Cocaine

Chemistry

Also known as

• Benzoylmethylecgonine
• Neurocaine
• L-Cocaine
• Kokain
• Cocain
• (-)-Cocaine
• Cocaina
• beta-Cocain

Stereoisomers

15 distinct stereoisomers are registered for this structure.

• Cocaine this area CID 446220
• methyl (1R,2R,3S,5R)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate CID 439497
• Pseudoallococaine CID 638023
• Pseudococaine CID 644005
• (S)-(+)-Cocaine CID 644017
• Methyl (1S,2R,3R,5R)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate CID 644018
• methyl (1R,2R,3R,5R)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate CID 6101676
• methyl (1S,2S,3R,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate CID 6918958
• methyl (1S,2S,3S,5R)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate CID 11779748
• 3h-Cocaine CID 13006129
• (R)-Allococaine CID 15558678
• methyl (1S,2R,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate CID 15558680
• methyl (1R,2S,3S,5R)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate CID 56840956
• methyl (1S,2S,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate CID 98078900
• methyl (1R,2S,3R,5R)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate CID 124909386
• Methyl 3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate mixture CID 2826

The cocaine in coca leaf, and therefore in every illicit sample, is a single natural stereoisomer — (−)-cocaine. Its four stereocentres allow fifteen others in principle; they are synthetic curiosities, far less active, and nobody encounters them.