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Gramine

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Name

Gramine

EINECS 201-749-8
CAS No. 87-52-5 Density 1.099 g/cm3
PSA 19.03000 LogP 2.22950
Solubility PRACTICALLY INSOLUBLE Melting Point 132-134 °C(lit.)
Formula C11H14N2 Boiling Point 293.9 °C at 760 mmHg
Molecular Weight 174.246 Flash Point 131.5 °C
Transport Information N/A Appearance beige powder
Safety 45-36/37/39-26 Risk Codes 34
Molecular Structure Molecular Structure of 87-52-5 (Gramine) Hazard Symbols CorrosiveC
Synonyms

Gramine(6CI);Indole, 3-[(dimethylamino)methyl]-(8CI);3-(N,N-Dimethylaminomethyl)indole;3-[(Dimethylamino)methyl]-1H-indole;3-[(Dimethylamino)methyl]indole;N,N-Dimethyl-1H-indole-3-methylamine;

Article Data 49

Gramine Consensus Reports

Reported in EPA TSCA Inventory.

Gramine Specification

The Donaxine with CAS registry number of 87-52-5 is also called 3-[(Dimethylamino)methyl]indole. Its EINECS registry number is 201-749-8. The IUPAC name is 1-(1H-indol-3-yl)-N,N-dimethylmethanamine. In addition, the molecular formula is C11H14N2 and the molecular weight is 174.24. It is a kind of beige powder and belongs to the classes of Pharmaceutical Intermediates; Indoles and derivatives; Indole; Indoles; Alkaloids; Biochemistry; Indole Alkaloids; Simple Indoles.

Physical properties about this chemical are: (1)ACD/LogP: 1.90; (2)ACD/LogD (pH 5.5): -1.15; (3)ACD/LogD (pH 7.4): -0.17; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 2.2; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 2; (11)Polar Surface Area: 8.17 Å2; (12)Index of Refraction: 1.63; (13)Molar Refractivity: 56.43 cm3; (14)Molar Volume: 158.4 cm3; (15)Polarizability: 22.37 ×10-24cm3; (16)Surface Tension: 46 dyne/cm; (17)Density: 1.099 g/cm3; (18)Flash Point: 131.5 °C; (19)Enthalpy of Vaporization: 53.35 kJ/mol; (20)Boiling Point: 293.9 °C at 760 mmHg; (21)Vapour Pressure: 0.00168 mmHg at 25°C.

Preparation of Donaxine: it can be prepared by indole, methanal and dicarboamine. And it is a condensation reaction. Firstly, cool the dicarboamine to -5 °C, and add it into glacial acetic acid. Then add indole and methanal into the dicarboamine at the temperature about 5 °C. The reaction time is 8 hours at reaction temperature of 30-40 °C. Via a series of cooling, acidification, crystallization you can get the product.

Uses of Donaxine: it is used for the production of anion-exchange resin. And it can react with acetic acid anhydride to get 3-acetoxymethyl-1-acetyl-indole. The reaction time is 45 minutes by heating. The yield is about 80%.

Donaxine can react with acetic acid anhydride to get 3-acetoxymethyl-1-acetyl-indole

When you are using this chemical, please be cautious about it as the following:
This chemical can cause burns. During using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.).

You can still convert the following datas into molecular structure:
(1)SMILES: c1cccc2c1c(cn2)CN(C)C
(2)InChI: InChI=1/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3
(3)InChIKey: OCDGBSUVYYVKQZ-UHFFFAOYAK

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 122mg/kg (122mg/kg)   Psychopharmacologia Vol. 16, Pg. 385, 1970.
mouse LD50 intravenous 46mg/kg (46mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT
Journal of Pharmacology and Experimental Therapeutics. Vol. 105, Pg. 130, 1952.
rat LDLo intraperitoneal 250mg/kg (250mg/kg)   National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 11, 1953.

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