2, 5-Dimethoxy-4-methylamphetamine

Silverman, P.B., and Ho, B.T. The discriminative stimulus properties of 2,5-dimethoxy-4-methylamphetamine (DOM) Differentiation from amphetamine. Psychopharmacology (Berlin) 68 209-215, 1980. 

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. 

Commissaris, R. L., Lyness, W. H., Cordon, J. J., Moore, K. E., and Rech, R. H. (1980) The effects of d-lysergic acid diethylamide (LSD), 2,5-dimethoxy-4-methylamphetamine (DOM) and d-amphetamine on operant responding in control and 6-hydroxydopamine-treated rats. Pharmacol. Biochem. Behav., 13 621-626. 

Harvey, J. A., Gormezano, I., and Cool, V. A. (1982) Effects of d-lysergic acid diethylamide, d-2-bromo-lysergic acid diethylamide, d-l-2-5-dimethoxy-4-methylamphetamine and d-am-... 

Cheng, H. C., Long, J. P., Nichols, D. E., and Barfknecht, C. F. (1974) Effects of psychotomimetics on vascular strips Studies of methoxylated amphetamines and optical isomers of 2,5-dimethoxy-4-methylamphetamine and 2,5-dimethoxy-4-bromoamphetamine. J. Pharmacol. Exp. Ther., 188 114-123. 

Snyder, S. H., Weingartner, H., and Faillace, L. A. (1970) DOET (2,5-dimethoxy-4-ethylam-phetamine) and DOM (STP) (2,5-dimethoxy-4-methylamphetamine), new psychotropic agents Ther effects in man. In Psychotomimetic Drugs, edited by D. Efron, pp. 247-264. Raven Press, New York. 

It is probably best to avoid p-methoxyamphetamine (PMA) and 2,5-dimethoxy-4-methylamphetamine (STP), the former because it seems to have a high toxicity and the latter because it lasts too long (e.g., 24 hours for a minimum dose). Other 4-alkyl amphetamines also seem to be toxic. A number of apparent fatalities due to MDA have been noted, but the reports usually involve very large amounts, often in combination with other drugs (e.g., 7 g MDA plus barbiturates) and screening for other, more toxic drugs (in particular, PMA) has not been done. 

Sagales T, Erill S, Domino EF. (1975). Effects of repeated doses of scopolamine on the electroencephalographic stages of sleep in normal volunteers. Clin Pharmacol Ther. 18(06) ITJ-yi. Sanders-Bush E, Burris KD, Knoth K. (1988). Lysergic acid diethylamide and 2,5-dimethoxy-4-methylamphetamine are partial agonists at serotonin receptors linked to phosphoinositide hydrolysis. J Pharmacol Exp Ther. 246(3) 924-28. 

V4. Van Vunakis, H., Bradvica, H., Benda, P., and Levine, L., Production and specificity of antibodies directed toward 3,4,5-trimethoxyphenylethylamine, 3,4-dimethoxyphenylethylamine and 2,5-dimethoxy-4-methylamphetamine. Biochem. Pharmacol. 18, 393-404 (1969). 

SYNTHESIS A fused sample of 5.0 g of white, crystalline free base 2,5-dimethoxy-4-methylamphetamine, DOM, was treated with 10 mL ethyl formate, and held at reflux on the steam bath for several h. Removal of the solvent gave 5.5 g of a white solid, which could be recrystallized from 15 mL MeOH to give 3.8 g of fine white crystals of 2,5-dimethoxy-N-formyl-4-methylamphetamine. An analytical sample from ethyl formate gave granular white crystals. 

DOB (2, 5-dimethoxy-4 bromoamphetamine) and DOM (2, 5-dimethoxy-4-methylamphetamine). DOM, also known as STP, gained a considerable following in the 1960s, despite its association with violent behavior. 2-CB is distantly related to MDMA (ecstasy). 

Sanders-Bush E, Burris KD, Knoth K. Lysergic acid diethylamide and 2,5-dimethoxy-4-methylamphetamine are partial agonists at serotonin receptors linked to phosphoinositide hydrolysis. J Pharmacol Exp Ther 1988 246 924-928. 

Muschamp JW, Regina MJ, Hull EM, Winter JC, Rabin RA. Lysergic acid diethylamide and [-]-2,5-dimethoxy-4-methylamphetamine increase extracellular glutamate in rat prefrontal cortex. Brain Res 2004 1023(1) 134—140. 

Synonym. 2,5-Dimethoxy-4-methylamphetamine 2,5-Dimethoxy-4,a-dimethylphenethylamine Cl 2H19NO2 = 209.3 CAS—15588-95-1... 

The behavioural effects of 2,5-dimethoxy-4 methylamphetamine (DOM), 2,5, dimethoxy-4-ethylamphetamine (DOET) and a series of 6 substituted phenyl amino-butanes, were compared with the behavioural effects of lysergic acid diethylamide (LSD), mescaline and (+ )-amphetamine. 

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