Structure via PubChem · Public domain (PubChem)
ecgonine methyl ester
Sign in to saveAlso known as Methyl ecgonine, methyl (2R,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate, Methylecgonine
Methylecgonine, also known as ecgonine methyl ester is a prominent tropane alkaloid found in coca leaves. It is metabolite of cocaine, and may be used as a precursor for it. It also occurs as minor alkaloid in roots of many Datura species such as Datura stramonium and Datura innoxia. ==Alkaloids== Cocamine (a-Truxilline) aka isatropylcocaine [490-17-5] and isococamine (beta-Truxilline) [490-15-3] are alkaloids present in Erythroxylun truxillense Rusby. The Victorian era references disclosed in John Glasby's dictionary of alkaloids indicate the longevity of these compounds. Although these citat
In the Vinony graph
Within Vinony's link graph, ecgonine methyl ester is referenced by 7 other articles, and connects out to cocaine, digital object identifier and chemical formula.
Vinony files it under Beta-Amino acids, Chemical articles with multiple compound IDs and Chemical articles with multiple PubChem CIDs.
Its subject is documented across 6 Wikipedia language editions.
Chemical data
- Formula
- C10H17NO3
- Molecular weight
- 199.25 g/mol
- IUPAC name
- methyl (1R,2R,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
- SMILES
- CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)O)C(=O)OC
- InChIKey
- QIQNNBXHAYSQRY-UYXSQOIJSA-N
- XLogP
- 0.6
- Polar surface area
- 49.8 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
358 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
- Simultaneous determination of cocaine, ecgonine methyl ester, benzoylecgonine, cocaethylene and norcocaine in dried blood spots by ultra-performance liquid chromatography coupled to tandem mass spectrometry.Forensic science international · 2019
via PubMed
Wikidata facts
- Has part
- hydrogen
- Mass
- 199.121
Show 5 more facts
- chemical formula
- C₁₀H₁₇NO₃
- isomeric SMILES
- CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)O)C(=O)OC
- canonical SMILES
- CN1C2CCC1C(C(C2)O)C(=O)OC
- subject has role
- psychoactive drug
- found in taxon
- Homo sapiens
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
5 sectionsContents
- Alkaloids
- Biosynthesis
- Animal study
- See also
- References
Methylecgonine, also known as ecgonine methyl ester is a prominent tropane alkaloid found in coca leaves. It is metabolite of cocaine, and may be used as a precursor for it. It also occurs as minor alkaloid in roots of many Datura species such as Datura stramonium and Datura innoxia. ==Alkaloids== Cocamine (a-Truxilline) aka isatropylcocaine [490-17-5] and isococamine (beta-Truxilline) [490-15-3] are alkaloids present in Erythroxylun truxillense Rusby. The Victorian era references disclosed in John Glasby's dictionary of alkaloids indicate the longevity of these compounds. Although these citations are outdated, a newer citation proposes different structures. These compounds are understood to be esters of truxillic acid and/or truxinic acid that are formed as a consequence of methylecgonine cinnamate photodimerizing. Cocamine was reported to be a heart poison in later work.
== Biosynthesis == It is the last step before cocaine is biosynthesized in coca plants with the help of BAHD acyltransferase.
Excerpted from Wikipedia’s “ecgonine methyl ester” article, available under the CC BY-SA 4.0 licence.