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Methylecgonine information


Methylecgonine
Names
IUPAC name
methyl 3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Other names
  • Ecgonine methyl ester
  • EME
  • Methyl ecgonine
Identifiers
CAS Number
  • 7143-09-1 ☒N
3D model (JSmol)
  • Interactive image
  • unspecified sterocentres: Interactive image
ChEMBL
  • ChEMBL305331
ChemSpider
  • 94674
PubChem CID
  • 104904
  • unspecified sterocentres: 251884
UNII
  • Y35FJB3QBJ
CompTox Dashboard (EPA)
  • DTXSID00891435 Edit this at Wikidata
InChI
  • InChI=1S/C10H17NO3/c1-11-6-3-4-7(11)9(8(12)5-6)10(13)14-2/h6-9,12H,3-5H2,1-2H3/t6-,7+,8-,9+/m0/s1
  • Key: QIQNNBXHAYSQRY-UYXSQOIJSA-N
  • unspecified sterocentres: InChI=1S/C10H17NO3/c1-11-6-3-4-7(11)9(8(12)5-6)10(13)14-2/h6-9,12H,3-5H2,1-2H3
    Key: QIQNNBXHAYSQRY-UHFFFAOYSA-N
SMILES
  • CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)O)C(=O)OC
  • unspecified sterocentres: CN1C2CCC1C(C(C2)O)C(=O)OC
Properties
Chemical formula
C10H17NO3
Molar mass 199.250 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Methylecgonine, also known as ecgonine methyl ester is a prominent tropane alkaloid found in coca leaves.[1] It is metabolite of cocaine,[2] 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[3] and Datura innoxia.[4]

  1. ^ Johnson, Emanuel L.; Emche, Stephen D. (1994). "Variation of Alkaloid Content in Erythroxylum coca Leaves from Leaf Bud to Leaf Drop". Annals of Botany. 73 (6): 645–650. doi:10.1006/anbo.1994.1081. JSTOR 42759059.
  2. ^ Ambre JJ, Ruo TI, Smith GL, Backes D, Smith CM (1982). "Ecgonine methyl ester, a major metabolite of cocaine". Journal of Analytical Toxicology. 6 (1): 26–9. doi:10.1093/jat/6.1.26. PMID 7078101.
  3. ^ El Bazaoui A, Bellimam MA, Soulaymani A (March 2011). "Nine new tropane alkaloids from Datura stramonium L. identified by GC/MS". Fitoterapia. 82 (2): 193–7. doi:10.1016/j.fitote.2010.09.010. PMID 20858536.
  4. ^ El Bazaoui, Ahmed; Bellimam, My Ahmed; Soulaymani, Abdelmajid (2012). "Tropane Alkaloids of Datura innoxia from Morocco". Zeitschrift für Naturforschung C. 67 (1–2): 8–14. doi:10.1515/znc-2012-1-202. ISSN 1865-7125. PMID 22486036. S2CID 21953079.

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