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Chemical compound From Wikipedia, the free encyclopedia
1-Methyltryptophan is a chemical compound that is an inhibitor of the tryptophan catabolic enzyme indoleamine 2,3-dioxygenase (IDO or INDO EC 1.13.11.52).[1] It is a chiral compound that can exist as both D- and L-enantiomers.
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Preferred IUPAC name
2-Amino-3-(1-methyl-1H-indol-3-yl)propanoic acid | |
Other names
1-Methyl-DL-tryptophan; DL-1-Methyltryptophan; ARBRIN; Indoximod | |
Identifiers | |
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3D model (JSmol) |
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ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.043.765 |
PubChem CID |
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CompTox Dashboard (EPA) |
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Properties | |
C12H14N2O2 | |
Molar mass | 218.256 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The L-isomer (L-1MT) inhibits IDO weakly but also serves as an enzyme substrate.
The D-isomer (D-1MT) does not inhibit IDO at all, but it can inhibit the IDO-related enzyme IDO2[2] and restore mTOR signaling in cells starved of tryptophan due to IDO activity.[3] D-1MT is also known as indoximod and is currently in clinical trials for cancer treatment, such as for advanced melanoma.[4]
A U.S. patent covering salt and prodrug formulations of indoximod was issued to NewLink Genetics on August 15, 2017 providing exclusivity until at least 2036.[5][6]
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