alpha-Methyltryptophan

Base Information

• Chemical Name: alpha-Methyltryptophan
• CAS No.: 153-91-3
• Deprecated CAS: 13510-08-2,17411-53-9
• Molecular Formula: C12H14N2O2
• Molecular Weight: 218.255
• NSC Number: 9948
• UNII: 260VJL1C6Q
• Wikidata: Q27074404
• Pharos Ligand ID: 73B6SN3AXBH5
• ChEMBL ID: CHEMBL559578
• Mol file: 153-91-3.mol

Synonyms:alpha-(11C)methyl-L-tryptophan;alpha-(14C)methyl-tryptophan;alpha-methyl-L-tryptophan;alpha-methyltryptophan;alpha-methyltryptophan, (+)-isomer;alpha-methyltryptophan, (-)-isomer;alpha-methyltryptophan, (D)-isomer;alpha-methyltryptophan, (DL)-isomer;alpha-methyltryptophan, (L)-isomer

Chemical Property of alpha-Methyltryptophan

Chemical Property:

• Melting Point: 234 °C(Solv: ethanol, 60% (64-17-5))
• Boiling Point: 444 °C at 760 mmHg
• PKA: 2.34±0.10(Predicted)
• Flash Point: 222.3 °C
• PSA: 79.11000
• Density: 1.314 g/cm³
• LogP: 2.21270
• Storage Temp.: 2-8°C
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 218.105527694
• Heavy Atom Count: 16
• Complexity: 282

Purity/Quality:

98%,99%, ^*data from raw suppliers

DL-alpha-Methyltryptophan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC1=CNC2=CC=CC=C21)(C(=O)O)N
• Uses: α-methyl-DL-tryptophan is used as a blocker of ATBo, an amino acid transporter whose expression is upregulated in cancer. It is also a substrate or non-transported inhibitor of the amino acid transporter PAT2 (slc36a2).

Technology Process of alpha-Methyltryptophan

There total 3 articles about alpha-Methyltryptophan which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

5-indol-3-ylmethyl-5-methyl-imidazolidine-2,4-dione (54585-06-7) → DL-α-methyltryptophan (153-91-3,13510-08-2)

Guidance literature:

With sodium hydroxide;

Reference yield:

3-(1H-indolyl)acetone (1201-26-9) → DL-α-methyltryptophan (153-91-3,13510-08-2)

Guidance literature:

Multi-step reaction with 2 steps

1: aqueous ethanol

2: aqueous NaOH

With sodium hydroxide; ethanol;

Reference yield:

→ DL-α-methyltryptophan (153-91-3,13510-08-2)

Guidance literature:

α-Isocyanopropionat 6, Graminmethiodid 4;

upstream raw materials:

5-indol-3-ylmethyl-5-methyl-imidazolidine-2,4-dione

3-(1H-indolyl)acetone

Downstream raw materials:

N-Boc-DL-α-methyl tryptophan

N-Amoc-DL-α-methyl tryptophan

N-(Fmoc)-DL-α-methyltryptophal

N-(1-hydroxy-3-(1H-indol-3-yl)-2-methylpropan-2-yl)-8,9-dimethoxy-3-phenyl-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxamide