ECGONINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H15NO3
Molecular Weight	185.2203
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1[C@H]2CC[C@@H]1[C@H]([C@@H](O)C2)C(O)=O

InChI

InChIKey=PHMBVCPLDPDESM-FKSUSPILSA-N

InChI=1S/C9H15NO3/c1-10-5-2-3-6(10)8(9(12)13)7(11)4-5/h5-8,11H,2-4H2,1H3,(H,12,13)/t5-,6+,7-,8+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C9H15NO3
Molecular Weight	185.2203
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Human liver carboxylesterase hCE-1: binding specificity for cocaine, heroin, and their metabolites and analogs.	1997 Sep	9311626
Ecgonine is an important marker for cocaine use in inadequately preserved specimens.	2001 Apr	11327356
In vitro stability of cocaine in whole blood and plasma including ecgonine as a target analyte.	2001 Apr	11294520
A catalytic antibody against cocaine attenuates cocaine's cardiovascular effects in mice: a dose and time course analysis.	2001 Jun	11407313
2'-substituted analogs of cocaine: synthesis and dopamine transporter binding potencies.	2001 Sep	11688137
Analysis of cocaine, benzoylecgonine, ecogonine methyl ester, and ecgonine by high-pressure liquid chromatography-API mass spectrometry and application to a short-term degradation study of cocaine in plasma.	2001 Sep	11550815
Synthesis and dopamine transporter binding of 2beta-isopropyl ester analogs of cocaine.	2002 Feb	11858849
Determination of the highest no-effect dose (HNED) and of the elimination pattern for cocaine in horses.	2002 Mar-Apr	11920936
Three-dimensional quantitative structure-activity relationship modeling of cocaine binding by a novel human monoclonal antibody.	2004 Jan 1	14695827
Determination of cocaine, its metabolites, pyrolysis products, and ethanol adducts in postmortem fluids and tissues using Zymark automated solid-phase extraction and gas chromatography-mass spectrometry.	2004 Jul 5	15171923
Gender differences in cocaine pharmacokinetics in CF-1 mice.	2005 Jan 15	15585357
Concentration profiles of cocaine, pyrolytic methyl ecgonidine and thirteen metabolites in human blood and urine: determination by gas chromatography-mass spectrometry.	2005 Nov	15841503
Simultaneous analyses of cocaine, cocaethylene, and their possible metabolic and pyrolytic products.	2006 Feb 10	16428007
Bioanalytical procedures for determination of drugs of abuse in blood.	2007 Aug	17468860
Cocaine and metabolites urinary excretion after controlled smoked administration.	2007 Oct	17988460
Can cocaine use be evaluated through analysis of wastewater? A nation-wide approach conducted in Belgium.	2009 May	19344443
Urinary excretion of ecgonine and five other cocaine metabolites following controlled oral, intravenous, intranasal, and smoked administration of cocaine.	2010 Mar	20223096
Quantification of drugs of abuse in municipal wastewater via SPE and direct injection liquid chromatography mass spectrometry.	2010 Nov	20865408

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:46:18 GMT 2025` Edited by `admin` on `Mon Mar 31 17:46:18 GMT 2025`
Record UNII	DX2E9E17AV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IDS-NE-001

Preferred Name

English

ECGONINE

Common Name

English

ECGONINE [MI]

Common Name

English

3.BETA.-HYDROXY-1.ALPHA.H,5.ALPHA.H-TROPANE-2.BETA.-CARBOXYLIC ACID

Common Name

English

3.BETA.-HYDROXY-2.BETA.-TROPANECARBOXYLIC ACID

Common Name

English

Ecgonine [WHO-DD]

Common Name

English

(1R,2R,3S,5S)-3-HYDROXY-8-METHYL-8-AZABICYCLO(3.2.1)OCTANE-2-CARBOXYLIC ACID

Systematic Name

English

EKGONIN

Common Name

English

Classification Tree Code System Code

DEA NO.

9180