| Identification | Back Directory | [Name]
L-ABRINE | [CAS]
21339-55-9 | [Synonyms]
ABRINE
Precasin
L-ABRINE
H-METRP-OH
ABRINE, L-
N-ME-TRP-OH
(S)-Indoximod
H-Trp(1-Me)-OH
N-ME-TRYPTOPHAN
N-METHYLTRYPTOPHAN
1-methyltryptophan
1-methyl-l-tryptopha
L-1-Methyltryptophan
1-METHYL-L-TRYPTOPHAN
N-METHYL-L-TRYPTOPHAN
1-Methyl-L-tryptophane
N-A-METHYL-L-TRYPTOPHAN
L-(-)-1-Methyltryptophan
N-ALPHA-METHYL-L-TRYPTOPHAN
Abrine/1-Methyl-L-tryptophan
1-Methyl-L-tryptophan
N ALPHA-METHYL-L(+)-TRYPTOPHAN
1-Methyl-L-tryptophan USP/EP/BP
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
(2S)-2-amino-3-(1-methylindol-3-yl)propanoic acid
(S)-2-amino-3-(1-methyl-1H-indol-3-yl)propanoic acid
(2S)-2-amino-3-(1-methyl-1H-indol-3-yl)propanoic acid | [EINECS(EC#)]
208-388-5 | [Molecular Formula]
C12H14N2O2 | [MDL Number]
MFCD00005645 | [MOL File]
21339-55-9.mol | [Molecular Weight]
218.25 |
| Chemical Properties | Back Directory | [Melting point ]
>300 °C (dec.)(lit.)
| [Boiling point ]
429.3±35.0 °C(Predicted) | [density ]
1.28 | [storage temp. ]
2-8°C | [solubility ]
Aqueous Acid (Slightly, Sonicated), Aqueous Base (Slightly, Sonicated), DMSO (Slightly） | [form ]
White to off-white powder. | [pka]
2.26±0.10(Predicted) | [color ]
Off-White to Pale Beige | [Optical Rotation]
[α]24/D 8.0°, c = 2 in acetic acid | [Major Application]
peptide synthesis | [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-/m0/s1 | [InChIKey]
ZADWXFSZEAPBJS-JTQLQIEISA-N | [SMILES]
Cn1cc(C[C@H](N)C(O)=O)c2ccccc12 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white crystalline powder, soluble in methanol, slightly soluble in water, insoluble in ether, soluble in dilute acid and dilute alkali, derived from the seeds of Abrus precatorius and Abrus fruticulosus of the leguminous plants. | [Uses]
Competitive inhibitor of indoleamine 2,3-dioxygenase (IDO). | [Definition]
ChEBI: 1-methyl-L-tryptophan is an indolyl carboxylic acid. | [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
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 |
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| Company Name: |
Energy Chemical
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| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
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