3.4- Methylenedioxyamphetamine, structure

One of the structural features of MDMA that is somewhat unusual is the fact that it is 3,4-disubstituted. Both 3,4-methylenedioxyamphetamine (MDA) (figure 2) and MDMA possess the 3,4-methylenedioxy function, and there apparently are no other active compounds known that fall within the... 

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. 

XTC, and Adam [22]. Its name is effectively used with a nonselective form and is applied to 3,4-methylenedioxyamphetamine (MDA), and to 3,4-methylenedioxy-ethylamphetamine (MDEA) that is also known on the streets as Eve. These three compounds are quite similar in their chemical compositions and biological effects [23]. Their structures and m/z values are shown in Figure 16.6a-c. 

Amphetamine, methamphetamine, MDA (3,4-methylenedioxyamphetamine), and MDMA (3,4-methylenedioxy methamphetamine) are examples that have similar structures to catecholamines, as shown in Fig. 17.10. The strnctnral similarity snggests that they may interfere with catecholamines pathways. Amphetamine is known to bind to and block the re-nptake mechanism (i.e., reabsorb the nenrorans-mitter such as dopamine back into the presynaptic cell) and increase the level of the nenrotransmitter in the synapse. Methamphetamine seems to have a similar effect bnt even stronger than that of amphetamine. 

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