Record Information |
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Version | 1.0 |
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Created at | 2021-06-20 19:31:45 UTC |
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Updated at | 2021-06-30 00:07:55 UTC |
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NP-MRD ID | NP0036327 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | N-methyltryptamine |
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Provided By | JEOL Database |
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Description | N-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. It was first documented in 1977 (PMID: 22091). Based on a literature review a significant number of articles have been published on N-Methyltryptamine (PMID: 11763413) (PMID: 23394630) (PMID: 6574135) (PMID: 8747157). |
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Structure | [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=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 |
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Synonyms | Value | Source |
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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 | 3-(2-(Methylamino)ethyl)indole | HMDB | Dipterine | HMDB | DL-Methyltryptamine | HMDB | Methyltryptamine | HMDB | N-Omega-methyltryptamine | HMDB | N-Methyltryptamine oxalate | HMDB | N-Methyltryptamine hydrochloride | HMDB |
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Chemical Formula | C11H14N2 |
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Average Mass | 174.2423 Da |
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Monoisotopic Mass | 174.11570 Da |
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IUPAC Name | [2-(1H-indol-3-yl)ethyl](methyl)amine |
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Traditional Name | methyltryptamine |
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CAS Registry Number | Not Available |
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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] |
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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 |
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InChI Key | NCIKQJBVUNUXLW-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Indoles and derivatives |
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Sub Class | Tryptamines and derivatives |
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Direct Parent | Tryptamines and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - 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 ]
- 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 ]
- 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 ]
- 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. doi: 10.1097/00001756-199511270-00024. [PubMed:8747157 ]
- 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 ]
- Penez, N., et al. (2011). Penez, N., et al, J. Nat. Prod. 74, 2304 (2011). J. Nat. Prod..
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