Clinical data | |
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Other names | Ciramadol, WY-15705 |
Routes of administration | Oral |
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CompTox Dashboard ( EPA) | |
Chemical and physical data | |
Formula | C15H23NO2 |
Molar mass | 249.354 g·mol−1 |
3D model ( JSmol) | |
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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]
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).
Clinical data | |
---|---|
Other names | Ciramadol, WY-15705 |
Routes of administration | Oral |
ATC code |
|
Identifiers | |
| |
CAS Number | |
PubChem CID | |
ChemSpider | |
UNII | |
KEGG | |
ChEMBL | |
CompTox Dashboard ( EPA) | |
Chemical and physical data | |
Formula | C15H23NO2 |
Molar mass | 249.354 g·mol−1 |
3D model ( JSmol) | |
| |
| |
(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]
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).