| Record Information |
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| Version | 5.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2005-11-16 15:48:42 UTC |
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| Update Date | 2023-05-30 20:55:49 UTC |
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| HMDB ID | HMDB0000303 |
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| Secondary Accession Numbers | - HMDB00303
- HMDB0060064
- HMDB60064
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| Metabolite Identification |
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| Common Name | Tryptamine |
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| Description | Tryptamine, also known as TrpN, is a catabolite of tryptophan converted by the gut microbiota. After absorption through the intestinal epithelium, tryptophan catabolites enter the bloodstream and are later excreted in the urine. Both Clostridium sp. and Ruminococcus sp. have been found to convert tryptophan into tryptamine (PMID: 30120222 ). Tryptamine is a monoamine compound that is a common precursor molecule to many hormones and neurotransmitters. Biosynthesis generally proceeds from the amino acid tryptophan, with tryptamine acting as a precursor for other compounds. Substitutions to the tryptamine molecule give rise to a group of compounds collectively known as tryptamines. The most well-known tryptamines are serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle. Tryptamine has been detected, but not quantified in, several different foods, such as onion-family vegetables, acerola, Japanese walnuts, custard apples, and green zucchinis. This could make tryptamine a potential biomarker for the consumption of these foods. |
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| Structure | InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2 |
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| Synonyms | | Value | Source |
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| 1H-Indole-3-ethanamine | ChEBI | | 2-(1H-indol-3-yl)ETHANAMINE | ChEBI | | 2-(3-Indolyl)ethylamine | ChEBI | | 3-(2-Aminoethyl)indole | ChEBI | | (3-Indolyl)ethylamine | HMDB | | 2-(1H-indol-3-yl)Ethylamine | HMDB | | 2-indol-3-yl-Aethylamin | HMDB | | 2-indol-3-yl-Ethylamine | HMDB | | 3-(2-Aminoethyl)-1H-indole | HMDB | | 3-Indoleethanamine | HMDB | | 3-Indoleethylamine | HMDB | | Tryptamin | HMDB | | 2-(1H-indol-3-yl)Ethan-1-amine | HMDB | | beta-(3-Indolyl)ethylamine | HMDB | | Β-(3-indolyl)ethylamine | HMDB | | TRPN | HMDB | | Tryptamine | HMDB |
| Show more...
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| Chemical Formula | C10H12N2 |
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| Average Molecular Weight | 160.2157 |
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| Monoisotopic Molecular Weight | 160.100048394 |
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| IUPAC Name | 2-(1H-indol-3-yl)ethan-1-amine |
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| Traditional Name | tryptamine |
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| CAS Registry Number | 61-54-1 |
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| SMILES | NCCC1=CNC2=C1C=CC=C2 |
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| InChI Identifier | InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2 |
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| InChI Key | APJYDQYYACXCRM-UHFFFAOYSA-N |
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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
- 2-arylethylamine
- Aralkylamine
- Substituted pyrrole
- Benzenoid
- Pyrrole
- Heteroaromatic compound
- Azacycle
- Hydrocarbon derivative
- Organopnictogen compound
- Amine
- Primary amine
- Organonitrogen compound
- Primary aliphatic amine
- Organic nitrogen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Physiological effect | Not Available |
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| Disposition | |
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| Process | |
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| Role | |
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| Physical Properties |
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| State | Solid |
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| Experimental Molecular Properties | | Property | Value | Reference |
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| Melting Point | 114 - 119 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | 1.55 | HANSCH,C ET AL. (1995) |
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| Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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| Predicted Molecular Properties | | Show more...
