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Revision as of 18:28, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 449580662 of page 5-Fluoro-AMT for the Chem/Drugbox validation project (updated: 'CAS_number').  Latest revision as of 13:31, 8 December 2024 edit Citation bot (talk | contribs)Bots5,424,288 edits Alter: url, issue. URLs might have been anonymized. Add: isbn, series, bibcode, doi-access. Formatted dashes. | Use this bot. Report bugs. | Suggested by Ira Leviton | Category:CS1 maint: unflagged free DOI | #UCB_Category 19/25 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| verifiedrevid = 413276928 | verifiedrevid = 477224287
| IUPAC_name = 1-(5-fluoro-1H-indol-3-yl)propan-2-amine | IUPAC_name = 1-(5-fluoro-1H-indol-3-yl)propan-2-amine
| image = 5-fluoro-alpha-methyltryptamine.svg | image = 5-fluoro-alpha-methyltryptamine.svg
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| legal_US = | legal_US =
| legal_status = | legal_status =
| routes_of_administration = | routes_of_administration =


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
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| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = <!-- blanked - oldvalue: 712-08-3 --> | CAS_number = 712-08-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = P46235ZAP7
| ATC_prefix = | ATC_prefix =
| ATC_suffix = | ATC_suffix =
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| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 96816 | ChEMBL = 96816
| synonyms = 5-Fluoro-α-methyltryptamine; 5-Fluoro-alpha-methyltryptamine; 5-Fluoro-αMT; 5-Fluoro-AMT; 5F-AMT; PAL-212; PAL-544


<!--Chemical data--> <!--Chemical data-->
| C=11 | H=13 | F=1 | N=2 | C=11 | H=13 | F=1 | N=2
⚫ | SMILES = Fc1cc2c(cc1)cc2CC(N)C
| molecular_weight = 192.233 g/mol
⚫ | smiles = Fc1cc2c(cc1)ncc2CC(N)C
| InChI = 1/C11H13FN2/c1-7(13)4-8-6-14-11-3-2-9(12)5-10(8)11/h2-3,5-7,14H,4,13H2,1H3
| InChIKey = CTGFDWBZMCPVED-UHFFFAOYAZ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C11H13FN2/c1-7(13)4-8-6-14-11-3-2-9(12)5-10(8)11/h2-3,5-7,14H,4,13H2,1H3 | StdInChI = 1S/C11H13FN2/c1-7(13)4-8-6-14-11-3-2-9(12)5-10(8)11/h2-3,5-7,14H,4,13H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CTGFDWBZMCPVED-UHFFFAOYSA-N | StdInChIKey = CTGFDWBZMCPVED-UHFFFAOYSA-N
| melting_point =
| melting_high =
}} }}

'''5-Fluoro-α-methyltryptamine''' ('''5-Fluoro-αMT''', '''5F-AMT'''), also known as '''PAL-212'''<ref name="BloughLandavazoDecker2014">{{cite journal | vauthors = Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB | title = Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes | journal = Psychopharmacology (Berl) | volume = 231 | issue = 21 | pages = 4135–4144 | date = October 2014 | pmid = 24800892 | pmc = 4194234 | doi = 10.1007/s00213-014-3557-7 | url = }}</ref><ref name="BloughLandavazoPartilla2014" /> or '''PAL-544''',<ref name="BanksBauerBlough2014">{{cite journal | vauthors = Banks ML, Bauer CT, Blough BE, Rothman RB, Partilla JS, Baumann MH, Negus SS | title = Abuse-related effects of dual dopamine/serotonin releasers with varying potency to release norepinephrine in male rats and rhesus monkeys | journal = Experimental and Clinical Psychopharmacology | volume = 22 | issue = 3 | pages = 274–284 | date = June 2014 | pmid = 24796848 | pmc = 4067459 | doi = 10.1037/a0036595 }}</ref><ref name="IsomerDesign">{{cite web | title=5-Fluoro-AMT | website=Isomer Design | date=11 November 2024 | url=https://isomerdesign.com/pihkal/explore/5104 | access-date=7 December 2024}}</ref> is a putative ], ], and ] ] ] related to ] (αMT).

