Amphetamine, chemical 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 ... 

Chemical Structures. Figure 1 shows the chemical structures for 14 phenylethylamine compounds. Nine of these compounds are used clinically as anorectics (ii-amphetamine, phentermine, diethylpropion, phenmetrazine, phendimetrazine, clotermine, chlorphentermine, benzphetamine, and fenfluramine). Four of these compounds are not approved for clinical use and are reported to have hallucinogenic properties (MDA, PMA, DOM, and DOET). The final compound ( /-ephedrine) is used clinically for bronchial muscle relaxation, cardiovascular, and mydriatic effects. Figure 2 shows the chemical structure for MDMA, the methyl analog of MDA. MDMA is not approved for clinical use and has been reported to produce both LSD-like and cocaine-like effects. 

Figure 4.1 The chemical structure of amphetamine and fenfluramine are illustrated here. Fenfluramine (bottom) is a diet pill that is very similar in structure to amphetamine (top). Fenfluramine is an appetite suppressant, like amphetamine, but it does not have stimulant effects. Fenfluramine was proposed as a safer alternative to amphetamine and was very effective in causing weight loss, especially when used in combination with phentermine. Unfortunately, fenfluramine eventually led to devastating side effects, which led to its being withdrawn from the U.S. market.

In terms of chemical structure, amphetamines are very close to epinephrine (adrenaline), norepinephrine (noradrenaline), and dopamine, differing in the absence of a hydroxyl group in the aromatic ring and in the aliphatic chain. 

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.

A number of antidepressants do not fit neatly into the other classes. Among these are bupropion,mirtazapine, amoxapine, and maprotiline (Figure 30-5). Bupropion has a unicyclic aminoketone structure. Its unique structure results in a different side-effect profile than most antidepressants (described below). Bupropion somewhat resembles amphetamine in chemical structure and like the stimulant, has central nervous system (CNS) activating properties. 

Current MAOIs include the hydrazine derivatives phenelzine and isocarboxazid and the non-hydrazines tranylcypromine, selegiline, and moclobemide (the latter is not available in the USA). The hydrazines and tranylcypromine bind irreversibly and nonselectively with MAO-A and -B, whereas other MAOIs may have more selective or reversible properties. Some of the MAOIs such as tranylcypromine resemble amphetamine in chemical structure, whereas other MAOIs such as selegiline have amphetamine-like metabolites. As a result, these MAOIs tend to have substantial CNS-stimulating effects. 

All amphetamines are synthetic, or manufactured, substances derived from alpha-methyl-beta-phenyl-ethyl-amine, a colorless liquid consisting of carbon, hydrogen, and nitrogen. In terms of their chemical structures, amphetamines are related to two natural substances known to boost energy within the human body. Those substances are ephedrine and adrenaline. Ephedrine is a natural stimulant found in plants of the genus Ephedra. It... 

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. 

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. 

Gordon Alles, a pharmacologist associated with the Medical School of the University of California in Los Angeles and the initial sponsor of Edward Anderson s peyote studies, was very interested in this area of chemistry and eventually synthesized a number of psychoactive compounds that have chemical structures similar to that of mescaline. The best known of these are amphetamine and MDA. His discoveries inspired further investigations that led to the creation of quite a number of "one-ring substituted phenyl-isopropylamines, which look much like mescaline on the molecular level but so far rarely have been found in the natural world. Many of these compounds will be discussed in Chapter Five. 

Fig. 1. A. Chemical structure of key molecules involved in the key steps in intracerebral synthesis and metabolism of dopamine. The successive steps are regulated by the enzymes tyrosine hydroxylase (TH), aromatic amino acid decarboxylase (AADC), monoamine oxidase (MAO) and dopamine-p-hydroxylase (DBH). B. Structure of key toxins and other drugs acting on dopamine neurones, including 6-hydroxydopamine (6-OHDA), a-methyl tyrosine, and amphetamine. For further details see Iversen and Iversen (1981) or Cooper et al. (1996).

Amphetamines are synthetic stimulants that were invented in Germany in the 1930vS. Their chemical structures resemble those of adrenaline and noradrenaline, the body s own stimulants. Their effects resemble those of cocaine but arc much longer lasting. A single oral dose of amphetamine usually stimulates the body for at least four hours. 

Look-alikes contain caffeine, ephedrine, or phenylpropanolamine, either singly or in combination. Ephedrine is a natural stimulant with a chemical structure resembling adrenaline that produces more anxiety and less euphoria than amphetamines. It... 

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. 

Many sympathomimetics have strong excitatory effects on the central nervous system. These are mostly synthetic compounds and include amphetamines. The chemical structures and abusive potential of amphetamines are discussed separately in the following section. 

Indeed, PDC catalyzes mainly the reaction of pyruvate with benzaldehyde for the formation of (R)-PAC 27. This C—C bond formation, a two-carbon unit elongation, is coupled to the concomitant decarboxylation of pyruvate 26. This reaction is industrially developed for the synthesis of (—)-ephedrine by adding a second step, a reductive amination. Ephedrine (marketed by Merck especially) is a sympathomimetic amine commonly used as a stimulant, appetite suppressant, concentration aid, and decongestant, and it is used to treat hypotension associated with anesthesia. It is similar in structure to the (semisynthetic) derivatives amphetamine and meth-amphetamine. Chemically, it is an alkaloid derived from various plants in the genus Ephedra (family Ephedra-ceae). It works mainly by increasing the activity of noradrenaline on adrenergic receptors. ... 

Structural Formula A complex of amphetamine, C HsCHjCHlCHsiNHj and tannic acid Chemical Abstracts Registry No. 1407-85-8... 

The hallucinogens generally fall into two chemical classes. The indole alkylamines include LSD, psilocybin, psilocin, dimethyltryptamine (DMT), and diethyltrypta-mine (DET), all of which are structurally similar to serotonin. The other chemical subclass of hallucinogens contains phenylethylamine derivatives such as mescaline, MDMA, MDA, and DOM (dimethoxymethyl amphetamine). A related stimulatory hallucinogen, PCP, is a piperidine analogue that produces unique effects. 

The hair treatment with concentrated solutions of sodium hydroxide allows the complete dissolution of the keratin structure by chemical hydrolysis of proteins in about 1 h. Under these conditions, some drugs such as amphetamines are volatile and thus there may be losses of the analyte. In more basic solutions occurs the complete hydrolysis of molecules such as cocaine, heroin, and 6-MAM [51]. Concentrated solutions of hydrochloric acid are also used it eliminates the problem of volatile basic compounds, but increases the time of dissolution. 

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