Tryptamine

Tryptamine
Names
	Preferred IUPAC name 2-(1H-Indol-3-yl)ethan-1-amine
Identifiers
CAS Number	61-54-1 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	125513
ChEBI	CHEBI:16765;
ChEMBL	ChEMBL6640 ;
ChemSpider	1118 ;
DrugBank	DB08653;
ECHA InfoCard	100.000.464
IUPHAR/BPS	125;
KEGG	C00398;
PubChem CID	1150;
UNII	422ZU9N5TV ;
CompTox Dashboard (EPA)	DTXSID2075340 ;
	InChI InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2 Key: APJYDQYYACXCRM-UHFFFAOYSA-N ; InChI=1/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2 Key: APJYDQYYACXCRM-UHFFFAOYAU;
	SMILES c1ccc2c(c1)c(c[nH]2)CCN;
Properties
Chemical formula	C10H12N2
Molar mass	160.220 g·mol−1
Appearance	white to orange needles
Melting point	118˚C
Boiling point	137 °C (279 °F; 410 K) (0.15 mmHg)
Solubility in water	negligible solubility in water
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tryptamine is an indolamine metabolite of the essential amino acid, tryptophan.^[2]^[3] 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).^[2] The structure of tryptamine is a shared feature of certain aminergic neuromodulators including melatonin, serotonin, bufotenin and psychedelic derivatives such as dimethyltryptamine (DMT), psilocybin, psilocin and others.^[4]^[5]^[6]

Tryptamine has been shown to activate serotonin receptors^[7]^[8] and trace amine-associated receptors expressed in the mammalian brain, and regulates the activity of dopaminergic, serotonergic and glutamatergic systems.^[9]^[10] In the human gut, symbiotic bacteria convert dietary tryptophan to tryptamine, which activates 5-HT₄ receptors and regulates gastrointestinal motility.^[3]^[11]^[12]

Multiple tryptamine-derived drugs have been developed to treat migraines, while trace amine-associated receptors are being explored as a potential treatment target for neuropsychiatric disorders.^[13]^[14]^[15]

Natural occurrences

For a list of plants, fungi and animals containing tryptamines, see List of psychoactive plants and List of naturally occurring tryptamines.

Mammalian brain

Endogenous levels of tryptamine in the mammalian brain are less than 100 ng per gram of tissue.^[16]^[17] However, elevated levels of trace amines have been observed in patients with certain neuropsychiatric disorders taking medications, such as bipolar depression and schizophrenia.^[18]

Mammalian gut microbiome

Tryptamine is relatively abundant in the gut and feces of humans and rodents.^[19]^[20] Commensal bacteria, including Ruminococcus gnavus and Clostridium sporogenes in the gastrointestinal tract, possess the enzyme tryptophan decarboxylase, which aids in the conversion of dietary tryptophan to tryptamine.^[19] Tryptamine is a ligand for gut epithelial serotonin type 4 (5-HT₄) receptors and regulates gastrointestinal electrolyte balance through colonic secretions.^[20]

Metabolism

Biosynthesis

To yield tryptamine in vivo, tryptophan decarboxylase removes the carboxylic acid group on the α-carbon of tryptophan.^[21] Synthetic modifications to tryptamine can produce serotonin and melatonin; however, these pathways do not occur naturally as the main pathway for endogenous neurotransmitter synthesis.^[22]

Catabolism

Monoamine oxidases A and B are the primary enzymes involved in tryptamine metabolism to produce indole-3-acetaldehyde, however it is unclear which isoform is specific to tryptamine degradation.^[23]

Mechanisms of action and biological effects

Neuromodulation

Tryptamine is known to act as a serotonin receptor agonist, although its potency is limited by rapid inactivation by monoamine oxidases.^[7]^[8]^[24]^[25] It has specifically been found to act as a full agonist of the serotonin 5-HT_2A receptor (EC₅₀Tooltip half-maximal effective concentration = 7.36 ± 0.56 nM; E_max = 104 ± 4%).^[7] Tryptamine was of much lower potency in stimulating the 5-HT_2A receptor β-arrestin pathway (EC₅₀ = 3,485 ± 234 nM; E_max = 108 ± 16%).^[7] In contrast to the 5-HT_2A receptor, tryptamine was found to be inactive at the serotonin 5-HT_1A receptor.^[7] Alexander Shulgin tested tryptamine at high doses intravenously and found that it produced weak serotonergic psychedelic-like effects as well as peripheral nervous system changes.^[7]^[26]

