Cocaethylene

Title: Cocaethylene
CAS Registry Number: 529-38-4
CAS Name: [1R-(exo,exo)]-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid ethyl ester
Additional Names: ecgonine ethyl ester benzoate (ester); O-benzoyl-l-ecgonine ethyl ester; ethylbenzoylecgonine
Trademarks: Homocaine
Molecular Formula: C18H23NO4
Molecular Weight: 317.38
Percent Composition: C 68.12%, H 7.30%, N 4.41%, O 20.16%
Literature References: Homolog of cocaine. Prepn: Merck, Ber. 18, 2952 (1885); Einhorn, ibid. 21, 47 (1888).
Properties: Prisms from alcohol, mp 109°. Almost insol in water. Sol in alcohol, ether.
Melting point: mp 109°
Therap-Cat: Anesthetic (local).
Keywords: Anesthetic (Local).
Cocaine Cocillana Coclaurine Cocoa Coconut Oil

Cocaethylene
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Systematic (IUPAC) name
ethyl (2R,3S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Clinical data
Pregnancy cat. C
Legal status CD (UK) Not scheduled specifically, could be prosecuted as an analogue of a scheduled substance.
Dependence liability Moderate to High
Routes Produced from ingestion of cocaine and ethanol
Identifiers
CAS number 529-38-4
ATC code None
PubChem CID 65034
ChemSpider 559082
ChEMBL CHEMBL608806
Synonyms benzoylecgonine ethyl ester, ethylbenzoylecgonine,
Chemical data
Formula C18H23NO4 
Mol. mass 317.38 g/mol

Cocaethylene (ethylbenzoylecgonine) is the ethyl ester of benzoylecgonine. It is structurally similar to cocaine, which is the methyl ester of benzoylecgonine. Cocaethylene is formed in vivo by the liver when cocaine and ethanol coexist in the blood.[1]