5-Hydroxytryptophan: Difference between revisions

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| ''[[5-HTP/Summary|Summary sheet: 5-HTP]]''

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'''5-Hydroxytryptophan''', also known as '''5-HTP''' and '''oxitriptan''', is a naturally occurring amino acid and chemical precursor as well as a metabolic intermediate in the biosynthesis of the neurotransmitters [[serotonin]] and [[melatonin]] from [[tryptophan]]. It is available over the counter in the United States, United Kingdom, and Canada as a dietary supplement and often used as an [[antidepressant]], sleep aid, and appetite suppressant. In some European countries, it is marketed as a prescription ~~substance~~ 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-Hydroxytryptophan''', also known as '''5-HTP''' and '''oxitriptan''', is a naturally occurring amino acid and chemical precursor as well as a metabolic intermediate in the biosynthesis of the neurotransmitters [[serotonin]] and [[melatonin]] from [[tryptophan]]. It is available over the counter in the United States, United Kingdom, and Canada as a dietary supplement and often used as an [[antidepressant]], sleep aid, and appetite suppressant. In some European countries, it is marketed 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 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 drug'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 depletes both 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 after 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 synergistically increase brain's serotonin levels to dangerous degrees -- resulting in a potentially life-threatening condition called [[serotonin syndrome]].

5-HTP should not be taken until 12 hours after one's last dose of MDMA because combining the two drugs could synergistically increase brain's serotonin levels to dangerous degrees -- resulting in a potentially life-threatening condition called [[serotonin syndrome]].

==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 R3 to an amino group via an ethyl side chain. 5-HTP is substituted at R5 of its indole heterocycle with a hydroxy (OH) functional group. It also contains propanoic acid group bound to the terminal amine RN 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 RN, and is converted by the body into serotonin by metabolic reactions.

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Due to the conversion of 5-HTP into serotonin by the liver, with prolonged use, there may be a significant risk of heart valve disease from serotonin's effect on the heart, which is thought to be due to agonism of the 5-HT2B receptor present on it.<ref>https://www.ncbi.nlm.nih.gov/pubmed/15781732 | Long-term serotonin administration induces heart valve disease in rats.</ref><ref>https://www.ncbi.nlm.nih.gov/pubmed/12466135 | Serotonin mechanisms in heart valve disease II: the 5-HT2 receptor and its signaling pathway in aortic valve interstitial cells.</ref>

It has been suggested that 5-HTP may cause eosinophilia-myalgia syndrome (EMS), a serious condition which results in extreme muscle tenderness, myalgia, and blood abnormalities. However, there is evidence to show that EMS was likely caused by a contaminant in certain 5-HTP supplements instead of the ~~substance~~ itself.<ref>https://www.ncbi.nlm.nih.gov/pubmed/7699627 | An eosinophilia-myalgia syndrome related disorder associated with exposure to L-5-hydroxytryptophan.</ref>

It has been suggested that 5-HTP may cause eosinophilia-myalgia syndrome (EMS), a serious condition which results in extreme muscle tenderness, myalgia, and blood abnormalities. However, there is evidence to show that EMS was likely caused by a contaminant in certain 5-HTP supplements instead of the drug itself.<ref>https://www.ncbi.nlm.nih.gov/pubmed/7699627 | An eosinophilia-myalgia syndrome related disorder associated with exposure to L-5-hydroxytryptophan.</ref>

===Dangerous interactions===

Although many ~~substances~~ are safe on their own, they can become dangerous and even life-threatening when combined with other substances. The list below contains some common potentially dangerous combinations, but may not include all of them. Certain combinations may be safe in low doses of each but still increase the potential risk of death. Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.

Although many drugs are safe on their own, they can become dangerous and even life-threatening when combined with other substances. The list below contains some common potentially dangerous combinations, but may not include all of them. Certain combinations may be safe in low doses of each but still increase the potential risk of death. Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.

Combinations in the list below may increase the amount of neurotransmitters, such as serotonin, to dangerous or even fatal levels, resulting in life-threatening [[serotonin syndrome]].

