Gramine

Base Information

• Chemical Name: Gramine
• CAS No.: 87-52-5
• Molecular Formula: C11H14N2
• Molecular Weight: 174.246
• Hs Code.: 29339900
• European Community (EC) Number: 201-749-8
• NSC Number: 16892
• UNII: FGQ8A78L14
• DSSTox Substance ID: DTXSID3058955
• Nikkaji Number: J10.618F
• Wikipedia: Gramine
• Wikidata: Q420118
• NCI Thesaurus Code: C64181
• Pharos Ligand ID: RBBW41X9A8PM
• Metabolomics Workbench ID: 47044
• ChEMBL ID: CHEMBL254348
• Mol file: 87-52-5.mol

Synonyms:3-(dimethylaminomethyl)indole;gramine

Chemical Property of Gramine

Chemical Property:

• Appearance/Colour: beige powder
• Vapor Pressure: 0.00168mmHg at 25°C
• Melting Point: 132-134 °C(lit.)
• Refractive Index: 1.63
• Boiling Point: 293.9 °C at 760 mmHg
• PKA: 17.00±0.30(Predicted)
• Flash Point: 131.5 °C
• PSA: 19.03000
• Density: 1.099 g/cm³
• LogP: 2.22950
• Storage Temp.: Refrigerator (+4°C)
• Solubility.: almost transparency in Methanol
• Water Solubility.: PRACTICALLY INSOLUBLE
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 174.115698455
• Heavy Atom Count: 13
• Complexity: 168

Purity/Quality:

99% ^*data from raw suppliers

Gramine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 45-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CC1=CNC2=CC=CC=C21
• Uses: Reactant 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

Technology Process of Gramine

There total 25 articles about Gramine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

indole (120-72-9) + formaldehyd (50-00-0,30525-89-4,61233-19-0) + dimethyl amine (124-40-3) → 3-(Dimethylaminomethyl)indole (87-52-5)

Guidance literature:

With zinc(II) chloride; In ethanol; at 20 ℃; for 1.5h;

DOI:10.1080/00397910600602503

Reference yield: 98.0%

indole (120-72-9) + N,N-dimethyl(methylene)ammonium chloride (30354-18-8) → 3-(Dimethylaminomethyl)indole (87-52-5)

Guidance literature:

In dichloromethane; for 0.166667h;

Reference yield: 96.0%

indole (120-72-9) + bis-(dimethylamino)methane (51-80-9) → 3-(Dimethylaminomethyl)indole (87-52-5)

Guidance literature:

With sulfur dioxide; In acetonitrile; for 96h;

DOI:10.1016/0040-4039(88)85070-6

upstream raw materials:

indole

bis-(dimethylamino)methane

N,N-dimethyl(methylene)ammonium chloride

formaldehyd

Downstream raw materials:

3,3'-diindolylmethane

3-(2-Nitro-2-phenylethyl)indole

3-(2-nitroethyl)indole

isopropylidene benzyl<(3-indolyl)methyl>malonate

Refernces

• 1、 O'Donovan,Leete. "-". . p. 461. Retrieved 1963.
• 2、 Alzweiri, Muhammed,A. Alsegiani, Amsha,Karaj, Endri,A. Almarghalani, Daniyah,Tabaza, Yahia,A. Shah, Zahoor,Tillekeratne, L.M. Viranga. "The structural simplification of lysergic acid as a natural lead for synthesizing novel anti-Alzheimer agents". supporting information. . Retrieved 2021/06/26.
• 3、 Nimbarte, Vijaykumar D.,Wirmer-Bartoschek, Julia,Gande, Santosh L.,Alshamleh, Islam,Seibert, Marcel,Nasiri, Hamid Reza,Schnütgen, Frank,Serve, Hubert,Schwalbe, Harald. "Synthesis and in Vitro Evaluation of Novel 5-Nitroindole Derivatives as c-Myc G-Quadruplex Binders with Anticancer Activity". . p. 1667 - 1679. Retrieved 2021/03/24.