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Tryptamine

Lianyungang Klinechem Co.,Ltd | Updated: Nov 22, 2018

Plants containing tryptamine

Many plants contain small amounts of tryptamine. It is a feedstock for the metabolic pathways which influence plant growth and microbiome. For example, it is found as a possible intermediate in one biosynthetic pathway to the plant hormone indole-3-acetic acid.[5] Higher concentrations can be found in many Acacia species.

Pharmacology

Tryptamine is an agonist of hTAAR1.[3] It acts as a non-selective serotonin receptor agonist and serotonin-norepinephrine-dopamine releasing agent (SNDRA), with a preference for evoking serotonin and dopamine release over norepinephrine release.[6][7][8]

Tryptamine has been shown to act as a noncompetitive inhibitor of serotonin N-acetyltransferase (SNAT) in mosquitoes.[9] SNAT catalyzes the anabolic metabolism of serotonin into N-acetylserotonin, another neuromodulator (specifically a neurotrophic factor via TrkB agonism) and the immediate precursor for melatonin.

Tryptamine is rapidly metabolized by MAO-A and MAO-B,[10] and for this reason, has a very short in vivo half-life.

Synthesis

The Abramovitch–Shapiro tryptamine synthesis is an organic reaction for the synthesis of tryptamine.[11]

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See also

·         Substituted tryptamine

·         Phenethylamine

References

1.     Jump up to:a b c d ehttp://www.chemicalbook.com/ProductChemicalPropertiesCB8192006_EN.htm[full citation needed]

2.     Jump up^ Jones R.S. (1982). "Tryptamine: a neuromodulator or neurotransmitter in mammalian brain?". Progress in Neurobiology. 19 (1&ndash, 2): 117&ndash, 139. doi:10.1016/0301-0082(82)90023-5.

3.     Jump up to:a b Khan MZ, Nawaz W (October 2016). "The emerging roles of human trace amines and human trace amine-associated receptors (hTAARs) in central nervous system". Biomed. Pharmacother. 83: 439–449. doi:10.1016/j.biopha.2016.07.002PMID 27424325.

4.     Jump up^ Jiang, Zhen; Mutch, Elaine; Blain, Peter G.; Williams, Faith M. (2006). "Conversion of trichloroethylene to chloral using occupationally relevant levels". Toxicology. 226 (1): 76–77. doi:10.1016/j.tox.2006.05.102.

5.     Jump up^ Nobutaka Takahashi (1986). Chemistry of Plant HormonesCRC PressISBN 9780849354700.

6.     Jump up^ Wölfel, Reinhard; Graefe, Karl-Heinz (1992). "Evidence for various tryptamines and related compounds acting as substrates of the platelet 5-hydroxytryptamine transporter". Naunyn-Schmiedeberg's Archives of Pharmacology. 345 (2): 129–36. doi:10.1007/BF00165727PMID 1570019.

7.     Jump up^ Shimazu, S; Miklya, I (2004). "Pharmacological studies with endogenous enhancer substances: Beta-phenylethylamine, tryptamine, and their synthetic derivatives". Progress in Neuro-psychopharmacology & Biological Psychiatry. 28 (3): 421–7. doi:10.1016/j.pnpbp.2003.11.016PMID 15093948.

8.     Jump up^ Blough, Bruce E.; Landavazo, Antonio; Partilla, John S.; Decker, Ann M.; Page, Kevin M.; Baumann, Michael H.; Rothman, Richard B. (2014). "Alpha-ethyltryptamines as dual dopamine–serotonin releasers". Bioorganic & Medicinal Chemistry Letters. 24 (19): 4754–4758. doi:10.1016/j.bmcl.2014.07.062ISSN 0960-894XPMC 4211607PMID 25193229.

9.     Jump up^ Khoo HG, Wong KP (1994). "Acetyl CoA generation and N-acetylation of serotonin (5HT) in the mosquito, Aedes togoi". Insect Biochemistry and Molecular Biology. 24 (5): 445–51. doi:10.1016/0965-1748(94)90039-6PMID 7911372.

10.  Jump up^ Sullivan, James P.; McDonnell, Leonard; Hardiman, Orla M.; Farrell, Michael A.; Phillips, Jack P.; Tipton, Keith F. (1986). "The oxidation of tryptamine by the two forms of monoamine oxidase in human tissues". Biochemical Pharmacology. 35 (19): 3255–60. doi:10.1016/0006-2952(86)90421-1PMID 3094536.

11.  Jump up^ Abramovitch, R. A.; Shapiro, D. (1956). "880. Tryptamines, carbolines, and related compounds. Part II. A convenient synthesis of tryptamines and β-carbolines". Journal of the Chemical Society: 4589–92. doi:10.1039/JR9560004589.


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