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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. It is related to the amino acid phenylalanine and to the phenethylamine psychostimulants β-phenethylamine (phenylethylamine) and amphetamine (α-methylphenethylamine).

D-Phenylalanine is a psychostimulant and selective norepinephrine releasing agent (NRA) or norepinephrine-preferring norepinephrine–dopamine releasing agent (NDRA). The EC₅₀Tooltip half-maximal effective concentration values of D-phenylalanine for monoamine release are 106 nM for norepinephrine, 1,355 nM for dopamine, and >10,000 nM for serotonin in rat brain synaptosomes. It is dramatically less potent as an MRA than phenethylamine or amphetamine. The potency of D-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 D-phenylalanine 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 (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. 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 transporters that transport phenylalanine, such as LAT3.

References

1. ^ Kohut SJ, Jacobs DS, Rothman RB, Partilla JS, Bergman J, Blough BE (December 2017). "Cocaine-like discriminative stimulus effects of "norepinephrine-preferring" monoamine releasers: time course and interaction studies in rhesus monkeys". Psychopharmacology (Berl). 234 (23–24): 3455–3465. doi:10.1007/s00213-017-4731-5. PMC 5747253. PMID 28889212.
2. ^ de Moura, Fernando Barreto; Sherwood, Alexander; Prisinzano, Thomas Edward; Kohut, Stephen John; Bergman, Jack (2018). "Intravenous Self-Administration of Synthetic Cathinones in Rhesus Monkeys". The FASEB Journal. 32 (S1). doi:10.1096/fasebj.2018.32.1_supplement.550.3. ISSN 0892-6638.
3. ^ "DL-Phenylalaninol". PubChem. Retrieved 15 January 2025.
4. Blough B (July 2008). "Dopamine-releasing agents" (PDF). In Trudell ML, Izenwasser S (eds.). Dopamine Transporters: Chemistry, Biology and Pharmacology. Hoboken : Wiley. pp. 305–320. ISBN 978-0-470-11790-3. OCLC 181862653. OL 18589888W.
5. Yang J, Gao J (August 2019). "Solriamfetol for the treatment of excessive daytime sleepiness associated with narcolepsy". Expert Rev Clin Pharmacol. 12 (8): 723–728. doi:10.1080/17512433.2019.1632705. PMID 31215815.
6. Fejős I, Tóth G, Várnai B, Szabó ZI, Köteles I, Malanga M, Béni S (September 2021). "Enantioseparation of solriamfetol and its major impurity phenylalaninol by capillary electrophoresis using sulfated gamma cyclodextrin". Electrophoresis. 42 (17–18): 1818–1825. doi:10.1002/elps.202100076. PMID 34109644.
7. "phenylalaninol". ChemSpider. 10 June 2024. Retrieved 15 January 2025.
8. Shimomura K, Fukushima T, Danno T, Matsumoto K, Miyoshi M (August 1975). "Inhibition of intestinal absorption of phenylalanine by phenylalaninol". J Biochem. 78 (2): 269–275. doi:10.1093/oxfordjournals.jbchem.a130904. PMID 1228171.
9. Babu E, Kanai Y, Chairoungdua A, Kim DK, Iribe Y, Tangtrongsup S, Jutabha P, Li Y, Ahmed N, Sakamoto S, Anzai N, Nagamori S, Endou H (October 2003). "Identification of a novel system L amino acid transporter structurally distinct from heterodimeric amino acid transporters". J Biol Chem. 278 (44): 43838–45. doi:10.1074/jbc.M305221200. PMID 12930836.

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