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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 17:43:18 UTC

Update Date

2023-02-21 17:17:01 UTC

HMDB ID

HMDB0004370

Secondary Accession Numbers

HMDB04370

Metabolite Identification

Common Name

N-Methyltryptamine

Description

N-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      55.991 -22.351   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0      53.527 -28.074   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      55.512 -23.814   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      54.005 -24.132   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      52.070 -27.605   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      53.527 -25.596   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      52.070 -26.065   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      54.426 -26.835   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      50.736 -28.375   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      50.736 -25.295   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      49.402 -27.605   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      49.402 -26.065   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      56.925 -22.154   0.000  0.00  0.00           C+0
CONECT    1    3   13                                                       
CONECT    2    5    8                                                       
CONECT    3    1    4                                                       
CONECT    4    3    6                                                       
CONECT    5    2    7    9                                                  
CONECT    6    4    7    8                                                  
CONECT    7    5    6   10                                                  
CONECT    8    2    6                                                       
CONECT    9    5   11                                                       
CONECT   10    7   12                                                       
CONECT   11    9   12                                                       
CONECT   12   10   11                                                       
CONECT   13    1                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

COMPND    HMDB0004370
HETATM    1  C1  UNL     1       3.539   0.352   0.424  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.488   0.181  -0.594  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.851  -1.117  -0.361  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.073  -1.085   0.947  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.031  -0.066   0.948  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.066   1.159   1.568  1.00  0.00           C  
HETATM    7  N2  UNL     1      -1.083   1.820   1.329  1.00  0.00           N  
HETATM    8  C6  UNL     1      -1.884   1.033   0.549  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.147   1.283   0.054  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.752   0.294  -0.725  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.082  -0.877  -0.971  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.822  -1.099  -0.464  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.189  -0.132   0.317  1.00  0.00           C  
HETATM   14  H1  UNL     1       3.055   0.575   1.394  1.00  0.00           H  
HETATM   15  H2  UNL     1       4.236   1.142   0.109  1.00  0.00           H  
HETATM   16  H3  UNL     1       4.094  -0.605   0.519  1.00  0.00           H  
HETATM   17  H4  UNL     1       2.994   0.094  -1.506  1.00  0.00           H  
HETATM   18  H5  UNL     1       1.248  -1.442  -1.204  1.00  0.00           H  
HETATM   19  H6  UNL     1       2.673  -1.846  -0.218  1.00  0.00           H  
HETATM   20  H7  UNL     1       0.615  -2.113   1.041  1.00  0.00           H  
HETATM   21  H8  UNL     1       1.815  -0.998   1.756  1.00  0.00           H  
HETATM   22  H9  UNL     1       0.853   1.612   2.176  1.00  0.00           H  
HETATM   23  H10 UNL     1      -1.361   2.773   1.661  1.00  0.00           H  
HETATM   24  H11 UNL     1      -3.656   2.223   0.266  1.00  0.00           H  
HETATM   25  H12 UNL     1      -4.740   0.472  -1.122  1.00  0.00           H  
HETATM   26  H13 UNL     1      -3.596  -1.611  -1.582  1.00  0.00           H  
HETATM   27  H14 UNL     1      -1.317  -2.022  -0.671  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   17
CONECT    3    4   18   19
CONECT    4    5   20   21
CONECT    5    6    6   13
CONECT    6    7   22
CONECT    7    8   23
CONECT    8    9    9   13
CONECT    9   10   24
CONECT   10   11   11   25
CONECT   11   12   26
CONECT   12   13   13   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(2-Methylaminoethyl)indole	ChEBI
N-Methyl-1H-indole-3-ethanamine	ChEBI
N-Monomethyltryptamine	ChEBI
N(Omega)-methyltryptamine	ChEBI
N-Methylindoleethylamine	Kegg
1-Methyl-2-(3-indolyl)ethylamine	Kegg
2-(1H-indol-3-yl)-N-Methylethanamine	HMDB, MeSH
3-(2-(methylamino)Ethyl)indole	HMDB
Dipterine	HMDB
DL-Methyltryptamine	HMDB
Methyltryptamine	HMDB
N-Omega-methyltryptamine	HMDB
N-Methyltryptamine oxalate	MeSH, HMDB
N-Methyltryptamine hydrochloride	MeSH, HMDB

Chemical Formula

C₁₁H₁₄N₂

Average Molecular Weight

174.2423

Monoisotopic Molecular Weight

174.115698458

IUPAC Name

[2-(1H-indol-3-yl)ethyl](methyl)amine

Traditional Name

methyltryptamine

CAS Registry Number

61-49-4

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 Key

NCIKQJBVUNUXLW-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Tryptamines 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

tryptamine alkaloid (CHEBI:28136 )
tryptamines (CHEBI:28136 )
Indole alkaloids (C06213 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 11763413)

Source

Exogenous

Exogenous (HMDB: HMDB0004370)

Food

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Endogenous

Plant

Plant (HMDB: HMDB0004370)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tryptophan Metabolism (PathBank: SMP0063693)
Tryptophan Metabolism (HMDB: HMDB0004370)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	87 - 89 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	143.0	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000478

