Introduction：Basic information about Gramine CAS 87-52-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Gramine Basic information
| Product Name: | Gramine |
| Synonyms: | n,n-dimethyl-1h-indole-3-methanamine;indol-3-ylmethyldimethylamine;GCLH / for Cefixime;3-(dimethylaninomethy)in dole;Indole, 3-[(dimethylamino)methyl]-;n,n-dimethyl-1h-indole-3-methanamin;N,N-Dimethyl-1H-indole-3-methylamine;TIMTEC-BB SBB003799 |
| CAS: | 87-52-5 |
| MF: | C11H14N2 |
| MW: | 174.24 |
| EINECS: | 201-749-8 |
| Product Categories: | Indole;Indoles;Pharmaceutical Intermediates;indole derivative;Indoles and derivatives;Alkaloids;Biochemistry;Indole Alkaloids;Simple Indoles;Inhibitors;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract |
| Mol File: | 87-52-5.mol |
|
Gramine Chemical Properties
| Melting point | 132-134 °C (lit.) |
| Boiling point | 295.23°C (rough estimate) |
| density | 1.0715 (rough estimate) |
| refractive index | 1.5500 (estimate) |
| Fp | 167 °C |
| storage temp. | Refrigerator (+4°C) |
| solubility | almost transparency in Methanol |
| pka | 17.00±0.30(Predicted) |
| form | Powder |
| color | Beige |
| Water Solubility | PRACTICALLY INSOLUBLE |
| Merck | 14,4533 |
| BRN | 140521 |
| InChI | 1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3 |
| InChIKey | OCDGBSUVYYVKQZ-UHFFFAOYSA-N |
| SMILES | CN(C)Cc1c[nH]c2ccccc12 |
| LogP | 2.177 (est) |
| CAS DataBase Reference | 87-52-5(CAS DataBase Reference) |
| NIST Chemistry Reference | 1H-Indole-3-methanamine, N,N-dimethyl-(87-52-5) |
| EPA Substance Registry System | 1H-Indole-3-methanamine, N,N-dimethyl- (87-52-5) |
Safety Information
| Hazard Codes | C |
| Risk Statements | 34 |
| Safety Statements | 45-36/37/39-26 |
| WGK Germany | 3 |
| RTECS | NL7525000 |
| TSCA | TSCA listed |
| HS Code | 29339900 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Dermal
Acute Tox. 4 Oral |
Gramine Usage And Synthesis
| Chemical Properties | ?3-(Dimethylaminomethyl)indole [87-52-5], gramine, C11H14N2, Mr 174.25, mp 138 – 139 ℃, forms colorless needles. The compound is soluble in ethanol, diethyl ether, and chloroform and insoluble in water. It can be synthesized from indole by the Mannich reaction with dimethyl-amine and formaldehyde. Gramine is used to synthesize D,L-tryptophan, the plant growth regulators indole-3-acetic acid and indole-3-butanoic acid as well as the intermediate tryptamine. |
| Uses | Reactant for preparation of:
- Dopamine D2 receptor antagonists
- Anti-malarial drugs
- 5-indolyl-Mannich bases
- Proliferation inhibitors
- Inhibitors of human mast cell chymase
- Preparation of DL-tryptophan
- Potential detoxification inhibitors of the crucifer phytoalexin brassinin
- 3-vinylindoles
- Serotonin 5-HT6 receptor ligand templates
- Selective protein kinase c delta (PKCδ) down regulators
|
| Definition | ChEBI: Gramine is an aminoalkylindole that is indole carrying a dimethylaminomethyl substituent at postion 3. It has a role as a plant metabolite, a serotonergic antagonist, an antiviral agent and an antibacterial agent. It is an aminoalkylindole, an indole alkaloid and a tertiary amino compound. It is a conjugate base of a gramine(1+). |
| General Description | This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG |
| storage | Room temperature |
| Purification Methods | Crystallise gramine from diethyl ether, ethanol or acetone. It sublimes at 59o/0.001mm. The hydrochloride crystallises from EtOH/Et2O with m 190.5-191.0o(dec). [Culvenor et al. Aust J Chem 17 1301 1964, Beilstein 22 III/IV 4302, 22/10 V 25.] |
Gramine Preparation Products And Raw materials
| Raw materials | Dimethylamine-->Indole-->Methanamine, 1-ethoxy-N,N-dimethyl--->GRAMINE, N-OXIDE-->N,N-dimethyl-1H-indole-3-carboxamide-->ESCHENMOSER'S SALT-->Indole-3-carboxaldehyde-->N,N,N',N'-TETRAMETHYLDIAMINOMETHANE-->Formaldehyde-->Uracil |
| Preparation Products | DL-Tryptophan-->3-Indoleacetonitrile-->Indol-1-ylmethyl-dimethyl-amine-->Indole-3-carbinol |
