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860646

Sigma-Aldrich

1-Methyl-DL-tryptophan

97%

Synonym(s):

1-Methyl-DL-tryptophan, 1-Methyltryptophan, 2-Amino-3-(1-methyl-1H-indol-3-yl)propanoic acid, 2-Amino-3-(1-methyl-1H-indol-3-yl)propanoicacid, 2-Amino-3-(1-methylindol-3-yl)propanoic acid, DL-1-Methyltryptophan, N′-Methyl-DL-tryptophan

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About This Item

Empirical Formula (Hill Notation):
C12H14N2O2
CAS Number:
26988-72-7
Molecular Weight:
218.25
EC Number:
248-157-6
MDL number:
MFCD00005803
UNSPSC Code:
12352100
PubChem Substance ID:
24888516
NACRES:
NA.22

Quality Level

100

assay

97%

form

solid

mp

250 °C (dec.) (lit.)

functional group

amine
carboxylic acid

SMILES string

Cn1cc(CC(N)C(O)=O)c2ccccc12

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)

InChI key

ZADWXFSZEAPBJS-UHFFFAOYSA-N

Related Categories

Application

1-Methyl-DL-tryptophan, a competitive inhibitor of indoleamine 2,3 dioxygenase-1 (IDO1), has been used to study inflammation-induced depression in mice and syncytial virus induced bronchiolitis.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCB6083
MKCC6956
MKBJ4016V
MKBC7435V
MKBC7435

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Motivational changes that develop in a mouse model of inflammation-induced depression are independent of indoleamine 2, 3 dioxygenase.
Vichaya, Elisabeth G et al.
Neuropsychopharmacology (2018)
Seung-Ha Yang et al.
Experimental & molecular medicine, 41(5), 315-324 (2009-03-25)
Mesenchymal stem cells (MSCs) can inhibit T cell proliferation; however, the underlying mechanisms are not clear. In this study, we investigated the mechanisms of the immunoregulatory activity of MSCs on T cells. Irradiated MSCs co-cultured with either na?ve or pre-activated
Qi-Xiang Ye et al.
Experimental and therapeutic medicine, 14(3), 1884-1891 (2017-10-01)
Cytotoxic T-lymphocyte-associated protein 4 immunoglobulin (CTLA4Ig) and anti-cluster of differentiation 154 (anti-CD154) are able to block B7/CD28 and CD40/CD154 co-stimulatory signals in T cells. Additionally, they promote hematopoietic stem cell transplantation (HSCT) in sensitized recipients and are able to induce
Gavin Carr et al.
Journal of medicinal chemistry, 51(9), 2634-2637 (2008-04-09)
Synthetic analogues of the sponge natural product exiguamine A (3) have been prepared and evaluated for their ability to inhibit indoleamine 2,3-dioxygenase in vitro.
Neda Milosavljevic et al.
Liver transplantation : official publication of the American Association for the Study of Liver Diseases and the International Liver Transplantation Society, 23(8), 1040-1050 (2017-05-10)
Mesenchymal stem cells (MSCs) are, due to immunomodulatory characteristics, considered as novel agents in the treatment of immune-mediated acute liver failure. Although it is known that MSCs can regulate activation of T lymphocytes, their capacity to modulate function of neutrophils
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