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Revision as of 18:30, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,052 edits Saving copy of the {{chembox}} taken from revid 474930461 of page 5-Hydroxytryptophan for the Chem/Drugbox validation project (updated: '').		Latest revision as of 19:09, 2 January 2025 edit Arthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fixes
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			{{Use dmy dates|date=September 2015}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
			{{Distinguish|5-hydroxytryptamine}}
	{{chembox
			{{About|5-hydroxytryptophan as a biological compound|its role as a medication and supplement|Oxitriptan}}
	| verifiedrevid = 443355009
			{{Chembox
	|ImageFile=5-Hydroxy-L-Tryptophan_(5-HTP).svg
			| Verifiedfields = changed
	|ImageSize=
			| Watchedfields = changed
	|ImageFile2=5-htp-3d.png
			| verifiedrevid = 477224677
	|IUPACName=2-amino-3- (5-hydroxy-1H-indol-3-yl) propanoic acid
			| ImageFile = 5-Hydroxy-L-Tryptophan (5-HTP).svg
	|OtherNames=
			| ImageClass = skin-invert
	|Section1= {{Chembox Identifiers
			| ImageAlt = Skeletal formula
	| UNII_Ref = {{fdacite|correct|FDA}}
			| ImageFile1 = 5-Hydroxy-L-tryptophan-3D-balls.png
			| ImageAlt1 = Ball-and-stick model
			| IUPACName = 2-amino-3-(5-hydroxy-1''H''-indol-3-yl)propanoic acid
			| OtherNames = 5-HTP; Oxitriptan
			|Section1={{Chembox Identifiers
			| IUPHAR_ligand = 4671
			| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = C1LJO185Q9		| UNII = C1LJO185Q9
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
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	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = LDCYZAJDBXYCGN-VIFPVBQESA-N		| StdInChIKey = LDCYZAJDBXYCGN-VIFPVBQESA-N
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|changed|CAS}}
	| CASNo=56-69-9		| CASNo = 56-69-9
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 388413		| ChemSpiderID = 388413
	| PubChem=144		| PubChem = 144
	| ChEBI_Ref = {{ebicite|correct|EBI}}		| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 17780		| ChEBI = 17780
	| SMILES = O=C(O)(N)Cc2c1cc(O)ccc1nc2		| SMILES = O=C(O)(N)Cc2c1cc(O)ccc1c2
	| MeSHName=5-Hydroxytryptophan		| MeSHName = 5-Hydroxytryptophan
	}}		}}
	|Section2= {{Chembox Properties		|Section2={{Chembox Properties
			| C=11 | H=12 | N=2 | O=3
	| Formula=C<sub>11</sub>H<sub>12</sub>N<sub>2</sub>O<sub>3</sub>
			| Appearance=
	| MolarMass=220.23 g/mol
			| Density=1.484 g/mL
	| Appearance=
			| MeltingPtC = 298 to 300
	| Density=
			| BoilingPtC=520.6
	| MeltingPt=
	| BoilingPt=		| Solubility=
	| Solubility=
	}}		}}
	|Section3= {{Chembox Hazards		|Section7={{Chembox Hazards
	| MainHazards=		| MainHazards=
	| FlashPt=		| FlashPtC=
			| AutoignitionPtC =
	| Autoignition=
	}}		}}
	}}		}}
			'''5-Hydroxytryptophan''' ('''5-HTP'''), used medically as '''oxitriptan''', is a ] ] and ] ] as well as a ] in the ] of the ] ].
			5-HTP can be manufactured and used as a ] and supplement with the {{Abbrlink|INN|International Nonproprietary Name}} '']''. Brand names include Cincofarm, Levothym, Levotonine, Oxyfan, Telesol, Tript-OH, and Triptum. As a drug, it is used in the treatment of ] and for certain other indications.
