ContaminantDB: Cocaethylene

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 18:39:39 UTC

Update Date

2016-11-09 01:17:32 UTC

Accession Number

CHEM022563

Identification

Common Name

Cocaethylene

Class

Small Molecule

Description

Cocaethylene is a recreational drug with stimulant, euphoriant, anorectic, sympathomimetic and local anesthetic properties. Three monoamine neurotransmitters known as serotonin (5-HT), norepinephrine (NE), and dopamine (DA) play an important role in cocaethylene's action. Cocaethylene increases the level of serotonergic, noradrenergic, and dopaminergic neurotransmission by inhibiting the action of the serotonin transporter (SERT), norepinephrine transporter (NET), and dopamine transporter (DAT) which makes cocaethylene a serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI).[Note 1]; Normally cocaine's metabolism produces two major and biologically inactive metabolites, benzoylecogonine and ecgonine methyl ester. Carboxylesterase is an important part of cocaine's metabolism because it acts as the catalyst for the hydrolysis of cocaine which produces the inactive metabolites. If ethanol is present during the metabolism of cocaine, a portion of the cocaine undergoes transesterification with ethanol, instead of undergoing hydrolysis with water, which results in cocaethylene.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Ethylbenzoylecgonine	HMDB
Homocaine	HMDB
Thylbenzoylecgonine (cocaethylene)	HMDB
Coca-ethylene	HMDB
Benzoylecgonine ethyl ester	HMDB
Ethylcocaine	HMDB
Ethyl 3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid	HMDB

Chemical Formula

C₁₈H₂₃NO₄

Average Molecular Mass

317.380 g/mol

Monoisotopic Mass

317.163 g/mol

CAS Registry Number

529-38-4

IUPAC Name

ethyl 3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

Traditional Name

ethyl 3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

SMILES

CCOC(=O)C1C2CCC(CC1OC(=O)C1=CC=CC=C1)N2C

InChI Identifier

InChI=1S/C18H23NO4/c1-3-22-18(21)16-14-10-9-13(19(14)2)11-15(16)23-17(20)12-7-5-4-6-8-12/h4-8,13-16H,3,9-11H2,1-2H3

InChI Key

NMPOSNRHZIWLLL-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Piperidinecarboxylic acid
Tropane alkaloid
Benzoyl
Dicarboxylic acid or derivatives
Piperidine
N-alkylpyrrolidine
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Amine
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.16 g/L	ALOGPS
logP	2.53	ALOGPS
logP	2.64	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	8.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	55.84 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	85.91 m³·mol⁻¹	ChemAxon
Polarizability	33.98 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-8920000000-d0ddc15ce1ec524cf976	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0759000000-f20aaaa4f88d5b7cf690	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-1921000000-1878f9aace099de4a6c3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-4900000000-be7bbb1ffce7c7bc543f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-1289000000-b238799d629e81c3c636	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00fu-3692000000-c1f442d41b90cc38c257	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00bc-3910000000-a07725f187dbed3eaf87	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0359000000-d47ddbfec015e5a77ccc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9600000000-a92ad0fa27f4215bc086	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9200000000-ea006683d2c3924fdb8d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0249000000-2e8ceb65026abfa3b686	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-0941000000-aa625de4aa67ad9ce25c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-1900000000-1f8eb4e4bd0801741731	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0041860

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Cocaethylene

Chemspider ID

2723

ChEBI ID

Not Available

PubChem Compound ID

2825

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Cocaethylene (CHEM022563)

Structure for CHEM022563: Cocaethylene