Ciramadol

Title: Ciramadol
CAS Registry Number: 63269-31-8
CAS Name: 3-[(R)-(Dimethylamino)[(1R,2R)-2-hydroxycyclohexyl]methyl]phenol
Additional Names: (-)-cis-2-(a-dimethylamino-m-hydroxybenzyl)cyclohexanol
Manufacturers' Codes: Wy-15705
Molecular Formula: C15H23NO2
Molecular Weight: 249.35
Percent Composition: C 72.25%, H 9.30%, N 5.62%, O 12.83%
Literature References: Analgesic with narcotic agonist-antagonist properties. Prepn: J. P. Yardley, P. B. Russel, DE 2317183; eidem, US 3928626, US 4017637 (1973, 1975 and 1977 all to Am. Home). Synthesis, relative stereochemistry, biological activity: J. P. Yardley et al., Experientia 34, 1124 (1978). Abs config: W. Stallings, Jr., J. Donohue, J. Cryst. Mol. Struct. 11, 59 (1981). Determn in pharmaceutical dosage forms: H. K. Chan, A. G. Fogg, Anal. Chim. Acta 105, 423 (1979). Metabolism: C. O. Tio et al., Fed. Proc. 38, 2717 (1979). Respiratory effects in man: H. P. Wuest, Arch. Int. Pharmacodyn. Ther. 240, 45 (1979). Analgesic effect in chronic pain: M. J. Staquet, Curr. Med. Res. Opin. 6, 475 (1980).
Properties: Cryst from acetone/hexane, mp 191-193°. [a]D25 -46.92° (c = 1.061 in methanol).
Melting point: mp 191-193°
Optical Rotation: [a]D25 -46.92° (c = 1.061 in methanol)
Derivative Type: Hydrochloride
CAS Registry Number: 63323-46-6
Trademarks: Ciradol (Wyeth)
Molecular Formula: C15H23NO2.HCl
Molecular Weight: 285.81
Percent Composition: C 63.04%, H 8.46%, N 4.90%, O 11.20%, Cl 12.40%
Properties: Cryst from acetone/methanol, mp 255-257° (effervescence). [a]D25 -15.31° (c = 1.067 in methanol).
Melting point: mp 255-257° (effervescence)
Optical Rotation: [a]D25 -15.31° (c = 1.067 in methanol)
Therap-Cat: Analgesic.
Keywords: Analgesic (Non-Narcotic).
Status: This monograph has been retired and is no longer subject to revision or update.
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Ciramadol
Ciramadol.svg
Systematic (IUPAC) name
3-{(R)-dimethylamino-[(1R,2R)-2-hydroxycyclohexyl]}methyl]phenol
Clinical data
Legal status  ?
Routes Oral
Identifiers
CAS number 63269-31-8 YesY
ATC code None
PubChem CID 44463
ChemSpider 40461 YesY
UNII 9NQ109OW0G YesY
KEGG D03523 YesY
Synonyms Ciramadol, WY-15705
Chemical data
Formula C15H23NO2 
Mol. mass 249.349 g/mol
 YesY (what is this?)  (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]