Methylecgonine

Source: Wikipedia, the free encyclopedia.
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
3D model (
JSmol
)
ChEMBL
ChemSpider
UNII
  • 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
  • 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
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).

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]

Biosynthesis

It is the last step before cocaine is biosynthesized in coca plants with the help of BAHD acyltransferase.[5]

Animal study

Animals study suggest that it has beneficial effect on cognition and protects against cocaine lethality.[6][7] It showed inhibition of sodium channels only at very high dosages.[8]

See also

References

  1. JSTOR 42759059
    .
  2. PMID 7078101
    .
  3. PMID 20858536
    .
  4. S2CID 21953079
    .
  5. PMID 25406120
    .
  6. S2CID 211054455
    .
  7. S2CID 34545574
    .
  8. PMID 6303347
    .
Stub icon

This article about an alkaloid is a stub. You can help Wikipedia by expanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Methylecgonine&oldid=1215460007"