1-Methyl-L-tryptophan

Product Name: 1-Methyl-L-tryptophan
CAS No.: 21339-55-9
Chemical Name: 1-Methyl-L-tryptophan
Synonyms: ABRINE;Precasin;ABRINE, L-;H-METRP-OH;N-ME-TRP-OH;(S)-NLG-8189;(S)-Indoximod;H-Trp(1-Me)-OH;N-ME-TRYPTOPHAN;1-methyltryptophan
CBNumber: CB6744979
Molecular Formula: C12H14N2O2
Formula Weight: 218.25
MOL File: 21339-55-9.mol

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1-Methyl-L-tryptophan Property

Melting point:: >300 °C (dec.)(lit.)
Boiling point:: 429.3±35.0 °C(Predicted)
Density: 1.28
storage temp.: Keep in dark place,Inert atmosphere,Room temperature
solubility: Aqueous Acid (Slightly, Sonicated), Aqueous Base (Slightly, Sonicated), DMSO (Slightly）
pka: 2.26±0.10(Predicted)
form: White to off-white powder.
color: Off-White to Pale Beige
optical activity: [α]24/D 8.0°, c = 2 in acetic acid

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Safety

Hazard Codes: Xn
Risk Statements: 20/21/22
Safety Statements: 36
WGK Germany: 3
RTECS: YN7135000

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 447439
Product name: 1-Methyl-L-tryptophan
Purity: 95%
Packaging: 1g
Price: $45.84
Updated: 2025/07/31

Sigma-Aldrich

Product number: 447439
Product name: 1-Methyl-L-tryptophan
Purity: 95%
Packaging: 5g
Price: $180
Updated: 2025/07/31

TCI Chemical

Product number: M3815
Product name: 1-Methyl-L-tryptophan
Packaging: 200MG
Price: $49
Updated: 2025/07/31

TCI Chemical

Product number: M3815
Product name: 1-Methyl-L-tryptophan
Packaging: 1G
Price: $147
Updated: 2025/07/31

TRC

Product number: A613855
Product name: (S)-2-Amino-3-(1-methyl-1h-indol-3-yl)propanoicAcid
Packaging: 50mg
Price: $80
Updated: 2021/12/16

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1-Methyl-L-tryptophan Chemical Properties,Usage,Production

Chemical Properties

Off-white crystalline powder, soluble in methanol, slightly soluble in water, insoluble in ether, soluble in dilute acids and dilute bases, from the seeds of the legume Acacia precatorius, Chickweed Abrus fruticulosus.

Uses

1-Methyl-L-tryptophan can be used:

In the preparation of L-tryptophan-based ligand for regioselective copper catalyzed N²-arylation of 1,2,3-triazoles.
As a key starting material for the total synthesis of (?)-ardeemin.
In the synthesis of cyclic peptide-capped gold nanoparticles as drug delivery systems.

Definition

ChEBI: 1-methyl-L-tryptophan is an indolyl carboxylic acid.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

73-22-3

74-88-4

21339-55-9

The general procedure for the synthesis of acacia alkaloids from L-tryptophan and iodomethane was as follows: 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 for a controlled time of 30 minutes. After the dropwise addition, 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. Filtered 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 standard methods. The analytical results (not shown) confirmed that the resulting solid was 1-methyltryptophan with 100% purity.

in vivo

(S)-Indoximod (5 mg/day, i.p. for 3 weeks) reverses the Bacillus Calmette-Guerin (BCG)-induced neurotoxicity in mice^[3].
(S)-Indoximod (200 mg/kg, oral gavage) shows delayed, lasts longer renoprotective effect than D isomer, and increases survival in the IRI rat model^[4].
(S)-Indoximod (1-9 mg/kg, i.p.) reverses cognitive, anxiety, and depressive-like behavior in bile duct ligation (BDL) rats^[5].

Animal Model:	Bile duct ligation (BDL) rats^[5]
Dosage:	1-9 mg/kg
Administration:	i.p., After the rats recovered for 7 days from BDL surgery.
Result:	Increased the sucrose preference. Prevents the increased number of buried marbles. Improved learning and memory function.

