Structure via PubChem · Public domain (PubChem)
اکگونین
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
Wikidata facts
- Subclass of
- carboxylic acid
- Has part
- hydrogen
- Mass
- 185.105193
Show 7 more facts
- chemical formula
- C₉H₁₅NO₃
- canonical SMILES
- CN1C2CCC1C(C(C2)O)C(=O)O
- isomeric SMILES
- CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)O)C(=O)O
- found in taxon
- Duboisia hopwoodii
- subject has role
- narcotic
- Commons category
- Ecgonine
- described by source
- Encyclopædia Britannica 11th edition
Sources (2)
via Wikidata · CC0