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Latest revision as of 02:53, 14 June 2024 edit undoAnomieBOT (talk | contribs)Bots6,575,307 editsm Dating maintenance tags: {{Mcn}} |
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{{Short description|Chemical compound}} |
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{{mcn|date=June 2024}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 403491898 |
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| verifiedrevid = 449870718 |
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| IUPAC_name = 6-(3,4-dihydro-1<nowiki>'</nowiki>''H'',2''H''-spiro-1'-yl)-4,4-diphenylhexan-3-one |
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| IUPAC_name = 6-{3,4-dihydro-2''H''-spiro-1'-yl}-4,4-diphenylhexan-3-one |
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| image = R-4066.png |
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| image = R-4066.svg |
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<!--Clinical data--> |
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<!--Clinical data--> |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| index2_label = oxalate |
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| CAS_number = 101564-56-1 |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| CAS_number = 66194-36-3 |
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| CAS_number2_Ref = {{cascite|correct|CAS}} |
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| CAS_number2 = 101564-56-1 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = L4YPY81SBM |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| UNII2 = DL9M9L165Z |
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| ATC_suffix = |
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| ATC_suffix = |
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| PubChem = 380029 |
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| PubChem = 380029 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 2010535 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 336763 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=32 | H=37 | N=1 | O=1 |
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| C=32 | H=37 | N=1 | O=1 |
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| molecular_weight = 451.641 |
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| molecular_weight = |
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| smiles = CCC(=O)C(CCN1CCC2(CCCC3=CC=CC=C32)CC1)(C4=CC=CC=C4)C5=CC=CC=C5 |
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| smiles = CCC(=O)C(CCN1CCC2(CCCC3=CC=CC=C32)CC1)(C4=CC=CC=C4)C5=CC=CC=C5 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C32H37NO/c1-2-30(34)32(27-14-5-3-6-15-27,28-16-7-4-8-17-28)22-25-33-23-20-31(21-24-33)19-11-13-26-12-9-10-18-29(26)31/h3-10,12,14-18H,2,11,13,19-25H2,1H3 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = ZVFXEHSJPKPKDW-UHFFFAOYSA-N |
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| synonyms = <small>''N''-(3,3-diphenyl-4-oxohex-1-yl)-7,8-benzo-3-azaspiroundecane</small> |
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| synonyms = <small>''N''-(3,3-diphenyl-4-oxohex-1-yl)-7,8-benzo-3-azaspiroundecane</small> |
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}} |
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'''R-4066''' ('''Spirodone''') is a drug which is an ] of the ] ] ], wherein the ] has been replaced by a tricyclic ] ]. Developed by Janssen Pharmaceutica,<ref>{{US patent|3125580}}</ref> it is around 212× more potent than methadone as an analgesic in animal tests, with an effective oral dosage of 0.07 mg/kg, but is shorter acting, with a duration of action of around 3 hours. If the ketone function is reduced and acetylated, the racemate has a potency of 106× that of methadone and has an analgesic duration of 20.5 hours compared to 8 hours for methadone.<ref>{{cite journal | vauthors = Frincke JM, Henderson GL | title = Synthesis and analgesic activity of some long-acting piperidinospiro derivatives of methadone | journal = Journal of Medicinal Chemistry | volume = 21 | issue = 5 | pages = 474–6 | date = May 1978 | pmid = 660594 | doi = 10.1021/jm00203a014 }}</ref> |
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'''R-4066''' is a drug which is an ] of the ] ] ], where the metabolically labile dimethylamino group has been replaced by a piperidinospiro group. Developed by Janssen Pharmacutica<ref>{{ cite patent |
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| country = US |
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| number = 3125580 |
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| status = patent |
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| title = N-(3,3-DIPHENYL-3-ALKANOYL)PROPYLSPIRO(TETRALIN-1,4'-PIPERIDINES) AND RELATED COMPOUNDS |
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| pubdate = 1961-10-10 |
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| gdate = 1964-03-17 |
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| inventor = Paul A. J. Janssen. |
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}}</ref>, it is around 212x more potent than methadone as an analgesic in animal tests, with an effective oral dosage of 0.07mg/kg, but is slightly shorter acting, with a duration of action of around 3 hours.<ref>Frincke JM, Henderson GL, Janssen PAJ, Van der Eycken CAM. Synthesis and analgesic activity of some long-acting piperidinospiro derivatives of methadone. ''Journal of Medicinal Chemistry''. 1978 May;21(5):474-6. PMID 660594</ref> |
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R-4066 has never been used in humans, but would be expected to produce effects similar to those of other potent opioid agonists, including strong ], ], ], ], ] and ] which could be harmful or fatal. |
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R-4066 has not been researched in humans, but would be expected to produce effects similar to those of ], including strong ], ], ], ], ] and ] which could be harmful or fatal.{{cn|date=June 2024}} |
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== References == |
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{{Reflist}} |
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{{Opioidergics}} |
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==References== |
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<references/> |
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{{Opioids}} |
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