Phenylalaninol
Psychoactive stimulant and norepinephrine releasing agent
From Wikipedia, the free encyclopedia
Phenylalaninol (code name PAL-329), or DL-phenylalaninol, also known as phenylmethylethanolamine or as α-(hydroxymethyl)phenethylamine, is a psychostimulant and monoamine releasing agent (MRA) of the phenethylamine family.[1][2] It is related to the amino acid phenylalanine and to the phenethylamine psychostimulants β-phenethylamine (phenylethylamine) and amphetamine (α-methylphenethylamine).[3]
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| Other names | DL-Phenylalaninol; Phenylmethylethanolamine; Benzylethanolamine; DL-Phenylglycinol; α-(Hydroxymethyl)phenethylamine; PAL-329; PAL329 |
| Drug class | Psychostimulant; Norepinephrine releasing agent; Norepinephrine–dopamine releasing agent |
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| ECHA InfoCard | 100.106.984 |
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| Formula | C9H13NO |
| Molar mass | 151.209 g·mol−1 |
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Phenylalaninol is a psychostimulant and selective norepinephrine releasing agent (NRA) or norepinephrine-preferring norepinephrine–dopamine releasing agent (NDRA).[1][2] The EC50 values of phenylalaninol for monoamine release are 106 nM for norepinephrine, 1,355 nM for dopamine, and >10,000 nM for serotonin in rat brain synaptosomes.[1] It is dramatically less potent as an MRA than phenethylamine or amphetamine.[1][4] The potency of phenylalaninol in inducing norepinephrine release is 13-fold higher than its potency in inducing dopamine release.[1] Similarly to other dopamine releasers like amphetamine, the drug shows cocaine-like effects and reinforcing properties in rhesus monkeys.[1][2] 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.[1][2]
The clinically used stimulant, wakefulness-promoting agent, and well-balanced norepinephrine–dopamine reuptake inhibitor (NDRI) solriamfetol (brand name Sunosi; O-carbamoyl-D-phenylalaninol) is a derivative of phenylalaninol with a carbamoyl substitution at the hydroxyl group of the molecule.[5] Phenylalaninol is a known impurity in chemical synthesis of solriamfetol.[6]
The predicted log P of phenylalaninol is 0.7 to 0.77 and hence it is relatively hydrophilic.[3][7] The compound appears to be actively transported in the body by some of the same transporters that transport phenylalanine, such as LAT3.[8][9]
