Ecgonidine is an alkaloid

Alkaloid

Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...

 related to ecgonine

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...

 and 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...

. It has a structure with a cycloheptene

Cycloheptene

Cycloheptene is a 7-membered cycloalkene with a flash point of -6 C°. It is a raw material in organic chemistry and a monomer in polymer synthesis. Cycloheptene can exist as either the cis- or the trans-isomer.- trans-Cycloheptene :...

 ring, with a nitrogen bridge, and a carboxylic acid

Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of at least one carboxyl group. The general formula of a carboxylic acid is R-COOH, where R is some monovalent functional group...

 side chain

Side chain

In organic chemistry and biochemistry, a side chain is a chemical group that is attached to a core part of the molecule called "main chain" or backbone. The placeholder R is often used as a generic placeholder for alkyl group side chains in chemical structure diagrams. To indicate other non-carbon...

.

Methylecgonidine

Methylecgonidine

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...

 is produced by 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...

 in the process of smoking 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...

, and then subsequently metabolised to ecgonidine, and so these two compounds can be tested for as a specific biomarker for crack cocaine use. Ecgonidine is formed 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...

of methylecgonidine, and so the relative concentrations of the two compounds can be used to gauge how recently crack cocaine was smoked. If levels of methylecgonidine are higher, then the drug was smoked recently; however after a longer time period mainly ecgonidine will be present. Ecgonidine has a half-life in the body of around 94–137 minutes, and so can be used to detect use of crack cocaine up to 8–10 hours after the drug is consumed.