15588-95-1Relevant articles and documents
Stereospecific synthesis of amphetamines
Wagner, Jared M.,McElhinny Jr., Charles J.,Lewin, Anita H.,Carroll, F. Ivy
, p. 2119 - 2125 (2007/10/03)
Regioselective addition of aryl lithium to commercially available (S)-(+)-propylene oxide provides the corresponding (S)-aryl-2-propanol. The (R)-amphetamine is obtained by conversion of the alcohol to the tosylate followed by azide displacement and hydrogenation. Mitsunobu conversion of the alcohol to the (R)-bromide followed by azide displacement and hydrogenation affords the (S)-amphetamine.
Binding of Phenylalkylamine Derivatives at 5-HT1C and 5-HT2 Serotonin Receptors: Evidence for a Lack of Selectivity
Glennon, Richard A.,Raghupathi, Reva,Bartyzel, Piotr,Teitler, Milt,Leonhardt, Sigrun
, p. 734 - 740 (2007/10/02)
Certain phenyalkylamine derivatives have been considered to bind selectively at 5-HT2 serotonin receptors.It is now recognized that the most widely used derivatives, i.e., 1-(2,5-dimethoxy-4-X-phenyl)-2-aminopropanes where X = Me (DOM), Br (DOB), and I (DOI) (1-3, respectively) also bind at the more recently identified population of serotonin 5-HT1C receptors.The purpose of the present investigation was to determine whether simple phenylalkylamines bind selectively at one population of receptors over the other.An examination of 34 derivatives reveals (i) similar structure-affinity relationships and (ii) a significant correlation (r = >0.9, n = 25) between 5-HT1C and 5-HT2 affinity.None of the compounds included in the present study displayed more than a 10-fold selectivity for one population of these receptors over the other; the results suggest that these compounds (including the widely used 5-HT2 agonists DOB and DOI) are 5-HT1C/5-HT2 agents.