Tryptamine (BioCAD00000018974)

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Metabolite Card

Formula: C10H12N2 (160.1)
SMILES: NCCC1=CNC2=C1C=CC=C2

Synonyms [en]

tryptamine; 3-(2-aminoethyl)indole; 1H-Indole-3-ethanamine; 2-(1H-Indol-3-yl)ethanamine; 2-(3-Indolyl)ethylamine; triptamine

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Tryptamine. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000018974). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

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.

Cytoplasm
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 61-54-1
  • PubChem: 1150
  • PubChem: 3688
  • ChEBI: ChEBI:16765
  • HMDB: HMDB0000303
  • KEGG: C00398
  • BioCyc: TRYPTAMINE
  • NCBI MeSH: tryptamine
  • Wikipedia: Tryptamine
  • DrugBank: DB08653
  • RefMet: RM0049799
  • MoNA: Alkaloids000007
  • MoNA: BAF_UVA_POS001432
  • MoNA: BAF_UVA_POS001433
  • MoNA: BAF_UVA_POS001434
  • MoNA: BAF_UVA_POS001467
  • MoNA: CCMSLIB00000578057
  • MoNA: CCMSLIB00004752867
  • MoNA: CCMSLIB00005464109
  • MoNA: CCMSLIB00005720198
  • MoNA: CCMSLIB00005720506
  • MoNA: EMBL-MCF_spec138818
  • MoNA: EMBL-MCF_spec138875
  • MoNA: FiehnHILIC000823
  • MoNA: FiehnHILIC002391
  • MoNA: GLS00090
  • MoNA: HMDB0000303_c_ms_1875
  • MoNA: HMDB0000303_c_ms_1878
  • MoNA: HMDB0000303_ms_ms_516
  • MoNA: HMDB0000303_ms_ms_517
  • MoNA: HMDB0000303_ms_ms_518
  • MoNA: JP002028
  • MoNA: KO004142
  • MoNA: KO004143
  • MoNA: KO004144
  • MoNA: KO004145
  • MoNA: KO004146
  • MoNA: KZ000271
  • MoNA: KZ000272
  • MoNA: MoNA011379
  • MoNA: MoNA011380
  • MoNA: MoNA011381
  • MoNA: MoNA011382
  • MoNA: MoNA023873
  • MoNA: MoNA023881
  • MoNA: MoNA032345
  • MoNA: MoNA032346
  • MoNA: MoNA032347
  • MoNA: MoNA034352
  • MoNA: MoNA034354
  • MoNA: MoNA034355
  • MoNA: MoNA036249
  • MoNA: MoNA036251
  • MoNA: MoNA036252
  • MoNA: MoNA037259
  • MoNA: MoNA037985
  • MoNA: MoNA038632
  • MoNA: OUF00478
  • MoNA: PR010102
  • MoNA: PR010103
  • MoNA: PS006901
  • MoNA: PS006902
  • MoNA: PS006903
  • MoNA: PS006904
  • MoNA: TOF_alkaloids_pos000007
  • MoNA: VF-NPL-QEHF002590
  • MoNA: VF-NPL-QEHF002591
  • MoNA: VF-NPL-QEHF002592
  • MoNA: VF-NPL-QEHF002593
  • MoNA: VF-NPL-QEHF002594
  • MoNA: VF-NPL-QEHF002595
  • MoNA: WA002432
  • MoNA: WA002433
  • MoNA: WA002434
  • MoNA: WA002435
  • MoNA: WA002436
  • Metlin: METLIN_325
  • Coconut NaturalProduct: CNP0329876.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R00685 4.1.1.28 L-tryptophan decarboxy-lyase
KEGG:R02173 1.4.3.4 tryptamine:oxygen oxidoreductase(deaminating)
KEGG:R02174 2.1.1.49 S-adenosyl-L-methionine:amine N-methyltransferase
KEGG:R03738 3.5.99.13 3-alpha(S)-strictosidine tryptamine-lyase
KEGG:R05895 C11816 + C00398<=>C11817
KEGG:R08481 C00398<=>C06535
KEGG:R08482 C00398<=>C09209
KEGG:R08483 C00398<=>C09089
KEGG:R08484 C00398<=>C06536
KEGG:R08604 1.14.13.- tryptamine,NADPH:oxygen oxidoreductase (N-hydroxylating)
KEGG:R11912 1.14.99.59 tryptamine,hydrogen-donor:oxygen oxidoreductase (4-hydroxylating)
KEGG:R12659 1.14.-.- C00398 + C03024 + C00007<=>C00780 + C03161 + C00001
BioCyc:RXN-19089 1.14.99.59 TRYPTAMINE + Red-NADPH-Hemoprotein-Reductases + OXYGEN-MOLECULE --> CPD-20575 + Ox-NADPH-Hemoprotein-Reductases + WATER
BioCyc:RXN-9316 TRYPTAMINE --> CPD-9938
BioCyc:RXN-19641 4.3.3.2 TRYPTAMINE + SECOLOGANATE --> CPD-21271 + WATER
BioCyc:RXN-1405 TRYPTAMINE + OXYGEN-MOLECULE + NADPH --> N-HYDROXYL-TRYPTAMINE + WATER + NADP
BioCyc:STRICTOSIDINE-SYNTHASE-RXN 4.3.3.2 TRYPTAMINE + SECOLOGANIN-CPD --> STRICTOSIDINE + WATER
BioCyc:RXN-8707 1.14.14.- TRYPTAMINE + Red-NADPH-Hemoprotein-Reductases + OXYGEN-MOLECULE --> SEROTONIN + Ox-NADPH-Hemoprotein-Reductases + WATER
BioCyc:RXN-1401 1.4.3.4 TRYPTAMINE + WATER + OXYGEN-MOLECULE --> AMMONIUM + INDOLE_ACETALDEHYDE + HYDROGEN-PEROXIDE
BioCyc:AROMATIC-L-AMINO-ACID-DECARBOXYLASE-RXN 4.1.1.28 TRP + PROTON --> TRYPTAMINE + CARBON-DIOXIDE
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Organism Source