It can also weakly activate the trace amine-associated receptor, TAAR1 (hTAAR1 in humans).^[27]^[28]^[29] Limited studies have considered tryptamine to be a trace neuromodulator capable of regulating the activity of neuronal cell responses without binding to the associated postsynaptic receptors.^[29]^[30]

Tryptamine has been found to act as a monoamine releasing agent.^[7]^[31] It is a releaser of serotonin, dopamine, and norepinephrine, in that order of potency (EC₅₀ = 32.6 ± 2.6 nM, 164 ± 16 nM, and 716 ± 46 nM, respectively).^[7]^[31] It is also a monoaminergic activity enhancer of these neurotransmitters.^[32]^[33]

hTAAR1

hTAAR1 is a stimulatory G-protein coupled receptor (GPCR) that is weakly expressed in the intracellular compartment of both pre- and postsynaptic neurons.^[34] Tryptamine and other hTAAR1 agonists can increase neuronal firing by inhibiting neurotransmitter recycling through cAMP-dependent phosphorylation of the monoamine reuptake transporter.^[35]^[30] This mechanism increases the amount of neurotransmitter in the synaptic cleft, subsequently increasing postsynaptic receptor binding and neuronal activation.^[30] Conversely, when hTAAR1 are colocalized with G protein-coupled inwardly-rectifying potassium channels (GIRKs), receptor activation reduces neuronal firing by facilitating membrane hyperpolarization through the efflux of potassium ions.^[30] The balance between the inhibitory and excitatory activity of hTAAR1 activation highlights the role of tryptamine in the regulation of neural activity.^[36]

Activation of hTAAR1 is under investigation as a novel treatment for depression, addiction, and schizophrenia.^[37] hTAAR1 is primarily expressed in brain structures associated with dopamine systems, such as the ventral tegmental area (VTA) and serotonin systems in the dorsal raphe nuclei (DRN).^[37] Additionally, the hTAAR1 gene is localized at 6q23.2 on the human chromosome, which is a susceptibility locus for mood disorders and schizophrenia.^[38] Activation of TAAR1 suggests a potential novel treatment for neuropsychiatric disorders, as TAAR1 agonists produce anti-depressive activity, increased cognition, reduced stress and anti-addiction effects.^[36]^[38]

Monoaminergic activity enhancer

Tryptamine is a monoaminergic activity enhancer (MAE) of serotonin, norepinephrine, and dopamine in addition to its serotonin receptor agonism.^[32]^[33] That is, it enhances the action potential-mediated release of these monoamine neurotransmitters.^[32]^[33] The MAE actions of tryptamine and other MAEs may be mediated by TAAR1 agonism.^[39]^[40] Synthetic and more potent MAEs like benzofuranylpropylaminopentane (BPAP) and indolylpropylaminopentane (IPAP) have been derived from tryptamine.^[32]^[33]^[41]^[42]^[43]

Gastrointestinal motility

Tryptamine produced by mutualistic bacteria in the human gut activates serotonin GPCRs ubiquitously expressed along the colonic epithelium.^[44] Upon tryptamine binding, the activated 5-HT₄ receptor undergoes a conformational change which allows its G_s alpha subunit to exchange GDP for GTP, and its liberation from the 5-HT₄ receptor and βγ subunit.^[44] GTP-bound G_s activates adenylyl cyclase, which catalyzes the conversion of ATP into cyclic adenosine monophosphate (cAMP).^[44] cAMP opens chloride and potassium ion channels to drive colonic electrolyte secretion and promote intestinal motility.^[45]^[46]

Pharmacodynamics

TAAR1 Activation (EC₅₀) and Binding Affinity (K_i) of Tryptamines^[47]
Tryptamine	Human TAAR1		Mouse TAAR1		Rat TAAR
	EC₅₀	K_i	EC₅₀	K_i	EC₅₀	K_i
Tryptamine	21	N/A	2.7	1.4	0.41	0.13
Serotonin	>50	N/A	>50	N/A	5.2	N/A
Psilocin	>30	N/A	2.7	17	0.92	1.4
DMT	>10	N/A	1.2	3.3	1.5	22
EC₅₀ and K_i values are in micromolar (μM). EC₅₀ reflects the amount of tryptamine required to elicit 50% of the maximum TAAR1 response. The smaller the K_i value, the stronger the tryptamine binds to the receptor.

