Pharmacology of Cocaine

Abstract

Chemically, cocaine is a [1R, 2R, 3S, 5S]-3-(benzoyloxy)-8-methyl-8-azabicyclo-­[3.2.1] octane-2-carboxylic acid methyl ester, or the methyl ester of benzoylecgonine. It appears as cocaine base (CAS-50-36-2) and the hydrochloride salt (CAS-53-21-4). There the three components of the molecule, the dotted lines around each component in the drawing mark important parts: ecgonine, methyl alcohol, and benzoic acid (Fig. 30).

Cocaine is still classified as a narcotic by the federal government. It is found in Schedule II of the Controlled Substances Act of 1970, and is subject to all the restrictions placed on opioids also found in Schedule II. Cocaine is at present only approved for topical administration. Its primary use is in ENT surgery, particularly of the nose, pharynx, etc. The esters and derivatives of ecgonine, which are convertible to ecgonine and cocaine, are also controlled according to that Convention. Coca leaf is separately listed in Schedule I and is defined by Article 1, Paragraph 1, as: “The leaf of the coca bush, except a leaf from which all ecgonine, cocaine and any other ecgonine alkaloids have been removed”. Cocaine is part of the alkaloids contained in the leaves (folia coca) of the coca bush Erythroxylon coca. It is a white, crystal-like powder, and when in the form of crack, cocaine base usually occurs as small (100–200 mg) lumps (‘rocks’).