Taxonomy Source

  1. Acacia baileyana [ncbi taxid: 383632]
  2. Acacia rigidula [ncbi taxid: ]
  3. Acia ferruginea [ncbi taxid: ]
  4. Aeollanthus parvifolius [ncbi taxid: ]
  5. Agastaches rugosa [ncbi taxid: ]
  6. Agave gracilipes [ncbi taxid: ]
  7. Ailanthus altissima [ncbi taxid: ]
  8. Aloe vela [ncbi taxid: ]
  9. Alstroemeria aurea [ncbi taxid: 56742]
  10. Andrographis paniculatus [ncbi taxid: ]
  11. Angelica sinensis [ncbi taxid: 165353]
  12. Arabidopsis thaliana [ncbi taxid: 3702]
  13. Arctostaphylos uva-ursi [ncbi taxid: 84009]
  14. Arnebia euchroma [ncbi taxid: 373122]
  15. Artemisia oranensis [ncbi taxid: 1903224]
  16. Artemisis anna [ncbi taxid: ]
  17. Aruncus dioicus [ncbi taxid: 32220]
  18. Aspergillus fumigatus [ncbi taxid: 746128]
  19. Babreum coscluea [ncbi taxid: ]
  20. Beta vulgaris [ncbi taxid: 161934]
  21. Brickellia kellermanii [ncbi taxid: ]
  22. Bufo bufo [ncbi taxid: 8384]
  23. Bufo gargarizans [ncbi taxid: 30331]
  24. Bufo melanostictus [ncbi taxid: ]
  25. Buxus sempervirens [ncbi taxid: 4002]
  26. Cabucala madagascariensis [ncbi taxid: ]
  27. Centaurea amara [ncbi taxid: ]
  28. Centaurea imperialis [ncbi taxid: 75648]
  29. Chenopodium rubrum [ncbi taxid: ]
  30. Cinchona pubescens [ncbi taxid: 50278]
  31. Cistanche deserticola [ncbi taxid: 161395]
  32. Citrullus lanatus [ncbi taxid: 3654]
  33. Citrus reticulata [ncbi taxid: 85571]
  34. Coprinus micaceus [ncbi taxid: ]
  35. Coptis chinensis [ncbi taxid: 261450]
  36. Cortinarius rubellus [ncbi taxid: 86073]
  37. Coruns officinalis [ncbi taxid: ]
  38. Cucumis sativus [ncbi taxid: 3659]
  39. Cupressus macrocarpa [ncbi taxid: ]
  40. Curcuma aeruginosa [ncbi taxid: 136205]
  41. Dendranthema morifolium [ncbi taxid: ]
  42. Dendrobium wardianum [ncbi taxid: 172646]
  43. Desmodium elegans [ncbi taxid: ]
  44. Desmodium styracifolium [ncbi taxid: ]
  45. Dicorynia guianensis [ncbi taxid: 162748]
  46. Didymosphaeria mori-albae [ncbi taxid: ]
  47. Dioscorea alata [ncbi taxid: 55571]
  48. Duttaphrynus melanostictus [ncbi taxid: 30335]
  49. Dysoxylum lenticellatum [ncbi taxid: ]
  50. Epimedium brevicornum [ncbi taxid: ]
  51. Eucalyptus macrocarpa [ncbi taxid: 1711389]
  52. Eucalyptus sieberi [ncbi taxid: 87684]
  53. Eucommia ulmoides [ncbi taxid: 4392]
  54. Forsythia suspensa [ncbi taxid: 126418]
  55. Galdenia jasminoides [ncbi taxid: ]
  56. Gavia immer [ncbi taxid: 37039]
  57. Gentiana macrophylla [ncbi taxid: 50765]
  58. Gentiana scabra [ncbi taxid: 292393]
  59. Glycyrrhiza uralensis [ncbi taxid: 74613]
  60. Haematomma ventosum [ncbi taxid: ]
  61. Halimeda macroloba [ncbi taxid: 170422]
  62. Haplopappus venetus [ncbi taxid: ]
  63. Homo sapiens [ncbi taxid: 9606]
  64. Hordeum vulgare [ncbi taxid: 4513]
  65. Hordeum vulgare L. s.l. (H. vulgare L. s.str. and H. vulgare subsp. hexastichon (L.) Celak.) [ncbi taxid: ]
  66. Hypericum perforatum [ncbi taxid: 65561]
  67. Isatis indigotica [ncbi taxid: 3242077]
  68. Isis minorbrachyblasta [ncbi taxid: ]
  69. Kochia trichophylla [ncbi taxid: ]
  70. Lactarius atlanticus [ncbi taxid: 1032834]
  71. Lecanora conizaeoides [ncbi taxid: 128387]
  72. Lens culinaris [ncbi taxid: 3864]
  73. Lens esculenta [ncbi taxid: ]
  74. Leonurus japonicus [ncbi taxid: ]
  75. Lobelia chinensis [ncbi taxid: 368926]
  76. Lonicera japonica [ncbi taxid: 105884]
  77. Lophartherum gracile [ncbi taxid: ]
  78. Lupinus albus [ncbi taxid: 3870]
  79. Lycium barbarum [ncbi taxid: 112863]