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.47 g/L	ALOGPS
logP	2.02	ALOGPS
logP	1.92	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	17.17	ChemAxon
pKa (Strongest Basic)	10.31	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	27.82 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	55.15 m³·mol⁻¹	ChemAxon
Polarizability	20.42 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	138.366	31661259
DarkChem	[M-H]-	137.392	31661259
DeepCCS	[M-2H]-	170.303	30932474
DeepCCS	[M+Na]+	145.682	30932474
AllCCS	[M+H]+	138.4	32859911
AllCCS	[M+H-H2O]+	134.0	32859911
AllCCS	[M+NH4]+	142.5	32859911
AllCCS	[M+Na]+	143.7	32859911
AllCCS	[M-H]-	142.6	32859911
AllCCS	[M+Na-2H]-	143.2	32859911
AllCCS	[M+HCOO]-	143.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.37 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8816 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.75 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	72.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	978.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	306.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	116.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	177.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	132.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	294.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	280.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	430.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	730.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	288.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	935.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	234.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	246.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	527.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	329.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	65.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Methyltryptamine	CNCCC1=CNC2=CC=CC=C12	2851.0	Standard polar	33892256
N-Methyltryptamine	CNCCC1=CNC2=CC=CC=C12	1769.7	Standard non polar	33892256
N-Methyltryptamine	CNCCC1=CNC2=CC=CC=C12	1823.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Methyltryptamine,1TMS,isomer #1	CN(CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C	1962.9	Semi standard non polar	33892256
N-Methyltryptamine,1TMS,isomer #1	CN(CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C	1946.6	Standard non polar	33892256
N-Methyltryptamine,1TMS,isomer #1	CN(CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C	2301.0	Standard polar	33892256
N-Methyltryptamine,1TMS,isomer #2	CNCCC1=CN([Si](C)(C)C)C2=CC=CC=C12	1767.8	Semi standard non polar	33892256
N-Methyltryptamine,1TMS,isomer #2	CNCCC1=CN([Si](C)(C)C)C2=CC=CC=C12	1834.2	Standard non polar	33892256
N-Methyltryptamine,1TMS,isomer #2	CNCCC1=CN([Si](C)(C)C)C2=CC=CC=C12	2107.4	Standard polar	33892256
N-Methyltryptamine,2TMS,isomer #1	CN(CCC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C	2045.3	Semi standard non polar	33892256
N-Methyltryptamine,2TMS,isomer #1	CN(CCC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C	2049.1	Standard non polar	33892256
N-Methyltryptamine,2TMS,isomer #1	CN(CCC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C	2092.0	Standard polar	33892256
N-Methyltryptamine,1TBDMS,isomer #1	CN(CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2201.1	Semi standard non polar	33892256
N-Methyltryptamine,1TBDMS,isomer #1	CN(CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2169.8	Standard non polar	33892256
N-Methyltryptamine,1TBDMS,isomer #1	CN(CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2415.7	Standard polar	33892256
N-Methyltryptamine,1TBDMS,isomer #2	CNCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2003.7	Semi standard non polar	33892256
N-Methyltryptamine,1TBDMS,isomer #2	CNCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2044.0	Standard non polar	33892256
N-Methyltryptamine,1TBDMS,isomer #2	CNCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2237.6	Standard polar	33892256
N-Methyltryptamine,2TBDMS,isomer #1	CN(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2456.1	Semi standard non polar	33892256
N-Methyltryptamine,2TBDMS,isomer #1	CN(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2476.7	Standard non polar	33892256
N-Methyltryptamine,2TBDMS,isomer #1	CN(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2334.3	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tryptophan metabolism	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.0026 (0.000045-0.00010) umol/mmol creatinine	Adult (>18 years old)	Both	Surgical patients	11763413	details
Urine	Detected and Quantified	0.0049 (0.000018-0.000094) umol/mmol creatinine	Adult (>18 years old)	Both	Psychiatric disorder	11763413	details

Associated Disorders and Diseases

Disease References

Major depressive disorder
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

608516 (Major depressive disorder)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

N-Methyltryptamine

METLIN ID

7057

PubChem Compound

6088

PDB ID

Not Available

ChEBI ID

28136

Food Biomarker Ontology

Not Available

VMH ID

M02605

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Manske, 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

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 ]
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 ]
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 ]
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

Enzyme Details

1. Indolethylamine N-methyltransferase

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-Methyltryptamine	details

Showing metabocard for N-Methyltryptamine (HMDB0004370)

MOL for HMDB0004370 (N-Methyltryptamine)

3D MOL for HMDB0004370 (N-Methyltryptamine)

3D SDF for HMDB0004370 (N-Methyltryptamine)

3D-SDF for HMDB0004370 (N-Methyltryptamine)

PDB for HMDB0004370 (N-Methyltryptamine)

3D PDB for HMDB0004370 (N-Methyltryptamine)

SMILES for HMDB0004370 (N-Methyltryptamine)

INCHI for HMDB0004370 (N-Methyltryptamine)

Structure for HMDB0004370 (N-Methyltryptamine)

3D Structure for HMDB0004370 (N-Methyltryptamine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions