Trimethoxy-amphetamine

Hallucinogenic effects from nutmeg can be achieved from doses of 5-30 g. Also, elemicin and myristicin, which are present in this familiar spice, can be converted by transamination reactions to the two phenylethylamines 3,4,5-trimethoxy-amphetamine (TMA) and 3-methoxy-4,5-methylenedioxyamphet-amine (MMDA), whose psychoactive effects are well known (see Fig. 6-1). Nutmeg oil is also consumed in closed wards and prisons [3,15]. 

In these amphetamine derivatives, the hallucinogenic effects are predominant, exceeding those of the phenylethylamines many times over. Thus, for example, 2,5-dimethoxy-4-methylamphetamine (DOM) has approximately 100 times the effect of mescalin [11]. Its effects of serenity, tranquility, and peace give the product its scene name STP . All substances, including 3,4,5-trimethoxy-amphetamine (TMA), which is also a metabolite of elemicine (a constituent of nutmeg), and 4-bromo-2,5-dimethoxyamphetamine (DOB), have been almost completely displaced by the methylenedioxyamphetamines and today play an insignificant role in the drug scene. 

Fig. 9. Psychotomimetic agents derived from -phenyiethyiamine. TMA trimethoxy-amphetamine DOM 2,5-dimethoxy-4-methylamphetamine MDA methylenedioxy-...

These compounds are analogs of the trimethoxy type compounds. They produce a pleasant, euphoric trip, much like a cross between mescaline and crank. The starting material (benzene ring) makes considerable difference in the potency of the final product of this or any other amphetamine. Below is a list of benzenes and their potency in M.U. (mescaline units). Also, the modification to the ring can create, more or less, a psychedelic effect. 

The enzymic oxidative deamination of simple phenethylamines is exemplified by the reported bio transformations of mescaline (146) (114, 115) and ephedrine (148) (116). Mescaline is metabolized to 3,4,5-trimethoxy-phenylacetic acid by tissue homogenates of mouse brain, liver, kidney, and heart (114,115). 3,4,5-Trimethoxybenzoic acid is also formed as a minor metabolite. The formation of jV-acetylmescaline (147), a significant metabolite in vivo, was not observed in the in vitro studies. Both D-(—)-and L-(+)-ephedrine have been incubated with enzyme preparations from rabbit liver norephedrine (149), benzoic acid, and 1-phenyl-1,2-propanediol were characterized as metabolites (116). The D-(—)-isomer was the better substrate, being more rapidly converted. Similar results were previously reported with rabbit liver slices as the source of enzyme (153,154). The enzymic degradation of the side chain of /i-phenethylamines has been extensively investigated with nonalkaloid substrates such as amphetamine (151) and jV-methylamphetamine (150) (10,155-157), and the reader is referred to these studies for a more comprehensive coverage of this aspect of the subject. 

Material A chemical related to mescaline and the amphetamines found in the roots of sweet flag ( Acorus calamus ) and Asarum spp. It is chemically the precusor of TMA-2 (2,4,5-trimethoxy-a-methyl-4,5-methylenedioxyphenylethylamine), a hallucinogen with 18 times the gram potency of mescaline. Asarone is converted to TMA-2 in the body by aminization which takes place shortly after ingestion. 

A solution of 15 g 3,4,5-trimethoxy propiophenone in a little absolute alcohol is stirred in, under warming in a bath (of saturated chlorine calcium solution), alternating with larger pieces sodium and alcohol, whereby at least 75 g sodium and 600 ccm absolute alcohol is necessary. After the sodium disappears in the mixture, is diluted with water (2L), acidified with hydrochloric acid, the alcohol distilled and then extracted with ether. Evaporation of the ether leaves 9 g of Divarin dimethylether. Source Asahina 1936 For use of selenium dioxide to crack off para methoxy group see page 180 in Amphetamine Syntheses Industrial. 

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