Cocaine reverse ester

Cocaine reverse ester
Identifiers
	IUPAC name [(2R,3S)-2-Acetyloxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] benzoate;
CAS Number	33780-46-0;
PubChem CID	9995139;
ChemSpider	8170720;
Chemical and physical data
Formula	C17H21NO4
Molar mass	303.358 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(=O)O[C@H]1[C@H](CC2CCC1N2C)OC(=O)C3=CC=CC=C3;
	InChI InChI=1S/C17H21NO4/c1-11(19)21-16-14-9-8-13(18(14)2)10-15(16)22-17(20)12-6-4-3-5-7-12/h3-7,13-16H,8-10H2,1-2H3/t13?,14?,15-,16+/m0/s1; Key:QAVJUWLVUKNZFV-SSHXOBKSSA-N;

Cocaine reverse ester, (also known as Reverse ester cocaine or REC) is a tropane derivative drug which is a reverse ester of cocaine, with the 2-COOCH₃ methoxycarbonyl group swapped to an isomeric OCOCH₃ acetoxy group. It was synthesised because of the observation that the reverse ester pairs of several structurally related substances show similar activity to each other (see e.g. methylphenidate vs phacetoperane, pethidine vs desmethylprodine). Cocaine reverse ester however did not produce cocaine-like stimulant effects in animal studies,^[1] and is also illegal in many jurisdictions as a structural isomer of cocaine; nevertheless it has attracted attention from vendors of quasi-legal designer drugs as a potential alternative to cocaine.

References[edit]

^ Daum SJ, Martini CM, Kullnig RK, Clarke RL (May 1972). "Compounds affecting the central nervous system. I. Tropane-2 ,3 -diol derivatives. A reverse ester of cocaine". The Journal of Organic Chemistry. 37 (10): 1665–9. doi:10.1021/jo00975a045. PMID 5031343.

[pmid5031343-1] Daum SJ, Martini CM, Kullnig RK, Clarke RL (May 1972). "Compounds affecting the central nervous system. I. Tropane-2 ,3 -diol derivatives. A reverse ester of cocaine". The Journal of Organic Chemistry. 37 (10): 1665–9. doi:10.1021/jo00975a045. PMID 5031343.

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