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5-Hydroxytryptophan: Difference between revisions
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{{distinguish2|[[Serotonin]] ('''5'''-'''h'''ydroxy'''t'''ryptamine, '''5-HT''')}} | {{distinguish2|[[Serotonin]] ('''5'''-'''h'''ydroxy'''t'''ryptamine, '''5-HT''')}} | ||
{{ | {{SummarySheet}} | ||
{ | {{SubstanceBox/5-HTP}} | ||
5- | '''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 should not be taken until 12 hours after one's last dose of MDMA because combining the two | 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>{{cite book | vauthors=((Society, S. P.)) | date= 2000 | title=Index Nominum 2000: International Drug Directory | publisher=Taylor & Francis | isbn=9783887630751}}</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 substance's [[duration|come down]] period, including [[anxiety]], [[depression]], and [[cognitive fatigue]].<ref>h{{cite journal | vauthors=((Wang, X.)), ((Baumann, M. H.)), ((Dersch, C. M.)), ((Rothman, R. B.)) | journal=Neuroscience | title=Restoration of 3,4-methylenedioxymethamphetamine-induced 5-HT depletion by the administration of l-5-hydroxytryptophan | volume=148 | issue=1 | pages=212–220 | date=10 August 2007 | url=https://www.sciencedirect.com/science/article/pii/S0306452207006732 | issn=0306-4522 | doi=10.1016/j.neuroscience.2007.05.024}}</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>{{cite journal | vauthors=((Stone, D. M.)), ((Johnson, M.)), ((Hanson, G. R.)), ((Gibb, J. W.)) | journal=European Journal of Pharmacology: Molecular Pharmacology | title=Acute inactivation of tryptophan hydroxylase by amphetamine analogs involves the oxidation of sulfhydryl sites | volume=172 | issue=1 | pages=93–97 | date= March 1989 | url=https://linkinghub.elsevier.com/retrieve/pii/0922410689900485 | issn=09224106 | doi=10.1016/0922-4106(89)90048-5}}</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. | ||
==Pharmacology== | ==Pharmacology== | ||
The psychoactive action of 5-HTP is derived from its increase in production of [[serotonin]] in central nervous system tissue. 5-HTP is decarboxylated to serotonin (5-hydroxytryptamine or 5-HT) by the enzyme 'aromatic-L-amino-acid decarboxylase', with the help of vitamin B<sub>6</sub>.<ref> | The psychoactive action of 5-HTP is derived from its increase in production of [[serotonin]] in central nervous system tissue. 5-HTP is decarboxylated to serotonin (5-hydroxytryptamine or 5-HT) by the enzyme 'aromatic-L-amino-acid decarboxylase', with the help of vitamin B<sub>6</sub>.<ref>{{cite journal | vauthors=((Rahman, M. K.)), ((Nagatsu, T.)), ((Sakurai, T.)), ((Hori, S.)), ((Abe, M.)), ((Matsuda, M.)) | journal=Japanese Journal of Pharmacology | title=Effect of pyridoxal phosphate deficiency on aromatic L-amino acid decarboxylase activity with L-DOPA and L-5-hydroxytryptophan as substrates in rats | volume=32 | issue=5 | pages=803–811 | date= October 1982 | issn=0021-5198 | doi=10.1254/jjp.32.803}}</ref> This reaction occurs both in nervous tissue and in the liver.<ref>{{cite journal | vauthors=((Bouchard, S.)), ((Bousquet, C.)), ((Roberge, A. G.)) | journal=Journal of Neurochemistry | title=Characteristics of dihydroxyphenylalanine/5-hydroxytryptophan decarboxylase activity in brain and liver of cat | volume=37 | issue=3 | pages=781–787 | date= September 1981 | issn=0022-3042 | doi=10.1111/j.1471-4159.1982.tb12555.x}}</ref> 5-HTP crosses the blood–brain barrier, while 5-HT (serotonin) does not.<ref>{{cite journal | vauthors=((Nakatani, Y.)), ((Sato-Suzuki, I.)), ((Tsujino, N.)), ((Nakasato, A.)), ((Seki, Y.)), ((Fumoto, M.)), ((Arita, H.)) | journal=The European Journal of Neuroscience | title=Augmented brain 5-HT crosses the blood-brain barrier through the 5-HT transporter in rat | volume=27 | issue=9 | pages=2466–2472 | date= May 2008 | issn=1460-9568 | doi=10.1111/j.1460-9568.2008.06201.x}}</ref> | ||
