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5-Hydroxytryptophan: Difference between revisions
>Unity The order goes: 5-HTP -> Serotonin -> Melatonin. The reference to melatonin biosynthesis is insufficiently precise. |
>Unity Streamline wording of introduction. |
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{{SubstanceBox/5-HTP}} | {{SubstanceBox/5-HTP}} | ||
'''5-Hydroxytryptophan''' (also known as '''5-HTP''' and '''oxitriptan''') is a naturally occurring | '''5-Hydroxytryptophan''' (also known as '''5-HTP''' and '''oxitriptan''') is a naturally occurring chemical substance and a metabolic intermediate in the biosynthesis of [[serotonin]] in the human body.{{citation needed}} | ||
5-HTP is | 5-HTP is available over the counter in the United States, United Kingdom, and Canada as a dietary supplement and is sometimes used as an [[antidepressant]], sleep aid, and appetite suppressant. It is marketed in some European countries as a prescription drug for the treatment of major depression.<ref>https://books.google.com/books?id=5GpcTQD_L2oC&lpg=PA1528&pg=PA773&hl=en#v=onepage&q&f=false | Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. ISBN 3-88763-075-0.</ref> | ||
5-HTP should not be taken until 12 hours after one's last dose of MDMA because combining the two substances could | 5-HTP is also popularly consumed by users of [[MDMA]] and other serotonin-releasing agents to try to reduce the negative [[MDMA#After_effects|after effects]] that begin during the substance's [[duration|come down]] period, including [[anxiety]], [[depression]], and [[cognitive fatigue]].<ref>http://www.sciencedirect.com/science/article/pii/S0306452207006732 | Wang, X.; Baumann, M. H.; Dersch, C. M.; Rothman, R. B. (2007-08-10). "Restoration of 3,4-methylenedioxymethamphetamine-induced 5-HT depletion by the administration of l-5-hydroxytryptophan". Neuroscience. 148 (1): 212–220. doi:10.1016/j.neuroscience.2007.05.024. PMID 17629409.</ref> | ||
Since 5-HTP is a precursor for the neurotransmitter [[serotonin]] and MDMA administration both depletes serotonin levels in the brain as well as inhibit the enzyme needed to produce it (i.e. tryptophan hydroxylase) for a short period after,<ref>Acute inactivation of tryptophan hydroxylase by amphetamine analogs involves the oxidation of sulfhydryl sites | http://www.maps.org/images/pdf/1989_stone_1.pdf</ref> it is believed that taking 5-HTP in the days after coming down will speed up the production of serotonin and decrease the time needed to recover (though there are many popular misconceptions and controversies as to just how effective it is for this purpose).{{Citation needed}} | |||
5-HTP should not be taken until 12 hours after one's last dose of MDMA because combining the two substances could interact to increase the brain's serotonin levels to dangerous levels, which can result in a potentially life-threatening condition called [[serotonin syndrome]]. | |||
==Chemistry== | ==Chemistry== | ||
5-HTP or 5-Hydroxytryptophan is a synthetic indole alkaloid molecule of the [[tryptamine]] class. Tryptamines share a core structure comprised of a bicyclic indole heterocycle attached at R<sub>3</sub> to an amino group via an ethyl side chain. 5-HTP is substituted at R<sub>5</sub> of its indole heterocycle with a hydroxy (OH) functional group. It also contains propanoic acid group bound to the terminal amine R<sub>N</sub> of its tryptamine backbone. 5-HTP is the 5-hydroxy analog of [[tryptophan]], and is sold in its levorotary isomer form. 5-HTP contains the core structure of [[serotonin]] with the addition of a propanoic acid at R<sub>N</sub>, and is converted by the body into serotonin by metabolic reactions. | 5-HTP or 5-Hydroxytryptophan is a synthetic indole alkaloid molecule of the [[tryptamine]] class. Tryptamines share a core structure comprised of a bicyclic indole heterocycle attached at R<sub>3</sub> to an amino group via an ethyl side chain. 5-HTP is substituted at R<sub>5</sub> of its indole heterocycle with a hydroxy (OH) functional group. It also contains propanoic acid group bound to the terminal amine R<sub>N</sub> of its tryptamine backbone. 5-HTP is the 5-hydroxy analog of [[tryptophan]], and is sold in its levorotary isomer form. 5-HTP contains the core structure of [[serotonin]] with the addition of a propanoic acid at R<sub>N</sub>, and is converted by the body into serotonin by metabolic reactions. | ||