Basic information
- CAS
87-52-5- Standard SMILES
CN(C)Cc1c[nH]c2ccccc12- InChIKey
OCDGBSUVYYVKQZ-UHFFFAOYSA-N- Molecular formula
- C11H14N2
- Average molar mass
- 174.24 g/mol
- Monoisotopic mass
- 174.11569845
Overview
Gramine is an aminoalkylindole that is indole carrying a dimethylaminomethyl substituent at postion 3. It has a role as an antiviral agent, an antibacterial agent, a serotonergic antagonist and a plant metabolite. It is an aminoalkylindole, an indole alkaloid and a tertiary amino compound. It is a conjugate base of a gramine(1+).
Names & identifiers
- Preferred name
- Gramine
- IUPAC
- 1-(1H-indol-3-yl)-N,N-dimethylmethanamine
- English name
- Gramine
- Molecular formula
- C11H14N2
- Molecular weight
- 174.24
Names & synonyms
Gramine87-52-53-(Dimethylaminomethyl)indoleDonaxineDonaxinGramin1-(1H-indol-3-yl)-N,N-dimethylmethanamine1H-Indole-3-methanamine, N,N-dimethyl-beta-DimethylaminomethylindoleN,N-Dimethyl-1H-indole-3-methanamine3-(N,N-Dimethylaminomethyl)indole(1H-indol-3-ylmethyl)dimethylamine
Show more names
DoranineNSC 16892GRAMINE(RG)Gramine >Gramine,>99%
3-[(Dimethylamino)methyl]indoleN,N-Dimethyl-1H-indole-3-methylamineFGQ8A78L14DTXSID3058955NSC-16892CHEBI:289483-((DIMETHYLAMINO)METHYL)INDOLE3-[Dimethylaminomethyl]indole
Database identifiers
- CAS
87-52-5- PubChem CID
- 6890
- DTXSID
DTXSID3058955- ChEMBL
CHEMBL254348- ChEBI
CHEBI:28948- UNII
- FGQ8A78L14
- EC Number
Properties
Computed structural properties
- XLogP
- 1.8
- Topological polar surface area
- 19 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 2
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 167
Experimental & physicochemical properties
Melting Point138 - 139 °C
Physical DescriptionSolid
Collision Cross Section
138.42 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
134.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 132 · 132-134 °C (lit.)
- Boiling point
- 295.23 °C · 295.23°C (rough estimate)
- Density
- 1.0715 · 1.0715 (rough estimate)
- refractive index
- 1.55 · 1.5500 (estimate)
- Flash point
- 167 °C · 167 °C
- storage temp.
- Refrigerator (+4°C)
- solubility
- almost transparency in Methanol
- pka
- 17 · 17.00±0.30(Predicted)
- form
Safety & regulation
GHS classification
GHS Classification
Danger
H314 (93.8%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 32 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information1H-Indole-3-methanamine, N,N-dimethyl-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Corr. 1B (93.8%)
Safety data
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- NL7525000
- hs_code
- 29339900
- risk_code
- 34
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- C
- safety_code
- 45-36/37/39-26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302+H312
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 Oral
- Precautionary statements
- P264-P270-P280-P301+P312-P302+P352+P312-P362+P364
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
General Manufacturing Information1H-Indole-3-methanamine, N,N-dimethyl-: ACTIVE
Applications
UsesReactant for preparation of:Dopamine D2 receptor antagonistsAnti-malarial drugs5-indolyl-Mannich basesProliferation inhibitorsInhibitors of human mast cell chymasePreparation of DL-tryptophanPotential detoxification inhibitors of the crucifer phytoalexin brassinin3-vinylindolesSerotonin 5-HT6 receptor ligand templatesSelective protein kinase c delta (PKCδ) down regulators
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
Upstream & downstream products
Upstream raw materials
Related reactions
19 records
Compound notes
Loading…