It has been found to act as a fairly balanced ] (SNDRA),<ref name="BanksBauerBlough2014" /><ref name="BloughLandavazoDecker2014" /> as a ] ] ],<ref name="BloughLandavazoDecker2014" /><ref name="ChairungsrilerdFurukawaTadano1998">{{cite journal | vauthors = Chairungsrilerd N, Furukawa K, Tadano T, Kisara K, Ohizumi Y | title = Effect of gamma-mangostin through the inhibition of 5-hydroxy-tryptamine2A receptors in 5-fluoro-alpha-methyltryptamine-induced head-twitch responses of mice | journal = British Journal of Pharmacology | volume = 123 | issue = 5 | pages = 855–862 | date = March 1998 | pmid = 9535013 | pmc = 1565246 | doi = 10.1038/sj.bjp.0701695 }}</ref> and as a ] and specific ].<ref name="WagmannBrandtKavanagh2017">{{cite journal | vauthors = Wagmann L, Brandt SD, Kavanagh PV, Maurer HH, Meyer MR | title = In vitro monoamine oxidase inhibition potential of alpha-methyltryptamine analog new psychoactive substances for assessing possible toxic risks | journal = Toxicol Lett | volume = 272 | issue = | pages = 84–93 | date = April 2017 | pmid = 28302559 | doi = 10.1016/j.toxlet.2017.03.007 | url = https://researchonline.ljmu.ac.uk/id/eprint/5909/1/TOXLET-D-17-00086R1_accepted_uncorected.pdf}}</ref><ref>{{cite journal | vauthors = Kinemuchi H, Arai Y | title = Selective inhibition of monoamine oxidase A and B by two substrate-analogues, 5-fluoro-alpha-methyltryptamine and p-chloro-beta-methylphenethylamine | journal = Research Communications in Chemical Pathology and Pharmacology | volume = 54 | issue = 1 | pages = 125–8 | date = October 1986 | pmid = 3797802 | doi = 10.1016/0028-3908(91)90057-i | s2cid = 34761939 }}</ref><ref>{{cite journal | vauthors = Kim SK, Toyoshima Y, Arai Y, Kinemuchi H, Tadano T, Oyama K, Satoh N, Kisara K | display-authors = 6 | title = Inhibition of monoamine oxidase by two substrate-analogues, with different preferences for 5-hydroxytryptamine neurons | journal = Neuropharmacology | volume = 30 | issue = 4 | pages = 329–35 | date = April 1991 | pmid = 1852266 | doi = 10.1016/0028-3908(91)90057-i |s2cid = 34761939 }}</ref><ref>{{cite journal | vauthors = Corne SJ, Pickering RW | title = A possible correlation between drug-induced hallucinations in man and a behavioural response in mice | journal = Psychopharmacologia | volume = 11 | issue = 1 | pages = 65–78 | year = 1967 | pmid = 5302272 | doi = 10.1007/bf00401509 | s2cid = 3148623 }}</ref><ref>{{cite journal | vauthors = Yamamoto T, Ueki S | title = The role of central serotonergic mechanisms on head-twitch and backward locomotion induced by hallucinogenic drugs | journal = Pharmacology, Biochemistry, and Behavior | volume = 14 | issue = 1 | pages = 89–95 | date = January 1981 | pmid = 6258178 | doi = 10.1016/0091-3057(81)90108-8 | s2cid = 45561708 }}</ref> Its {{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}} values in terms of ] are 14 to 19{{nbsp}}nM for serotonin, 78 to 126{{nbsp}}nM for ], and 32 to 37{{nbsp}}nM for ].<ref name="BanksBauerBlough2014" /><ref name="BloughLandavazoDecker2014" /><ref name="BloughLandavazoPartilla2014" /> Its {{Abbr|EC<sub>50</sub>|half-maximal effective concentration}} at the serotonin 5-HT<sub>2A</sub> receptor is 8.47{{nbsp}}nM and its {{Abbrlink|E<sub>max</sub>|maximal efficacy}} at the receptor is 107%.<ref name="BloughLandavazoPartilla2014">{{cite journal | vauthors = Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, Rothman RB | title = Alpha-ethyltryptamines as dual dopamine-serotonin releasers | journal = Bioorg Med Chem Lett | volume = 24 | issue = 19 | pages = 4754–4758 | date = October 2014 | pmid = 25193229 | pmc = 4211607 | doi = 10.1016/j.bmcl.2014.07.062 | url = }}</ref>

