ChemicalBook > CAS DataBase List > 1-METHYL-D-TRYPTOPHAN

1-METHYL-D-TRYPTOPHAN

Product Name
1-METHYL-D-TRYPTOPHAN
CAS No.
110117-83-4
Chemical Name
1-METHYL-D-TRYPTOPHAN
Synonyms
Me-D-Trp;NLG-8189;IndoxiMod;1-Me-D-Trp;D-Trp(Me)-OH;H-D-Trp(1-Me)-OH;Indoximod (NLG-8189）;1-METHYL-D-TRYPTOPHAN;1-Methyl-D-tryptophane;D-Tryptophan, 1-methyl-
CBNumber
CB0467553
Molecular Formula
C12H14N2O2
Formula Weight
218.25
MOL File
110117-83-4.mol
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1-METHYL-D-TRYPTOPHAN Property

Melting point:
242-245 °C(lit.)
alpha 
12.4o (C = 2 IN ACETIC ACID)
Boiling point:
429.3±35.0 °C(Predicted)
Density 
1.28
storage temp. 
Keep in dark place,Sealed in dry,Room Temperature
solubility 
Soluble in DMSO (greater than 25 mg/ml).
pka
2.26±0.10(Predicted)
form 
White to light brown crystalline powder.
color 
White
optical activity
[α]22/D +12.4°, c = 2 in acetic acid
Water Solubility 
Soluble to 5 mM in water with gentle warming
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
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)/t10-/m1/s1
InChIKey
ZADWXFSZEAPBJS-SNVBAGLBSA-N
SMILES
C(O)(=O)[C@@H](CC1C2=C(C=CC=C2)N(C)C=1)N
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Safety

WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
452483
Product name
1-Methyl-D-tryptophan
Purity
95%
Packaging
1g
Price
$139.83
Updated
2025/07/31
Sigma-Aldrich
Product number
452483
Product name
1-Methyl-D-tryptophan
Purity
95%
Packaging
10g
Price
$877.24
Updated
2025/07/31
TCI Chemical
Product number
M3336
Product name
1-Methyl-D-tryptophan
Packaging
200MG
Price
$66
Updated
2025/07/31
TCI Chemical
Product number
M3336
Product name
1-Methyl-D-tryptophan
Packaging
1G
Price
$198
Updated
2025/07/31
Cayman Chemical
Product number
16456
Product name
1-methyl-D-Tryptophan
Purity
≥95%
Packaging
1g
Price
$115
Updated
2024/03/01
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1-METHYL-D-TRYPTOPHAN Chemical Properties,Usage,Production

Description

Indoleamine 2,3-dioxygenase (IDO) metabolizes tryptophan to kynurenine, leading to the production of NAD+ via the kynurenine pathway. The overexpression of IDO in tumors and tumor-draining lymph nodes induces immune tolerance and enhances tumor growth in vivo. 1-methyl-D-Tryptophan is an inhibitor of IDO (IC50 = 7 μM) that is effective in vivo. In mice, 1-methyl-D-tryptophan prevents T-cell anergy triggered by dendritic cells overexpressing IDO. It augments the antitumor and antiviral immunoresponse of CD8+ T-cells and reduces tumor volume in mice with xenografts overexpressing IDO. 1-methyl-D-Tryptophan, in combination with chemotherapy, causes regression of tumors and prolongs survival. Surprisingly, 1-methyl-D-tryptophan induces the expression of IDO in human ovarian carcinoma SKOV3 cells in culture.

Uses

Indoleamine 2,3-dioxygenase (IDO) metabolizes tryptophan to kynurenine, leading to the production of NAD+ via the kynurenine pathway. The overexpression of IDO in tumors and tumor-draining lymph nodes induces immune tolerance and enhances tumor growth in vivo. 1-methyl-D-Tryptophan is an inhibitor of IDO (IC50 = 7 μM) that is effective in vivo. In mice, 1-methyl-D-tryptophan prevents T-cell anergy triggered by dendritic cells overexpressing IDO. It augments the antitumor and antiviral immunoresponse of CD8+ T-cells and reduces tumor volume in mice with xenografts overexpressing IDO. 1-methyl-D-Tryptophan, in combination with chemotherapy, causes regression of tumors and prolongs survival. Surprisingly, 1-methyl-D-tryptophan induces the expression of IDO in human ovarian carcinoma SKOV3 cells in culture.

Uses

1-Methyl-D-tryptophan is used in biological studies to determine the effect of IDO2 enzyme (indoleamine-(2,3)-dioxygenase) activity and IDO2-mediated arrest of human T cell proliferation. It reverses IDO-mediated immune suppression

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

73-22-3

74-88-4

21339-55-9

General procedure for the synthesis of acacia alkaloids from L-tryptophan and iodomethane: 10.2 g of L-tryptophan was dissolved in 130 mL of dimethylsulfoxide (DMSO), and 5 g of sodium hydroxide was added in batches over a 30-minute period under nitrogen protection. After addition, the reaction system was stirred at room temperature for 1 h. Subsequently, the reaction system was cooled to 0 °C. A 30 mL solution of DMSO with 7.46 g of iodomethane was slowly added dropwise over 30 min. After the dropwise addition was completed, the reaction was continued for 15 hours. After completion of the reaction, 50 mL of water was added to the system to quench the reaction. The reaction mixture was poured into 400 mL of ether and a large solid was precipitated and filtered. The resulting solid was dissolved in water and the pH was adjusted to 6-7 with concentrated hydrochloric acid, and the solid was again precipitated. Filtering was extracted and dried to give 8.7 g of white powdery product (80% yield, melting point 269°C). The product was analyzed by 1H-NMR, 13C-NMR, IR spectroscopy and mass spectrometry according to the method of Example 1. The results showed that the resulting solid product was 1-methyltryptophan with 100% purity.