Tryptamine-based therapeutics

Drug	Mechanism	Treatment	Effect	Structure
Sumatriptan^[48]	5-HT_1B and 5-HT_1D agonist	Migraine Headaches	Vasoconstriction of brain blood vessels	Sumatriptan
Rizatriptan^[48]	5-HT_1B and 5-HT_1D agonist	Migraine Headaches	Vasoconstriction of brain blood vessels	Rizatriptan
Zolmitriptan^[48]	5-HT_1B and 5-HT_1D agonist	Migraine Headaches	Vasoconstriction of brain blood vessels	Zolmitriptan
Almotriptan^[48]	5-HT_1B and 5-HT_1D agonist	Migraine Headaches	Vasoconstriction of brain blood vessels	Almotriptan
Eletriptan^[48]	5-HT_1B and 5-HT_1D agonist	Migraine Headaches	Vasoconstriction of brain blood vessels	Eletriptan
Frovatriptan^[48]	5-HT_1B and 5-HT_1D agonist	Migraine Headaches	Vasoconstriction of brain blood vessels	Frovatriptan
Naratriptan^[48]	5-HT_1B and 5-HT_1D agonist	Migraine Headaches	Vasoconstriction of brain blood vessels	Naratriptan

References

^ Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (85th ed.). CRC Press. p. 3-564. ISBN 978-0-8493-0484-2.
^ ^a ^b "Tryptamine". pubchem.ncbi.nlm.nih.gov. Retrieved 2020-12-01.
^ ^a ^b Jenkins, Trisha A.; Nguyen, Jason C. D.; Polglaze, Kate E.; Bertrand, Paul P. (2016-01-20). "Influence of Tryptophan and Serotonin on Mood and Cognition with a Possible Role of the Gut-Brain Axis". Nutrients. 8 (1): 56. doi:10.3390/nu8010056. ISSN 2072-6643. PMC 4728667. PMID 26805875.
^ Tylš, Filip; Páleníček, Tomáš; Horáček, Jiří (2014-03-01). "Psilocybin – Summary of knowledge and new perspectives". European Neuropsychopharmacology. 24 (3): 342–356. doi:10.1016/j.euroneuro.2013.12.006. ISSN 0924-977X. PMID 24444771. S2CID 10758314.
^ Tittarelli, Roberta; Mannocchi, Giulio; Pantano, Flaminia; Romolo, Francesco Saverio (2015). "Recreational Use, Analysis and Toxicity of Tryptamines". Current Neuropharmacology. 13 (1): 26–46. doi:10.2174/1570159X13666141210222409. ISSN 1570-159X. PMC 4462041. PMID 26074742.
^ "The Ayahuasca Phenomenon". MAPS. 21 November 2014. Retrieved 2020-10-03.
^ ^a ^b ^c ^d ^e ^f ^g ^h Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB (October 2014). "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology (Berl). 231 (21): 4135–4144. doi:10.1007/s00213-014-3557-7. PMC 4194234. PMID 24800892.
^ ^a ^b Mousseau DD (March 1993). "Tryptamine: a metabolite of tryptophan implicated in various neuropsychiatric disorders". Metab Brain Dis. 8 (1): 1–44. doi:10.1007/BF01000528. PMID 8098507.
^ Khan, Muhammad Zahid; Nawaz, Waqas (2016-10-01). "The emerging roles of human trace amines and human trace amine-associated receptors (hTAARs) in central nervous system". Biomedicine & Pharmacotherapy. 83: 439–449. doi:10.1016/j.biopha.2016.07.002. ISSN 0753-3322. PMID 27424325.
^ Berry, Mark D.; Gainetdinov, Raul R.; Hoener, Marius C.; Shahid, Mohammed (2017-12-01). "Pharmacology of human trace amine-associated receptors: Therapeutic opportunities and challenges". Pharmacology & Therapeutics. 180: 161–180. doi:10.1016/j.pharmthera.2017.07.002. ISSN 0163-7258. PMID 28723415. S2CID 207366162.
^ Bhattarai, Yogesh; Williams, Brianna B.; Battaglioli, Eric J.; Whitaker, Weston R.; Till, Lisa; Grover, Madhusudan; Linden, David R.; Akiba, Yasutada; Kandimalla, Karunya K.; Zachos, Nicholas C.; Kaunitz, Jonathan D. (2018-06-13). "Gut Microbiota-Produced Tryptamine Activates an Epithelial G-Protein-Coupled Receptor to Increase Colonic Secretion". Cell Host & Microbe. 23 (6): 775–785.e5. doi:10.1016/j.chom.2018.05.004. ISSN 1931-3128. PMC 6055526. PMID 29902441.