Excess 5-HTP, especially when administered with vitamin B<sub>6</sub>, is thought to be metabolized and excreted.<ref>Biochemical properties and kinetic parameters of | Excess 5-HTP, especially when administered with vitamin B<sub>6</sub>, is thought to be metabolized and excreted.<ref>{{cite journal | vauthors=((Bouchard, S.)), ((Roberge, A. G.)) | journal=Canadian Journal of Biochemistry | title=Biochemical properties and kinetic parameters of dihydroxyphenyialanine – 5-hydroxytryptophan decarboxylase in brain, liver, and adrenals of cat | volume=57 | issue=7 | pages=1014–1018 | date=1 July 1979 | url=http://www.nrcresearchpress.com/doi/10.1139/o79-126 | issn=0008-4018 | doi=10.1139/o79-126}}</ref><ref>{{cite journal | vauthors=((Amamoto, T.)), ((Sarai, K.)) | journal=Hiroshima Journal of Medical Sciences | title=On the tryptophan-serotonin metabolism in manic-depressive disorders. Changes in plasma 5-HT and 5-HIAA levels and urinary 5-HIAA excretion following oral loading of L-5HTP in patients with depression | volume=25 | issue=2–3 | pages=135–140 | date= September 1976 | issn=0018-2052}}</ref> | ||
==Subjective effects== | ==Subjective effects== | ||
{{EffectStub}} | {{EffectStub}} | ||
{{effects/base | |||
|{{effects/physical| | |||
For some individuals, 5-HTP can cause the following side effects (although rare, and typically at higher dosages). | For some individuals, 5-HTP can cause the following side effects (although rare, and typically at higher dosages). | ||
*'''[[Effect::Sedation]]''' | |||
*'''[[Effect::Stimulation]]''' | |||
*'''[[Effect::Bodily control enhancement]]''' | |||
*'''[[Effect::Abnormal heartbeat]]''' | *'''[[Effect::Abnormal heartbeat]]''' | ||
*'''[[Effect::Appetite suppression]]''' | *'''[[Effect::Appetite suppression]]''' | ||
*'''[[Effect::Diarrhea]]''' | *'''[[Effect::Diarrhea]]''' | ||
*'''[[Effect::Dizziness]] | *'''[[Effect::Dizziness]] | ||
| Line 34: | Line 37: | ||
*'''[[Effect::Increased heart rate]]''' | *'''[[Effect::Increased heart rate]]''' | ||
*'''[[Effect::Nausea]] and vomiting''' | *'''[[Effect::Nausea]] and vomiting''' | ||
*'''[[Effect::Stomach bloating]]''' | *'''[[Effect::Stomach bloating]]''' | ||
*'''[[Effect::Stomach cramps]]''' | *'''[[Effect::Stomach cramps]]''' | ||
*'''[[Effect::Teeth grinding]]''' | *'''[[Effect::Teeth grinding]]''' | ||
}} | |||
{{effects/visual| | |||
Visual distortions have been reported at heavy doses and consistent usage of 5-HTP. They are usually mild. | |||
*'''[[Effect::Tracers]]''' | |||
*'''[[Effect::Color enhancement]]''' | |||
*'''[[Effect::Drifting]]''' | |||
*'''[[Effect::Depth perception distortions]]''' | |||
}} | |||
|{{effects/cognitive| | |||
*'''[[Effect::Cognitive euphoria]]''' - Although mild, this effect is present at heavier dosages, but may also come with it a number of peripheral side effects due to peripheral serotonin activity (mostly on the gut). | *'''[[Effect::Cognitive euphoria]]''' - Although mild, this effect is present at heavier dosages, but may also come with it a number of peripheral side effects due to peripheral serotonin activity (mostly on the gut). | ||
*'''[[Effect::Anxiety suppression]]''' | *'''[[Effect::Anxiety suppression]]''' | ||
| Line 49: | Line 59: | ||
*'''[[Effect::Thought acceleration]]''' or '''[[Effect::Thought deceleration]]''' | *'''[[Effect::Thought acceleration]]''' or '''[[Effect::Thought deceleration]]''' | ||
}} | |||
