Cocaethylene

Cocaethylene
Clinical data


Pregnancy category	C
Dependence liability	Moderate to High
Routes of administration	Produced from ingestion of cocaine and ethanol
ATC code	none
Legal status
Legal status	UK: Controlled Drug US: Analogue to a Schedule I/II drug (possibly) Not scheduled
Identifiers
IUPAC name ethyl (2R,3S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Synonyms	benzoylecgonine ethyl ester, ethylbenzoylecgonine,
CAS Number	529-38-4
PubChem CID	65034
ChemSpider	559082
ChEMBL	CHEMBL608806
ECHA InfoCard	100.164.816
Chemical and physical data
Formula	C₁₈H₂₃NO₄
Molar mass	317.38 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(O[C@H]1C[C@H]2N(C)[C@@H]([C@H]1C(=O)OCC)CC2)c3ccccc3

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

Cocaethylene is the byproduct of concurrent consumption of alcohol and cocaine as metabolized by the liver. Normally, metabolism of cocaine produces two primarily biologically inactive metabolites—benzoylecgonine and ecgonine methyl ester. The hepatic enzyme carboxylesterase is an important part of cocaine's metabolism because it acts as a catalyst for the hydrolysis of cocaine in the liver, which produces these inactive metabolites. If ethanol is present during the metabolism of cocaine, a portion of the cocaine undergoes transesterification with ethanol, rather than undergoing hydrolysis with water, which results in the production of cocaethylene.

Cocaethylene is largely considered a recreational drug in and of itself, with stimulant, euphoriant, anorectic, sympathomimetic, and local anesthetic properties. The monoamine neurotransmitters serotonin, norepinephrine, and dopamine play important roles in cocaethylene's action in the brain. Cocaethylene increases the levels of serotonergic, noradrenergic, and dopaminergic neurotransmission in the brain by inhibiting the action of the serotonin transporter, norepinephrine transporter, and dopamine transporter. These pharmacological properties make cocaethylene a serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI; also known as a "triple reuptake inhibitor").

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