3.4- Methylenedioxymethamphetamine, structure

Recent controversy about the recreational abuse and potential therapeutic use of designer drugs has focused attention on MDA (methylenedioxyampheta-mine HCl) and structurally related phenylisopropylamine compounds, including MDMA istructural analogs of the psychomotor stimulant amphetamine and the hallucinogen mescaline, and produce stimulant and/or hallucinogenic effects (Shulgin 1978). 

By far the most important synthetic analog of amphetamine currently in illicit use is 3,4-methylenedioxymethamphetamine (MDMA). The formulas below show the close structural relationship of amphetamine, methamphetamine, and MDMA. 

Tenamfetamine ( ecstasy, MDMA methylenedioxymethamphetamine) is structurally related to mescaline as well as to amphetamine. It was originally patented in 1914 as an appetite suppressant and has recently achieved widespread popularity as a dance drug at rave parties (where it is deemed necessary to keep pace with the beat and duration of the music popular names reflect the appearance of the tablets and capsules and include White Dove, White Burger, Red and Black, Denis the Menace). Tenamfetamine stimulates central and peripheral a-and p-adrenoceptors thus the pharmacological effects are compounded by those of physical exertion, dehydration and heat. In susceptible individuals (poor metabolisers who exhibit the CYP450 2D6 polymorphism) a severe and fatal idiosyncratic reaction may occur with fulminant hyperthermia, convulsioirs, disseminated intravascular coagulation, rhabdomyolysis, and acute renal and hepatic failure. Treatment includes activated charcoal, diazepam for convulsions, P-blockade (atenolol) for tachycardia, a-blockade (phentolamine) for hypertension, and dantrolene if the rectal temperature exceeds 39°C. 

ECSTASY" (also known as "XTC" or "E") is the "street" name of one member of a family of amphetamine related drugs which first became popular in the "rave" or modem dance music culture across Europe in the 1980s (Table 1). Its chemical name is 3,4-methylenedioxymethamphetamine (MDMA) closely related drugs include methylenedioxyamphetamine (MDA) and methylene-dioxyethylamphetamine (MDEA). The chemical structure of this series of drugs and their relationship to older better known stimulants of abuse, amphetamine and methamphetamine, is shown in Figure 1. 

Figure 3.1 Structures of selected stimulants ephedrine (1), amphetamine (2), meth-amphetamine (3), 3,4-methylenedioxymethamphetamine (4), nikethamide (5), phen-termine (6), benzphetamine (7), strychnine (8), and cocaine (9).

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