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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 17:43:18 UTC
Update Date2020-11-09 23:17:29 UTC
HMDB IDHMDB0004370
Secondary Accession Numbers
  • HMDB04370
Metabolite Identification
Common NameN-Methyltryptamine
DescriptionN-Methyltryptamine 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. Based on a literature review a small amount of articles have been published on N-Methyltryptamine.
Structure
Data?1582752307
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
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point87 - 89 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
AllCCS[M+H]+ExperimentalNot Available143.0http://allccs.zhulab.cn/database/detail?ID=AllCCS00000478
DarkChem[M+H]+PredictedNot Available138.36631661259
DarkChem[M-H]-PredictedNot Available137.39231661259

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, Positivesplash10-0006-9300000000-cda1856cd3f9a9be8be52017-09-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
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
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-e5d0ebf20455b6c0a9532021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-1900000000-cfcdbac3cdba755294fb2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-4900000000-6351c35b44904458dd172021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-7bf47db63971154d9fbc2021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-1f3eefe4c85b6d6c9d852021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0900000000-03ee0845d8a2e12d5c982021-09-09View Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 References
Major depressive disorder
  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 ]
Associated OMIM IDs
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
Food Biomarker OntologyNot Available
VMH IDM02605
MarkerDB IDNot Available
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. 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. [PubMed:6574135 ]
  3. 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 ]
  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