Amphetamines and its derivatives

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INTRODUCTION

Amphetamine-type stimulants (ATS) are a group of drugs, mostly synthetic in origin, that are structurally derived from β-phenethylamine (Figure 1).

Amphetamine (AMP, “Speed”) was initially synthesized in Berlin in 1887 as 1-methyl-2-phenethylamine. It was the first of several chemicals, including methamphetamine (MET, “Ice”) and 3,4-methylenedioxymethamphetamine (MDMA, “Ecstasy”), which have similar structures and biological properties, and are referred to collectively as “amphetamines” (Cody, 2005). Since 1887, amphetamine was thought to be a human invention (Berman et al., 2009), but the compound was found in 1997, along with methamphetamine, nicotine and mescaline, within two species of Texas acacia bushes (Clement, Goff and Forbes, 1998). AMP and MET are most commonly abused drugs. They have asymmetric centre and exists as one of the two possible enantiomers (see Figure 2) (Cody, 2005).

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In attempt to maintain anorexic activity while limiting undesirable side effects, substitutions have been made to amphetamine and methamphetamine. Others have been made to enhance the stimulatory activity or to avoid legal restrictions on the manufacture and use of the drugs (Cody, 2005). The related groups of amphetamine derivatives are shown in Figures 3 and 4. Figure 5 shows another group of precursor drugs that is metabolized by the body into AMP and MET.

Administration and neurotoxicity of amphetamines

Amphetamines are generally administered as oral capsules. This route results in a gradual increase in drug concentration, which peaks in around an hour and maintains effective drug levels for 8 – 12 hours. Amphetamines can also be injected into the circulation (Parrott et al., 2004). Amphetamines readily cross the blood-brain barrier to reach the sites (Berman et al., 2009) of action in the brain. The acute administration of amphetamines produce a wide range of dose-dependent behavioral changes, including increased arousal or wakefulness, anorexia, hyperactivity, perseverative movements, and, in particular, a state of pleasurable affect, elation, and euphoria, which can lead to the abuse of the drug (Berman, 2009). This causes amphetamines to be associated with acts of violence. Acute drug abusers will develop tolerance, where the same dose of drug has diminishing physiological and psychological effects. They need to increase their dosage if they wish to generate the same strength of effect. Cross-tolerance will also occur as tolerance to one drug affects another drug with similar neurochemical profile. As a result, drug abusers will seek for another class of drug and become polydrug users (Parrott et al., 2004). Chronic drug abusers usually take in amphetamines through injection or smoking ice amphetamines. These abusers suffer many health problems and a reduced life expectancy. They are more susceptible to HIV (human immunodeficiency virus), AIDS (acquired immunity deficiency syndrome) and SIDS (sudden infant death syndrome) (Parrott at al., 2004).

Clinical uses

In accordance with the Convention on Psychotropic Substances of 1971,

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