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]

Other namesα-MePhe; α-Me-Phe; α-Methyl-Phe; AMPA; α-Methyl-L-Phenylalanine

Drug classTyrosine hydroxylase inhibitor; Phenylalanine hydroxylase inhibitor; Catecholamine depleting agent; Catecholamine releasing agent

CAS Number

• 23239-35-2

PubChem CID

• 2724754

Quick facts Clinical data, Other names ...

α-Methylphenylalanine

Clinical data
Other names	α-MePhe; α-Me-Phe; α-Methyl-Phe; AMPA; α-Methyl-L-Phenylalanine
Drug class	Tyrosine hydroxylase inhibitor; Phenylalanine hydroxylase inhibitor; Catecholamine depleting agent; Catecholamine releasing agent
Identifiers
IUPAC name (2S)-2-amino-2-methyl-3-phenylpropanoic acid
CAS Number	23239-35-2
PubChem CID	2724754
ChemSpider	2006873
UNII	W4V7K5BM5T
ChEBI	CHEBI:141138
ChEMBL	ChEMBL4249392
Chemical and physical data
Formula	C10H13NO2
Molar mass	179.219 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@](CC1=CC=CC=C1)(C(=O)O)N
InChI InChI=1S/C10H13NO2/c1-10(11,9(12)13)7-8-5-3-2-4-6-8/h2-6H,7,11H2,1H3,(H,12,13)/t10-/m0/s1 Key:HYOWVAAEQCNGLE-JTQLQIEISA-N

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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]