L-Tryptophan, 1-methyl-
1-Methyl-L-tryptophan
CAS: 21339-55-9
Molecular Formula: C12H14N2O2
L-Tryptophan, 1-methyl- - Names and Identifiers
| Name | 1-Methyl-L-tryptophan |
| Synonyms | N-ME-TRP-OH N-ME-TRYPTOPHAN 1-Methyltryptophan N-METHYLTRYPTOPHAN 1-methyl-l-tryptopha L-1-Methyltryptophan 1-Methyl-L-tryptophan DL-1-Methyltryptophan N-METHYL-L-TRYPTOPHAN L-tryptophan, 1-methyl- L-Tryptophan, 1-methyl- N-A-METHYL-L-TRYPTOPHAN L-(-)-1-Methyltryptophan N-ALPHA-METHYL-L-TRYPTOPHAN N ALPHA-METHYL-L(+)-TRYPTOPHAN (S)-2-Amino-3-(1-methyl-1H-indol-3-yl)propanoic acid |
| CAS | 21339-55-9 |
| EINECS | 208-388-5 |
| InChI | InChI=1/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 |
L-Tryptophan, 1-methyl- - Physico-chemical Properties
| Molecular Formula | C12H14N2O2 |
| Molar Mass | 218.25 |
| Density | 1.28 |
| Melting Point | >300°C (dec.)(lit.) |
| Boling Point | 429.3±35.0 °C(Predicted) |
| Specific Rotation(α) | D21 +44° (0.28 g in 10 ml 0.5N HCl)；65 ° (C=1, 0.5mol/L NaOH) |
| Flash Point | 213.4°C |
| Solubility | H2O : 2 mg/mL (9.16 mM; ultrasonic and adjust pH to 10 with NaOH) |
| Vapor Presure | 3.92E-08mmHg at 25°C |
| Appearance | Off-white to light yellow (Solid) |
| Color | Off-White to Pale Beige |
| pKa | 2.26±0.10(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
| Refractive Index | 1.625 |
| MDL | MFCD00005645 |
| Physical and Chemical Properties | White-like crystalline powder, soluble in methanol, slightly soluble in water, insoluble in ether, soluble in dilute acid and dilute alkali, derived from the legume Acacia Abrus precatorius seeds, Abrus Abrus fruticulosus. |
L-Tryptophan, 1-methyl- - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | 36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | YN7135000 |
L-Tryptophan, 1-methyl- - Reference
| Reference Show more | 1. Li Chenghao, Wang Meng, Ren Xiaoliang. Solubilization of Sulfonated Calix6 Aroene on Monomer Components of Four Types of Traditional Chinese Medicine and Its Mechanism [J]. Modern Chinese Medicine, 2020,22(12):2032-2038. |
L-Tryptophan, 1-methyl- - Reference Information
| effect | intraperitoneal injection of abrin can reduce the inflammatory reaction caused by staphylococcal toxin in the shoulder of mice, high concentration can inhibit the lysis of sheep red blood cells. The combination of 1-methyltryptophan (abradine) with a range of existing clinical chemotherapy drugs such as cyclophosphamide, cisplatin, doxorubicin, or paclitaxel showed excellent synergistic effects, become a promising chemical, immune combination therapy drugs. 1-methyltryptophan is expected to play an important role in anti-cancer therapy, and the development of its synthetic method will bring favorable social and economic benefits. |
| preparation | in a three-necked flask with an ice water bath, 10.2g of tryptophan was added to ML of tetrahydrofuran (THF), under the condition of nitrogen protection, within 50min, 5g of commercial sodium amino acid was added in batches, and after adding the sodium amino acid, the ice water bath was removed to stir at room temperature (about 25 ° C) for 2 hours, the temperature of the reaction system was then reduced to 0 °c using an ice-water bath. A solution of 7.46G of methyl iodide in 50ml of THF was added dropwise to the above mixed solution with a constant-pressure dropping funnel within 30min, and after completion of the dropwise addition, the reaction was continued with stirring for 15 hours. After completion of the reaction, 30ml of water was added at room temperature to quench the reaction. The reaction mixture was poured into 6.5 ml of ether, and a large amount of solid was observed to precipitate. The solid was filtered with a Buchner funnel, and the obtained solid was dissolved in ml of water to obtain a solution, and 25ml of concentrated hydrochloric acid was added to adjust the pH, the precipitated solid was filtered off with suction again and dried over anhydrous sodium sulfate to obtain a white solid powder product, 8.5g (yield 78%,m. P. 269 °c). |
| efficacy and role of Acacia seeds | [medicinal parts] from the legume seeds of acacia. [chemical composition] containing triterpene glycoside A, triterpene glycoside B, triterpene glycoside C, triterpene glycoside D, lectin-a, lectin-B, abrin protein Ⅰ, abrin protein Ⅱ, abrin protein Ⅲ, abrin, abrin, abrin, abrin, choline, methyl cation of N-dimethyltryptophan methyl ester, decanone base, etc. [sexual taste and Meridian tropism] the nature was flat, with bitter taste. It belongs to the meridian of large intestine, stomach and heart. [efficacy and role] emetic, insecticidal, swelling. It is an insecticide and antipruritic drug. [clinical application] external use, should not be taken orally to prevent poisoning. Topically applied to the affected area. With the treatment of scabies, psoriasis, swelling. [contraindication] This product is toxic and should not be taken orally. |
| biological activity | (S)-Indoximod (1-methyll-l-tryptophan) is indoleamine-2, 3-dioxygenase (IDO) inhibitors. (S)-Indoximod can be used in cancer research. |
| Target | Indoleamine 2,3-Dioxygenase (IDO) |
| Chemical properties | off-white crystalline powder, soluble in methanol, slightly soluble in water, insoluble in ether, soluble in dilute acid and dilute alkali, it is derived from the seeds of Abrus premiorius, Abrus ruticulosus. |
| Usage | abrin has the effects of anti-liver injury and immune enhancement. |
Last Update：2024-04-09 02:00:02
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