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Tryptamine

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Tryptamine
Names
IUPAC name
2-(1H-Indol-3-yl)ethanamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.464 Edit this at Wikidata
UNII
  • InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2 ☒N
    Key: APJYDQYYACXCRM-UHFFFAOYSA-N ☒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
  • c1ccc2c(c1)c(c[nH]2)CCN
Properties
C10H12N2
Molar mass 160.220 g·mol−1
Appearance white to orange crystalline powder[1]
Melting point 113-116˚C[1]
Boiling point 137 °C (279 °F; 410 K) (0.15 mmHg)[1]
negligible solubility in water[1]
Hazards
Flash point 185˚C[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Tryptamine is a monoamine alkaloid. It contains an indole ring structure, and is structurally similar to the amino acid tryptophan, from which the name derives. Tryptamine is found in trace amounts in the brains of mammals and is hypothesized to play a role as a neuromodulator or neurotransmitter.[2] Similar to other trace amines, tryptamine binds to human trace amine-associated receptor 1 (TAAR1) as an agonist.[3]

Tryptamine is the common functional group in a set of compounds termed collectively substituted tryptamines. This set includes many biologically active compounds, including neurotransmitters and psychedelic drugs.

The concentration of tryptamine in rat brains is about 3.5 pmol/g.[4]

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]

See also

References

  1. ^ a b c d e http://www.chemicalbook.com/ProductChemicalPropertiesCB8192006_EN.htm[full citation needed]
  2. ^ Jones R.S. (1982). "Tryptamine: a neuromodulator or neurotransmitter in mammalian brain?". Progress in Neurobiology. 19 (1–2): 117–139. doi:10.1016/0301-0082(82)90023-5.
  3. ^ 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.2016.07.002. PMID 27424325.
  4. ^ 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. ^ Nobutaka Takahashi (1986). Chemistry of Plant Hormones. CRC Press. ISBN 9780849354700.
  6. ^ 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/BF00165727. PMID 1570019.
  7. ^ 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.2003.11.016. PMID 15093948.
  8. ^ 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.2014.07.062. ISSN 0960-894X. PMC 4211607. PMID 25193229.
  9. ^ 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)90039-6. PMID 7911372.
  10. ^ 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)90421-1. PMID 3094536.
  11. ^ 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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