Phenylalaninol
Phenylalaninol, or DL-phenylalaninol, also known as phenylmethylethanolamine or as α-phenethylamine, is a psychostimulant and monoamine releasing agent of the phenethylamine family. It is related to the amino acid phenylalanine and to the phenethylamine psychostimulants β-phenethylamine and amphetamine.
Phenylalaninol is a psychostimulant and selective norepinephrine releasing agent or norepinephrine-preferring norepinephrine–dopamine releasing agent. The values of phenylalaninol for monoamine release are 106nM for norepinephrine, 1,355nM for dopamine, and >10,000nM for serotonin in rat brain synaptosomes. It is dramatically less potent as an MRA than phenethylamine or amphetamine. The potency of phenylalaninol in inducing norepinephrine release is 13-fold higher than its potency in inducing dopamine release. Similarly to other dopamine releasers like amphetamine, the drug shows cocaine-like effects and reinforcing properties in rhesus monkeys. The much greater potency of phenylalaninol in inducing norepinephrine over inducing dopamine release does not appear to interfere with its dopamine release-mediated reinforcing effects.
The clinically used stimulant, wakefulness-promoting agent, and well-balanced norepinephrine–dopamine reuptake inhibitor solriamfetol is a derivative of phenylalaninol with a carbamoyl substitution at the hydroxyl group of the molecule. Phenylalaninol is a known impurity in chemical synthesis of solriamfetol.
The predicted log P of phenylalaninol is 0.7 to 0.77 and hence it is relatively hydrophilic. The compound appears to be actively transported in the body by some of the same membrane [transport protein|transporter]s that transport phenylalanine, such as LAT3.