  80. Lycopersicon esculentum [ncbi taxid: ]
  81. Lycopersicon esculentum Mill. [ncbi taxid: ]
  82. Lytanthus salicinus [ncbi taxid: ]
  83. Mahonia bealei [ncbi taxid: ]
  84. Malbranchea cinnamomea [ncbi taxid: 5041]
  85. Melochia pyramidata [ncbi taxid: 2895626]
  86. Mimosa scabrella [ncbi taxid: 648482]
  87. Mimosa somnians [ncbi taxid: 367329]
  88. Morus alba [ncbi taxid: 3498]
  89. Mucuna pruriens [ncbi taxid: 157652]
  90. Mus musculus [ncbi taxid: 10090]
  91. Musa spp. [ncbi taxid: ]
  92. Nicotiana tabacum [ncbi taxid: 4097]
  93. Nicotiana tabacum L. [ncbi taxid: ]
  94. Nicotiana tobacum [ncbi taxid: ]
  95. Ophiopogon japonicus [ncbi taxid: 100506]
  96. Ophiorrhiza pumila [ncbi taxid: 157934]
  97. Panax notoginsneg [ncbi taxid: ]
  98. Patrinia scabiosifolia [ncbi taxid: 300888]
  99. Penicillium expansum [ncbi taxid: 27334]
  100. Pentaceras australis [ncbi taxid: ]
  101. Petalostylis labicheoides [ncbi taxid: 162878]
  102. Pharbitis nil [ncbi taxid: ]
  103. Phebalium ozothamnoides [ncbi taxid: ]
  104. Phellodendron amurense [ncbi taxid: 68554]
  105. Piper futokadsura [ncbi taxid: ]
  106. Piptadenia peregrina [ncbi taxid: ]
  107. Pirola decorata [ncbi taxid: ]
  108. Pleurotus citrinopileatus [ncbi taxid: 98342]
  109. Polygala tenuifolia [ncbi taxid: 355332]
  110. Polygonatum sibiricum [ncbi taxid: 261423]
  111. Polygonum multiflorum [ncbi taxid: ]
  112. Poria cocos [ncbi taxid: ]
  113. Potentilla multifida [ncbi taxid: 210859]
  114. Prosopis alba [ncbi taxid: ]
  115. Prosopis nigra [ncbi taxid: ]
  116. Prunella vulgaris [ncbi taxid: 39358]
  117. Prunus cerasus [ncbi taxid: 140311]
  118. Psilocybe arcana [ncbi taxid: ]
  119. Psilocybe bohemica [ncbi taxid: ]
  120. Psilocybe semilanceata [ncbi taxid: 181775]
  121. Pueraria lobata [ncbi taxid: ]
  122. Punica granatum [ncbi taxid: 22663]
  123. Punica granatum L. [ncbi taxid: ]
  124. Pyrola chlorantha [ncbi taxid: 93824]
  125. Raphanus sativus [ncbi taxid: 3726]
  126. Rehmannia glutinosa [ncbi taxid: 99300]
  127. Rhaponticum carthamoides [ncbi taxid: ]
  128. Rheum palmatum [ncbi taxid: 137221]
  129. Rubus chingii [ncbi taxid: 714495]
  130. Salvia miltiorrhiza [ncbi taxid: 226208]
  131. Saposhmikovia divaricata [ncbi taxid: ]
  132. Saururus cernuus [ncbi taxid: 13260]
  133. Schisondra chinensis [ncbi taxid: ]
  134. Scrophularia ningpoensis [ncbi taxid: 291326]
  135. Scutellaria amoena [ncbi taxid: 1052904]
  136. Scutellaria baicalensis [ncbi taxid: 65409]
  137. Solanum lycopersicum [ncbi taxid: 4081]
  138. Solanum lycopersicum L. [ncbi taxid: ]
  139. Solanum tuberosum [ncbi taxid: 4113]
  140. Solanum tuberosum L. [ncbi taxid: ]
  141. Sophora flavescens [ncbi taxid: 49840]
  142. Spongia cerebriformis [ncbi taxid: ]
  143. Streptomyces plumbeus [ncbi taxid: 285475]
  144. Strychnos fendleri [ncbi taxid: 1040884]
  145. Symplocos lancifolia [ncbi taxid: 239704]
  146. Syzygium aromaticum [ncbi taxid: 219868]
  147. Tachigali paniculata [ncbi taxid: 53928]
  148. Tanacetum parthenium [ncbi taxid: 127999]
  149. Taxillus chinensis [ncbi taxid: 227909]
  150. Uncaria rhynchophylla [ncbi taxid: 43575]
  151. Valeriana jatamansi [ncbi taxid: 59170]
  152. Vellozia epidendroides [ncbi taxid: 1051480]
  153. Vernonia hirsuta [ncbi taxid: ]
  154. Vicia villosa [ncbi taxid: 3911]
  155. Viola philipica [ncbi taxid: ]
  156. Vitex megapotamica [ncbi taxid: 1365883]
  157. Zea mays [ncbi taxid: 4577]
  158. Ziziphus jujuba [ncbi taxid: 326968]

