Stimulants cathinone

Khat produces effects similar to those of other monoamine stimulants, (i.e., increases in mental stimulation, physical endurance, elevated mood) (Widler etal. 1994 Kalix 1994 Brenneisen etal. 1990). Stimulus generalization occurs between cathinone, amphetamine, and cocaine, suggesting similar subjective effects (Huang and Wilson 1986). Similar to other monoamine stimulants, cathinone causes dose-dependent reductions in eating and body weight (Islam et al. 1990 Zelger and Carlini 1980). Oral cathinone increases sexual arousal in rats, but does not affect erectile or ejaculatory responses (Taha et al. 1995). 

Psilocin Stimulants Cathinone Ephedrine Phentermine Anabolic steroids Methandrostenolone Nandrolone Stanozolol... 

Cathinone An amphetamine derivative found in khat extracted from Catha edulis growing in the Horn of Africa, where it is widely used as a recreational stimulant. 

There are more than 40 alkaloids, glycosides, tannins, and terpenoids in khat (Elmi 1983). Two phenylalkylamines, namely, cathine (norpseudoephedrine) and cathinone [S(-)-alpha-aminopropiophenone] well account for the CNS stimulant effects (Kalix 1988) (figure 4.17). The... 

Animals self-administer cathinone in a pattern common to abuses of monoamine stimulants such as cocaine (Woolverton and Johanson 1984). Cathinone can induce a conditioned place preference in rats (Schechter 1991). Withdrawal symptoms of khat include lethargy, depression, nightmares, and mild tremor (Kalix 1994). /V-methylated cathinone (methcathinone) is more potent, and has become available on the illegal market. It was subsequently scheduled as a controlled substance (Glennon et al. 1995). 

As would be expected, khat overuse produces symptoms similar to those of other monoamine stimulants, such as cocaine or amphetamine, including signs of sympathetic overarousal. In the extreme this can involve a toxic psychosis. Disorders more frequently associated with chronic khat use in males are headaches, anorexia, insomnia, constipation, and respiratory illnesses (Kennedy et al. 1983). Females report higher incidences of acute gastritis, jaundice, bronchitis and hepatic diseases. Also, cathinone has toxic reproductive effects in humans and experimental animals (Islam et al. 1990). It decreases sperm count and motility, and increases the number of abnormal sperm cells. It also decreases plasma testosterone in rats. 

Khat Catha edulis Leaves Alkaloids cathinone, cathine Chewed, tea Stimulant Yemenis, Ethiopians, Somalis etc. East Arabia, East Africa, Madagascar... 

DRUG CLASSIFICATIONS Cathinone Schedule I, stimulant cathine Schedule IV, stimulant... 

In the 1990s, methcathinone—called by various street names such as cat, goob, Jeff, speed, bathtub speed, mulka, gaggers, the C, wild cat, Cadillac express, and ephedrine—appeared as a drug of abuse on the black market. Methcathinone, a synthetic form of cathinone, is an even more potent stimulant than its natural counterpart and is illegal in the United States. 

Although the Catha edulis plant contains a number of chemicals, vitamins, and minerals, its main active ingredient is cathinone, an alkaloid with a chemical structure similar to ephedrine and d-amphetamine. Like amphetamine, it increases the levels of dopamine in the brain and acts as a mild stimulant. For this reason, khat is sometimes referred to as a natural amphetamine. 

The fresh leaves of the khat shrub (Catha edulis) are chewed by several millions of people in East Africa and the Arabian peninsula for their euphoric and stimulating properties (284). The rather newly discovered alkaloid cathinone [(S)-a-aminopropiophenone] is responsible for the stimulating properties of khat (284). It has been shown that cathinone induces release at physiological catecholamine storage sites in a manner similar to that of amphetamine. Further results suggest that cathinone and amphetamine produce their stimulant effects via the same dopaminergic mechanism (599). The more recently discovered khat constituents merucathinone, merucathine, and pseudomerucathine were found to have only weak dopamine-releasing effects and were therefore considered unlikely to play an important role in the stimulatory actions of khat leaves (414). 

