Cocaine reverse ester

Short description: Chemical compound

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.

## See also

* 3-(p-Fluorobenzoyloxy)tropane
* 4′-Fluorococaine
* Benzoylecgonine
* Methylecgonine cinnamate
* Salicylmethylecgonine

## References

1. ↑ "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. May 1972. doi:10.1021/jo00975a045. PMID 5031343.

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*[CID]: Compound ID