Α-Methylphenylalanine Explained

α-Methylphenylalanine (α-MePhe or AMPA) is an artificial amino acid and a phenethylamine and amphetamine derivative.[1] It is the α-methylated analogue of phenylalanine, the precursor of the catecholamine neurotransmitters, and the amino acid analogue of amphetamine (α-methylphenethylamine), a psychostimulant and monoamine releasing agent.

α-MePhe is a tyrosine hydroxylase inhibitor, thereby preventing the transformation of tyrosine into L-DOPA, and results in depletion of the catecholamine neurotransmitters.[2] It is also an inhibitor of phenylalanine hydroxylase, and in conjunction with phenylalanine administration, induces hyperphenylalaninemia analogous to that in phenylketonuria in animals.[3] [4] [5] [6] [7] The drug is known to produce metaraminol (3,β-dihydroxyamphetamine), a catecholamine releasing agent, as an active metabolite in animals, and this metabolite contributes to its effects.[8]

α-MePhe is a substrate of the L-type amino acid transporter 1 (LAT1), which transports it across the blood–brain barrier into the central nervous system.[9] [10]

See also

Notes and References

  1. Web site: alpha-methyl-L-phenylalanine . 8 October 2024 . PubChem.
  2. Torchiana ML, Porter CC, Stone CA, Hanson HM . May 1970 . Some biochemical and pharmacological actions of α-methylphenylalanine . Biochem Pharmacol . 19 . 5 . 1601–1614 . 10.1016/0006-2952(70)90148-6 . 4998458.
  3. Wyse AT, Dos Santos TM, Seminotti B, Leipnitz G . June 2021 . Insights from Animal Models on the Pathophysiology of Hyperphenylalaninemia: Role of Mitochondrial Dysfunction, Oxidative Stress and Inflammation . Mol Neurobiol . 58 . 6 . 2897–2909 . 10.1007/s12035-021-02304-1 . 33550493.
  4. Alexander SP, Fabbro D, Kelly E, Mathie A, Peters JA, Veale EL, Armstrong JF, Faccenda E, Harding SD, Pawson AJ, Sharman JL, Southan C, Davies JA . December 2019 . THE CONCISE GUIDE TO PHARMACOLOGY 2019/20: Enzymes . Br J Pharmacol . 176 Suppl 1 . Suppl 1 . S297–S396 . 10.1111/bph.14752 . 6844577 . 31710714.
  5. Benevenga NJ, Steele RD . 1984 . Adverse effects of excessive consumption of amino acids . Annu Rev Nutr . 4 . 157–181 . 10.1146/annurev.nu.04.070184.001105 . 6235826.
  6. Greengard O, Yoss MS, Del Valle JA . June 1976 . Alpha-methylphenylalanine, a new inducer of chronic hyperphenylalaninemia in sucling rats . Science . 192 . 4243 . 1007–1008 . 10.1126/science.944951 . 944951.
  7. Huether G, Neuhoff V . 1981 . Use of alpha-methylphenylalanine for studies of brain development in experimental phenylketonuria . J Inherit Metab Dis . 4 . 2 . 67–68 . 10.1007/BF02263594 . 6790851.
  8. Bollinger FW . April 1971 . Resolution of DL-alpha-methylphenylalanine . J Med Chem . 14 . 4 . 373–375 . 10.1021/jm00286a028 . 5553758.
  9. Zhang J, Xu Y, Li D, Fu L, Zhang X, Bao Y, Zheng L . 2020 . Review of the Correlation of LAT1 With Diseases: Mechanism and Treatment . Front Chem . 8 . 564809 . 10.3389/fchem.2020.564809 . 7606929 . 33195053 . free.
  10. Chen S, Jin C, Ohgaki R, Xu M, Okanishi H, Kanai Y . February 2024 . Structure-activity characteristics of phenylalanine analogs selectively transported by L-type amino acid transporter 1 (LAT1) . Sci Rep . 14 . 1 . 4651 . 10.1038/s41598-024-55252-w . 10897196 . 38409393.

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