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