The synthesis of enantiomers of a series of methoxy- and alkyl- substituted phenylisopropylamines is described. The synthesis comprises reducing the imines, formed by the reaction of appropriate phenylacetones with either (+)- or (-)-α-methylbenzylamine, by low-pressure reduction techniques, and subsequently subjecting the optically active N-(α-phenethyl)phenylisopropylamine derivative to hydrogenolysis. The hydrogenolysis products are characterized by enantiomeric purities in the range of 96 - 99%. Yields of products are approximately 60%.
A homologous series of 4 alkyl 2,5 dimethoxyphenylisopropylamines (alkyl = H through n C5H11 and t C4H9) was synthesized and compared with mescaline as serotonin agonists in a sheep umbilical preparation. The three carbon homolog 6d was found to be the most potent of the straight chain series in accordance with its observed psychotomimetic effectiveness in man.
Shulgin,Dyer
p. 1201 - 1204
(2007/10/06)
Asymmetric synthesis of psychotomimetic phenylisopropylamines.
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Nichols,Barfknecht,Rusterholz,Benington,Morin
p. 480 - 483
(2007/10/05)
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