R-4066

R-4066 (Spirodone) is a drug which is a derivative of the opioid analgesic norpipanone, wherein the piperidine ring has been replaced by a tricyclic spiro heterocycle.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,^[1] 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.^[2]

Other namesN-(3,3-diphenyl-4-oxohex-1-yl)-7,8-benzo-3-azaspiro[5.5]undecane

CAS Number

• 66194-36-3 ^Y
• oxalate: 101564-56-1 ^Y

PubChem CID

• 380029

ChemSpider

• 336763 ^N

Quick facts Clinical data, Other names ...

R-4066

Clinical data
Other names	N-(3,3-diphenyl-4-oxohex-1-yl)-7,8-benzo-3-azaspiro[5.5]undecane
Identifiers
IUPAC name 6-{3,4-dihydro-2H-spiro[naphthalene-1,4'-piperidine]-1'-yl}-4,4-diphenylhexan-3-one
CAS Number	66194-36-3 Y oxalate: 101564-56-1 Y
PubChem CID	380029
ChemSpider	336763 N
UNII	L4YPY81SBM oxalate: DL9M9L165Z Y
ChEMBL	ChEMBL2010535 N
CompTox Dashboard (EPA)	DTXSID101018281 DTXSID10906347, DTXSID101018281
Chemical and physical data
Formula	C32H37NO
Molar mass	451.654 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCC(=O)C(CCN1CCC2(CCCC3=CC=CC=C32)CC1)(C4=CC=CC=C4)C5=CC=CC=C5
InChI InChI=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 N Key:ZVFXEHSJPKPKDW-UHFFFAOYSA-N N
NY (what is this?)  (verify)

Close

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]}

Other related compounds include R-4837 [59708-47-3] & R-5260 [1109-69-9].^[3]