Editing Tryptamine (section)

{{short description|Metabolite of the amino acid tryptophan}}
{{about|the specific substance|the class of substances|substituted tryptamine}}
{{chembox
| ImageFile = Tryptamine structure.svg
| ImageClass = skin-invert-image
| ImageSize = 200px
| ImageFile2 = Tryptamine molecule from xtal ball.png
| PIN= 2-(1''H''-Indol-3-yl)ethan-1-amine
| OtherNames = T; Triptamine; β-(3-Indolyl)ethylamine; Indolylethylamine; Indolethylamine; PAL-235; PAL235
|Section1={{Chembox Identifiers
| CASNo = 61-54-1
| CASNo_Ref = {{cascite|correct|CAS}}
| Beilstein = 125513
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 422ZU9N5TV
| PubChem=1150
| ChEBI = 16765
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 6640
| DrugBank = DB08653
| IUPHAR_ligand = 125
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 1118
| KEGG = C00398
| SMILES = c1ccc2c(c1)c(c[nH]2)CCN
| InChI = 1/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2
| InChIKey = APJYDQYYACXCRM-UHFFFAOYAU
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2
| StdInChIKey_Ref = {{stdinchicite|correc|chemspider}}
| StdInChIKey = APJYDQYYACXCRM-UHFFFAOYSA-N
 }}
|Section2={{Chembox Properties
|Properties_ref =<ref>{{cite book |title=CRC Handbook of Chemistry and Physics |date=2005 |editor-last=Lide |editor-first=D. R. |edition=85th |publisher=[[CRC Press]] |isbn=978-0-8493-0484-2 |pages=3–564}}</ref>
| C=10 | H=12 | N=2
| Appearance=white to orange needles
| Density=
| MeltingPt=118˚C
| BoilingPtC=137
| BoilingPt_notes= (0.15 mmHg)
| Solubility=negligible solubility in water
 }}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
 }}
|Section6 = {{Chembox Pharmacology
| Drug_class = [[Serotonin receptor agonist]]; [[Trace amine-associated receptor 1]] (TAAR1) [[agonist]]; [[Serotonin–norepinephrine–dopamine releasing agent]]; [[Serotonergic psychedelic]]; [[Hallucinogen]]
| AdminRoutes = [[Intravenous injection|Intravenous]]<ref name="MartinSloan1977" /><ref name="ShulginShulgin1997" /><ref name="MartinSloan1970" />
| Bioavail = Very low
| Excretion = [[Urine]]<ref name="MartinSloan1970" /><ref name="FranzenGross1965" /><ref name="Price1975" />
| DurationOfAction = Very short<ref name="Jones1982" /><ref name="BloughLandavazoDecker2014" /><ref name="ShulginShulgin1997" /><ref name="MartinSloan1970" />
| HalfLife = Very short<ref name="Jones1982" /><ref name="BloughLandavazoDecker2014" /><ref name="ShulginShulgin1997" /><ref name="MartinSloan1970" />
| Metabolism = Very rapid ([[oxidative deamination]] by {{Abbrlink|MAO|monoamine oxidase}})<ref name="Jones1982" /><ref name="BloughLandavazoDecker2014" /><ref name="ShulginShulgin1997" /><ref name="MartinSloan1970" />
| Metabolites = [[Indole-3-acetic acid]] (IAA)
| OnsetOfAction = Very rapid<ref name="Jones1982" /><ref name="BloughLandavazoDecker2014" /><ref name="ShulginShulgin1997" /><ref name="MartinSloan1970" />
| ProteinBound = 
| Legal_status = Legal or unregulated
 }}
}}

'''Tryptamine''' is an [[Indolamines|indolamine]] metabolite of the essential amino acid [[tryptophan]].<ref name=NML>{{Cite web |title=Tryptamine|url=https://pubchem.ncbi.nlm.nih.gov/compound/1150|access-date=2020-12-01|website=pubchem.ncbi.nlm.nih.gov}}</ref><ref name=":32">{{Cite journal|last1=Jenkins|first1=Trisha A.|last2=Nguyen|first2=Jason C. D.|last3=Polglaze|first3=Kate E.|last4=Bertrand|first4=Paul P.|date=2016-01-20|title=Influence of Tryptophan and Serotonin on Mood and Cognition with a Possible Role of the Gut-Brain Axis|journal=Nutrients|volume=8|issue=1|page=56|doi=10.3390/nu8010056|issn=2072-6643|pmc=4728667|pmid=26805875|doi-access=free}}</ref> The chemical structure is defined by an [[indole]]—a fused [[benzene]] and [[pyrrole]] ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the first one being the [[heterocyclic]] nitrogen).<ref name="NML"/> The structure of tryptamine is a shared feature of certain aminergic [[Neuromodulation|neuromodulators]] including [[melatonin]], [[serotonin]], [[bufotenin]] and psychedelic derivatives such as [[N,N-Dimethyltryptamine|dimethyltryptamine]] (DMT), [[psilocybin]], [[psilocin]] and [[List of naturally occurring tryptamines|others]].<ref name=":6">{{Cite journal|last1=Tylš|first1=Filip|last2=Páleníček|first2=Tomáš|last3=Horáček|first3=Jiří|date=2014-03-01|title=Psilocybin – Summary of knowledge and new perspectives|url=http://www.sciencedirect.com/science/article/pii/S0924977X13003519|journal=European Neuropsychopharmacology|language=en|volume=24|issue=3|pages=342–356|doi=10.1016/j.euroneuro.2013.12.006|pmid=24444771|s2cid=10758314|issn=0924-977X|url-access=subscription}}</ref><ref name=":03">{{Cite journal|last1=Tittarelli|first1=Roberta|last2=Mannocchi|first2=Giulio|last3=Pantano|first3=Flaminia|last4=Romolo|first4=Francesco Saverio|date=2015|title=Recreational Use, Analysis and Toxicity of Tryptamines|journal=Current Neuropharmacology|volume=13|issue=1|pages=26–46|doi=10.2174/1570159X13666141210222409|issn=1570-159X|pmc=4462041|pmid=26074742}}</ref><ref name=":5">{{Cite web|title=The Ayahuasca Phenomenon|url=https://maps.org/articles/5408-the-ayahuasca-phenomenon|access-date=2020-10-03|website=MAPS| date=21 November 2014 |language=en-gb}}</ref>

