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Showing Compound 3-(Dimethylaminomethyl)indole (FDB014498)

Record Information
Version1.0
Creation date2010-04-08 22:11:18 UTC
Update date2019-11-26 03:10:10 UTC
Primary IDFDB014498
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-(Dimethylaminomethyl)indole
Description3-(Dimethylaminomethyl)indole, also known as donaxin or (1H-indol-3-ylmethyl)dimethylamine, belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. 3-(Dimethylaminomethyl)indole is a very strong basic compound (based on its pKa). 3-(Dimethylaminomethyl)indole has been detected, but not quantified in, several different foods, such as barley, brassicas, cereals and cereal products, common wheats, and lupines. This could make 3-(dimethylaminomethyl)indole a potential biomarker for the consumption of these foods.
CAS Number87-52-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(1H-indol-3-Ylmethyl)dimethylamineChEBI
3-(N,N-Dimethylaminomethyl)indoleChEBI
3-[(Dimethylamino)methyl]indoleChEBI
beta-DimethylaminomethylindoleChEBI
DonaxinChEBI
DonaxineChEBI
GraminChEBI
indol-3-YlmethyldimethylamineChEBI
N,N-Dimethyl-1H-indole-3-methanamineChEBI
(1H-indol-3-yl)-N,N-DimethylmethanamineKegg
b-DimethylaminomethylindoleGenerator
Β-dimethylaminomethylindoleGenerator
(1H-indol-3-Ylmethyl)-dimethyl-amineHMDB
(indol-3-Ylmethyl)dimethylamineHMDB
1-(1H-indol-3-yl)-N,N-DimethylmethanamineHMDB
1H-indol-3-yl-N,N-DimethylmethanamineHMDB
3-((Dimethylamino)methyl)-indoleHMDB
3-Dimethylaminomethylindol (gramin)HMDB
3-[(Dimethylamino)methyl]-indoleHMDB
b-(Dimethylaminomethyl)indoleHMDB
beta -DimethylaminomethylindoleHMDB
DoranineHMDB
Indolalkylamine der.HMDB
N,N-Dimethyl-1H-indole-3-methanamine, 9ciHMDB
N,N-Dimethyl-1H-indole-3-methylamineHMDB
3-(Dimethylaminomethyl)indoleChEBI
(1H-Indol-3-ylmethyl)-dimethyl-aminebiospider
(Indol-3-ylmethyl)dimethylaminebiospider
β-dimethylaminomethylindolebiospider
1-(1H-indol-3-yl)-N,N-dimethylmethanaminebiospider
1H-Indol-3-yl-N,N-dimethylmethanaminebiospider
1H-Indole-3-methanamine, N,N-dimethyl-biospider
3-((dimethylamino)Methyl)-indoleHMDB
3-[(dimethylamino)Methyl]-indoleHMDB
B-(dimethylaminomethyl)indolebiospider
Beta-dimethylaminomethylindolebiospider
Graminedb_source
Indol-3-ylmethyldimethylaminebiospider
Indole, 3-((dimethylamino)methyl)-biospider
Indole, 3-[(dimethylamino)methyl]-biospider
N,N-Dimethyl-1H-indole-3-methanamine, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility3.43 g/LALOGPS
logP2.01ALOGPS
logP2.01ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)15.97ChemAxon
pKa (Strongest Basic)8.99ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area19.03 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity55.69 m³·mol⁻¹ChemAxon
Polarizability20.24 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H14N2
IUPAC name[(1H-indol-3-yl)methyl]dimethylamine
InChI IdentifierInChI=1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3
InChI KeyOCDGBSUVYYVKQZ-UHFFFAOYSA-N
Isomeric SMILESCN(C)CC1=CNC2=CC=CC=C12
Average Molecular Weight174.2423
Monoisotopic Molecular Weight174.115698458
Classification
Description Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Aralkylamine
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 75.82%; H 8.10%; N 16.08%DFC
Melting PointMp 138-139°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKapKa 16 (25°,NH, aq. KOH)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-001i-3900000000-d1d9e746dd89f8340e66Spectrum
Predicted GC-MS3-(Dimethylaminomethyl)indole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-053r-2900000000-e16912ed7a8b64df55c8Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0059-0900000000-46a2a8bc6df733c63b6eSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-002b-0900000000-d62fe8bf9fe908b6c657Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-7ddf4cc8719b5bb02438Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-8a648696af7414a85f14Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-a15c86c98c024930425aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-1900000000-18494e76b11d09a6db0aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9600000000-ad30c2cd79b87e7cf3d8Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-f9f2e8362c42c7d0ac11Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004i-0900000000-d2c4aaf90ad86d48951eSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0900000000-b9adc728e65f3947056cSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0910000000-4d9be164e6468558ee0eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-67c885f9800d6d095f14Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003r-0900000000-414a182f24f2887b5111Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000000-59033a77b0437b7c7b6aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-2f44253b46777aef2f62Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-3b82d8097f71c789b8a5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06r6-7900000000-078092839a6793aa904fSpectrum
NMR
TypeDescriptionView
1D NMR13C NMR SpectrumSpectrum
ChemSpider ID6625
ChEMBL IDCHEMBL254348
KEGG Compound IDC08304
Pubchem Compound ID6890
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35762
CRC / DFC (Dictionary of Food Compounds) IDJRK41-S:JRK41-S
EAFUS IDNot Available
Dr. Duke IDGRAMINE
BIGG IDNot Available
KNApSAcK IDC00001411
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti arrhythmic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti feedantDUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
vasopressorDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.