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)

Flash point:

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

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

HS Code 

29339900

MSDS

• Language:English Provider:3-(Dimethylaminomethyl)indole
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

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(87-52-5)Related Product Information

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• Dimethyl ether
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• Dimethyl fumarate
• 2-Methylindole
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• Indole