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 | ''[[5-HTP/Summary|Summary sheet: 5-HTP]]''
 |}
-'''5-Hydroxytryptophan''', also known as '''5-HTP''' and '''oxitriptan''', is a naturally occurring amino acid and chemical precursor as well as a metabolic intermediate in the biosynthesis of the neurotransmitters [[serotonin]] and [[melatonin]] from [[tryptophan]]. It is available over the counter in the United States, United Kingdom, and Canada as a dietary supplement and often used as an [[antidepressant]], sleep aid, and appetite suppressant. In some European countries, it is marketed as a prescription substance 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-Hydroxytryptophan''', also known as '''5-HTP''' and '''oxitriptan''', is a naturally occurring amino acid and chemical precursor as well as a metabolic intermediate in the biosynthesis of the neurotransmitters [[serotonin]] and [[melatonin]] from [[tryptophan]]. It is available over the counter in the United States, United Kingdom, and Canada as a dietary supplement and often used as an [[antidepressant]], sleep aid, and appetite suppressant. In some European countries, it is marketed 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>
 -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 drug'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 depletes both 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 after 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}}
--HTP should not be taken until 12 hours after one's last dose of MDMA because combining the two substances could synergistically increase brain's serotonin levels to dangerous degrees -- resulting in a potentially life-threatening condition called [[serotonin syndrome]].
+-HTP should not be taken until 12 hours after one's last dose of MDMA because combining the two drugs could synergistically increase brain's serotonin levels to dangerous degrees -- resulting in a potentially life-threatening condition called [[serotonin syndrome]].
 ==Chemistry==
 -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.
@@ Line 51: / Line 51: @@
 Due to the conversion of 5-HTP into serotonin by the liver, with prolonged use, there may be a significant risk of heart valve disease from serotonin's effect on the heart, which is thought to be due to agonism of the 5-HT<sub>2B</sub> receptor present on it.<ref>https://www.ncbi.nlm.nih.gov/pubmed/15781732 | Long-term serotonin administration induces heart valve disease in rats.</ref><ref>https://www.ncbi.nlm.nih.gov/pubmed/12466135 | Serotonin mechanisms in heart valve disease II: the 5-HT2 receptor and its signaling pathway in aortic valve interstitial cells.</ref>
-It has been suggested that 5-HTP may cause eosinophilia-myalgia syndrome (EMS), a serious condition which results in extreme muscle tenderness, myalgia, and blood abnormalities. However, there is evidence to show that EMS was likely caused by a contaminant in certain 5-HTP supplements instead of the substance itself.<ref>https://www.ncbi.nlm.nih.gov/pubmed/7699627 | An eosinophilia-myalgia syndrome related disorder associated with exposure to L-5-hydroxytryptophan.</ref>
+It has been suggested that 5-HTP may cause eosinophilia-myalgia syndrome (EMS), a serious condition which results in extreme muscle tenderness, myalgia, and blood abnormalities. However, there is evidence to show that EMS was likely caused by a contaminant in certain 5-HTP supplements instead of the drug itself.<ref>https://www.ncbi.nlm.nih.gov/pubmed/7699627 | An eosinophilia-myalgia syndrome related disorder associated with exposure to L-5-hydroxytryptophan.</ref>
 ===Dangerous interactions===
-Although many substances are safe on their own, they can become dangerous and even life-threatening when combined with other substances. The list below contains some common potentially dangerous combinations, but may not include all of them. Certain combinations may be safe in low doses of each but still increase the potential risk of death. Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.
+Although many drugs are safe on their own, they can become dangerous and even life-threatening when combined with other substances. The list below contains some common potentially dangerous combinations, but may not include all of them. Certain combinations may be safe in low doses of each but still increase the potential risk of death. Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.
 Combinations in the list below may increase the amount of neurotransmitters, such as serotonin, to dangerous or even fatal levels, resulting in life-threatening [[serotonin syndrome]].