Showing metabocard for N-Methyltryptamine (BMDB0004370)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:09:23 UTC
Update Date2020-05-21 16:27:05 UTC
MCDB ID BMDB0004370
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
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-cda1856cd3f9a9be8be52017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-0900000000-9f3d3580f44ff890d9482017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-822848a623cb945205992017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0900000000-aeca37a42c6e04d4325c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00kf-1900000000-d53eab471c68809fb7c82017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00kf-5900000000-f4083668545bda8552102017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-355e913a45ee33e9295c2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00kf-5900000000-1b4d8e3ddf4ea31ba73e2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00kf-5900000000-fbbe54b40b8af9d897c62021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-0e2a8616131b493185b52021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-1c80db89940328726fb22021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-4d1da80c5173955a75502021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-5de268ec5bd72e565bca2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014r-5900000000-8c15e85abc899ccef9592021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-1eed92d8ef02bbec784e2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00b9-0900000000-429679de84f745409dc62021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00b9-0900000000-1f7051f1660d63ba423f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-715b206cdf07055bc0302021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0900000000-4d5e4238b68a10b624f62016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-1900000000-eee318bc268c45febfc32016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015c-2900000000-1a64ba33dbf7376a39fe2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-4c2bf25ab0e52c7eea972016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-ccc8d0f0f96ce2885b892016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-015c-2900000000-03489d7c3b16f79c38682016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-e5d0ebf20455b6c0a9532021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-1900000000-cfcdbac3cdba755294fb2021-09-23View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0004370
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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)Download (PDF)
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 ]