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Record Information
Version4.0
Creation Date2006-08-13 17:43:18 UTC
Update Date2017-09-27 08:24:28 UTC
HMDB IDHMDB0004370
Secondary Accession Numbers
  • HMDB04370
Metabolite Identification
Common NameN-Methyltryptamine
DescriptionN-Methyltryptamine (NMT), or monomethyltryptamine, is a tryptamine alkaloid that has been found in the bark, shoots and leaves of numerous plants. (wikipedia). N-Methyltryptamine was detected in urine from all autistic patients with mental retardation and epilepsy and many autistic patients (32/47) with mental retardation (PubMed ID 8747157 ).
Structure
Thumb
Synonyms
ValueSource
3-(2-Methylaminoethyl)indoleChEBI
N-Methyl-1H-indole-3-ethanamineChEBI
N-MonomethyltryptamineChEBI
N(Omega)-methyltryptamineChEBI
1-Methyl-2-(3-indolyl)ethylamineHMDB
2-(1H-indol-3-yl)-N-MethylethanamineHMDB
3-(2-(methylamino)Ethyl)indoleHMDB
DipterineHMDB
DL-MethyltryptamineHMDB
MethyltryptamineHMDB
N-MethylindoleethylamineHMDB
N-Omega-methyltryptamineHMDB
N-Methyltryptamine oxalateMeSH
N-Methyltryptamine hydrochlorideMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as tryptamines and derivatives. These are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassIndoles 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
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Biofluid and excreta:

Source:

  Biological:

    Plant:

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
Water Solubility0.47 g/LALOGPS
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 RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
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
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Tryptophan MetabolismPw000163Pw000163 greyscalePw000163 simpleMap00380
Displaying 1 entry
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.0026 (0.000045-0.00010) umol/mmol creatinineAdult (>18 years old)BothSurgical patients details
UrineDetected and Quantified0.0049 (0.000018-0.000094) umol/mmol creatinineAdult (>18 years old)BothPsychiatric disorder details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023368
KNApSAcK IDNot Available
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. Takeda N, Ikeda R, Ohba K, Kondo M: Bufotenine reconsidered as a diagnostic indicator of psychiatric disorders. Neuroreport. 1995 Nov 27;6(17):2378-80. [PubMed:8747157 ]
  2. 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 ]
  3. 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. [PubMed:6574135 ]
  4. 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. [PubMed:22091 ]

Enzymes

General function:
Involved in methyltransferase activity
Specific function:
Functions as thioether S-methyltransferase and is active with a variety of thioethers and the corresponding selenium and tellurium compounds, including 3-methylthiopropionaldehyde, dimethyl selenide, dimethyl telluride, 2-methylthioethylamine, 2-methylthioethanol, methyl-n-propyl sulfide and diethyl sulfide. Plays an important role in the detoxification of selenium compounds (By similarity). Catalyzes the N-methylation of tryptamine and structurally related compounds.
Gene Name:
INMT
Uniprot ID:
O95050
Molecular weight:
28833.695
Reactions
S-Adenosylmethionine + Tryptamine → S-Adenosylhomocysteine + N-Methyltryptaminedetails