5-Hydroxytryptophan: Difference between revisions

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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 ~~drugs~~ 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 substances 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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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 ~~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.

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.

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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 -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 drugs 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 substances 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 53: / Line 53: @@
 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 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.
+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.
 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]].