Khat Pseudoephedrine

During the isolation of cathinone, 3,6-dimethyl-2,5-diphenyl pyrazine (3) was also found (14). This is doubtless an artifact, the product of oxidative dimerization of cathinone which involves the formation of condensation product 4 as an intermediate (18). Also found was the diketone (5) and the cinnamoyl compound (6) (14), later shown to have the (S) stereochemistry illustrated and named merucathinone (6,19,20). Merucathine (7) has also been isolated (6,21,22), and this and merucathinone are minor components. (-)-Norephedrine (8) also occurs in khat (14), and its iV-formyl derivative (9) has been found in plant material of South Arabian origin (23). Despite earlier positive reports, ephedrine and pseudoephedrine have not been verified as components of khat (14). HPLC has been employed to separate and quantify mixtures of the khatamines cathinone, (+)-norpseudoephedrine, and (—)-norephedrine in connection with a study of their distribution in different parts of the khat plant and in specimens of different geographical origin (20,21). 

KHAT OR QAT Catha edulis (Vahl) Forsk. Ex. Endl., family Celastraceae, grows in East Africa. It is cultivated in the mountainous regions (above 1,500 m) in Ethiopia, and Kenya. In countries such as Yemen, the fresh leaves are chewed or used for preparing tea, which is used as a stimulant. Khat counteracts fatigue, facilitates strenuous muscular work, and causes talkativeness. These effects depend on the occurrence in the fresh leaves of the labile alkaloid cathinone, which quickly breaks down into pseudoephedrine. The effects of cathinone are similar to those of amphetamine and there... 

All ephedra plants contain phenylalanine-derived alkaloids. These include (-)-ephedrine, (+)-pseudoephedrine, (-)-norephedrine, (+)-norpseudo-ephedrine (also called cathine because it is a major alkaloid of Catha edulis or khat, a plant used as a stimulant in North Africa), (-)-A-methylephedrine and (+)-A-methylpseudoephedrine, (+)-pseudoephedrine, and (+/-)-norephedrine (phenylpropanolamine). Significant enantioselective differences with regard to both pharmacokinetic and pharmacodynamic effects of these agents are possible. All of these alkaloids have important effects on the cardiovascular and respiratory systems, but not to the same degree. 

An updated section an aryl derivatives of amino-alcohols is included in the latest volume of Rodd. A review of the chemistry and pharmacology of the drug Khat (Catha edulis), whose main active constituent is (+)-nor-pseudoephedrine, includes... 

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