in vivo

The D isomer is more efficacious as an anticancer agent in chemo-immunotherapy regimens using NSC-26271, NSC 125973, or LY 188011, when tested in mouse models of transplantable melanoma and transplantable and autochthonous breast cancer. The D isomer of 1-methyl-tryptophan specifically targets the IDO gene because the antitumor effect of d-1-methyl-tryptophan is completely lost in mice with a disruption of the IDO gene (IDO-knockout mice). Oral administration of dl-1-methyl-tryptophan in combination with NSC 125973 can elicit regression of autochthonous breast tumors[1].

IC 50

IDO: 19 μM (Ki)

storage

Store at -20°C

References

[1] DE-YAN HOU. Inhibition of indoleamine 2,3-dioxygenase in dendritic cells by stereoisomers of 1-methyl-tryptophan correlates with antitumor responses.[J]. Cancer research, 2007, 67 2: 792-801. DOI:10.1158/0008-5472.can-06-2925
[2] HATEM SOLIMAN  Scott A  Melanie Mediavilla Varela. Indoleamine 2,3-dioxygenase: is it an immune suppressor?[J]. Cancer journal, 2010, 16 4: 354-359. DOI:10.1097/ppo.0b013e3181eb3343
[3] MARIA FRIBERG. Indoleamine 2,3-dioxygenase contributes to tumor cell evasion of T cell-mediated rejection[J]. International Journal of Cancer, 2002, 101 2: 151-155. DOI:10.1002/ijc.10645
[4] RICHARD METZ. IDO inhibits a tryptophan sufficiency signal that stimulates mTOR: A novel IDO effector pathway targeted by D-1-methyl-tryptophan.[J]. Oncoimmunology, 2012, 1 9: 1460-1468. DOI:10.4161/onci.21716

1-METHYL-D-TRYPTOPHAN Preparation Products And Raw materials

Raw materials

Preparation Products

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1-METHYL-D-TRYPTOPHAN Suppliers

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View Lastest Price from 1-METHYL-D-TRYPTOPHAN manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
1-Methyl-D-tryptophan 110117-83-4
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
98%min
Supply Ability
500kg
Release date
2021-08-24
Zhuozhou Wenxi import and Export Co., Ltd
Product
1-Methyl-D-tryptophan 95% 110117-83-4
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-06-27
Career Henan Chemical Co
Product
1-METHYL-D-TRYPTOPHAN 110117-83-4
Price
US $7.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
1000kg
Release date
2020-01-13

110117-83-4, 1-METHYL-D-TRYPTOPHANRelated Search:

5-METHYL-DL-TRYPTOPHAN 1-METHYL-D-TRYPTOPHAN 1-METHYL-DL-TRYPTOPHAN Fmoc-D-Trp(Boc)-OH 5-METHYL-DL-TRYPTOPHAN HYDRATE α-Methyl-(S)-tryptophan,ALPHA-METHYL-L-TRYPTOPHAN 1-METHYL-L-TRYPTOPHAN D(+)-Tryptophan L-Abrine BOC-D-TPI(FOR)-OH Z-D-TRP(BOC)-OH FMOC-D-TRP(ME)-OH H-D-TRP(BOC)-OH 7-METHOXY-1-METHYL-D-TRYPTOPHAN ETHYL ESTER BOC-D-TRP(FOR)-OH H-D-TRP(FOR)-OH HCL BOC-N-ALPHA-METHYL-DL-TRYPTOPHAN 4-METHYL-DL-TRYPTOPHAN

  • 1-METHYL-D-TRYPTOPHAN
  • 1-Methyl-D-tryptophane
  • 1-METHYL-D-TRYPTOPHAN 95%
  • (R)-2-amino-3-(1-methyl-1H-indol-3-yl)propanoic acid
  • IndoxiMod
  • Indoximod (NLG-8189）
  • NLG-8189
  • Me-D-Trp
  • 1-Me-D-Trp
  • D-Trp(Me)-OH
  • H-D-Trp(1-Me)-OH
  • INDOXIMOD;1-METHYL-D-TRYPTOPHAN;1-METHYL-D-TRYPTOPHANE
  • (2R)-2-amino-3-(1-methyl-1H-indol-3-yl)propanoic acid
  • D-Tryptophan, 1-methyl-
  • 1-METHYL-D-TRYPTOPHAN USP/EP/BP
  • (2R)-2-amino-3-(1-methylindol-3-yl)propanoic acid
  • Indoximod, Indoleamine 2,3-dioxygenase (IDO) inhibitor
  • 1-Methyl-<sc>D</sc>-tryptophan
  • 110117-83-4
  • Amino Acid Derivatives
  • Peptide Synthesis
  • Specialty Synthesis
  • Tryptophan
  • Inhibitors
  • Amino Acid Derivatives
  • Peptide Synthesis
  • Tryptophan