References

[1] Journal of Organic Chemistry, 2009, vol. 74, # 1, p. 298 - 304
[2] Patent: CN105367477, 2016, A. Location in patent: Paragraph 0047; 0048; 0049
[3] Chemistry - A European Journal, 2014, vol. 20, # 46, p. 15021 - 15030
[4] Organic and Biomolecular Chemistry, 2006, vol. 4, # 2, p. 291 - 298

1-Methyl-L-tryptophan Preparation Products And Raw materials

Raw materials

Preparation Products

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1-Methyl-L-tryptophan Suppliers

China 188 Germany 1 India 2 Japan 2 Switzerland 2 United Kingdom 1 United States 14 Global 210

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View Lastest Price from 1-Methyl-L-tryptophan manufacturers

Wuhan Nutra Biotechnology Co.,Ltd

Product: 1-Methyl-L-tryptophan;L-abrine 21339-55-9
Price: US $150.00-0.00/g
Min. Order: 1g
Purity: 98%+
Supply Ability: 100kgs
Release date: 2021-05-19

Zhuozhou Wenxi import and Export Co., Ltd

Product: 1-Methyl-L-tryptophan 95% 21339-55-9
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: L-ABRINE 21339-55-9
Price: US $1.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 25kg
Release date: 2019-07-12

21339-55-9, 1-Methyl-L-tryptophanRelated Search:

BOC-TRP(FOR)-OH FMOC-METRP(BOC)-OH H-TRP(BOC)-OH Fmoc-Trp(Boc)-OH BOC-TRP(BOC)-OH 1-Methyl-L-tryptophan Z-TRP(BOC)-OH DCHA DL-5-METHYLTRYPTOPHAN L-a-Methyltryptophan,S-2-METHYLTRYPTOPHAN,L-α-Methyltryptophan L-Tryptophan TRYPTAMINE HYDROCHLORIDE L-Abrine ABRINE, L-(P),ABRINE, L-(RG) BOC-TRP(HOC) BOC-TPI(FOR)-OH H-TRP(BOC)-OTBU HCL FMOC-TRP(BOC)-OPFP FMOC-METRP-OH

1-methyl-l-tryptopha

N-A-METHYL-L-TRYPTOPHAN

N ALPHA-METHYL-L(+)-TRYPTOPHAN

N-ALPHA-METHYL-L-TRYPTOPHAN

N-METHYLTRYPTOPHAN

N-ME-TRP-OH

N-ME-TRYPTOPHAN

N-METHYL-L-TRYPTOPHAN

(2S)-2-amino-3-(1-methyl-1H-indol-3-yl)propanoic acid

(2S)-2-amino-3-(1-methylindol-3-yl)propanoic acid

1-methyltryptophan

ABRINE

ABRINE, L-

1-Methyl-L-tryptophane

Precasin

H-METRP-OH

(S)-2-amino-3-(1-methyl-1H-indol-3-yl)propanoic acid

2-amino-3-(1-methylindol-3-yl)propanoic acid

2-amino-3-(1-methylindol-3-yl)propionic acid

2-azanyl-3-(1-methylindol-3-yl)propanoic acid

(αS)-1-Methyl-α-amino-1H-indole-3-propanoic acid

(αS)-α-Amino-1-methyl-1H-indole-3-propanoic acid

L-(-)-1-Methyltryptophan

L-1-Methyltryptophan

H-Trp(1-Me)-OH

1-Methyl-<SC>L</SC>-tryptophan

1-METHYL-L-TRYPTOPHAN

Abrine/1-Methyl-L-tryptophan

1-Methyl-L-tryptophan USP/EP/BP

(S)-Indoximod

(2S)-2-amino-3-(1-methylindol-3-yl)propanoicaci

(S)-NLG-8189

21339-55-9

21339-55-1

C10H9NNHCH3COOH

Amino Acid Derivatives

Tryptophans

Indoles

N-Methyl Amino Acids

Peptide Synthesis

Specialty Synthesis

Unnatural Amino Acid Derivatives

Tryptophan

Indoles and derivatives

Amino Acid Derivatives

Peptide Synthesis

Tryptophan

amino acid