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Record Information
Version2.0
Created at2021-06-20 19:31:45 UTC
Updated at2021-06-30 00:07:55 UTC
NP-MRD IDNP0036327
Secondary Accession NumbersNone
Natural Product Identification
Common NameN-methyltryptamine
Provided ByJEOL DatabaseJEOL Logo
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. In humans, N-methyltryptamine is involved in the tryptophan metabolism pathway. N-Methyltryptamine has been detected, but not quantified in, milk (cow). This could make N-methyltryptamine a potential biomarker for the consumption of these foods. N-Methyltryptamine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. N-methyltryptamine is found in Acacia confusa, Acacia maidenii, Anadenanthera peregrina, Mimosa ophthalmocentra, Mimosa somnians, Nectandra megapotamica, Paramuricea clavata, Tachigali paniculata, Vachellia rigidula and Virola sebifera. N-methyltryptamine was first documented in 1977 (PMID: 22091). Based on a literature review a small amount of articles have been published on N-Methyltryptamine (PMID: 11763413) (PMID: 6574135).
Structure
Thumb
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
3-(2-(Methylamino)ethyl)indoleHMDB
DipterineHMDB
DL-MethyltryptamineHMDB
MethyltryptamineHMDB
N-Omega-methyltryptamineHMDB
N-Methyltryptamine oxalateHMDB
N-Methyltryptamine hydrochlorideHMDB
Chemical FormulaC11H14N2
Average Mass174.2423 Da
Monoisotopic Mass174.11570 Da
IUPAC Name[2-(1H-indol-3-yl)ethyl](methyl)amine
Traditional Namemethyltryptamine
CAS Registry NumberNot Available
SMILES
[H]N(C([H])([H])[H])C([H])([H])C([H])([H])C1=C([H])N([H])C2=C1C([H])=C([H])C([H])=C2[H]
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acacia confusaLOTUS Database
Acacia maideniiLOTUS Database
Acacia rigidulaKNApSAcK Database
Anadenanthera peregrinaLOTUS Database
Chimonanthus fragransKNApSAcK Database
Mimosa ophthalmocentraLOTUS Database
Mimosa somniansLOTUS Database
Nectandra megapotamicaLOTUS Database
Paramuricea clavataJEOL database
    • Penez, N., et al, J. Nat. Prod. 74, 2304 (2011)
Prosopis nigraKNApSAcK Database
Tachigali paniculataLOTUS Database
Taxus chinensisKNApSAcK Database
Vachellia rigidulaLOTUS Database
Virola sebiferaLOTUS Database
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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot 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 RuleNoChemAxon
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
Good Scents IDNot Available
References
General References
  1. Forsstrom T, Tuominen J, Karkkainen J: Determination of potentially hallucinogenic N-dimethylated indoleamines in human urine by HPLC/ESI-MS-MS. Scand J Clin Lab Invest. 2001;61(7):547-56. [PubMed:11763413 ]
  2. VandenHeuvel WJ, Carlin JR, Walker RW: Biochemical and biomedical applications of capillary column GLC using SIM. J Chromatogr Sci. 1983 Mar;21(3):119-24. doi: 10.1093/chromsci/21.3.119. [PubMed:6574135 ]
  3. Oon MC, Murray RM, Rodnight R, Murphy MP, Birley JL: Factors affecting the urinary excretion of endogenously formed dimethyltryptamine in normal human subjects. Psychopharmacology (Berl). 1977 Oct 20;54(2):171-5. doi: 10.1007/BF00426775. [PubMed:22091 ]
  4. Penez, N., et al. (2011). Penez, N., et al, J. Nat. Prod. 74, 2304 (2011). J. Nat. Prod..