1-Methyltryptophan

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.

Quick facts Names, Identifiers ...

1-Methyltryptophan

Names
IUPAC name 1-Methyltryptophan
Systematic 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
CAS Number	26988-72-7 (D/L) N 21339-55-9 (L) Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL504816 N ChEMBL514172 Y
ChemSpider	88584 Y
ECHA InfoCard	100.043.765
IUPHAR/BPS	4694
PubChem CID	98112
CompTox Dashboard (EPA)	DTXSID601314131
InChI InChI=1S/C12H14N2O2/c1-14-7-8(6-10(13)12(15)16)9-4-2-3-5-11(9)14/h2-5,7,10H,6,13H2,1H3,(H,15,16) Y Key: ZADWXFSZEAPBJS-UHFFFAOYSA-N Y InChI=1S/C12H14N2O2/c1-14-7-8(6-10(13)12(15)16)9-4-2-3-5-11(9)14/h2-5,7,10H,6,13H2,1H3,(H,15,16) Key: ZADWXFSZEAPBJS-UHFFFAOYSA-N
SMILES O=C(O)C(N)Cc2c1ccccc1n(c2)C
Properties
Chemical formula	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). N verify (what is YN ?) Infobox references

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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 it was in clinical trials for cancer treatment, such as for advanced melanoma, in 2017.^{[4][needs update]}

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]