^ Field, Michael (2003). "Intestinal ion transport and the pathophysiology of diarrhea". Journal of Clinical Investigation. 111 (7): 931–943. doi:10.1172/JCI200318326. ISSN 0021-9738. PMC 152597. PMID 12671039.
^ "Serotonin Receptor Agonists (Triptans)", LiverTox: Clinical and Research Information on Drug-Induced Liver Injury, Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases, 2012, PMID 31644023, retrieved 2020-10-15
^ "New Compound Related to Psychedelic Ibogaine Could Treat Addiction, Depression". UC Davis. 2020-12-09. Retrieved 2020-12-11.
^ ServiceDec. 9, Robert F. "Chemists re-engineer a psychedelic to treat depression and addiction in rodents". Science | AAAS. Retrieved 2020-12-11.{{cite web}}: CS1 maint: numeric names: authors list (link)
^ Tittarelli, Roberta; Mannocchi, Giulio; Pantano, Flaminia; Romolo, Francesco Saverio (2015). "Recreational Use, Analysis and Toxicity of Tryptamines". Current Neuropharmacology. 13 (1): 26–46. doi:10.2174/1570159X13666141210222409. ISSN 1570-159X. PMC 4462041. PMID 26074742.
^ Berry, Mark D.; Gainetdinov, Raul R.; Hoener, Marius C.; Shahid, Mohammed (2017-12-01). "Pharmacology of human trace amine-associated receptors: Therapeutic opportunities and challenges". Pharmacology & Therapeutics. 180: 161–180. doi:10.1016/j.pharmthera.2017.07.002. ISSN 0163-7258. PMID 28723415. S2CID 207366162.
^ Miller, Gregory M. (2011). "The Emerging Role of Trace Amine Associated Receptor 1 in the Functional Regulation of Monoamine Transporters and Dopaminergic Activity". Journal of Neurochemistry. 116 (2): 164–176. doi:10.1111/j.1471-4159.2010.07109.x. ISSN 0022-3042. PMC 3005101. PMID 21073468.
^ ^a ^b Jenkins, Trisha A.; Nguyen, Jason C. D.; Polglaze, Kate E.; Bertrand, Paul P. (2016-01-20). "Influence of Tryptophan and Serotonin on Mood and Cognition with a Possible Role of the Gut-Brain Axis". Nutrients. 8 (1): 56. doi:10.3390/nu8010056. ISSN 2072-6643. PMC 4728667. PMID 26805875.
^ ^a ^b Bhattarai, Yogesh; Williams, Brianna B.; Battaglioli, Eric J.; Whitaker, Weston R.; Till, Lisa; Grover, Madhusudan; Linden, David R.; Akiba, Yasutada; Kandimalla, Karunya K.; Zachos, Nicholas C.; Kaunitz, Jonathan D. (2018-06-13). "Gut Microbiota-Produced Tryptamine Activates an Epithelial G-Protein-Coupled Receptor to Increase Colonic Secretion". Cell Host & Microbe. 23 (6): 775–785.e5. doi:10.1016/j.chom.2018.05.004. ISSN 1931-3128. PMC 6055526. PMID 29902441.
^ Tittarelli, Roberta; Mannocchi, Giulio; Pantano, Flaminia; Romolo, Francesco Saverio (2015). "Recreational Use, Analysis and Toxicity of Tryptamines". Current Neuropharmacology. 13 (1): 26–46. doi:10.2174/1570159X13666141210222409. ISSN 1570-159X. PMC 4462041. PMID 26074742.
^ "Serotonin Synthesis and Metabolism". Sigma Aldrich. 2020.
^ "MetaCyc L-tryptophan degradation VI (via tryptamine)". biocyc.org. Retrieved 2020-12-11.
^ Anwar MA, Ford WR, Broadley KJ, Herbert AA (April 2012). "Vasoconstrictor and vasodilator responses to tryptamine of rat-isolated perfused mesentery: comparison with tyramine and β-phenylethylamine". Br J Pharmacol. 165 (7): 2191–2202. doi:10.1111/j.1476-5381.2011.01706.x. PMC 3413856. PMID 21958009.
^ Bradley PB, Humphrey PP, Williams RH (April 1985). "Tryptamine-induced vasoconstrictor responses in rat caudal arteries are mediated predominantly via 5-hydroxytryptamine receptors". Br J Pharmacol. 84 (4): 919–925. doi:10.1111/j.1476-5381.1985.tb17386.x. PMC 1987057. PMID 3159458.
