Phenylalaninol
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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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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.106.984 |
| Chemical and physical data | |
| Formula | C9H13NO |
| Molar mass | 151.209 g·mol−1 |
| 3D model (JSmol) | |
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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.[1][2] It is related to the amino acid phenylalanine and to the phenethylamine psychostimulants β-phenethylamine (phenylethylamine) and amphetamine (α-methylphenethylamine).[3]
D-Phenylalanine is a psychostimulant and selective norepinephrine releasing agent (NRA) or norepinephrine-preferring norepinephrine–dopamine releasing agent (NDRA).[1][2] The EC50 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.[1] It is dramatically less potent as an MRA than phenethylamine or amphetamine.[1][4] The potency of D-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 D-phenylalanine 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]
References
[edit]- ^ a b c d e f g 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. 234 (23–24): 3455–3465. doi:10.1007/s00213-017-4731-5. PMC 5747253. PMID 28889212.
- ^ a b c d de Moura FB, Sherwood A, Prisinzano TE, Kohut SJ, Bergman J (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.
- ^ a b "DL-Phenylalaninol". PubChem. Retrieved 15 January 2025.
- ^ Blough B (July 2008). "Dopamine-releasing agents" (PDF). In Trudell ML, Izenwasser S (eds.). Dopamine Transporters: Chemistry, Biology and Pharmacology. Hoboken [NJ]: Wiley. pp. 305–320. ISBN 978-0-470-11790-3. OCLC 181862653. OL 18589888W.
- ^ 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.
- ^ 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.
- ^ "phenylalaninol". ChemSpider. 10 June 2024. Retrieved 15 January 2025.
- ^ 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.
- ^ 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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