Tryptamine

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Tryptamine
Tryptamine structure.png
Tryptamine-3d-sticks.png
Identifiers
CAS number 61-54-1 YesY
PubChem 1150
ChEMBL CHEMBL6640 N
IUPHAR ligand 125
Jmol-3D images Image 1
Properties
Molecular formula 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]
Solubility in water negligible solubility in water[1]
Hazards
Flash point 185˚C[1]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Tryptamine is a monoamine alkaloid found in plants, fungi, and animals. 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]

Plants containing tryptamine[edit]

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[edit]

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 [edit]

The Abramovitch–Shapiro tryptamine synthesis is an organic reaction for the synthesis of tryptamines.[10]

General structure of substituted tryptamines

See also[edit]

References[edit]

  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. doi:10.1016/0301-0082(82)90023-5. 
  3. ^ Jiang, Zhen; Mutch, Elaine; Blain, Peter G.; Williams, Faith M. (2006). "Conversion of trichloroethylene to chloral using occupationally relevant levels". Toxicology 226: 76. doi:10.1016/j.tox.2006.05.102. 
  4. ^ Nobutaka Takahashi (1986). Chemistry of Plant Hormones. CRC Press. ISBN 9780849354700. 
  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. doi:10.1007/BF00165727. PMID 1570019. 
  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. doi:10.1016/j.pnpbp.2003.11.016. PMID 15093948. 
  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. doi:10.1016/j.bmcl.2014.07.062. ISSN 0960-894X. 
  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. doi:10.1016/0006-2952(86)90421-1. PMID 3094536. 
  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. doi:10.1039/JR9560004589. 

External links[edit]