Khat is purchased as bundles of dried and fresh leaves and buds. For transport purposes, it is usually wrapped in plastic bags or banana skins to preserve its moisture content - loss of activity is observed after 48 h if the plant material dries out. However, the drug can also be obtained as dried crushed leaves or in powdered form. These materials are either chewed or used to prepare an infusion which is drunk like tea. The major part of the pharmacological action is due to cathinone, which acts as a central nervous system (CNS) stimulant, promoting excitation, reducing the need to sleep and enhancing communication. 

Chewing the leaves of Catha edulis (khat, qat) results in subjective mental stimulation, increased physical endurance, and increased self-esteem and social interaction. Until recently, this habit was confined to Arabian and East African countries, because only fresh leaves are active, but because of increased air transportation, khat is now also chewed in other parts of the world. Although cathine (norpseudoephedrine) is quantitatively the main alkaloid, the amphetamine-hke euphorigenic and sympathomimetic cardiovascular effects of khat are primarily attributed to cathinone (1). In Yemen chewers of khat produced in fields where chemical pesticides are used regularly have more sjmptoms than chewers of khat produced in fields where chemical pesticides are rarely or never used (2). 

The most common route of khat administration is chewing the fresh leaves of the plant. The juices are swallowed and contain two stimulants cathine and cathinone. These substances produce effects that are very similar to cocaine and amphetamine mediated by actions on the monoamine neurotransmitter systems. Users report that... 

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... 

Khat is a plant material widely chewed in East Africa and Yemen for its stimulant properties these are due to the alka-loidal cathinone, a compound similar to amphetamine. Methcathinone, a congener with similar effects, has been synthesized in clandestine laboratories, but widespread use in North America has not been reported. MDMA ( ecstasy ) also has stimulant properties. 

KhaL Chat quat. Leaves of Caiha edulis Forsk, Celastraceae widely used in E. Africa and Yemen as an amphetamine-like stimulant. Most important consriruent is the alkaloid cathinone, q.v. also norpseudoephedrine, cathi-dine, cathedulin. lsoln and characterization of constituents of khat O. Wolfes, Arch. Pharm. 268, 81 (1930) H. Friebel, R, Bril la, Naturwiss. 50, 354 (1963) M. Cais el al. Tetrahedron 31, 2727 (1975) R. L. Baxter et al, Chem. Commun. 1976, 463. Pharmacology of khat extracts G. A. Alles et al, J. Med. Pharm. Chem, 3, 323 (1961). Reviews A. Geta-hun, A. D, Krikorian, Econ. Bot. 27, 353, 378 (1973) P, Kalix, Gen. Pharmacol. 15, 179 (1984). 

Bupropion (amfebutamone) is a phenylisopropylaminoketone that is structurally related to the phenylisopropylamine CNS stimulant, methamphetamine, and the phenylisopropylaminoketone, cathinone (a constituent in khat), and the anorexiant, diethylpropion (Fig. 21.21). Although structurally similar to the CNS stimulants, bupropion exhibits distinctive different pharmacologic and therapeutic effects. The absence of the tricyclic ring system in bupropion results in a better adverse-effect profile than with the TCAs. The tertiary butyl group in bupropion prevents its N-dealkylation to metabolites that could possess sympathomimetic and/or anorexigenic properties. 

An important step towards identification of C. edulis constituents was the discovery of (+)-norpseudoephedrine (cathine) in dried leaves by Wolfes in 1930 and during several decades this alkaloid was thought to be the main active principle of C. edulis [96]. However, as already pointed out by Brucke (1941), (+)-noipseudoephedrine is CNS stimulant of high potency and the amount of this substance that was present in a portion of C. edulis was insufficient to account for the symptoms observed after consumption of the material [97]. Subsequently, in the course of a reinvestigation of the constituents of C. edulis leaf, the United Nations Narcotics Laboratory identified this compound as a-aminopropiophenone and the name (-)-cathinone was proposed for the new alkaloid [98]. Since then, several researches on C. edulis constituents and its pharmacological effects have been recorded [99,100]. 

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