^ Shulgin, A.; Shulgin, A. (1997). Tihkal: The Continuation. Transform Press. #53. T. ISBN 978-0-9630096-9-2. Retrieved 17 August 2024. (with 250 mg, intravenously) "Tryptamine was infused intravenously over a period of up to 7.5 minutes. Physical changes included an increases in blood pressure, in the amplitude of the patellar reflex, and in pupillary diameter. The subjective changes are not unlike those seen with small doses of LSD. A point-by-point comparison between the tryptamine and LSD syndromes reveals a close similarity which is consistent with the hypothesis that tryptamine and LSD have a common mode of action."
^ Yu, Ai-Ming; Granvil, Camille P.; Haining, Robert L.; Krausz, Kristopher W.; Corchero, Javier; Küpfer, Adrian; Idle, Jeffrey R.; Gonzalez, Frank J. (2003-02-01). "The Relative Contribution of Monoamine Oxidase and Cytochrome P450 Isozymes to the Metabolic Deamination of the Trace Amine Tryptamine". Journal of Pharmacology and Experimental Therapeutics. 304 (2): 539–546. doi:10.1124/jpet.102.043786. ISSN 0022-3565. PMID 12538805. S2CID 18279145.
^ Khan, Muhammad Zahid; Nawaz, Waqas (2016-10-01). "The emerging roles of human trace amines and human trace amine-associated receptors (hTAARs) in central nervous system". Biomedicine & Pharmacotherapy. 83: 439–449. doi:10.1016/j.biopha.2016.07.002. ISSN 0753-3322. PMID 27424325.
^ ^a ^b Zucchi, R; Chiellini, G; Scanlan, T S; Grandy, D K (2006). "Trace amine-associated receptors and their ligands". British Journal of Pharmacology. 149 (8): 967–978. doi:10.1038/sj.bjp.0706948. ISSN 0007-1188. PMC 2014643. PMID 17088868.
^ ^a ^b ^c ^d Miller, Gregory M. (2011). "The Emerging Role of Trace Amine Associated Receptor 1 in the Functional Regulation of Monoamine Transporters and Dopaminergic Activity". Journal of Neurochemistry. 116 (2): 164–176. doi:10.1111/j.1471-4159.2010.07109.x. ISSN 0022-3042. PMC 3005101. PMID 21073468.
^ ^a ^b Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, Rothman RB (October 2014). "Alpha-ethyltryptamines as dual dopamine-serotonin releasers". Bioorg Med Chem Lett. 24 (19): 4754–4758. doi:10.1016/j.bmcl.2014.07.062. PMC 4211607. PMID 25193229.
^ ^a ^b ^c ^d Shimazu S, Miklya I (May 2004). "Pharmacological studies with endogenous enhancer substances: beta-phenylethylamine, tryptamine, and their synthetic derivatives". Progress in Neuro-Psychopharmacology & Biological Psychiatry. 28 (3): 421–427. doi:10.1016/j.pnpbp.2003.11.016. PMID 15093948. S2CID 37564231.
^ ^a ^b ^c ^d Knoll J (August 2003). "Enhancer regulation/endogenous and synthetic enhancer compounds: a neurochemical concept of the innate and acquired drives". Neurochem Res. 28 (8): 1275–1297. doi:10.1023/a:1024224311289. PMID 12834268.
^ Berry, Mark D.; Gainetdinov, Raul R.; Hoener, Marius C.; Shahid, Mohammed (2017-12-01). "Pharmacology of human trace amine-associated receptors: Therapeutic opportunities and challenges". Pharmacology & Therapeutics. 180: 161–180. doi:10.1016/j.pharmthera.2017.07.002. ISSN 0163-7258. PMID 28723415. S2CID 207366162.
^ Jing, Li; Li, Jun-Xu (2015-08-15). "Trace amine-associated receptor 1: a promising target for the treatment of psychostimulant addiction". European Journal of Pharmacology. 761: 345–352. doi:10.1016/j.ejphar.2015.06.019. ISSN 0014-2999. PMC 4532615. PMID 26092759.
^ ^a ^b Grandy, David K.; Miller, Gregory M.; Li, Jun-Xu (2016-02-01). ""TAARgeting Addiction" The Alamo Bears Witness to Another Revolution". Drug and Alcohol Dependence. 159: 9–16. doi:10.1016/j.drugalcdep.2015.11.014. ISSN 0376-8716. PMC 4724540. PMID 26644139.
