Structure via PubChem · Public domain (PubChem)
ecgonine
Sign in to saveAlso known as 3beta-hydroxy-1alphaH,5alphaH-tropane-2beta-carboxylic acid, [1R*-(Exo,exo)]-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid, 3beta-hydroxy-2beta-tropanecarboxylic acid, 1-Ecgonine, (-)-Ecgonine
Ecgonine is a tropane alkaloid (alkaloid derivative of tropane) found naturally in coca leaves. It has a close structural relation to cocaine: it is both a metabolite and a precursor, and as such, it is a controlled substance in many jurisdictions, as are some substances which can be used as precursors to ecgonine itself.
Chemical data
- Formula
- C9H15NO3
- Molecular weight
- 185.22 g/mol
- IUPAC name
- (1R,2R,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
- SMILES
- CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)O)C(=O)O
- InChIKey
- PHMBVCPLDPDESM-FKSUSPILSA-N
- XLogP
- -1.8
- Polar surface area
- 60.8 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
466 papers- Cocaine: An Updated Overview on Chemistry, Detection, Biokinetics, and Pharmacotoxicological Aspects including Abuse Pattern.Toxins · 2022
- Effects of ecgonine methyl ester on cognition in scopolamine-impaired and aged rats.Psychopharmacology · 2020
- Ecgonine methyl ester, a major metabolite of cocaine.Journal of analytical toxicology · 1982
- Urinary excretion of ecgonine methyl ester, a major metabolite of cocaine in humans.Journal of analytical toxicology · 1984
- Postmortem redistribution of cocaine and its metabolites, benzoylecgonine and ecgonine methyl ester in humans: Important variables that might be influencing the central blood / peripheral blood ratio.Forensic science international · 2023
via PubMed
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Encyclopedic overview
2 sectionsContents
- See also
- References
Ecgonine is a tropane alkaloid (alkaloid derivative of tropane) found naturally in coca leaves. It has a close structural relation to cocaine: it is both a metabolite and a precursor, and as such, it is a controlled substance in many jurisdictions, as are some substances which can be used as precursors to ecgonine itself.
Structurally, ecgonine is a cycloheptane derivative with a nitrogen bridge. It is obtained by hydrolysis of cocaine with acids or alkalis, and crystallizes with one molecule of water, the crystals melting at 198–199 °C. It is levorotary, and on warming with alkalis gives iso-ecgonine, which is dextrorotary.
Excerpted from Wikipedia’s “ecgonine” article, available under the CC BY-SA 4.0 licence.