p-Ethynylphenylalanine

• CAT Number: I015571
• CAS Number: 278605-15-5
• Molecular Formula: C11H11NO2
• Molecular Weight: 189.21
• Purity: ≥95%
• Synonyms: (2S)-2-amino-3-(4-ethynylphenyl)propanoic acid
• InChI: InChI=1S/C11H11NO2/c1-2-8-3-5-9(6-4-8)7-10(12)11(13)14/h1,3-6,10H,7,12H2,(H,13,14)/t10-/m0/s1
• InChIKey: PPDNGMUGVMESGE-JTQLQIEISA-N
• SMILES: C#CC1=CC=C(C=C1)CC(C(=O)O)N

p-Ethynylphenylalanine (4-Ethynyl-L-phenylalanine) is a potent, selective, reversible and competitive inhibitor of tryptophan hydroxylase (TPH), with a Ki of 32.6 μM[1]. p-Ethynylphenylalanine is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
p-Ethynylphenylalanine selectively and reversibly inhibits the biosynthesis of serotonin[1].?
p-Ethynylphenylalanine has a low affinity for various recombinant 5-HT receptors (5-HT1, 5-HT2, 5-HT4, 5-HT5, 5-HT6, and 5-HT7)[1].
p-Ethynylphenylalanine (30 mg/kg; i.p.) decreases in 5-HT and 5-HIAA levels in the rat midbrain but not in tissue[1].?
p-Ethynylphenylalanine does not inhibit the aromatic amino acid decarboxylase[1].

Reference

[1]. Stokes AH, et al. p-ethynylphenylalanine: a potent inhibitor of tryptophan hydroxylase. J Neurochem. 2000 May;74(5):2067-73.
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