Reference

Late intermediates in the biosynthesis of cocaine: 4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoate and methyl ecgonine

Late intermediates in the biosynthesis of cocaine: 4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoate and methyl ecgonine. Leete, Edward; Bjorklund, Jeffrey A.; Couladis, Maria M.; Kim, Sung Hoon (Dep. Chem., Univ. Minnesota, Minneapolis, MN 55455, USA). J. Am. Chem. Soc.There are some reagents with their cas registry numbers 532-24-1 and 52853-03-9 are used in this study., 113(24), 9286-92 (English) 1991. CODEN: JACSAT. ISSN: 0002-7863. DOCUMENT TYPE: Journal CA Section: 11 (Plant Biochemistry) Section cross-reference(s): 31 Me (RS)-[1,2-13C2,1-14C]-4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoate was synthesized from a mixt. of sodium [1,2-13C2]- and [1-14C]acetate. This b-keto ester was administered to intact Erythroxylum coca plants, resulting in the formation of labeled cocaine and Me ecgonine. The presence of contiguous 13C atoms in these alkaloids at C-2 and C-9 was established by 13C NMR spectroscopy, and the presence of 14C at C-9 was established by a chem. degrdn. These results are consistent with the hypothesis for the biosynthesis of cocaine, which involves the intermediacy of 4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoate (rather than 2-(1-methyl-2-pyrrolidinyl)-3-oxobutanoate) in the formation of the tropane moiety of cocaine. Support for this biogenetic scheme was also obtained by a biomimetic synthesis of 2-carbomethoxy-3-tropinone by the oxidn. of methyl-4-(1-methyl-2-pyrrolidinyl)-3-oxobutanoate with mercuric acetate. The formation of labeled cocaine and Me ecgonine in leaf cuttings of E. coca was obsd. after incubation with [9-14C]-2-carbomethoxy-3-tropinone. The degree of incorporation of this precursor into cocaine was significantly increased by the concomitant administration of the N-acetylcysteamine thioester of benzoic acid, with a corresponding redn. in the degree of incorporation into Me ecgonine. .

Carbon-13 NMR spectroscopy of atropine analogs and cocaine

Carbon-13 NMR spectroscopy of atropine analogs and cocaine. Avdovich, H. W.In this study， 532-24-1 and 51-34-3 are also used.; Neville, G. A. (Health Prot. Branch, Health Welfare Canada, Ottawa, ON K1A 0L2, Can.). Can. J. Spectrosc., 28(1), 1-8 (English) 1983. CODEN: CJSPAI. ISSN: 0045-5105. DOCUMENT TYPE: Journal CA Section: 4 (Toxicology) Whereas some recent 13C-NMR spectroscopic studies have been made for cocaine [50-36-2] and tropane alkaloids, various inaccuracies and contradictions exist in the literature. A series of atropine [51-55-8] analogs together with cocaine were, therefore, examd. by 13C-NMR spectrometry in D2O and CDCl3 solns. for clarification and consolidation of spectral information. .