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| Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized| Derivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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| Tryptamine,1TMS,isomer #1 | C[Si](C)(C)NCCC1=C[NH]C2=CC=CC=C12 | 1878.2 | Semi standard non polar | 33892256 | | Tryptamine,1TMS,isomer #1 | C[Si](C)(C)NCCC1=C[NH]C2=CC=CC=C12 | 1894.9 | Standard non polar | 33892256 | | Tryptamine,1TMS,isomer #1 | C[Si](C)(C)NCCC1=C[NH]C2=CC=CC=C12 | 2339.0 | Standard polar | 33892256 | | Tryptamine,1TMS,isomer #2 | C[Si](C)(C)N1C=C(CCN)C2=CC=CC=C21 | 1821.4 | Semi standard non polar | 33892256 | | Tryptamine,1TMS,isomer #2 | C[Si](C)(C)N1C=C(CCN)C2=CC=CC=C21 | 1863.6 | Standard non polar | 33892256 | | Tryptamine,1TMS,isomer #2 | C[Si](C)(C)N1C=C(CCN)C2=CC=CC=C21 | 2309.0 | Standard polar | 33892256 | | Tryptamine,2TMS,isomer #1 | C[Si](C)(C)N(CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C | 2104.3 | Semi standard non polar | 33892256 | | Tryptamine,2TMS,isomer #1 | C[Si](C)(C)N(CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C | 2123.9 | Standard non polar | 33892256 | | Tryptamine,2TMS,isomer #1 | C[Si](C)(C)N(CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C | 2275.2 | Standard polar | 33892256 | | Tryptamine,2TMS,isomer #2 | C[Si](C)(C)NCCC1=CN([Si](C)(C)C)C2=CC=CC=C12 | 1938.1 | Semi standard non polar | 33892256 | | Tryptamine,2TMS,isomer #2 | C[Si](C)(C)NCCC1=CN([Si](C)(C)C)C2=CC=CC=C12 | 1993.9 | Standard non polar | 33892256 | | Tryptamine,2TMS,isomer #2 | C[Si](C)(C)NCCC1=CN([Si](C)(C)C)C2=CC=CC=C12 | 2111.1 | Standard polar | 33892256 | | Tryptamine,3TMS,isomer #1 | C[Si](C)(C)N(CCC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C | 2185.9 | Semi standard non polar | 33892256 | | Tryptamine,3TMS,isomer #1 | C[Si](C)(C)N(CCC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C | 2210.8 | Standard non polar | 33892256 | | Tryptamine,3TMS,isomer #1 | C[Si](C)(C)N(CCC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C | 2118.2 | Standard polar | 33892256 | | Tryptamine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NCCC1=C[NH]C2=CC=CC=C12 | 2139.9 | Semi standard non polar | 33892256 | | Tryptamine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NCCC1=C[NH]C2=CC=CC=C12 | 2098.0 | Standard non polar | 33892256 | | Tryptamine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NCCC1=C[NH]C2=CC=CC=C12 | 2433.2 | Standard polar | 33892256 | | Tryptamine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C=C(CCN)C2=CC=CC=C21 | 2066.9 | Semi standard non polar | 33892256 | | Tryptamine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C=C(CCN)C2=CC=CC=C21 | 2045.9 | Standard non polar | 33892256 | | Tryptamine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C=C(CCN)C2=CC=CC=C21 | 2384.6 | Standard polar | 33892256 | | Tryptamine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C | 2552.8 | Semi standard non polar | 33892256 | | Tryptamine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C | 2519.2 | Standard non polar | 33892256 | | Tryptamine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(CCC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C | 2424.1 | Standard polar | 33892256 | | Tryptamine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12 | 2386.9 | Semi standard non polar | 33892256 | | Tryptamine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12 | 2399.2 | Standard non polar | 33892256 | | Tryptamine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12 | 2337.9 | Standard polar | 33892256 | | Tryptamine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C | 2807.1 | Semi standard non polar | 33892256 | | Tryptamine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C | 2776.9 | Standard non polar | 33892256 | | Tryptamine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C | 2420.6 | Standard polar | 33892256 |
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| Spectra |
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| GC-MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Experimental GC-MS | GC-MS Spectrum - Tryptamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-00dr-2900000000-037af42e76613b924496 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Tryptamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) | splash10-00di-1900000000-0f82cbf608e15678c41e | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Tryptamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-00di-2900000000-a7c4e80f196945c43f38 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Tryptamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-00di-7900000000-3900b703ce7b512e882b | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Tryptamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) | splash10-00di-8900000000-f45a71db0a2ef37bb21e | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Tryptamine GC-MS (3 TMS) | splash10-00di-2900000000-bd00339c48e04ebcf419 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Tryptamine GC-MS (2 TMS) | splash10-00di-2900000000-830c8a076e1bd787d36b | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Tryptamine EI-B (Non-derivatized) | splash10-001i-2900000000-b39aa63579c1df55320b | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Tryptamine EI-B (Non-derivatized) | splash10-00di-1900000000-ac580ff9d9d90ed4712f | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Tryptamine GC-EI-TOF (Non-derivatized) | splash10-00dr-2900000000-037af42e76613b924496 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Tryptamine GC-EI-TOF (Non-derivatized) | splash10-00di-1900000000-0f82cbf608e15678c41e | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Tryptamine GC-EI-TOF (Non-derivatized) | splash10-00di-2900000000-a7c4e80f196945c43f38 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Tryptamine GC-EI-TOF (Non-derivatized) | splash10-00di-7900000000-3900b703ce7b512e882b | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Tryptamine GC-EI-TOF (Non-derivatized) | splash10-00di-8900000000-f45a71db0a2ef37bb21e | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Tryptamine GC-MS (Non-derivatized) | splash10-00di-2900000000-bd00339c48e04ebcf419 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Tryptamine GC-MS (Non-derivatized) | splash10-00di-2900000000-830c8a076e1bd787d36b | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Tryptamine GC-MS (Non-derivatized) | splash10-00di-2900000000-bd00339c48e04ebcf419 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | | Experimental GC-MS | GC-MS Spectrum - Tryptamine GC-MS (Non-derivatized) | splash10-00di-2900000000-830c8a076e1bd787d36b | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - Tryptamine GC-MS (Non-derivatized) - 70eV, Positive | splash10-001i-6900000000-9eba5d47042c8fee1aeb | 2017-07-27 | Wishart Lab | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - Tryptamine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | | MS | Mass Spectrum (Electron Ionization) | splash10-001i-2900000000-6a48efe719d0f7482467 | 2015-03-01 | Not Available | View Spectrum |
MS/MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Experimental LC-MS/MS | LC-MS/MS Spectrum - Tryptamine Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-03di-0900000000-b73564ce7b9f5f38af40 | 2012-07-24 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tryptamine Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-00kf-0900000000-24ae4f71c6de13d45134 | 2012-07-24 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tryptamine Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-014l-7900000000-630a258032b083d5d676 | 2012-07-24 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tryptamine EI-B (MX-1303) , Positive-QTOF | splash10-001i-2900000000-b39aa63579c1df55320b | 2012-08-31 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tryptamine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF | splash10-0006-0900000000-0572e0c6753816d29646 | 2012-08-31 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tryptamine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF | splash10-0006-0900000000-a3617243f16ac1d19ca3 | 2012-08-31 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tryptamine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF | splash10-0006-0900000000-5198dc18989eb021ff2b | 2012-08-31 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tryptamine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF | splash10-014l-2900000000-3b3b79050401c23f0c22 | 2012-08-31 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tryptamine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF | splash10-014l-7900000000-b62047ba50e6464b146c | 2012-08-31 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tryptamine Linear Ion Trap , negative-QTOF | splash10-0002-9500000000-692ccea6512d337d1e9b | 2017-09-14 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tryptamine LC-ESI-QQ , positive-QTOF | splash10-0006-0900000000-0572e0c6753816d29646 | 2017-09-14 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tryptamine LC-ESI-QQ , positive-QTOF | splash10-0006-0900000000-a3617243f16ac1d19ca3 | 2017-09-14 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tryptamine LC-ESI-QQ , positive-QTOF | splash10-0006-0900000000-5198dc18989eb021ff2b | 2017-09-14 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tryptamine LC-ESI-QQ , positive-QTOF | splash10-014l-2900000000-3b3b79050401c23f0c22 | 2017-09-14 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tryptamine LC-ESI-QQ , positive-QTOF | splash10-014l-7900000000-b62047ba50e6464b146c | 2017-09-14 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tryptamine Linear Ion Trap , positive-QTOF | splash10-0006-0900000000-bb34ead00b4bce5008dc | 2017-09-14 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tryptamine , positive-QTOF | splash10-0006-0900000000-bb699b23c5872ac8e0fd | 2017-09-14 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tryptamine 10V, Positive-QTOF | splash10-0006-0900000000-0584fe53e5bb04749635 | 2021-09-20 | HMDB team, MONA | View Spectrum | | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tryptamine 20V, Positive-QTOF | splash10-0006-0900000000-10334c65fa0049224d2b | 2021-09-20 | HMDB team, MONA | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tryptamine 10V, Positive-QTOF | splash10-03dl-0900000000-7bc3b97123326f275789 | 2015-05-26 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tryptamine 20V, Positive-QTOF | splash10-0006-0900000000-5905ea387430fa86aaf0 | 2015-05-26 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tryptamine 40V, Positive-QTOF | splash10-014l-2900000000-efe6e15de34968102591 | 2015-05-26 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tryptamine 10V, Negative-QTOF | splash10-0a4i-0900000000-c52fec329f216423ec97 | 2015-05-27 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tryptamine 20V, Negative-QTOF | splash10-0a4i-0900000000-274ddaffc49a15406923 | 2015-05-27 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tryptamine 40V, Negative-QTOF | splash10-014l-2900000000-11fbc4d015c37419fca0 | 2015-05-27 | Wishart Lab | View Spectrum |
NMR Spectra| Spectrum Type | Description | Deposition Date | Source | View |
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| Experimental 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | 2012-12-04 | Wishart Lab | View Spectrum | | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
IR Spectra| Spectrum Type | Description | Deposition Date | Source | View |
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| Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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| Biological Properties |
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| Cellular Locations | - Cytoplasm (predicted from logP)
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| Biospecimen Locations | |
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| Tissue Locations | - Brain
- Intestine
- Neuron
- Platelet
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| Pathways | |
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| Normal Concentrations |
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| Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | Not Quantified | Infant (0-1 year old) | Not Available | Normal | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | Not Quantified | Infant (0-1 year old) | Not Specified | Normal | | details | | Feces | Detected but not Quantified | Not Quantified | Infant (0-1 year old) | Not Specified | Normal | | details | | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 0.026 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 0.098 (0.03-0.15) umol/mmol creatinine | Children (1-13 years old) | Both | Normal | - Geigy Scientific ...
