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
PubChem CID
ChemSpider
Chemical and physical data
FormulaC17H21NO4
Molar mass303.358 g·mol−1
3D model (JSmol)
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 livestock studies (not rats),[1] however use in humans grants the user a five hour long high, half the normal dose of cocaine and is generally very pure due to it's rarity. However it 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 greater alternative to cocaine.

See also

References

  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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