			==Production==
			5-HTP is produced from the amino acid ] through the action of the enzyme ]. Tryptophan hydroxylase is one of the ]. Production of 5-HTP is the rate-limiting step in 5-HT (serotonin) synthesis. 5-HTP is normally rapidly converted to 5-HT by amino acid decarboxylase.<ref>{{cite journal | vauthors = Turner EH, Loftis JM, Blackwell AD | title = Serotonin a la carte: supplementation with the serotonin precursor 5-hydroxytryptophan | journal = Pharmacology & Therapeutics | volume = 109 | issue = 3 | pages = 325–38 | date = March 2006 | pmid = 16023217 | doi = 10.1016/j.pharmthera.2005.06.004 | s2cid = 2563606 | url = https://escholarship.org/uc/item/58h866d5 }}</ref>
			==Metabolism==
			5-HTP is ] to ] (5-hydroxytryptamine or 5-HT) by the ] ] with the help of ].<ref>{{cite journal | vauthors = Rahman MK, Nagatsu T, Sakurai T, Hori S, Abe M, Matsuda M | title = Effect of pyridoxal phosphate deficiency on aromatic L-amino acid decarboxylase activity with L-DOPA and L-5-hydroxytryptophan as substrates in rats | journal = Japanese Journal of Pharmacology | volume = 32 | issue = 5 | pages = 803–11 | date = October 1982 | pmid = 6983619 | doi = 10.1254/jjp.32.803 | doi-access = free }}</ref> This reaction occurs both in nervous tissue and in the liver.<ref>{{cite journal | vauthors = Bouchard S, Bousquet C, Roberge AG | title = Characteristics of dihydroxyphenylalanine/5-hydroxytryptophan decarboxylase activity in brain and liver of cat | journal = Journal of Neurochemistry | volume = 37 | issue = 3 | pages = 781–7 | date = September 1981 | pmid = 6974228 | doi = 10.1111/j.1471-4159.1982.tb12555.x | s2cid = 43853143 }}</ref> 5-HTP crosses the ],<ref>{{cite journal | vauthors = Nakatani Y, Sato-Suzuki I, Tsujino N, Nakasato A, Seki Y, Fumoto M, Arita H | title = Augmented brain 5-HT crosses the blood-brain barrier through the 5-HT transporter in rat | journal = The European Journal of Neuroscience | volume = 27 | issue = 9 | pages = 2466–72 | date = May 2008 | pmid = 18445233 | doi = 10.1111/j.1460-9568.2008.06201.x | s2cid = 18940166 }}</ref> while 5-HT does not. 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 AG | title = Biochemical properties and kinetic parameters of dihydroxyphenylalanine--5-hydroxytryptophan decarboxylase in brain, liver, and adrenals of cat | journal = Canadian Journal of Biochemistry | volume = 57 | issue = 7 | pages = 1014–8 | date = July 1979 | pmid = 39668 | doi = 10.1139/o79-126 }}</ref><ref>{{cite journal | vauthors = Amamoto T, Sarai K | 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 | journal = Hiroshima Journal of Medical Sciences | volume = 25 | issue = 2–3 | pages = 135–40 | date = September 1976 | pmid = 1088369 }}</ref>
			]
			{{Enzymatic Reaction
			| forward_enzyme=]
			| reverse_enzyme=
			| substrate=5-HTP
			| product=]
			| reaction_direction_(forward/reversible/reverse)=forward
			| minor_forward_substrate(s)=]
			| minor_forward_product(s) =
			| minor_reverse_substrate(s)=
			| minor_reverse_product(s) =
			| substrate_image=5-Hydroxy-L-Tryptophan_(5-HTP).svg
			| substrate_image_size=160px
			| product_image=Serotonin (5-HT).svg
			| product_image_size=125px
			}}
			==Dietary sources==
			{{See also|Tryptophan#Dietary sources}}
			Though 5-HTP is found in food only in insignificant quantities, it is a chemical involved intermediately in the metabolism of tryptophan, an amino acid found in all unfractionated foods, with lower total amino acid content correlating with increased tryptophan absorption.<ref>{{cite web|url=http://www.umm.edu/altmed/articles/5-hydroxytryptophan-000283.htm|title=5-Hydroxytryptophan|access-date=21 January 2010|publisher=University of Maryland Medical Center| archive-url= https://web.archive.org/web/20100106132618/http://www.umm.edu/altmed/articles/5-hydroxytryptophan-000283.htm| archive-date= 6 January 2010 | url-status=dead}}</ref>
			==Use as a medication and supplement==
			{{Main|Oxitriptan}}
			5-HTP is used medically and as a supplement under the name '']'' in the treatment of ] and for certain other indications.