- West Cadwell, N.J...
- Basel, Switzerlan...
| details | | Urine | Detected and Quantified | 0.03 (0.01-0.049) umol/mmol creatinine | Adult (>18 years old) | Male | Normal | - Geigy Scientific ...
- West Cadwell, N.J...
- Basel, Switzerlan...
| details | | Urine | Detected and Quantified | 0.02 (0.02-0.03) umol/mmol creatinine | Adult (>18 years old) | Female | Normal | - Geigy Scientific ...
- West Cadwell, N.J...
- Basel, Switzerlan...
| details | | Urine | Detected and Quantified | 0.06 (0.04-0.08) umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details |
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| Abnormal Concentrations |
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| Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Irritable bowel syndrome | | details | | Urine | Detected and Quantified | 0.926 umol/mmol creatinine | Adult (>18 years old) | Female | Pregnancy | | details |
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| Associated Disorders and Diseases |
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| Disease References | | Irritable bowel syndrome |
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- Ponnusamy K, Choi JN, Kim J, Lee SY, Lee CH: Microbial community and metabolomic comparison of irritable bowel syndrome faeces. J Med Microbiol. 2011 Jun;60(Pt 6):817-27. doi: 10.1099/jmm.0.028126-0. Epub 2011 Feb 17. [PubMed:21330412 ]
| | Colorectal cancer |
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- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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| Associated OMIM IDs | |
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| External Links |
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| DrugBank ID | DB08653 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB000917 |
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| KNApSAcK ID | C00001434 |
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| Chemspider ID | 1118 |
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| KEGG Compound ID | C00398 |
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| BioCyc ID | TRYPTAMINE |
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| BiGG ID | Not Available |
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| Wikipedia Link | Tryptamine |
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| METLIN ID | Not Available |
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| PubChem Compound | 1150 |
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| PDB ID | Not Available |
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| ChEBI ID | 16765 |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | TRYPTA |
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| MarkerDB ID | Not Available |
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| Good Scents ID | Not Available |
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| References |
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| Synthesis Reference | Abramovitch, R. A.; Shapiro, D. Tryptamines, carbolines, and related compounds. II. A convenient synthesis of tryptamines and b-carbolines. Journal of the Chemical Society (1956), 4589-92. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - Radulovacki P, Djuricic-Nedelson M, Chen EH, Radulovacki M: Human tryptamine metabolism decreases during night sleep. Brain Res Bull. 1983 Jan;10(1):43-5. [PubMed:6186344 ]
- Mathew RJ, Ho BT, Kralik P, Weinman M, Claghorn JL: Anxiety and platelet MAO levels after relaxation training. Am J Psychiatry. 1981 Mar;138(3):371-3. [PubMed:7008633 ]
- Gilboa-Garber N, Katz-Bergman Y, Pinsky A: Comparative study of the sensitivity of acetylcholinesterases and cholinesterases from animal and bacterial sources to inhibition by serotonin and its derivatives. Experientia. 1978 Aug 15;34(8):992-3. [PubMed:100343 ]
