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
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.