Ciramadol

Opioid analgesic drug From Wikipedia, the free encyclopedia

Ciramadol

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]

Quick Facts Clinical data, Other names ...
Ciramadol
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Clinical data
Other namesCiramadol, WY-15705
Routes of
administration
Oral
ATC code
  • none
Identifiers
  • 3-{(R)-Dimethylamino-[(1R,2R)-2-hydroxycyclohexyl]}methyl]phenol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H23NO2
Molar mass249.354 g·mol−1
3D model (JSmol)
  • OC1=CC=CC([C@@H]([C@H]2CCCC[C@H]2O)N(C)C)=C1
  • 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 Y
  • Key:UVTLONZTPXCUPU-ZNMIVQPWSA-N Y
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Synthesis

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Ciramadol synthesis:[8][9] Patents:[10][11][12]

The Claisen-Schmidt condensation between 3-(methoxymethoxy)benzaldehyde [13709-05-2] (1) and cyclohexanone (2) afforded CID:54364197 (3). Michael addition of dimethylamine leads the aminoketone, i.e. 2-[dimethylamino-[3-(methoxymethoxy)phenyl]methyl]cyclohexan-1-one, CID21518320. Reduction of the ketone proceeds stereospecifically to afford the cis aminoalcohol [51356-58-2] (4). Mild hydrolysis of the product gives the free phenol ciramadol (5).

See also

References

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