Methylecgonidine
Encyclopedia
Methylecgonidine is a chemical intermediate derived from ecgonine
or cocaine
.
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
. 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. Methylecgonidine has been shown to be specifically more harmful to the body than other byproducts of cocaine; for example to the heart, lungs & liver.
It is also used in scientific research for the manufacture of phenyltropane
analogues
such as Troparil, Dichloropane, Iometopane 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. 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
.
Ecgonine
Ecgonine is an organic chemical and tropane alkaloid found naturally in coca leaves. It has a close structural relation to cocaine: it is both a metabolite and a precursor, and as such, it is a controlled substance, as are all known substances which can be used as precursors to ecgonine...
or cocaine
Cocaine
Cocaine is a crystalline tropane alkaloid that is obtained from the leaves of the coca plant. The name comes from "coca" in addition to the alkaloid suffix -ine, forming cocaine. It is a stimulant of the central nervous system, an appetite suppressant, and a topical anesthetic...
.
Methylecgonidine is a pyrolysis
Pyrolysis
Pyrolysis is a thermochemical decomposition of organic material at elevated temperatures without the participation of oxygen. It involves the simultaneous change of chemical composition and physical phase, and is irreversible...
product formed when crack cocaine
Crack cocaine
Crack cocaine is the freebase form of cocaine that can be smoked. It may also be termed rock, hard, iron, cavvy, base, or just crack; it is the most addictive form of cocaine. Crack rocks offer a short but intense high to smokers...
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
Metabolite
Metabolites are the intermediates and products of metabolism. The term metabolite is usually restricted to small molecules. A primary metabolite is directly involved in normal growth, development, and reproduction. Alcohol is an example of a primary metabolite produced in large-scale by industrial...
. Methylecgonidine has a relatively short half-life of 18-21 minutes, after which it is metabolised to ecgonidine
Ecgonidine
Ecgonidine is an alkaloid related to ecgonine and cocaine. It has a structure with a cycloheptene ring, with a nitrogen bridge, and a carboxylic acid side chain....
, meaning that the relative concentrations of the two compounds can be used to estimate how recently crack cocaine has been smoked. Methylecgonidine has been shown to be specifically more harmful to the body than other byproducts of cocaine; for example to the heart, lungs & liver.
It is also used in scientific research for the manufacture of phenyltropane
Phenyltropane
Phenyltropanes were originally developed to reduce cocaine addiction and dependency. In general these compounds act as inhibitors of the plasmalemmal monoamine reuptake transporters. Although RTI holds a strong position in this field, they are not the only researchers that have prepared these...
analogues
Analog (chemistry)
In chemistry, a structural analog , also known as chemical analog or simply analog, is a compound having a structure similar to that of another one, but differing from it in respect of a certain component. It can differ in one or more atoms, functional groups, or substructures, which are replaced...
such as Troparil, Dichloropane, Iometopane and CFT. Methylecgonidine could also theoretically be used to produce cocaine
Cocaine
Cocaine is a crystalline tropane alkaloid that is obtained from the leaves of the coca plant. The name comes from "coca" in addition to the alkaloid suffix -ine, forming cocaine. It is a stimulant of the central nervous system, an appetite suppressant, and a topical anesthetic...
and so may be a controlled substance
Controlled substance
A controlled substance is generally a drug or chemical whose manufacture, possession, or use are regulated by a government. This may include illegal drugs and prescription medications ....
in some countries.
When methylecgonidine is made synthetically for research purposes, it is usually produced by reacting cocaine or ecgonine with hydrochloric acid
Hydrochloric acid
Hydrochloric acid is a solution of hydrogen chloride in water, that is a highly corrosive, strong mineral acid with many industrial uses. It is found naturally in gastric acid....
, yielding ecgonidine
Ecgonidine
Ecgonidine is an alkaloid related to ecgonine and cocaine. It has a structure with a cycloheptene ring, with a nitrogen bridge, and a carboxylic acid side chain....
(anhydroecgonine), followed by methylation to yield methylecgonidine. 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
Methylamine
Methylamine is the organic compound with a formula of CH3NH2. This colourless gas is a derivative of ammonia, but with one H atom replaced by a methyl group. It is the simplest primary amine. It is sold as a solution in methanol, ethanol, THF, and water, or as the anhydrous gas in pressurized...
and sodium hydroxide, followed by reaction with a mixture of methanol
Methanol
Methanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...
and sulfuric acid
Sulfuric acid
Sulfuric acid is a strong mineral acid with the molecular formula . Its historical name is oil of vitriol. Pure sulfuric acid is a highly corrosive, colorless, viscous liquid. The salts of sulfuric acid are called sulfates...
.