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Ronald T. Coutts and Jerry L. Malicky. 
“The Synthesis of Some Analogs of the Hallucinogen 1-2,5-Dimethoxy-4-methylphenyl-2-aminopropane DOM”. 
Can. J. Chem.. 1973 Oct. 31;51:1402-9.
The synthesis of a series of 4-substituted 1-2,5-dimethoxypheny1-2-aminopropanes, in which the 4-substituent is Br, CI, I, NO,, NH,, and NHAc, is described. These compounds are analogs of 1-2,5-dimethoxy-4-methylpheny1-2-aminopropane DOM, a known hallucinogen. A synthesis of N-2,5-dimethoxy-4-methylphenethylhydroxylamine, the N-hydroxy homolog of DOM, is also reported. Brief reference is made to the preliminary pharmacology of these compounds.
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