Tryptamine has been shown to activate [[serotonin receptor]]s<ref name="BloughLandavazoDecker2014" /><ref name="Mousseau1993" /> and [[trace amine-associated receptor]]s expressed in the mammalian brain, and regulates the activity of [[Dopaminergic pathways|dopaminergic]], [[Serotonin pathway|serotonergic]] and [[Glutamic acid|glutamatergic]] systems.<ref name="KhanNawaz2016">{{Cite journal|last1=Khan|first1=Muhammad Zahid|last2=Nawaz|first2=Waqas|date=2016-10-01|title=The emerging roles of human trace amines and human trace amine-associated receptors (hTAARs) in central nervous system|url=http://www.sciencedirect.com/science/article/pii/S075333221630556X|journal=Biomedicine & Pharmacotherapy|language=en|volume=83|pages=439–449|doi=10.1016/j.biopha.2016.07.002|pmid=27424325|issn=0753-3322|url-access=subscription}}</ref><ref name="BerryGainetdinovHoener2017">{{Cite journal|date=2017-12-01|title=Pharmacology of human trace amine-associated receptors: Therapeutic opportunities and challenges|journal=Pharmacology & Therapeutics|language=en|volume=180|pages=161–180|doi=10.1016/j.pharmthera.2017.07.002|issn=0163-7258|last1=Berry|first1=Mark D.|last2=Gainetdinov|first2=Raul R.|last3=Hoener|first3=Marius C.|last4=Shahid|first4=Mohammed|pmid=28723415|s2cid=207366162|doi-access=free}}</ref> In the human gut, bacteria convert dietary tryptophan to tryptamine, which activates [[5-HT4 receptor|5-HT<sub>4</sub>]] receptors and regulates gastrointestinal motility.<ref name=":32"/><ref name=":103">{{Cite journal|last1=Bhattarai|first1=Yogesh|last2=Williams|first2=Brianna B.|last3=Battaglioli|first3=Eric J.|last4=Whitaker|first4=Weston R.|last5=Till|first5=Lisa|last6=Grover|first6=Madhusudan|last7=Linden|first7=David R.|last8=Akiba|first8=Yasutada|last9=Kandimalla|first9=Karunya K.|last10=Zachos|first10=Nicholas C.|last11=Kaunitz|first11=Jonathan D.|date=2018-06-13|title=Gut Microbiota-Produced Tryptamine Activates an Epithelial G-Protein-Coupled Receptor to Increase Colonic Secretion|url= |journal=Cell Host & Microbe|language=en|volume=23|issue=6|pages=775–785.e5|doi=10.1016/j.chom.2018.05.004|issn=1931-3128|pmid=29902441|pmc=6055526}}</ref><ref name=":152">{{Cite journal|last=Field|first=Michael|date=2003|title=Intestinal ion transport and the pathophysiology of diarrhea|journal=Journal of Clinical Investigation|volume=111|issue=7|pages=931–943|doi=10.1172/JCI200318326|issn=0021-9738|pmid=12671039|pmc=152597}}</ref>

Multiple tryptamine-derived drugs have been developed to treat [[migraine]]s, while trace amine-associated receptors are being explored as a potential treatment target for neuropsychiatric disorders.<ref name=":16">{{Citation|title=Serotonin Receptor Agonists (Triptans)|date=2012|url=http://www.ncbi.nlm.nih.gov/books/NBK548713/|work=LiverTox: Clinical and Research Information on Drug-Induced Liver Injury|place=Bethesda (MD)|publisher=National Institute of Diabetes and Digestive and Kidney Diseases|pmid=31644023|access-date=2020-10-15}}</ref><ref name=":7">{{Cite web|date=2020-12-09|title=New Compound Related to Psychedelic Ibogaine Could Treat Addiction, Depression|url=https://www.ucdavis.edu/news/new-compound-related-psychedelic-ibogaine-could-treat-addiction-depression|access-date=2020-12-11|website=UC Davis|language=EN}}</ref><ref name=":8">{{Cite web|last=ServiceDec. 9|first=Robert F.|title=Chemists re-engineer a psychedelic to treat depression and addiction in rodents|url=https://www.science.org/content/article/chemists-re-engineer-psychedelic-treat-depression-and-addiction-rodents|access-date=2020-12-11|website=Science {{!}} AAAS|language=en}}</ref>