Showing metabocard for N-Methyltryptamine (BMDB0004370)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:09:23 UTC
Update Date2020-05-21 16:27:05 UTC
BMDB IDBMDB0004370
Secondary Accession Numbers
  • BMDB04370
Metabolite Identification
Common NameN-Methyltryptamine
DescriptionN-Methyltryptamine, also known as dipterine, belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine. N-Methyltryptamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. N-Methyltryptamine and S-adenosylhomocysteine can be biosynthesized from tryptamine and S-adenosylmethionine through its interaction with the enzyme indolethylamine N-methyltransferase. In cattle, N-methyltryptamine is involved in the metabolic pathway called the tryptophan metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-(2-Methylaminoethyl)indoleChEBI
N-Methyl-1H-indole-3-ethanamineChEBI
N-MonomethyltryptamineChEBI
N(Omega)-methyltryptamineChEBI
N-MethylindoleethylamineKegg
1-Methyl-2-(3-indolyl)ethylamineKegg
2-(1H-indol-3-yl)-N-MethylethanamineHMDB, MeSH
3-(2-(methylamino)Ethyl)indoleHMDB
DipterineHMDB
DL-MethyltryptamineHMDB
MethyltryptamineHMDB
N-Omega-methyltryptamineHMDB
N-Methyltryptamine oxalateMeSH, HMDB
N-Methyltryptamine hydrochlorideMeSH, HMDB
Chemical FormulaC11H14N2
Average Molecular Weight174.2423
Monoisotopic Molecular Weight174.115698458
IUPAC Name[2-(1H-indol-3-yl)ethyl](methyl)amine
Traditional Namemethyltryptamine
CAS Registry Number61-49-4
SMILES
CNCCC1=CNC2=CC=CC=C12
InChI Identifier
InChI=1S/C11H14N2/c1-12-7-6-9-8-13-11-5-3-2-4-10(9)11/h2-5,8,12-13H,6-7H2,1H3
InChI KeyNCIKQJBVUNUXLW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentTryptamines and derivatives
Alternative Parents
Substituents
  • Tryptamine
  • 3-alkylindole
  • Indole
  • Aralkylamine
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Secondary aliphatic amine
  • Secondary amine
  • Azacycle
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point87 - 89 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.02ALOGPS
logP1.92ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)17.17ChemAxon
pKa (Strongest Basic)10.31ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area27.82 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity55.15 m³·mol⁻¹ChemAxon
Polarizability20.42 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-cda1856cd3f9a9be8be5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-0900000000-9f3d3580f44ff890d948View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-822848a623cb94520599View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-aeca37a42c6e04d4325cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00kf-1900000000-d53eab471c68809fb7c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00kf-5900000000-f4083668545bda855210View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-355e913a45ee33e9295cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00kf-5900000000-1b4d8e3ddf4ea31ba73eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00kf-5900000000-fbbe54b40b8af9d897c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-0e2a8616131b493185b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-1c80db89940328726fb2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-4d1da80c5173955a7550View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-5de268ec5bd72e565bcaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014r-5900000000-8c15e85abc899ccef959View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-1eed92d8ef02bbec784eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00b9-0900000000-429679de84f745409dc6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00b9-0900000000-1f7051f1660d63ba423fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-715b206cdf07055bc030View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0900000000-4d5e4238b68a10b624f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-1900000000-eee318bc268c45febfc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015c-2900000000-1a64ba33dbf7376a39feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-4c2bf25ab0e52c7eea97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-ccc8d0f0f96ce2885b89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-015c-2900000000-03489d7c3b16f79c3868View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-e5d0ebf20455b6c0a953View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-1900000000-cfcdbac3cdba755294fbView in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
HMDB IDHMDB0004370
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023368
KNApSAcK IDC00026521
Chemspider ID5863
KEGG Compound IDC06213
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Methyltryptamine
METLIN ID7057
PubChem Compound6088
PDB IDNot Available
ChEBI ID28136
References
Synthesis ReferenceManske, Richard H. F. Calycanthine. II. The degradation of calycanthine to N-methyltryptamine. Can. J. Research (1931), 4 275-82.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21. [PubMed:23394630 ]

Enzymes

Enzyme Details
1. Phenylethanolamine N-methyltransferase
General function:
Involved in phenylethanolamine N-methyltransferase acti
Specific function:
Converts noradrenaline to adrenaline.
Gene Name:
PNMT
Uniprot ID:
P10938
Molecular weight:
30918.0
Reactions
Tryptamine + S-Adenosylmethionine → N-Methyltryptamine + S-Adenosylhomocysteinedetails