^ ^a ^b Berry, Mark D.; Gainetdinov, Raul R.; Hoener, Marius C.; Shahid, Mohammed (2017-12-01). "Pharmacology of human trace amine-associated receptors: Therapeutic opportunities and challenges". Pharmacology & Therapeutics. 180: 161–180. doi:10.1016/j.pharmthera.2017.07.002. ISSN 0163-7258. PMID 28723415. S2CID 207366162.
^ ^a ^b Gainetdinov, Raul R.; Hoener, Marius C.; Berry, Mark D. (2018-07-01). "Trace Amines and Their Receptors". Pharmacological Reviews. 70 (3): 549–620. doi:10.1124/pr.117.015305. ISSN 0031-6997. PMID 29941461. S2CID 49411553.
^ Harsing LG, Knoll J, Miklya I (August 2022). "Enhancer Regulation of Dopaminergic Neurochemical Transmission in the Striatum". Int J Mol Sci. 23 (15): 8543. doi:10.3390/ijms23158543. PMC 9369307. PMID 35955676.
^ Harsing LG, Timar J, Miklya I (August 2023). "Striking Neurochemical and Behavioral Differences in the Mode of Action of Selegiline and Rasagiline". Int J Mol Sci. 24 (17): 13334. doi:10.3390/ijms241713334. PMC 10487936. PMID 37686140.
^ Knoll J (2001). "Antiaging compounds: (-)deprenyl (selegeline) and (-)1-(benzofuran-2-yl)-2-propylaminopentane, [(-)BPAP], a selective highly potent enhancer of the impulse propagation mediated release of catecholamine and serotonin in the brain". CNS Drug Rev. 7 (3): 317–45. doi:10.1111/j.1527-3458.2001.tb00202.x. PMC 6494119. PMID 11607046.
^ Yoneda F, Moto T, Sakae M, Ohde H, Knoll B, Miklya I, Knoll J (May 2001). "Structure-activity studies leading to (-)1-(benzofuran-2-yl)-2-propylaminopentane, ((-)BPAP), a highly potent, selective enhancer of the impulse propagation mediated release of catecholamines and serotonin in the brain". Bioorg Med Chem. 9 (5): 1197–1212. doi:10.1016/s0968-0896(01)00002-5. PMID 11377178.
^ Knoll J, Yoneda F, Knoll B, Ohde H, Miklya I (December 1999). "(-)1-(Benzofuran-2-yl)-2-propylaminopentane, [(-)BPAP], a selective enhancer of the impulse propagation mediated release of catecholamines and serotonin in the brain". British Journal of Pharmacology. 128 (8): 1723–1732. doi:10.1038/sj.bjp.0702995. PMC 1571822. PMID 10588928.
^ ^a ^b ^c Bhattarai, Yogesh; Williams, Brianna B.; Battaglioli, Eric J.; Whitaker, Weston R.; Till, Lisa; Grover, Madhusudan; Linden, David R.; Akiba, Yasutada; Kandimalla, Karunya K.; Zachos, Nicholas C.; Kaunitz, Jonathan D. (2018-06-13). "Gut Microbiota-Produced Tryptamine Activates an Epithelial G-Protein-Coupled Receptor to Increase Colonic Secretion". Cell Host & Microbe. 23 (6): 775–785.e5. doi:10.1016/j.chom.2018.05.004. ISSN 1931-3128. PMC 6055526. PMID 29902441.
^ Field, Michael (2003). "Intestinal ion transport and the pathophysiology of diarrhea". Journal of Clinical Investigation. 111 (7): 931–943. doi:10.1172/JCI200318326. ISSN 0021-9738. PMC 152597. PMID 12671039.
^ "Microbiome-Lax May Relieve Constipation". GEN - Genetic Engineering and Biotechnology News. 2018-06-15. Retrieved 2020-12-11.
^ Gainetdinov, Raul R.; Hoener, Marius C.; Berry, Mark D. (2018-07-01). "Trace Amines and Their Receptors". Pharmacological Reviews. 70 (3): 549–620. doi:10.1124/pr.117.015305. ISSN 0031-6997. PMID 29941461. S2CID 49411553.
^ ^a ^b ^c ^d ^e ^f ^g "Serotonin Receptor Agonists (Triptans)", LiverTox: Clinical and Research Information on Drug-Induced Liver Injury, Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases, 2012, PMID 31644023, retrieved 2020-10-15

