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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 has been detected, but not quantified in, several different foods, such as brassicas, barleys (Hordeum vulgare), common wheats (Triticum aestivum), breakfast cereal, and cereals and cereal products. This could make 3-(dimethylaminomethyl)indole a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 3-(Dimethylaminomethyl)indole.
CAS Number87-52-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
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-d1d9e746dd89f8340e662015-03-01View Spectrum
Predicted GC-MS3-(Dimethylaminomethyl)indole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-053r-2900000000-e16912ed7a8b64df55c8Spectrum
Predicted GC-MS3-(Dimethylaminomethyl)indole, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-(Dimethylaminomethyl)indole, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0059-0900000000-46a2a8bc6df733c63b6e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-002b-0900000000-d62fe8bf9fe908b6c6572017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-7ddf4cc8719b5bb024382017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-8a648696af7414a85f142017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-a15c86c98c024930425a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-1900000000-18494e76b11d09a6db0a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9600000000-ad30c2cd79b87e7cf3d82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-f9f2e8362c42c7d0ac112017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004i-0900000000-d2c4aaf90ad86d48951e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0900000000-b9adc728e65f3947056c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0910000000-4d9be164e6468558ee0e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001i-2900000000-0b8ed5267aeded5f760a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-001i-0900000000-b21eb9303021ba27c6a52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-e913804323f5982091482021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-cc77ee60897881ca34332021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-edce45bfa47c9f3c7cbe2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-93027cb8819607deda322021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001i-0900000000-b734096fe5125e8b81582021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-003r-6900000000-31b1a35b9a4b0478b41d2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-67c885f9800d6d095f142016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003r-0900000000-414a182f24f2887b51112016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000000-59033a77b0437b7c7b6a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-2f44253b46777aef2f622016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-3b82d8097f71c789b8a52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06r6-7900000000-078092839a6793aa904f2016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
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.