Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 5-Fluoro-DMT: Difference between pages
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Saving copy of the {{drugbox}} taken from revid 455740018 of page 5-Fluoro-DMT for the Chem/Drugbox validation project (updated: 'CAS_number'). |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid [{{fullurl:5-Fluoro-DMT|oldid=455740018}} 455740018] of page [[5-Fluoro-DMT]] with values updated to verified values.}} |
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{{Use dmy dates|date=January 2024}} |
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{{Drugbox |
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{{Infobox drug |
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| Watchedfields = changed |
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| IUPAC_name = 2-(5-fluoro-1H-indol-3-yl)-''N'',''N''-dimethylethanamine |
| IUPAC_name = 2-(5-fluoro-1H-indol-3-yl)-''N'',''N''-dimethylethanamine |
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| image = 5-Fluoro-DMT_structure.png |
| image = 5-Fluoro-DMT_structure.png |
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<!--Clinical data--> |
<!--Clinical data--> |
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| tradename = |
| tradename = |
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<!--Identifiers--> |
<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| CAS_number = |
| CAS_number = 22120-36-1 |
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| PubChem = 2762738 |
| PubChem = 2762738 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 2043436 |
| ChemSpiderID = 2043436 |
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| ChEMBL = 1630729 |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=12 | H=15 | F=1 | N=2 |
| C=12 | H=15 | F=1 | N=2 |
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| smiles = CN(C)CCC1=CNC2=C1C=C(C=C2)F |
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| molecular_weight = 206.259 g/mol |
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| smiles = Fc2ccc(c1c2)ncc1CCN(C)C |
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| InChI = 1/C12H15FN2/c1-15(2)6-5-9-8-14-12-4-3-10(13)7-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3 |
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| InChIKey = BXYDWQABVPBLBU-UHFFFAOYAA |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C12H15FN2/c1-15(2)6-5-9-8-14-12-4-3-10(13)7-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3 |
| StdInChI = 1S/C12H15FN2/c1-15(2)6-5-9-8-14-12-4-3-10(13)7-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3 |
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| StdInChIKey = BXYDWQABVPBLBU-UHFFFAOYSA-N |
| StdInChIKey = BXYDWQABVPBLBU-UHFFFAOYSA-N |
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}} |
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'''5-Fluoro-''N'',''N''-dimethyltryptamine''' ('''5-fluoro-DMT''', '''5F-DMT''') is a [[tryptamine]] derivative related to compounds such as [[5-bromo-DMT]] and [[5-MeO-DMT]].<ref>{{cite journal | vauthors = Chen CY, Senanayake CH, Bill TJ, Larsen RD, Verhoeven TR, Reider PJ | title = Improved Fischer indole reaction for the preparation of N, N-dimethyltryptamines: Synthesis of L-695,894, a potent 5-HT1D receptor agonist. | journal = The Journal of Organic Chemistry | date = July 1994 | volume = 59 | issue = 13 | pages = 3738–3741 | doi = 10.1021/jo00092a046 }}</ref> Fluorination of psychedelic tryptamines either reduces or has little effect on 5-HT<sub>2A/C</sub> receptor affinity or intrinsic activity, although 6-fluoro-DET is inactive as a psychedelic despite acting as a 5-HT<sub>2A</sub> agonist (cf. [[lisuride]]), while [[4-fluoro-5-methoxy-DMT]] is a much stronger agonist at 5-HT<sub>1A</sub> than 5-HT<sub>2A</sub>.<ref>{{cite journal | vauthors = Blair JB, Kurrasch-Orbaugh D, Marona-Lewicka D, Cumbay MG, Watts VJ, Barker EL, Nichols DE | title = Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines | journal = Journal of Medicinal Chemistry | volume = 43 | issue = 24 | pages = 4701–10 | date = November 2000 | pmid = 11101361 | doi = 10.1021/jm000339w }}</ref><ref>{{cite journal | vauthors = Rabin RA, Regina M, Doat M, Winter JC | title = 5-HT2A receptor-stimulated phosphoinositide hydrolysis in the stimulus effects of hallucinogens | journal = Pharmacology, Biochemistry, and Behavior | volume = 72 | issue = 1–2 | pages = 29–37 | date = May 2002 | pmid = 11900766 | doi = 10.1016/S0091-3057(01)00720-1 | s2cid = 6480715 }}</ref> |
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== See also == |
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* [[5-F-AMT|5-Fluoro-AMT]] |
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* [[5-Fluoro-DET]] |
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* [[5-Fluoro-MET]] |
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* [[6-fluoro-AMT]] |
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* [[6-Fluoro-DMT]] |
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* [[4-fluoro-5-methoxy-DMT]] |
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* [[6-Fluoro-DET]]([http://www.erowid.org/library/books_online/tihkal/tihkal03.shtml 6-Fluoro-DET]) |
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* [[O-4310]] |
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*It's worth noting that [[GR-159897]] is based on the same structure. |
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== References == |
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{{reflist}} |
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{{Hallucinogens}} |
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{{Tryptamines}} |
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{{DEFAULTSORT:5-Fluoro-Dmt}} |
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[[Category:Psychedelic tryptamines]] |
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[[Category:Tryptamines]] |
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[[Category:Fluoroarenes]] |
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[[Category:Dimethylamino compounds]] |
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{{Hallucinogen-stub}} |
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