Phenylalaninol

Not to be confused with Phenylalanine or DL-Phenylalanine.

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]

Phenylalaninol

Clinical data
Other names	DL-Phenylalaninol; Phenylmethylethanolamine; Benzylethanolamine; DL-Phenylglycinol; α-(Hydroxymethyl)phenethylamine; PAL-329; PAL329
Drug class	Psychostimulant; Norepinephrine releasing agent; Norepinephrine–dopamine releasing agent
Identifiers
IUPAC name 2-amino-3-phenylpropan-1-ol
CAS Number	16088-07-6
PubChem CID	76652
ChemSpider	69116
UNII	C8L8LX87R1
ChEMBL	ChEMBL21676
CompTox Dashboard (EPA)	DTXSID90863121
ECHA InfoCard	100.106.984
Chemical and physical data
Formula	C9H13NO
Molar mass	151.209 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1=CC=C(C=C1)CC(CO)N
InChI InChI=1S/C9H13NO/c10-9(7-11)6-8-4-2-1-3-5-8/h1-5,9,11H,6-7,10H2 Key:STVVMTBJNDTZBF-UHFFFAOYSA-N

Phenylalaninol is a psychostimulant and selective norepinephrine releasing agent (NRA) or norepinephrine-preferring norepinephrine–dopamine releasing agent (NDRA).^[1][2] The EC₅₀Tooltip half-maximal effective concentration 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]