidine
1171:
1138:
1137:
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1111:
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1055:
1049:
1048:
1016:
1010:
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1002:
996:
995:
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961:
960:
951:(9): 2444–2446.
945:J. Am. Chem. Soc
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913:
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877:
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860:
820:
814:
813:
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729:
724:
718:
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564:Enantioselective
545:Michael addition
538:
532:
480:and so may be a
401:Methylecgonidine
379:
373:
370:
369:
351:
336:
333:
327:
321:
314:Chemical formula
244:
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33:
26:
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889:(11): 1902–11.
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781:
737:
736:
732:
725:
721:
683:
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678:
673:
651:
534:
528:
516:with methanol.
490:
432:partial agonist
398:
391:
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384: ?)
375:
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12:
11:
5:
1177:
1175:
1167:
1166:
1161:
1156:
1146:
1145:
1140:
1139:
1128:(35): 4653–6.
1112:
1085:
1050:
1031:(5): 873–876.
1011:
997:
962:
935:
908:
872:
815:
796:(12): 1543–8.
779:
730:
719:
692:(3): 1179–87.
675:
674:
672:
669:
668:
667:
662:
657:
650:
647:
514:esterification
489:
486:
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360:standard state
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237:DTXSID20276220
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1164:Methyl esters
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978:(7): 2024–7.
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771:
766:
761:
757:
753:
750:(2): 451–60.
749:
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731:
728:
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588:
584:
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576:
573:synthesized (
572:
565:
561:
556:
552:
550:
546:
542:
537:
531:
521:
517:
515:
511:
507:
503:
502:pyrolytically
494:
487:
485:
483:
479:
475:
471:
467:
463:
459:
456:
455:phenyltropane
451:
449:
445:
442:, leading to
441:
437:
433:
429:
425:
421:
420:crack cocaine
417:
412:
410:
406:
402:
390:
383:
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355:
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156:ECHA InfoCard
153:
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61:
55:
51:
45:
41:
36:
32:
27:
19:
1159:Cycloalkenes
1125:
1121:
1115:
1098:
1095:J. Org. Chem
1094:
1088:
1063:
1059:
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1028:
1024:
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832:
828:
818:
793:
789:
782:
747:
743:
733:
722:
689:
685:
679:
665:Tropacocaine
642:
638:
634:
622:
618:
614:
606:
602:
598:
594:
590:
586:
578:
574:
570:
568:
526:
512:followed by
499:
466:dichloropane
452:
413:
400:
399:
83:Identifiers
73:Other names
63:
59:
1045:2268/237697
510:dehydration
307:Properties
162:100.164.719
1148:Categories
671:References
660:Anatoxin-a
506:hydrolysis
470:iometopane
434:effect at
428:ecgonidine
424:metabolite
345:Molar mass
208:58C337KP3E
135:ChemSpider
111:3D model (
100:43021-26-7
90:CAS Number
44:IUPAC name
1080:0040-4039
835:: 17555.
655:Arecoline
488:Synthesis
458:analogues
448:apoptosis
416:pyrolysis
58:Methyl (1
867:26626425
810:12482236
774:11159694
714:15619796
706:14561847
649:See also
549:atropine
462:troparil
460:such as
405:ecgonine
144:21106453
992:2362282
903:8575031
858:4667193
837:Bibcode
765:1572570
569:Davies
478:cocaine
409:cocaine
382:what is
380: (
350:181.235
175:PubChem
1078:
990:
901:
865:
855:
808:
772:
762:
712:
704:
571:et al.
560:Davies
472:, and
377:verify
374:
291:SMILES
188:119478
38:Names
710:S2CID
256:InChI
113:JSmol
1076:ISSN
988:PMID
899:PMID
863:PMID
806:PMID
770:PMID
702:PMID
627:TBAF
541:PhLi
438:and
199:UNII
1130:doi
1103:doi
1068:doi
1041:hdl
1033:doi
980:doi
953:doi
926:doi
891:doi
853:PMC
845:doi
798:doi
760:PMC
752:doi
748:132
694:doi
690:307
633:, (
474:CFT
407:or
225:EPA
178:CID
1150::
1126:30
1124:.
1099:56
1097:.
1074:.
1064:33
1062:.
1039:.
1029:46
1027:.
1023:.
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976:33
974:.
949:63
947:.
922:56
920:.
897:.
887:43
885:.
861:.
851:.
843:.
831:.
827:.
804:.
794:15
792:.
768:.
758:.
746:.
742:.
708:.
700:.
688:.
641:)-
621:)-
605:)-
562:.
468:,
464:,
450:.
436:M1
411:.
329:15
323:10
62:,5
1136:.
1132::
1109:.
1105::
1082:.
1070::
1047:.
1043::
1035::
1008:.
994:.
982::
959:.
955::
932:.
928::
905:.
893::
869:.
847::
839::
833:5
812:.
800::
776:.
754::
716:.
696::
643:5
639:S
637:/
635:R
623:4
619:S
617:/
615:R
607:8
603:S
601:/
599:R
595:1
591:N
587:2
579:S
577:/
575:R
508:/
372:N
338:2
335:O
332:N
326:H
320:C
227:)
223:(
115:)
64:S
60:R
20:.
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