			It can be potentiated in ] with a ] ] (AAAD) ] such as ] or ]. These agents increase the strength and duration of oxitriptan. An investigational combination formulation is ].
			==Research==
			===Psychedelic effects===
			{{See also|Tryptophan#Psychedelic effects}}
			5-HTP robustly produces the ] (HTR) in rodents when administered at relatively high doses.<ref name="KozlenkovGonzález-Maeso2013" /><ref name="SchmidBohn2018" /><ref name="JasterdelaFuenteRevengaGonzález-Maeso2022">{{cite journal | vauthors = Jaster AM, de la Fuente Revenga M, González-Maeso J | title = Molecular targets of psychedelic-induced plasticity | journal = J Neurochem | volume = 162 | issue = 1 | pages = 80–88 | date = July 2022 | pmid = 34741320 | pmc = 9068831 | doi = 10.1111/jnc.15536 | url = }}</ref><ref name="SchmidBohn2010">{{cite journal | vauthors = Schmid CL, Bohn LM | title = Serotonin, but not N-methyltryptamines, activates the serotonin 2A receptor via a β-arrestin2/Src/Akt signaling complex in vivo | journal = J Neurosci | volume = 30 | issue = 40 | pages = 13513–24 | date = October 2010 | pmid = 20926677 | pmc = 3001293 | doi = 10.1523/JNEUROSCI.1665-10.2010 | url = }}</ref> Similarly, ] of serotonin, but not peripheral administration of serotonin, produces the HTR.<ref name="SchmidBohn2018" /><ref name="KozlenkovGonzález-Maeso2013" /><ref name="SchmidBohn2010" /> The HTR is induced by ]s like ] (LSD) and ] and is a behavioral proxy of psychedelic effects.<ref name="CanalMorgan2012">{{cite journal | vauthors = Canal CE, Morgan D | title = Head-twitch response in rodents induced by the hallucinogen 2,5-dimethoxy-4-iodoamphetamine: a comprehensive history, a re-evaluation of mechanisms, and its utility as a model | journal = Drug Test Anal | volume = 4 | issue = 7-8 | pages = 556–576 | date = 2012 | pmid = 22517680 | pmc = 3722587 | doi = 10.1002/dta.1333 | url = }}</ref><ref name="KozlenkovGonzález-Maeso2013" />
			The HTR of 5-HTP is blocked by serotonin ] ]s, which block the ]ic effects of serotonergic psychedelics in humans, is prevented by ] (AAAD) ]s, which block conversion of 5-HTP into serotonin, and is potentiated by ] (MAO-A) ]s, which prevent the ] of serotonin and other ] ]s.<ref name="SchmidBohn2018">{{cite book | last=Schmid | first=Cullen L. | last2=Bohn | first2=Laura M. | title=5-HT2A Receptors in the Central Nervous System | chapter=βArrestins: Ligand-Directed Regulators of 5-HT2A Receptor Trafficking and Signaling Events | publisher=Springer International Publishing | publication-place=Cham | date=2018 | isbn=978-3-319-70472-2 | doi=10.1007/978-3-319-70474-6_2 | page=31–55}}</ref><ref name="KozlenkovGonzález-Maeso2013" /><ref name="JasterdelaFuenteRevengaGonzález-Maeso2022" /><ref name="SchmidBohn2010" /> In addition, the HTR of 5-HTP is abolished by ] (INMT) ]s, which block conversion of serotonin and other endogenous tryptamines into ''N''-] tryptamines, such as ] (NMS; norbufotenin), ] (5-hydroxy-''N'',''N''-dimethyltryptamine; 5-HO-DMT), and ] (DMT).<ref name="KozlenkovGonzález-Maeso2013">{{cite book | last=Kozlenkov | first=Alexey | last2=González-Maeso | first2=Javier | title=The Neuroscience of Hallucinations | chapter=Animal Models and Hallucinogenic Drugs | publisher=Springer New York | publication-place=New York, NY | date=2013 | isbn=978-1-4614-4120-5 | doi=10.1007/978-1-4614-4121-2_14 | page=253–277}}</ref><ref name="HalberstadtGeyer2018">{{cite journal | vauthors = Halberstadt AL, Geyer MA | title = Effect of Hallucinogens on Unconditioned Behavior | journal = Curr Top Behav Neurosci | volume = 36 | issue = | pages = 159–199 | date = 2018 | pmid = 28224459 | pmc = 5787039 | doi = 10.1007/7854_2016_466 | url = }}</ref><ref name="SchmidBohn2010" /> These ''N''-methylated tryptamines are well-known for their psychedelic effects, whereas serotonin itself, without ], does not seem to produce psychedelic effects.