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: 2024-11-19 20:33:22
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) |
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
New Products
4-Aminotetrahydropyran-4-carbonitrile Hydrochloride (R)-3-Aminobutanenitrile Hydrochloride 4-AMINO-TETRAHYDRO-PYRAN-4-CARBOXYLIC ACID HCL 4-(Dimethylamino)tetrahydro-2H-pyran-4-carbonitrile 3-((Dimethylamino)methyl)-5-methylhexan-2-one oxalate 1,4-Dioxa-8-azaspiro[4.5]decane 5-Bromo-2-nitropyridine Nimesulide BP Aceclofenac IP/BP/EP Mefenamic Acid IP/BP/EP/USP Diclofenac Sodium IP/BP/EP/USP Ornidazole IP Diclofenac Potassium SODIUM AAS SOLUTION ZINC AAS SOLUTION BUFFER SOLUTION PH 10.0(BORATE) GOOCH CRUCIBLE SINTERED AQUANIL 5 BERYLLIUM AAS SOLUTION 2-Bromo-1-(bromomethyl)-3-chloro-5-nitrobenzene 2-Bromo-3-nitroaniline N-(3-Hydroxypropyl)-N-methylacetamide 3-Bromo-6-chloropyridazine 4-ethyl-3-nitrobenzoic acidRelated products of tetrahydrofuran
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