Ciramadol

Ciramadol
Clinical data
Other names	Ciramadol, WY-15705
Routes of; administration	Oral
ATC code	none;
Identifiers
	IUPAC name 3-{(R)-Dimethylamino-[(1R,2R)-2-hydroxycyclohexyl]}methyl]phenol;
CAS Number	63269-31-8 ;
PubChem CID	44463;
ChemSpider	40461 ;
UNII	9NQ109OW0G;
KEGG	D03523 ;
ChEMBL	ChEMBL2104132;
CompTox Dashboard (EPA)	DTXSID601018412 ;
Chemical and physical data
Formula	C15H23NO2
Molar mass	249.354 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES OC1=CC=CC([C@@H]([C@H]2CCCC[C@H]2O)N(C)C)=C1;
	InChI InChI=1S/C15H23NO2/c1-16(2)15(11-6-5-7-12(17)10-11)13-8-3-4-9-14(13)18/h5-7,10,13-15,17-18H,3-4,8-9H2,1-2H3/t13-,14+,15-/m0/s1 ; Key:UVTLONZTPXCUPU-ZNMIVQPWSA-N ;
	(verify)

Ciramadol (WY-15,705) is an opioid analgesic that was developed in the late 1970s^[1] and is related to phencyclidine, tramadol, tapentadol and venlafaxine.^[2] It is a mixed agonist-antagonist for the μ-opioid receptor with relatively low abuse potential^[3] and a ceiling on respiratory depression^[4] which makes it a relatively safe drug. It has a slightly higher potency and effectiveness as an analgesic than codeine,^[5] but is weaker than morphine.^[6] Other side effects include sedation and nausea but these are generally less severe than with other similar drugs.^[7]

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Synthesis