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Dyer DC, Nichols DE, Rusterholz DB, Barfknecht CF. 
“Comparative effects of stereoisomers of psychotomimetic phenylisopropylamines”. 
Life Sci. 1973 Oct 25;13(7):885-96.
Stereoisomers, R- and S+, of five psychotomimetic phenylisopropylamines contracted isolated strips of sheep umbilical arteries . The compounds exhibited the following order of potency : 2,5-dimeth- oxy-4-bromo-amphetamine DOB > 2,5-dimethoxy-4-ethyl-amphetamine DOET > 2,5-dimetho -4-methyl-amphetamine DOM > 2,5-dimethoxyamphetamine 2,5-DMA > 4-methoxy-amphetamine PMA . Stereoselectivity was observed in that the R- isomers were more active than the S+ isomers except for PMA . Evidence was obtained for the action of these hallucinogens on 5-hydroxytryptamine receptors . There was a general correlation of smooth muscle stimulating activity with known hallucinogenic activity .
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