Pathway Synthetic

pathway id name
BioCyc:LEISH_PWY-581 IAA biosynthesis I
Plant Reactome:R-OAU-2744345 Metabolism and regulation
Plant Reactome:R-TAE-1119486 IAA biosynthesis I
Plant Reactome:R-TAE-2744344 Secondary metabolism
Plant Reactome:R-TAE-1119344 Serotonin biosynthesis
Plant Reactome:R-MES-2744345 Metabolism and regulation
Plant Reactome:R-MES-2744341 Hormone signaling, transport, and metabolism
Plant Reactome:R-MES-1119438 Secologanin and strictosidine biosynthesis
Plant Reactome:R-TDI-2744345 Metabolism and regulation
Plant Reactome:R-DRO-2744345 Metabolism and regulation
Plant Reactome:R-DRO-1119486 IAA biosynthesis I
Plant Reactome:R-OGU-2744341 Hormone signaling, transport, and metabolism
Plant Reactome:R-OMI-1119438 Secologanin and strictosidine biosynthesis
Plant Reactome:R-PTI-2744345 Metabolism and regulation
Plant Reactome:R-PTI-2744341 Hormone signaling, transport, and metabolism
Plant Reactome:R-GMA-2744345 Metabolism and regulation
Plant Reactome:R-GMA-2744344 Secondary metabolism
Plant Reactome:R-GMA-1119438 Secologanin and strictosidine biosynthesis
Plant Reactome:R-PDA-2744345 Metabolism and regulation
Plant Reactome:R-PDA-1119438 Secologanin and strictosidine biosynthesis
View All Pathways