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Barfknecht CF, Nichols DE. 
“Potential psychotomimetics, Bromomethoxyamphetamines”. 
J Med Chem. 1971 Apr 07;14(4):370-2.
In they study of psychotomimetic amphetamines, 2,5- dimethoxy-4-methylamphetamine DOM is the most potent compound yet discovered 50-150 times mescaline.2 At least part of its potency is related to the nature of the para substituent. In light of Knoll's3 studies on the psychotomimetic effects of p-bromomethamphetamine and its cross- to LSD, the synthesis and evaluation of bromomethoxyamphetamines appeared to be a logical extension. Br has a comparable size, but different electronic character than Me. Kang and Green4 have recently demonstrated a correlation between the electronic character of the ring wild hallucinogenic potency of methoxylated amphetamines, The substitution of Br into various ring positions of methoxylated amphetamines allows for several electronic arrangements.
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