From 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
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
C 10 H 17 N O 3
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).
Chemical compound
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
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ Schmidt GW, Jirschitzka J, Porta T, Reichelt M, Luck K, Torre JC, Dolke F, Varesio E, Hopfgartner G, Gershenzon J, D'Auria JC (January 2015).
"The last step in cocaine biosynthesis is catalyzed by a BAHD acyltransferase" .
Plant Physiology . 167 (1): 89–101.
doi :
10.1104/pp.114.248187 .
PMC
4281001 .
PMID
25406120 .
^ Curry SH, Marler M (May 2020). "Effects of ecgonine methyl ester on cognition in scopolamine-impaired and aged rats".
Psychopharmacology . 237 (5): 1331–1342.
doi :
10.1007/s00213-020-05460-9 .
PMID
32034448 .
S2CID
211054455 .
^ Hoffman RS, Kaplan JL, Hung OL, Goldfrank LR (2004). "Ecgonine methyl ester protects against cocaine lethality in mice".
Journal of Toxicology. Clinical Toxicology . 42 (4): 349–54.
doi :
10.1081/clt-120039540 .
PMID
15461242 .
S2CID
34545574 .
^ Matthews JC, Collins A (February 1983). "Interactions of cocaine and cocaine congeners with sodium channels".
Biochemical Pharmacology . 32 (3): 455–60.
doi :
10.1016/0006-2952(83)90523-3 .
PMID
6303347 .