The {{Abbrlink|IC<sub>50</sub>|half-maximal inhibitory concentration}} of 5-fluoro-AMT for ] is 180 to 450{{nbsp}}nM.<ref name="Reyes-ParadaIturriaga-VasquezCassels2019">{{cite journal | vauthors = Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK | title = Amphetamine Derivatives as Monoamine Oxidase Inhibitors | journal = Front Pharmacol | volume = 10 | issue = | pages = 1590 | date = 2019 | pmid = 32038257 | pmc = 6989591 | doi = 10.3389/fphar.2019.01590 | doi-access = free | url = }}</ref><ref name="NakagawasaiAraiSatoh2004">{{cite journal | vauthors = Nakagawasai O, Arai Y, Satoh SE, Satoh N, Neda M, Hozumi M, Oka R, Hiraga H, Tadano T | title = Monoamine oxidase and head-twitch response in mice. Mechanisms of alpha-methylated substrate derivatives | journal = Neurotoxicology | volume = 25 | issue = 1–2 | pages = 223–232 | date = January 2004 | pmid = 14697897 | doi = 10.1016/S0161-813X(03)00101-3 | bibcode = 2004NeuTx..25..223N | url = }}</ref><ref name="WagmannBrandtKavanagh2017" /> This is similar to the potency of ] (PMA) and ] (4-MTA).<ref name="Reyes-ParadaIturriaga-VasquezCassels2019" />

The ] serotonin 5-HT<sub>2A</sub> receptor agonism of 5-fluoro-αMT suggests that it could be an active psychedelic in humans, although it is not known to have been tested in humans and could be dangerous due to its strong inhibition of ].<ref name="WagmannBrandtKavanagh2017" /> Accordingly, 5-fluoro-αMT induces the ], a behavioral proxy of psychedelic-like effects, in rodents.<ref name="HalberstadtGeyer2018">{{cite journal | vauthors = Halberstadt AL, Geyer MA | title = Effect of Hallucinogens on Unconditioned Behavior | journal = Curr Top Behav Neurosci | series = Current Topics in Behavioral Neurosciences | volume = 36 | issue = | pages = 159–199 | date = 2018 | pmid = 28224459 | pmc = 5787039 | doi = 10.1007/7854_2016_466 | isbn = 978-3-662-55878-2 | url = }}</ref><ref name="NakagawasaiAraiSatoh2004">{{cite journal | vauthors = Nakagawasai O, Arai Y, Satoh SE, Satoh N, Neda M, Hozumi M, Oka R, Hiraga H, Tadano T | title = Monoamine oxidase and head-twitch response in mice. Mechanisms of alpha-methylated substrate derivatives | journal = Neurotoxicology | volume = 25 | issue = 1–2 | pages = 223–232 | date = January 2004 | pmid = 14697897 | doi = 10.1016/S0161-813X(03)00101-3 | bibcode = 2004NeuTx..25..223N | url = }}</ref><ref name="TadanoNedaHozumi1995">{{cite journal | vauthors = Tadano T, Neda M, Hozumi M, Yonezawa A, Arai Y, Fujita T, Kinemuchi H, Kisara K | title = alpha-Methylated tryptamine derivatives induce a 5-HT receptor-mediated head-twitch response in mice | journal = Neuropharmacology | volume = 34 | issue = 2 | pages = 229–234 | date = February 1995 | pmid = 7617148 | doi = 10.1016/0028-3908(94)00119-d | url = }}</ref>

== See also ==
* ]
* ]
* ]
* ]
* ]
* ]
* ]
* ] (PAL-571)

== References ==
{{Reflist|30em}}

== Further reading ==
{{refbegin}}
* {{cite journal | vauthors = Nakagawasai O, Arai Y, Satoh SE, Satoh N, Neda M, Hozumi M, Oka R, Hiraga H, Tadano T | display-authors = 6 | title = Monoamine oxidase and head-twitch response in mice. Mechanisms of alpha-methylated substrate derivatives | journal = Neurotoxicology | volume = 25 | issue = 1–2 | pages = 223–32 | date = January 2004 | pmid = 14697897 | doi = 10.1016/S0161-813X(03)00101-3 | bibcode = 2004NeuTx..25..223N }}
{{refend}}

{{Entactogens}}
{{Hallucinogens}}
{{Stimulants}}
{{Serotonin receptor modulators}}
{{Monoamine releasing agents}}
{{Monoamine metabolism modulators}}
{{Tryptamines}}

{{DEFAULTSORT:F-AMT, 5-}}

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