{{Short description|Chemical compound}} {{more citations needed|date=June 2024}} {{Infobox drug | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 449870718 | IUPAC_name = 6-{3,4-dihydro-2''H''-spiro[naphthalene-1,4'-piperidine]-1'-yl}-4,4-diphenylhexan-3-one | image = R-4066.svg | image_class = skin-invert-image

<!--Clinical data--> | tradename = | pregnancy_category = | legal_US = | routes_of_administration =

<!--Pharmacokinetic data--> | bioavailability = | metabolism = | excretion =

<!--Identifiers--> | index2_label = oxalate | CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 66194-36-3 | CAS_number2_Ref = {{cascite|correct|CAS}} | CAS_number2 = 101564-56-1 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = L4YPY81SBM | UNII2_Ref = {{fdacite|correct|FDA}} | UNII2 = DL9M9L165Z | ATC_suffix = | PubChem = 380029 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 2010535 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 336763

<!--Chemical data--> | C=32 | H=37 | N=1 | O=1 | molecular_weight = | smiles = CCC(=O)C(CCN1CCC2(CCCC3=CC=CC=C32)CC1)(C4=CC=CC=C4)C5=CC=CC=C5 | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | 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 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = ZVFXEHSJPKPKDW-UHFFFAOYSA-N | synonyms = <small>''N''-(3,3-diphenyl-4-oxohex-1-yl)-7,8-benzo-3-azaspiro[5.5]undecane</small> }}

'''R-4066''' ('''Spirodone''') is a drug which is a derivative of the opioid analgesic norpipanone, wherein the piperidine ring has been replaced by a tricyclic spiro heterocycle. 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&nbsp;mg/kg, but is shorter acting, with a duration of action of around 3&nbsp;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&nbsp;hours compared to 8&nbsp;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>

R-4066 has not been researched in humans, but would be expected to produce effects similar to those of fentanyl, including strong analgesia, sedation, euphoria, constipation, itching and respiratory depression which could be harmful or fatal.{{citation needed|date=June 2024}}

Other related compounds include R-4837 [59708-47-3] & R-5260 [1109-69-9].<ref>{{cite journal | vauthors=((Leysen, J.)), ((Tollenaere, J. P.)), ((Koch, M. H. J.)), ((Laduron, P.)) | journal=European Journal of Pharmacology | title=Differentiation of opiate and neuroleptic receptor binding in rat brain | volume=43 | issue=3 | pages=253–267 | date= June 1977 | doi=10.1016/0014-2999(77)90025-5 | pmid=194781 }}</ref>

== References == {{Reflist}}

{{Opioidergics}}

Category:Opioids Category:Ketones Category:Nitrogen heterocycles Category:Mu-opioid receptor agonists Category:Spiro compounds Category:Abandoned drugs Category:Belgian inventions

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