{{effects/aftereffects| | |||
*'''[[Effect::Dream potentiation]]''' | *'''[[Effect::Dream potentiation]]''' | ||
*'''[[Effect::Physical fatigue]] | *'''[[Effect::Physical fatigue]] | ||
*'''[[Effect::Sleep paralysis]] | |||
}} | |||
{{effects/auditory| | |||
*'''[[Effect::Auditory hallucinations|Hallucinations]]''' - Auditory hallucinations have been reported on 5-HTP, however they are rare and only occur at high dosages. | |||
}} | |||
}} | |||
===Experience reports=== | |||
Anecdotal reports which describe the effects of this compound within our [[experience index]] include: | |||
{{#ask: [[Category:5-HTP]][[Category:Experience]]|format=ul|Columns=1}} | |||
Additional experience reports can be found here: | |||
*[https://www.erowid.org/experiences/subs/exp_Tryptophan_5HTP.shtml Erowid Experience Vaults: 5-HTP] | |||
==Toxicity and harm potential== | ==Toxicity and harm potential== | ||
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> receptors present on it.<ref> | 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> receptors present on it.<ref>{{cite journal | vauthors=((Gustafsson, B. I.)), ((Tømmerås, K.)), ((Nordrum, I.)), ((Loennechen, J. P.)), ((Brunsvik, A.)), ((Solligård, E.)), ((Fossmark, R.)), ((Bakke, I.)), ((Syversen, U.)), ((Waldum, H.)) | journal=Circulation | title=Long-term serotonin administration induces heart valve disease in rats | volume=111 | issue=12 | pages=1517–1522 | date=29 March 2005 | issn=1524-4539 | doi=10.1161/01.CIR.0000159356.42064.48}}</ref><ref>{{cite journal | vauthors=((Xu, J.)), ((Jian, B.)), ((Chu, R.)), ((Lu, Z.)), ((Li, Q.)), ((Dunlop, J.)), ((Rosenzweig-Lipson, S.)), ((McGonigle, P.)), ((Levy, R. J.)), ((Liang, B.)) | journal=The American Journal of Pathology | title=Serotonin mechanisms in heart valve disease II: the 5-HT2 receptor and its signaling pathway in aortic valve interstitial cells | volume=161 | issue=6 | pages=2209–2218 | date= December 2002 | issn=0002-9440 | doi=10.1016/S0002-9440(10)64497-5}}</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 | 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>{{cite journal | vauthors=((Michelson, D.)), ((Page, S. W.)), ((Casey, R.)), ((Trucksess, M. W.)), ((Love, L. A.)), ((Milstien, S.)), ((Wilson, C.)), ((Massaquoi, S. G.)), ((Crofford, L. J.)), ((Hallett, M.)) | journal=The Journal of Rheumatology | title=An eosinophilia-myalgia syndrome related disorder associated with exposure to L-5-hydroxytryptophan | volume=21 | issue=12 | pages=2261–2265 | date= December 1994 | issn=0315-162X}}</ref> | ||
===Dangerous interactions=== | ===Dangerous interactions=== | ||
Although many | 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]]. | 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]]. | ||
*'''[[DangerousInteraction:: | |||
*'''[[ | *'''[[DangerousInteraction::SSRIs]]''' - When combined with antidepressants of the SSRI class, high doses of 5-HTP can cause acute serotonin syndrome in rats.<ref name="one">{{cite journal | vauthors=((Ma, Z.)), ((Zhang, G.)), ((Jenney, C.)), ((Krishnamoorthy, S.)), ((Tao, R.)) | journal=European Journal of Pharmacology | title=Characterization of serotonin-toxicity syndrome (toxidrome) elicited by 5-hydroxy-l-tryptophan in clorgyline-pretreated rats | volume=588 | issue=2–3 | pages=198–206 | date=7 July 2008 | issn=0014-2999 | doi=10.1016/j.ejphar.2008.04.004}}</ref><ref name="two">{{cite journal | vauthors=((Izumi, T.)), ((Iwamoto, N.)), ((Kitaichi, Y.)), ((Kato, A.)), ((Inoue, T.)), ((Koyama, T.)) | journal=European Journal of Pharmacology | title=Effects of co-administration of a selective serotonin reuptake inhibitor and monoamine oxidase inhibitors on 5-HT-related behavior in rats | volume=532 | issue=3 | pages=258–264 | date=27 February 2006 | issn=0014-2999 | doi=10.1016/j.ejphar.2005.12.075}}</ref> | ||
*'''[[DangerousInteraction::Serotonin releasers]]''' such as '''[[MDMA]]''', '''[[4-FA]]''', '''[[MDAI]]''' and '''[[αMT]]''' - To prevent serotonin syndrome, 5-HTP should only be taken once the user has come down from the MDMA (or other serotonin releaser), roughly 12 hours after the last dose. | *'''[[DangerousInteraction::SNRIs]]''' | ||
*'''[[DangerousInteraction::Serotonin releasers]]''' such as '''[[MDMA]]''', '''[[mephedrone]]''', '''[[4-FA]]''', '''[[MDAI]]''' and '''[[αMT]]''' - To prevent serotonin syndrome, 5-HTP should only be taken once the user has come down from the MDMA (or other serotonin releaser), roughly 12 hours after the last dose. | |||
*'''[[DangerousInteraction::MAOIs]]''' such as '''[[syrian rue]]''', '''[[banisteriopsis caapi]]''', '''[[2C-T-2]]''', '''[[2C-T-7]]''', '''[[αMT]]''', and some '''[[antidepressants]]''' - When combined with antidepressants of the MAOI class, high doses of 5-HTP can cause acute serotonin syndrome in rats.<ref name="one" /><ref name="two" /> | *'''[[DangerousInteraction::MAOIs]]''' such as '''[[syrian rue]]''', '''[[banisteriopsis caapi]]''', '''[[2C-T-2]]''', '''[[2C-T-7]]''', '''[[αMT]]''', and some '''[[antidepressants]]''' - When combined with antidepressants of the MAOI class, high doses of 5-HTP can cause acute serotonin syndrome in rats.<ref name="one" /><ref name="two" /> | ||
*'''[[Tricyclic antidepressants]] (TCAs)''' | *'''[[DangerousInteraction::Tricyclic antidepressants]] (TCAs)''' | ||
*'''[[DangerousInteraction::Tramadol]]''' | *'''[[DangerousInteraction::Tramadol]]''' | ||
==Legal | ==Legal status== | ||
5-HTP is commonly sold over the counter as a dietary supplement in the United States, United Kingdom, and | 5-HTP is commonly sold over the counter as a dietary supplement in the United States, United Kingdom, Canada and most of Europe and is not subject to any illicit substance control laws. | ||
In some parts of Europe, where it prescribed as an | In some parts of Europe, where it prescribed as an anti-depressant, there may be some controls on its sale and distribution.{{citation needed}} | ||
==See also== | ==See also== | ||
*[[Serotonin syndrome]] | *[[Serotonin syndrome]] | ||
*[[Tryptamine]] | *[[Tryptamine]] | ||
*[[Neurotransmitter]] | *[[Neurotransmitter]] | ||
*[[MDMA]] | *[[MDMA]] | ||
*[[MDAI]] | *[[MDAI]] | ||
| Line 82: | Line 110: | ||
==External links== | ==External links== | ||
*[https://en.wikipedia.org/wiki/5-Hydroxytryptophan 5-Hydroxytryptophan (Wikipedia)] | *[https://en.wikipedia.org/wiki/5-Hydroxytryptophan 5-Hydroxytryptophan (Wikipedia)] | ||
*[https://isomerdesign.com/PiHKAL/explore.php?id=5149 5-Hydroxytryptophan (Isomer Design)] | |||
*[http://umm.edu/health/medical/altmed/supplement/5hydroxytryptophan-5htp 5-Hydroxytryptophan (UM Medical Center)] | *[http://umm.edu/health/medical/altmed/supplement/5hydroxytryptophan-5htp 5-Hydroxytryptophan (UM Medical Center)] | ||
*[https://go.drugbank.com/drugs/DB02959 5-HTP (DrugBank)] | |||
*[https://examine.com/supplements/5-htp/ 5-HTP (Examine.com)] | *[https://examine.com/supplements/5-htp/ 5-HTP (Examine.com)] | ||
*[https://www.drugs.com/npp/5-htp.html 5-HTP (Drugs.com)] | *[https://www.drugs.com/npp/5-htp.html 5-HTP (Drugs.com)] | ||
==References== | ==References== | ||
<references/> | <references /> | ||
[[Category:Psychoactive substance]] | |||
[[Category:Amino acid]] | |||
[[Category:Tryptamine]] | |||
[[Category:Antidepressant]] | [[Category:Antidepressant]] | ||
[[Category: | [[Category:Precursor]] | ||