<ref name="KozlenkovGonzález-Maeso2013" /><ref name="SchmidBohn2010" /> 5-HTP has not been found to produce psychedelic effects in humans, which has been attributed to the high doses required to produce such effects.<ref name="KozlenkovGonzález-Maeso2013" /><ref name="JasterdelaFuenteRevengaGonzález-Maeso2022" /> The 5-HTP doses that produce the HTR in rodents are orders of magnitude higher than the doses of 5-HTP that have been used safely and therapeutically in humans.<ref name="JasterdelaFuenteRevengaGonzález-Maeso2022" /> It remains unknown whether 5-HTP can produce psychedelic effects in humans.<ref name="HanksGonzález-Maeso2013">{{cite journal | vauthors = Hanks JB, González-Maeso J | title = Animal models of serotonergic psychedelics | journal = ACS Chem Neurosci | volume = 4 | issue = 1 | pages = 33–42 | date = January 2013 | pmid = 23336043 | pmc = 3547517 | doi = 10.1021/cn300138m | url = | quote = Following these initial studies, it was shown that a large dose of the serotonin precursor 5-hydroxytryptophan (5-HTP) induces head-twitch behavior in mice.32 However, to our knowledge, equivalent doses of 5-HTP have not been tested in healthy volunteers, and therefore, it remains unknown whether 5-HTP is psychedelic in humans. Subsequently, numerous psychedelic compounds were shown to induce head-twitch behavior.27,33−36}}</ref>
			The lack of the HTR and psychedelic effects with serotonin itself has been attributed to the fact that these effects appear to be dependent on activation of a population of ] 5-HT<sub>2A</sub> receptors expressed in ] ]s in the ] (mPFC) that lack the ] (SERT) and are inaccessible to serotonin.<ref name="Sapienza2023">{{cite journal | last=Sapienza | first=Jacopo | title=The Key Role of Intracellular 5-HT2A Receptors: A Turning Point in Psychedelic Research? | journal=Psychoactives | volume=2 | issue=4 | date=13 October 2023 | issn=2813-1851 | doi=10.3390/psychoactives2040018 | doi-access=free | pages=287–293}}</ref><ref name="VargasDunlapDong2023">{{cite journal | vauthors = Vargas MV, Dunlap LE, Dong C, Carter SJ, Tombari RJ, Jami SA, Cameron LP, Patel SD, Hennessey JJ, Saeger HN, McCorvy JD, Gray JA, Tian L, Olson DE | title = Psychedelics promote neuroplasticity through the activation of intracellular 5-HT2A receptors | journal = Science | volume = 379 | issue = 6633 | pages = 700–706 | date = February 2023 | pmid = 36795823 | pmc = 10108900 | doi = 10.1126/science.adf0435 | url = }}</ref> Serotonin itself is too ] to enter serotonergic neurons without the SERT, whereas serotonergic psychedelics and serotonin's ''N''-methylated ]s and ]s are ] and readily enter these neurons.<ref name="Sapienza2023" /><ref name="VargasDunlapDong2023" /> These findings may also explain why ]s (SSRIs) and related serotonergic agents do not produce psychedelic effects.<ref name="Sapienza2023" />
			==See also==
			* ]
			==References==
			{{Reflist}}
			{{Neurotransmitter metabolism intermediates}}
			{{Serotonin receptor modulators}}
			{{Tryptamines}}
			{{DEFAULTSORT:Hydroxytryptophan, 5-}}
			]
			]
			]
			]
			]