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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:47:01 UTC
Update Date2019-07-23 06:19:28 UTC
HMDB IDHMDB0035762
Secondary Accession Numbers
  • HMDB35762
Metabolite Identification
Common 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. An aminoalkylindole that is indole carrying a dimethylaminomethyl substituent at postion 3. 3-(Dimethylaminomethyl)indole is a very strong basic compound (based on its pKa). Outside of the human body, 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.
Structure
Data?1563862768
Synonyms
ValueSource
(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
Chemical FormulaC11H14N2
Average Molecular Weight174.2423
Monoisotopic Molecular Weight174.115698458
IUPAC Name[(1H-indol-3-yl)methyl]dimethylamine
Traditional Namegramin
CAS Registry Number87-52-5
SMILES
CN(C)CC1=CNC2=CC=CC=C12
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point138 - 139 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot 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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-2900000000-e16912ed7a8b64df55c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0059-0900000000-46a2a8bc6df733c63b6eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-002b-0900000000-d62fe8bf9fe908b6c657Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-7ddf4cc8719b5bb02438Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-8a648696af7414a85f14Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-a15c86c98c024930425aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-1900000000-18494e76b11d09a6db0aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9600000000-ad30c2cd79b87e7cf3d8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-f9f2e8362c42c7d0ac11Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004i-0900000000-d2c4aaf90ad86d48951eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0900000000-b9adc728e65f3947056cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0910000000-4d9be164e6468558ee0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-67c885f9800d6d095f14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003r-0900000000-414a182f24f2887b5111Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000000-59033a77b0437b7c7b6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-2f44253b46777aef2f62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-3b82d8097f71c789b8a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06r6-7900000000-078092839a6793aa904fSpectrum
MSMass Spectrum (Electron Ionization)splash10-001i-3900000000-d1d9e746dd89f8340e66Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014498
KNApSAcK IDC00001411
Chemspider ID6625
KEGG Compound IDC08304
BioCyc IDCPD-8915
BiGG IDNot Available
Wikipedia LinkGramine
METLIN IDNot Available
PubChem Compound6890
PDB IDNot Available
ChEBI ID28948
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .