Methylecgonine

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]

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
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

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

• Ecgonine