Ecstasy structure

The ecstasy molecule itself is just an amphetamine with a couple of extra things attached to it. The chemical structures of the major ecstasy class drugs and speed class drugs can be seen in the preceding schematic ... 

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). 

Figure 1.1 The chemical structure of Ecstasy, shown here, is quite similar to the chemical structure of amphetamine (see inner boxed portion of chemical structure). Ecstasy s chemical structure is also similar to the chemical structure of hallucinogens and, not surprisingly, it—like all hallucinogens—is a psychoactive, mind-altering drug.

Designer drugs" include amphetamines which have been modified for heightened psychoactive effects. The use of MDMA or Ecstasy has become popular over the past few years, especially after some psychiatrists attested to its beneficial use in alleviating anxiety and emotional trauma in their patients. MDA, a structural sister to MDMA, has been found to produce destruction of serotonergic neurons in rat brain. 

Some designer drugs are mescaline analogs, meaning they are similar in chemical structure. The most popular mescaline analog is 3,4-methylenediozy-methamphetamine (MDMA or Ecstasy). Other analogs of mescaline include amphetamines and metham-phetamines. 

Not much is known about hallucinogens in general and mescaline in particular. While much of the research has pointed to the close ties with serotonin, others are now looking at the similarity between mescaline and amphetamine, with which it shares an even closer similar structure. This is especially evident in the mescaline analogs such as ecstasy, which has an extreme amphetamine-like effect on users. Amphetamines affect the adrenal system. 

Figure 15.5. Structures of some "designer drugs" of abuse. Compare the structure of alpha-methyl fentanyl with that of fentanyl, MMP+ with that of pethidine, and ecstasy with that of methamphetamine.

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. 

Structurally-related drugs include dexamfet-amine (used for narcolepsy and in attention deficit hyperactivity disorder (ADHD) see p. 387), methylphenidate (used for ADHD), tenamfetamine (Ecstasy, see p. 189), phentermine, diethylpropion, and pemoline. 

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. 

The major pharmacological action of ecstasy involves its effect on the release of neurotransmitters from nerve endings in the brain particularly serotonin and dopamine. More prolonged effects (particularly following repeated doses) involve a loss of serotonin from fhe brain also a loss of serotonergic neuronal structures. It is unclear if any ofher neurofransmitter sysfems are involved. 

The chemical name for 2CB is 4-Bromo-2, 5-Dimethoxy-phenthylamine. This increasingly popular club drug is similar in chemical structure to Ecstasy and mescaline. 

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