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HomeProduct name listGramine

Gramine

Synonym(s):3-(Dimethylaminomethyl)indole;Donaxine;NSC 16892

  • CAS NO.:87-52-5
  • Empirical Formula: C11H14N2
  • Molecular Weight: 174.24
  • MDL number: MFCD00005629
  • EINECS: 201-749-8
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-06 18:33:45
Gramine Structural

What is Gramine?

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.

The Uses of Gramine

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

What are the applications of Application

Gramine is a useful compound for the preparation of D2 receptor antagonists

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.]

Properties of Gramine

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
form  Powder
pka 17.00±0.30(Predicted)
color  Beige
Water Solubility  PRACTICALLY INSOLUBLE
Merck  14,4533
BRN  140521
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 for Gramine

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

Computed Descriptors for Gramine

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