Hallucinogens entactogens

N-methylation greatly attenuates hallucinogenic activity, but has no significant effect on potency of entactogens. N-ethylation also seems to allow compounds to retain entactogenic activity. 

The more active stereochemistry of the entactogens is S, while that of the hallucinogenic amphetamines is R. 

Extension of the alpha-methyl to an alpha-ethyl abolishes hallucinogenic activity, but has only a minor effect on entactogens. 

Nichols, DE. Differences between the mechanisms of action of MDMA, MBDB, and the classical hallucinogens. Identification of a new therapeutic class Entactogens. J Psychoactive Drugs 18 305-313, 1986. 

Amphetamine and methamphetamine possess an essentially pure psychostimulant effect however, substituted derivatives in position 3 and 4 on benzene ring are defined as entactogene [14], This class of substances includes methylenedioxymethamphetamine (MDMA), methylenedioxyamphetamine (MDA), methylenedioxyethyl-amphetamine (MDEA), and others such as the /V-melhyl-l-(3-4-methylenedioxyphenyl)-2-butanamine (MBDB), methoxymethylenedioxyam-phetamine (MMDA) (Fig. 4). All of these substances are more active in the d form. There are also amphetamine-like substances which combine sympathomimetic (euphoric) and hallucinogen effects they are primary amines, trisubstituted on the benzene ring, that produce effects similar to mescaline. Among these the 2,5-dime-thoxy-4-methylamphetamine (DOM) is the most important. 

Entactogene and hallucinogenic amphetamines, furthermore, have an effect on the serotonin system by increasing the availability of serotonin, a neurotransmitter that controls sleep, mood, emotion, memory, perception, sexual behavior, and hunger [14],... 

These important products are not all synthetic. The oral consumption of 5-30 g nutmeg will produce hallucinogenic and entactogenic effects. The two constituents elemicine and myristicine (see Fig. 6-1) are converted by transamination in the liver to 3,4,5-trimethoxyamphetamine and MMDA [15]. 

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