Chemistry:Α-Methylphenylalanine
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.[1]
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.[2][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
- Fenclonine (para-chlorophenylalanine)
- Metirosine (α-methyl-para-tyrosine)
- Methyldopa (α-methyl-DOPA)
- α-Methyltryptophan
- 3,4-Dihydroxystyrene
References
- ↑ 1.0 1.1 "alpha-methyl-L-phenylalanine". https://pubchem.ncbi.nlm.nih.gov/compound/2724754.
- ↑ 2.0 2.1 "Some biochemical and pharmacological actions of α-methylphenylalanine". Biochem Pharmacol 19 (5): 1601–1614. May 1970. doi:10.1016/0006-2952(70)90148-6. PMID 4998458.
- ↑ "Insights from Animal Models on the Pathophysiology of Hyperphenylalaninemia: Role of Mitochondrial Dysfunction, Oxidative Stress and Inflammation". Mol Neurobiol 58 (6): 2897–2909. June 2021. doi:10.1007/s12035-021-02304-1. PMID 33550493.
- ↑ "THE CONCISE GUIDE TO PHARMACOLOGY 2019/20: Enzymes". Br J Pharmacol 176 Suppl 1 (Suppl 1): S297–S396. December 2019. doi:10.1111/bph.14752. PMID 31710714.
- ↑ "Adverse effects of excessive consumption of amino acids". Annu Rev Nutr 4: 157–181. 1984. doi:10.1146/annurev.nu.04.070184.001105. PMID 6235826.
- ↑ "Alpha-methylphenylalanine, a new inducer of chronic hyperphenylalaninemia in sucling rats". Science 192 (4243): 1007–1008. June 1976. doi:10.1126/science.944951. PMID 944951. Bibcode: 1976Sci...192.1007G.
- ↑ "Use of alpha-methylphenylalanine for studies of brain development in experimental phenylketonuria". J Inherit Metab Dis 4 (2): 67–68. 1981. doi:10.1007/BF02263594. PMID 6790851.
- ↑ "Resolution of DL-alpha-methylphenylalanine". J Med Chem 14 (4): 373–375. April 1971. doi:10.1021/jm00286a028. PMID 5553758.
- ↑ "Review of the Correlation of LAT1 With Diseases: Mechanism and Treatment". Front Chem 8. 2020. doi:10.3389/fchem.2020.564809. PMID 33195053. Bibcode: 2020FrCh....8..967Z.
- ↑ "Structure-activity characteristics of phenylalanine analogs selectively transported by L-type amino acid transporter 1 (LAT1)". Sci Rep 14 (1). February 2024. doi:10.1038/s41598-024-55252-w. PMID 38409393. Bibcode: 2024NatSR..14.4651C.
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