2.5- Dimethoxy-4-methyl-amphetamine

Commissaris, R. L., Lyness, W. H., Moore, M. E., and Rech, R. H. (1980) Enhancement of the behavioral effects of 2,5-dimethoxy-4-methyl-amphetamine (DOM) by pretreatment with p-chlorophenylalanine. Pharmacol. Biochem. Behav., 13 605-608. 

The phenylalkylamines mescaline, 2,5-dimethoxy-4-methyl amphetamine (DOM) and 3,4-dimethoxyphenylethylamine had no effects on caeruloplasmin — they were neither substrates nor did they modify the oxidation of known substrates. In other studies on the substrate specificity of caeruloplasmin it was noted that, in addition to being a substrate, 3-hydroxy-4-methoxyphenylethylamine accelerated the oxidation of both noradrenaline and 5-HT. Since demethylated metabolites of mescaline have been isolated by Musacchio and Goldstein (1967) from rats given this drug, it is possible that it is these metabolites which are the chemical species actually responsible for the observed central effects. In such a situation there should be a correlation between the central effects of the compound administered and the interaction of its demethylated metabolite with caeruloplasmin, but there would be no correlation between the central effects of the compounds and their effects on the enzyme. This point requires further experimental study. 

Idanpaan-Heikkila, J. E. and McIsaac, W. M. (1970) 2,5-Dimethoxy-4-methyl-amphetamine. Tissue distribution- and, neurochemical action. Biochem. Pharmacol., 19, 935-937. 

Snyder, S. H., Faillace, L. and Hollister, L. (1967) 2,5-Dimethoxy-4-methyl-amphetamine (STP). A new hallucinogenic drug. Science, 158,669-670. 

Amphetamine type of stimulants Methyl-amphetamine, 2, 5-dimethoxy-4-methyl amphetamine, methylene dioxy amphetamine Adsorption Corasil II Gradient system of ethanol/dioxan/ cyclohexylamine in hexane... 

Mescaline (3,4,5-frimethoxyphenylethylamine) and STP or DOM (2,5-dimethoxy-4-methyl amphetamine) were extracted with ether from alkaline aqueous solution. The ether extracts were mixed with CSj and allowed to stand for several hours or heated at 50 "C for 2 h, then evaporated to a small volume. 

Figure 22 HPTLC-FTIR spectra of 2,5-dimethoxy-4-methyl-phenylamine (DMMPEA, —) and 2,5-dimethoxy-4-methyl-amphetamine (DOM,...), aliphatic region (A) and aromatic region (B).

Garden City, NY, Medical Examination Publishing, 1981 Snyder SH, Faillace L 2,3-Dimethoxy-4-methyl-amphetamine (STP) a new hallucinogenic drug. Science 1388 669-670, 1967 Spielewoy C, Markou A Withdrawal from chronic phencyclidine treatment induces long-lasting depression in brain reward function. Neuropsychopharmacology 28 1106-1116,2003... 

Berger, U. Hung, G. Molliver, M.E. and Grzanna, R. Psychotropic amphetamines have different sites of action at serotonergic (5-HT) synapses A eomparison of p-chloroamphetamine (PCA) and 3,4-methyl-enedioxyamphetamine (MDA) with 2,5-dimethoxy-4-methylamphetamine (DOM). Abstr Soc Neurosci 13 906, 1987. 

EXTENSIONS AND COMMENTARY I can t remember the exact names of the companies that went with the oil additives. STP was, I believe, it s own thing, and originally stood for Scientifically Treated Petroleum. And F-310 was, I believe, a Chevron Oil product. F-320 was, of course, the product of the wild and happy chemists at the Pharmaceutical Chemistry Department at the University of California in San Francisco, playing with what they fondly called funny drugs. And when the 2,4,6-orientation became an obvious positional isomer, the Pennzoil Oil Company s additive, Z-7, was a natural to have its name volunteered to the cause. There was one additional isomer possible, with the methyl in the 2-position and the methoxyl groups at the 4- and 6-positions. This followed the more conventional aldehyde made from 3,5-dimethoxytoluene via the Vilsmeier process, with POCl3 and N-methylformanilide. This material (2,4-dimethoxy-6-methylbenzaldehyde with mp 64-65 °C from cyclohexane or from MeOH) is completely distinct from the isomer used above (2,6-dimethoxy-4-methy lbenzaldehyde with a mp of 92-93 °C from MeOH). The amphetamine from this isomer is 2,4-dimethoxy-6-methylamphetamine, and had been christened by the chemistry crowd as Z-7.1. 

SYNTHESIS To a solution of 6.0 g of the free base of 2,5-dimethoxy-N-mcthyl-amphetamine (see recipe under METHYL-DM A) in 30 mL glacial acetic acid there was added, dropwise and with good stirring, a solution of 5.5 g bromine in 15 mL acetic acid. The reaction became quite warm, and turned very dark. After stirring... 

The last of the butyl isomers, the tert-butyl compound, was made from a much more obvious starting material. This is the commercially available tert-butyl hydroquinone. It was methylated in sodium hydroxide with methyl iodide, and then carried through the above sequence (benzaldehyde. mp 124 °C from cyclohexane, nitrostyrene, yellow crystals from methanol, mp 95-96.5 °C, and lithium aluminum hydride reduction) to give 2,5-dimethoxy-4-(l,l-dimethylethyl)amphetamine hydrochloride (DOTB, mp 168 °C). Rats trained in a process called the Sidman Avoidance Schedule gave behavior that suggested that DOTB had no activity at all, and in human trials, doses of up to 25 milligrams were totally without effect. 

Amphetamines e.g. 2,S-dimethoxy-4-bromoamphetamine [S] /O Methyl esters of fatty acids [6] ... 

A number of compounds related to DOM had been synthesized and studied at the University of California at San Francisco, at about this time. Two of these were simply the juggling of the two methoxyl groups and the methyl group on the ring, still maintaining the 2,4,5-ness relative to the amphetamine chain. These are 2,4-dimethoxy-5-methylamphetamine and 4,5-dimethoxy-2-... 

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