13510-08-2

Basic information

• Product Name: alpha-methyltryptophan
• Synonyms: alpha-methyltryptophan;Nsc9948;Tryptophan, .alpha.-methyl-
• CAS NO: 13510-08-2
• Molecular Formula: C12H14 N2 O2
• Molecular Weight: 0
• Mol File: 13510-08-2.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 444°Cat760mmHg
• Flash Point: 222.3°C
• Appearance: /
• Density: 1.314g/cm³
• Vapor Pressure: 1.15E-08mmHg at 25°C
• Refractive Index: 1.675
• CAS DataBase Reference: alpha-methyltryptophan(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-methyltryptophan(13510-08-2)
• EPA Substance Registry System: alpha-methyltryptophan(13510-08-2)

Safety Data

• Hazardous Substances Data: 13510-08-2(Hazardous Substances Data)

Usage

Chemical compound

Alpha-methyltryptophan

Function

Inhibitor of the enzyme indoleamine 2,3-dioxygenase (IDO)

Role

Regulation of immune response

Therapeutic applications

Treatment of various diseases, including cancer and autoimmune disorders

Research

Subject of research for immunomodulatory properties

Results

Promising in preclinical studies

Need for further research

To understand potential therapeutic benefits and side effects in clinical settings

InChI:InChI=1/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)

Upstream product

• 1266681-04-2 tert-butyl 3-{[(3S,5aR,6aS,7aS)-2,3,5,5a,6,6a,7,7a-octahydro-3,6,6,7a-tetramethyl-2-oxobicyclo[4.1.0]hept-1⁽⁶⁾eno[3,4-b][1,4]oxazin-3-yl]methyl}-1H-indole-1-carboxylate 
• 116139-85-6 (2R,5S)-3-benzoyl-2-(tert-butyl)-4-(<1-(tert-butyloxycarbonyl)-1H-indol-3-yl>methyl)-4-methyl-5-oxazolidinon 
• 96551-21-2 1-(t-butyloxycarbonyl)-3-(bromomethyl)indole 
• 170458-97-6 (2R,4R)-2-(tert-Butyl)-3-(ethoxycarbonyl)-4-(indol-3-yl-methyl)-4-methyl-1,3-oxazolidin-5-one 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 200716-94-5 (2S,3aR,8aR)-2-Methyl-2,3,3a,8a-tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid tribenzyl ester 
• 200716-93-4 (2S,3aR,8aS)-2,3,3a,8a-Tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid tribenzyl ester 
• 69876-37-5 (S)-benzyl 2-(((benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propanoate 
• 153-91-3 DL-α-methyltryptophan 
• 116139-87-8 (S)-N²-benzoyl-2-methyltryptophan-methylester 
• 121704-33-4 2-(2-Chloro-acetylamino)-3-(1H-indol-3-yl)-2-methyl-propionic acid 
• 141784-94-3 2-Amino-3-(1H-indol-3-yl)-2-methyl-propionic acid butyl ester 
• 114524-80-0 methyl 2-(indol-3-ylmethyl)-2-aminopropionate 
• 136088-19-2 dimethyl (2R,3aS,8aR)-2-methyl-8-(p-tolylsulphonyl)-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-1,2-dicarboxylate 

Downstream Products

• 1428795-68-9 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 
• 114779-80-5 N-(Fmoc)-DL-α-methyltryptophal 
• 114779-81-6 N-Amoc-DL-α-methyl tryptophan 
• 114779-79-2 N-Boc-DL-α-methyl tryptophan 
• 142854-50-0 L-α-methyl-tryptophan methyl ester 

Related news

alpha-methyltryptophan (cas 13510-08-2) as a therapeutic agent08/10/2019

1. Alpha-methyltryptophan, on administration to experimental animals gives rise to cerebral alpha-methylserotonin, which substitutes for serotonin in certain behavioral and functional tests.2. Such results are consistent wich the similarity of the properties of the two indoleamlnes with respect ...detailed

Relevant articles and documents

Chiral ligand-exchange resolution of underivatized amino acids on a dynamically modified stationary phase for RP-HPTLC

The synthesis of Spi(τ-dec), derived from the selective alkylation of L-spinacine (4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid) at the τ-nitrogen of its heteroaromatic ring, with a linear hydrocarbon chain of 10 carbon atoms, is described here for the first time. Spi(τ-dec) was successfully employed in the past to prepare home-made chiral columns for chiral ligand-exchange high-performance liquid chromatography. In the present article a new method is described, using Spi(τ-dec) as a chiral selector in high-performance thin-layer chromatography (HPTLC): commercial hydrophobic plates were first coated with Spi(τ-dec) and then treated with copper sulfate. The performance of this new chiral stationary phase was tested against racemic mixtures of aromatic amino acids, after appropriate optimization of both the conditions of preparation of the plates and the mobile phase composition. The enantioselectivity values obtained for the studied compounds were higher than those reported in the literature for similar systems. The method employed here for the preparation of chiral HPTLC plates proved practical, efficient, and inexpensive. Chirality 26:313-318, 2014. 2014 Wiley Periodicals, Inc.

A facile method for the asymmetric synthesis of α-methyltryptophan

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Asymmetric synthesis of α-Methyl α-Amino Acids through diastereoselective alkylation under mild reaction conditions of an iminic alanine template with a 1,2,3,6-Tetrahydro-2-Pyrazinone structure

(6R)-6-Isopropyl-3-methyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone, obtained from (R)-valine and (S)-alanine, is highly diastereoselectively alkylated at room temperature by: a) activated alkyl halides under solid-liquid PTC conditions, b) non-activated alkyl halides with organic bases, c) electrophilic olefins employing both solid-liquid PTC conditions and organic bases, and d) allylic carbonates by means of palladium catalysis under neutral conditions. Enantiomerically pure (S)-α-methyl α-amino acids 8 are obtained by hydrolysis of the alkylated pyrazinones.