Ecgonine is an organic chemical and tropane alkaloid

Tropane alkaloid

Tropane alkaloids are a class of alkaloids and secondary metabolites that contain a tropane ring in their chemical structure...

 found naturally in coca

Coca

Coca, Erythroxylum coca, is a plant in the family Erythroxylaceae, native to western South America. The plant plays a significant role in many traditional Andean cultures...

 leaves. It has a close structural relation to 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 is both 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...

 and a precursor, and as such, it is 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 ....

, as are all known substances which can be used as precursors to ecgonine itself.

Structurally, ecgonine is a cycloheptane

Cycloheptane

Cycloheptane is a cycloalkane with the molecular formula C7H14. Cycloheptane is used as a nonpolar solvent for the chemical industry and as an intermediate in the manufacture of chemicals and pharmaceutical drugs. It may be derived by Clemmensen reduction from cycloheptanone. Cycloheptane vapour is...

 derivative with a nitrogen bridge. It is obtained by hydrolysis

Hydrolysis

Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...

 of 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...

 with acids or alkali

Alkali

In chemistry, an alkali is a basic, ionic salt of an alkali metal or alkaline earth metal element. Some authors also define an alkali as a base that dissolves in water. A solution of a soluble base has a pH greater than 7. The adjective alkaline is commonly used in English as a synonym for base,...

s, and crystallizes with one molecule of water, the crystals melting at 198–199 °C. It is levorotary, and on warming with alkalis gives iso-ecgonine, which is dextrorotary.

It is a tertiary base, and has the properties of an acid and an alcohol. It is the 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...

 corresponding to tropine

Tropine

Tropine is a derivative of tropane containing a hydroxyl group at third carbon. It is also called 3-tropanol.Benzatropine and etybenzatropine are derivatives of tropine. It is also a building block of atropine, a cholinergic drug prototypical of the muscarinic antagonist class.-External Links:*...

, for it yields the same products on oxidation, and by treatment with phosphorus pentachloride is converted into anhydroecgonine, C₉H₁₃NO₂, which, when heated to 280 °C 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....

, eliminates carbon dioxide

Carbon dioxide

Carbon dioxide is a naturally occurring chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom...

 and yields tropidine, C₈H₁₃N.

See also

• Anhydroecgonine
• Benzoylecgonine
  Benzoylecgonine
  Benzoylecgonine is a topical analgesic and the main metabolite of cocaine.-History:Benzoylecgonine is used as the main pharmaceutical ingredient in the prescription drug Esterom, a topical solution used for the relief of muscle pain....
  
  
• Cocaethylene
  Cocaethylene
  Cocaethylene is the ethyl ester of benzoylecgonine. It is structurally similar to cocaine, which is the methyl ester of benzoylecgonine. Cocaethylene is formed in vivo when cocaine and ethyl alcohol have been ingested simultaneously....
  
  
• 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...
  
  
• Cuscohygrine
  Cuscohygrine
  Cuscohygrine is a pyrrolidine alkaloid found in coca. It can be extracted from plants of the family Solanaceae as well, including Atropa belladonna , Datura inoxia and Datura stramonium...
  
  
• Dihydrocuscohygrine
• Hydroxytropacocaine
  Hydroxytropacocaine
  Hydroxytropacocaine is a tropane alkaloid found in Erythroxylum coca....
  
  
• Hygrine
  Hygrine
  Hygrine is a pyrrolidine alkaloid, found mainly in coca leaves . It was first isolated by Carl Liebermann in 1889 as an alkaloid accompanying cocaine in coca. Hygrine is extracted as a thick yellow oil, having a pungent taste and odor....
  
  
• 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...
  
  
• Salicylmethylecgonine
  Salicylmethylecgonine
  Salicylmethylecgonine, is a tropane derivative drug which is both a synthetic analogue and a possible active metabolite of cocaine...
  
  
• Tropinone
  Tropinone
  Tropinone is an alkaloid, famously synthesised in 1917 by Robert Robinson as a synthetic precursor to atropine, a scarce commodity during World War I. Tropinone and the alkaloids cocaine and atropine all share the same tropane core structure.-Synthesis:...
  
  
• Truxilline
• Tropacocaine
  Tropacocaine
  Tropacocaine is a cocaine related alkaloid....
  
  
• Troparil