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Tryptamine

Tryptamine
Names
IUPAC name
2-(1H-Indol-3-yl)ethanamine
Identifiers
 Y
ChEMBL  N
Jmol-3D images Image
PubChem
Properties
C10H12N2
Molar mass 160.22 g·mol−1
Appearance white to orange crystalline powder[1]
Melting point 113-116˚C[1] 
Boiling point 137˚C (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  (: Y/N?)

Tryptamine is a monoamine alkaloid. It contains an indole ring structure, and is structurally similar to the amino acid tryptophan, from which it derives its name. Tryptamine is found in trace amounts in the brains of mammals and is believed to play a role as a neuromodulator or neurotransmitter.[2]

The tryptamine chemical structure is the backbone for a group of compounds termed collectively substituted tryptamines. This group includes many biologically active compounds, including neurotransmitters and psychedelic drugs.

The concentration of tryptamine in rat brains is about 3.5 pmol/g.[3]

Contents

  • Plants containing tryptamine 1
  • Role in vertebrates 2
  • Synthesis 3
  • See also 4
  • References 5
  • External links 6

Plants containing tryptamine

Many plants contain small amounts of tryptamine, for example, as a possible intermediate in one biosynthetic pathway to the plant hormone indole-3-acetic acid.[4] Higher concentrations can be found in many Acacia species.

Role in vertebrates

Tryptamine 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.[5][6][7] It is rapidly metabolized by MAO-A and MAO-B,[8] and for this reason, has a very short in vivo half-life.

Tryptamine has also been observed to be a noncompetitive inhibitor of serotonin N-acetyltransferase (SNAT) in mosquitoes.[9] SNAT catalyzes the anabolic metabolism of serotonin into N-acetylserotonin, another neuromodulator and the immediate precursor for melatonin.

Synthesis

The Abramovitch–Shapiro tryptamine synthesis is an

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

External links

  1. ^ a b c d e "http://www.chemicalbook.com/ProductChemicalPropertiesCB8192006_EN.htm"
  2. ^ Jones R.S. (1982). "Tryptamine: a neuromodulator or neurotransmitter in mammalian brain?". Progress in neurobiology 19 (1–2): 117–139.  
  3. ^ 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.  
  4. ^ Nobutaka Takahashi (1986). Chemistry of Plant Hormones.  
  5. ^ 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.  
  6. ^ 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.  
  7. ^ 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.  
  8. ^ 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.  
  9. ^ http://www.ncbi.nlm.nih.gov/pubmed/7911372
  10. ^ Abramovitch, R. A.; Shapiro, D. (1956). "880. Tryptamines, carbolines, and related compounds. Part II. A convenient synthesis of tryptamines and ?-carbolines". Journal of the Chemical Society (Resumed): 4589.  

References

See also

General structure of substituted tryptamines

[10]

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