- Tsuchiya H, Ohtani S, Yamada K, Tajima K, Sato M: Formation of tetrahydro-beta-carbolines in human saliva. Biochem Pharmacol. 1995 Dec 22;50(12):2109-12. [PubMed:8849340 ]
- Tam WY, Chan MY, Lee PH: The menstrual cycle and platelet 5-HT uptake. Psychosom Med. 1985 Jul-Aug;47(4):352-62. [PubMed:4023163 ]
- Friedl W, Kruger J, Propping P: Intraindividual stability and extent of genetic determination of platelet monoamine oxidase activity. Pharmacopsychiatria. 1981 May;14(3):83-6. [PubMed:7196052 ]
- Sullivan JP, McDonnell L, Hardiman OM, Farrell MA, Phillips JP, Tipton KF: The oxidation of tryptamine by the two forms of monoamine oxidase in human tissues. Biochem Pharmacol. 1986 Oct 1;35(19):3255-60. [PubMed:3094536 ]
- al Mardini H, Harrison EJ, Ince PG, Bartlett K, Record CO: Brain indoles in human hepatic encephalopathy. Hepatology. 1993 Jun;17(6):1033-40. [PubMed:7685732 ]
- Young SN, Gauthier S: Effect of tryptophan administration on tryptophan, 5-hydroxyindoleacetic acid and indoleacetic acid in human lumbar and cisternal cerebrospinal fluid. J Neurol Neurosurg Psychiatry. 1981 Apr;44(4):323-8. [PubMed:6165809 ]
- Siwers B, Ringberger VA, Tuck JR, Sjoqvist F: Initial clinical trial based on biochemical methodology of zimelidine (a serotonin uptake inhibitor) in depressed patients. Clin Pharmacol Ther. 1977 Feb;21(2):194-200. [PubMed:837638 ]
- Sullivan JL, Coffey CE, Basuk B, Cavenar JO, Maltbie AA, Zung WW: Urinary tryptamine excretion in chronic schizophrenics with low platelet MAO activity. Biol Psychiatry. 1980 Feb;15(1):113-20. [PubMed:7357050 ]
- Tsuchiya H, Hayashi T, Tatsumi M, Hoshino Y, Ohtani S, Takagi N: High-performance liquid-chromatographic analysis for serotonin and tryptamine excreted in urine after oral loading with L-tryptophan. Clin Chem. 1989 Jan;35(1):43-7. [PubMed:2910580 ]
- Anderson GM, Gerner RH, Cohen DJ, Fairbanks L: Central tryptamine turnover in depression, schizophrenia, and anorexia: measurement of indoleacetic acid in cerebrospinal fluid. Biol Psychiatry. 1984 Oct;19(10):1427-35. [PubMed:6518200 ]
- Gaszner P, Miklya I: The use of the synthetic enhancer substances (-)-deprenyl and (-)-BPAP in major depression. Neuropsychopharmacol Hung. 2004 Dec;6(4):210-20. [PubMed:15825677 ]
- Dolusic E, Kowalczyk M, Magnus V, Sandberg G, Normanly J: Biotinylated indoles as probes for indole-binding proteins. Bioconjug Chem. 2001 Mar-Apr;12(2):152-62. [PubMed:11312675 ]
- Demisch L, von der Muhlen H, Bochnik HJ, Seiler N: Substrate-typic changes of platelet monoamine oxidase activity in sub-types of schizophrenia. Arch Psychiatr Nervenkr (1970). 1977 Dec 28;224(4):319-29. [PubMed:606205 ]
- Gaszner P, Miklya I: Major depression and the synthetic enhancer substances, (-)-deprenyl and R-(-)-1-(benzofuran-2-yl)-2-propylaminopentane. Prog Neuropsychopharmacol Biol Psychiatry. 2006 Jan;30(1):5-14. Epub 2005 Jul 14. [PubMed:16023777 ]
- Mousseau DD, Layrargues GP, Butterworth RF: Region-selective decreases in densities of [3H]tryptamine binding sites in autopsied brain tissue from cirrhotic patients with hepatic encephalopathy. J Neurochem. 1994 Feb;62(2):621-5. [PubMed:8294925 ]
- Anthenelli RM, Tipp J, Li TK, Magnes L, Schuckit MA, Rice J, Daw W, Nurnberger JI Jr: Platelet monoamine oxidase activity in subgroups of alcoholics and controls: results from the Collaborative Study on the Genetics of Alcoholism. Alcohol Clin Exp Res. 1998 May;22(3):598-604. [PubMed:9622437 ]
- Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
- Roager HM, Licht TR: Microbial tryptophan catabolites in health and disease. Nat Commun. 2018 Aug 17;9(1):3294. doi: 10.1038/s41467-018-05470-4. [PubMed:30120222 ]
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