Methylecgonine

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 ;
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

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]

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.

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[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.

[pmid7078101-2] 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.

[pmid20858536-3] 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.

[El_BazaouiBellimam2012-4] 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.

[pmid25406120-5] 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.

[pmid32034448-6] 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.

[pmid15461242-7] 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.

[pmid6303347-8] 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.

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Biosynthesis

Animal study

See also

References