Gramine

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
Gramine Structure
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
pka17.00±0.30(Predicted)
form Powder
color Beige
Water Solubility PRACTICALLY INSOLUBLE
Merck 14,4533
BRN 140521
LogP2.177 (est)
CAS DataBase Reference87-52-5(CAS DataBase Reference)
NIST Chemistry Reference1H-Indole-3-methanamine, N,N-dimethyl-(87-52-5)
EPA Substance Registry System1H-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 Information
ProviderLanguage
3-(Dimethylaminomethyl)indole English
ACROS English
SigmaAldrich English
Gramine Usage And Synthesis
Chemical Propertiesbeige powder
UsesReactant 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
DefinitionChEBI: 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 DescriptionThis 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
storageRoom temperature
Purification MethodsCrystallise 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.]
Metformin AURORA 16337 2-Methylindole N,N-Dimethylformamide 3-Dimethylaminopropylamine 5-METHOXYGRAMINE Flunixin meglumine 2-Dimethylaminoethanol 5-BENZYLOXYGRAMINE Meglumine Dimethyl fumarate Gramine Dimethyl sulfoxide 2-METHYL-3-N,N-DIMETHYLAMINOMETHYLINDOLE Dimethyl ether Dimethyl carbonate 2,5-Dimethylindole 2,3-Dimethylindole

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