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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:47:01 UTC
Update Date2021-09-07 17:05:35 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 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 Molecular Properties
PropertyValueReference
Melting Point138 - 139 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
AllCCS[M+H]+ExperimentalNot Available134.852http://allccs.zhulab.cn/database/detail?ID=AllCCS00001124
DarkChem[M+H]+PredictedNot Available139.19931661259
DarkChem[M-H]-PredictedNot Available136.95531661259

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-2900000000-e16912ed7a8b64df55c82017-07-27View Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-3900000000-d1d9e746dd89f8340e662015-03-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0059-0900000000-46a2a8bc6df733c63b6e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-002b-0900000000-d62fe8bf9fe908b6c6572017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-7ddf4cc8719b5bb024382017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-8a648696af7414a85f142017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-a15c86c98c024930425a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-1900000000-18494e76b11d09a6db0a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9600000000-ad30c2cd79b87e7cf3d82017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-f9f2e8362c42c7d0ac112017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004i-0900000000-d2c4aaf90ad86d48951e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0900000000-b9adc728e65f3947056c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0910000000-4d9be164e6468558ee0e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001i-2900000000-0b8ed5267aeded5f760a2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-001i-0900000000-b21eb9303021ba27c6a52021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-e913804323f5982091482021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-cc77ee60897881ca34332021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-edce45bfa47c9f3c7cbe2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-93027cb8819607deda322021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001i-0900000000-b734096fe5125e8b81582021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-003r-6900000000-31b1a35b9a4b0478b41d2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-67c885f9800d6d095f142016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003r-0900000000-414a182f24f2887b51112016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0900000000-59033a77b0437b7c7b6a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-2f44253b46777aef2f622016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-3b82d8097f71c789b8a52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06r6-7900000000-078092839a6793aa904f2016-08-03View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)2015-03-12View Spectrum
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 IDNot Available
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.. .