External links

Tryptamine FAQ
Tryptamine Hallucinogens and Consciousness
Tryptamind Psychoactives, reference site on tryptamine and other psychoactives.
Tryptamine (T) entry in TiHKAL • info

[1] Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (85th ed.). CRC Press. p. 3-564. ISBN 978-0-8493-0484-2.

[NML-2] "Tryptamine". pubchem.ncbi.nlm.nih.gov. Retrieved 2020-12-01.

[:3-3] Jenkins, Trisha A.; Nguyen, Jason C. D.; Polglaze, Kate E.; Bertrand, Paul P. (2016-01-20). "Influence of Tryptophan and Serotonin on Mood and Cognition with a Possible Role of the Gut-Brain Axis". Nutrients. 8 (1): 56. doi:10.3390/nu8010056. ISSN 2072-6643. PMC 4728667. PMID 26805875.

[:6-4] Tylš, Filip; Páleníček, Tomáš; Horáček, Jiří (2014-03-01). "Psilocybin – Summary of knowledge and new perspectives". European Neuropsychopharmacology. 24 (3): 342–356. doi:10.1016/j.euroneuro.2013.12.006. ISSN 0924-977X. PMID 24444771. S2CID 10758314.

[:0-5] Tittarelli, Roberta; Mannocchi, Giulio; Pantano, Flaminia; Romolo, Francesco Saverio (2015). "Recreational Use, Analysis and Toxicity of Tryptamines". Current Neuropharmacology. 13 (1): 26–46. doi:10.2174/1570159X13666141210222409. ISSN 1570-159X. PMC 4462041. PMID 26074742.

[:5-6] "The Ayahuasca Phenomenon". MAPS. 21 November 2014. Retrieved 2020-10-03.

[BloughLandavazoDecker2014-7] ^ ^a ^b ^c ^d ^e ^f ^g ^h Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB (October 2014). "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology (Berl). 231 (21): 4135–4144. doi:10.1007/s00213-014-3557-7. PMC 4194234. PMID 24800892.

[Mousseau1993-8] Mousseau DD (March 1993). "Tryptamine: a metabolite of tryptophan implicated in various neuropsychiatric disorders". Metab Brain Dis. 8 (1): 1–44. doi:10.1007/BF01000528. PMID 8098507.

[:2-9] Khan, Muhammad Zahid; Nawaz, Waqas (2016-10-01). "The emerging roles of human trace amines and human trace amine-associated receptors (hTAARs) in central nervous system". Biomedicine & Pharmacotherapy. 83: 439–449. doi:10.1016/j.biopha.2016.07.002. ISSN 0753-3322. PMID 27424325.

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Tryptamine

Natural occurrences

Mammalian brain

Mammalian gut microbiome

Metabolism

Biosynthesis

Catabolism

Mechanisms of action and biological effects

Neuromodulation

hTAAR1

Monoaminergic activity enhancer

Gastrointestinal motility

Pharmacodynamics

Tryptamine-based therapeutics

See also

References

External links

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