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Gramine

Basic information Safety Supplier Related

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
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • Inhibitors
  • standardized herbal extract
Mol File:
87-52-5.mol
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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
form 
Powder
pka
17.00±0.30(Predicted)
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)
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Safety Information

Hazard Codes 
C
Risk Statements 
34
Safety Statements 
45-36/37/39-26
WGK Germany 
3
RTECS 
NL7525000
HS Code 
29339900

MSDS

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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

Preparation Products

Raw materials

GramineSupplier

J & K SCIENTIFIC LTD.
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010-82848833 400-666-7788
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Meryer (Shanghai) Chemical Technology Co., Ltd.
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4006608290; 18621169109
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Chembest Research Laboratories Limited
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021-20908456
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TCI (Shanghai) Development Co., Ltd.
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021-67121386
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Ark Pharm, Inc.
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847-367-3680
Email
sales@arkpharminc.com