Description

α-Methyltryptophan (CAS: 16709-25-4) is a specialized tryptophan derivative featuring a methyl substitution at the alpha position, enhancing its biochemical stability and altering its metabolic pathways. With the molecular formula C₁₂H₁₄N₂O₂, this compound is widely utilized in neuroscience and pharmacology research, particularly in studies involving serotonin synthesis inhibition and neurotransmitter regulation. Available as a high-purity reagent, it is ideal for enzymatic assays, radiolabeling experiments (¹⁴C-labeled variants), and as a reference standard in analytical applications such as HPLC and LC-MS. Its unique structure makes it a valuable tool for investigating amino acid transport mechanisms and neurodegenerative disorders.

Properties

• CAS Number: 16709-25-4
• Complexity: 282
• IUPAC Name: (2S)-2-amino-3-(1H-indol-3-yl)-2-methyl-propanoic acid
• InChI: InChI=1S/C12H14N2O2/c1-12(13,11(15)16)6-8-7-14-10-5-3-2-4-9(8)10/h2-5,7,14H,6,13H2,1H3,(H,15,16)/t12-/m0/s1
• InChI Key: ZTTWHZHBPDYSQB-LBPRGKRZSA-N
• Exact Mass: 218.105527694
• Molecular Formula: C12H14N2O2
• Molecular Weight: 218.25
• SMILES: C[C@](CC1=CNC2=CC=CC=C21)(C(=O)O)N
• Topological: 79.1
• Monoisotopic Mass: 218.105527694
• Synonyms: 16709-25-4, alpha-Methyltryptophan, alpha-Methyl-L-tryptophan, 1F33TJ4ZOP, (-)-ALPHA-METHYLTRYPTOPHAN, UNII-1F33TJ4ZOP, L-ALPHA-METHYLTRYPTOPHAN, L-.ALPHA.-METHYLTRYPTOPHAN, .ALPHA.-METHYL-L-TRYPTOPHAN, L-TRYPTOPHAN, ALPHA-METHYL-, (-)-.ALPHA.-METHYLTRYPTOPHAN, L-TRYPTOPHAN, .ALPHA.-METHYL-, Tryptophan, alpha-methyl-, .alpha.-Methyltryptophan, UNII-260VJL1C6Q, DTXSID60350250, NSC 9948, NSC-9948, alpha-(14C)methyl-tryptophan, DTXCID70301319, ALPHA-METHYLTRYPTOPHAN, (+-), .ALPHA.-METHYLTRYPTOPHAN, (+-), A-METHYL-L-TRYPTOPHAN, (S)-2-Amino-3-(1H-indol-3-yl)-2-methylpropanoic acid, (2S)-2-amino-3-(1H-indol-3-yl)-2-methylpropanoic acid, H-alpha-Me-DL-Trp-OH, alpha-Methyl-L-tryptophane hemihydrate, ZIQ, beta-Me-L-Trp-OH, ?-Methyl-L-tryptophan, H–Me-DL-Trp-OH, Alfa-Methyl-DL-Tryptophan, alpha -Methyl-L-tryptophan, SCHEMBL162554, CHEBI:232371, AKOS015909511, AB07677, CS-0447803, G81879, (S)-2-Amino-3-(1H-indol-3-yl)-2-methylpropanoicacid

α-Methyltryptophan is primarily used in research to study serotonin biosynthesis, as it competitively inhibits tryptophan hydroxylase. It serves as a tracer in PET imaging to assess brain serotonin synthesis rates. Additionally, it aids in investigating amino acid transport across the blood-brain barrier. Its radiolabeled form (¹⁴C) is employed in metabolic pathway studies.

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