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Methylecgonidine



Methylecgonidine
IUPAC name Methyl (1S,5R)-8-methyl-8-azabicyclo[3.2.1]oct-3-ene-4-carboxylate
Other names Anhydromethylecgonine
Anhydroecgonine methyl ester
Identifiers
CAS number 43021-26-7
PubChem 119478
SMILES CN1[C@H]2CC[C@@H]1C(=CC2)C(=O)OC
Properties
Molecular formula C10H15NO2
Molar mass 181.232 g/mol
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Methylecgonidine (anhydromethylecgonine; anhydroecgonine methyl ester) is a chemical intermediate derived from ecgonine or cocaine.

Additional recommended knowledge

Methylecgonidine is a pyrolysis product formed when crack cocaine is smoked, making this substance a useful biomarker to specifically test for use of crack cocaine, as opposed to powder cocaine which does not form methylecgonidine as a metabolite.[1] Methylecgonidine has a relatively short half-life of 18-21 minutes, after which it is metabolised to ecgonidine, meaning that the relative concentrations of the two compounds can be used to estimate how recently crack cocaine has been smoked.

It is also used in scientific research for the manufacture of phenyltropane analogues such as Troparil, Lometopane and CFT. Methylecgonidine could also theoretically be used to produce cocaine and so may be a controlled substance in some countries.

When methylecgonidine is made synthetically for research purposes, it is usually produced by reacting cocaine or ecgonine with hydrochloric acid, yielding ecgonidine (anhydroecgonine), followed by methylation to yield methylecgonidine.[2] Alternatively it can be made in a two step reaction by reacting 2,4,6-cycloheptatriene-7-carboxylic acid with first a mixture of methylamine and sodium hydroxide, followed by reaction with a mixture of methanol and sulfuric acid.[3]

References

  1. ^ Scheidweiler KB, Plessinger MA, Shojaie J, Wood RW, Kwong TC. Pharmacokinetics and pharmacodynamics of methylecgonidine, a crack cocaine pyrolyzate. Journal of Pharmacology and Experimental Therapeutics. 2003 Dec;307(3):1179-87.
  2. ^ Satendra Singh. Chemistry, Design, and Structure-Activity Relationship of Cocaine Antagonists. Chemistry Reviews (2000); (100):925-1024
  3. ^ Kline RH, Wright J, Fox KM, Eldefrawi ME. Journal of Medicinal Chemistry. (1990); (33):2024
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Methylecgonidine". A list of authors is available in Wikipedia.
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