{{Chembox | ImageFile = Methyl ecgonine.svg | IUPACName = methyl 3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate | OtherNames = {{Unbulleted list | Ecgonine methyl ester | EME | Methyl ecgonine }} | Section1={{Chembox Identifiers | index1_label = unspecified sterocentres <!-- name --> | CASNo_Ref = {{Cascite|changed|CAS}} | CASNo = 7143-09-1 | ChEMBL = 305331 | ChemSpiderID = 94674 | PubChem = 104904 | PubChem1 = 251884 | UNII = Y35FJB3QBJ | StdInChI=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 | InChIKey = QIQNNBXHAYSQRY-UYXSQOIJSA-N | InChI1 = 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 | InChIKey1 = QIQNNBXHAYSQRY-UHFFFAOYSA-N | SMILES1 = CN1C2CCC1C(C(C2)O)C(=O)OC | SMILES = CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)O)C(=O)OC }} |Section2={{Chembox Properties | C=10 | H=17 | N=1 |O=3 }} }}
'''Methylecgonine''', also known as '''ecgonine methyl''' '''ester''' is a prominent tropane alkaloid found in coca leaves.<ref>{{cite journal|title=Variation of Alkaloid Content in Erythroxylum coca Leaves from Leaf Bud to Leaf Drop |jstor = 42759059|url=https://www.jstor.org/stable/42759059|last1 = Johnson|first1 = Emanuel L.|last2 = Emche|first2 = Stephen D.|journal = Annals of Botany|year = 1994|volume = 73|issue = 6|pages = 645–650|doi = 10.1006/anbo.1994.1081| bibcode=1994AnBot..73..645J |url-access = subscription}}</ref> It is metabolite of cocaine,<ref name="pmid7078101">{{cite journal |vauthors=Ambre JJ, Ruo TI, Smith GL, Backes D, Smith CM |title=Ecgonine methyl ester, a major metabolite of cocaine |journal=Journal of Analytical Toxicology |volume=6 |issue=1 |pages=26–9 |date=1982 |pmid=7078101 |doi=10.1093/jat/6.1.26 |url= |issn=}}</ref> 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''<ref name="pmid20858536">{{cite journal |vauthors=El Bazaoui A, Bellimam MA, Soulaymani A |title=Nine new tropane alkaloids from Datura stramonium L. identified by GC/MS |journal=Fitoterapia |volume=82 |issue=2 |pages=193–7 |date=March 2011 |pmid=20858536 |doi=10.1016/j.fitote.2010.09.010 |url= |issn=}}</ref> and ''Datura innoxia''.<ref name="El BazaouiBellimam2012">{{cite journal|last1=El Bazaoui|first1=Ahmed|last2=Bellimam|first2=My Ahmed|last3=Soulaymani|first3=Abdelmajid|title=Tropane Alkaloids of Datura innoxia from Morocco|journal=Zeitschrift für Naturforschung C|volume=67|issue=1–2|year=2012|pages=8–14|issn=1865-7125|doi=10.1515/znc-2012-1-202|pmid=22486036|s2cid=21953079 |doi-access=free}}</ref>
== Biosynthesis == It is the last step before cocaine is biosynthesized in coca plants with the help of BAHD acyltransferase.<ref name="pmid25406120">{{cite journal |vauthors=Schmidt GW, Jirschitzka J, Porta T, Reichelt M, Luck K, Torre JC, Dolke F, Varesio E, Hopfgartner G, Gershenzon J, D'Auria JC |title=The last step in cocaine biosynthesis is catalyzed by a BAHD acyltransferase |journal=Plant Physiology |volume=167 |issue=1 |pages=89–101 |date=January 2015 |pmid=25406120 |pmc=4281001 |doi=10.1104/pp.114.248187 |url= |issn=}}</ref>
== Animal study == Animals study suggest that it has beneficial effect on cognition and protects against cocaine lethality.<ref name="pmid32034448">{{cite journal |vauthors=Curry SH, Marler M |title=Effects of ecgonine methyl ester on cognition in scopolamine-impaired and aged rats |journal=Psychopharmacology |volume=237 |issue=5 |pages=1331–1342 |date=May 2020 |pmid=32034448 |doi=10.1007/s00213-020-05460-9 |s2cid=211054455 |url= |issn=}}</ref><ref name="pmid15461242">{{cite journal |vauthors=Hoffman RS, Kaplan JL, Hung OL, Goldfrank LR |title=Ecgonine methyl ester protects against cocaine lethality in mice |journal=Journal of Toxicology. Clinical Toxicology |volume=42 |issue=4 |pages=349–54 |date=2004 |pmid=15461242 |doi=10.1081/clt-120039540 |s2cid=34545574 |url= |issn=}}</ref> It showed inhibition of sodium channels only at very high dosages.<ref name="pmid6303347">{{cite journal |vauthors=Matthews JC, Collins A |title=Interactions of cocaine and cocaine congeners with sodium channels |journal=Biochemical Pharmacology |volume=32 |issue=3 |pages=455–60 |date=February 1983 |pmid=6303347 |doi=10.1016/0006-2952(83)90523-3 |url= |issn=}}</ref>
== See also == * Ecgonine
== References == {{Reflist}}
Category:Coca tropane alkaloids Category:Beta-Amino acids
{{Alkaloid-stub}}