Hydromorphinol
Hydromorphinol (RAM-320, 14-Hydroxydihydromorphine),[1] also is an opiate analogue that is a derivative of morphine, where the 14-position has been hydroxylated and the 7,8- double bond saturated.[2] It has similar effects to morphine such as sedation, analgesia and respiratory depression, but is twice as potent as morphine[3] and has a steeper dose-response curve and longer half-life.[4] It is used in medicine as the bitartrate salt (free base conversion ratio 0.643, molecular weight 471.5) and hydrochloride (free base conversion ratio 0.770, molecular weight 393.9)
Clinical data | |
---|---|
Other names | Hydromorphinol, 14-hydroxy-7,8-dihydromorphine, RAM-320 |
ATC code |
|
Legal status | |
Legal status |
|
Identifiers | |
IUPAC name
| |
CAS Number |
|
PubChem CID | |
ChemSpider | |
UNII | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.016.878 |
Chemical and physical data | |
Formula | C17H21NO4 |
Molar mass | 303.35 g/mol g·mol−1 |
3D model (JSmol) | |
SMILES
| |
InChI
| |
|
It is also called α-Oxymorphol, and oxymorphol is itself a mixture of hydromorphinol and 4,5α-Epoxy-17-methylmorphinan-3,6β,14-triol, β-Oxymorphol, which is different at position 6 on the morphine carbon skeleton.[5]
Hydromorphinol was developed in Austria in 1932. In the United States, it was never available and is classified as a Schedule I drug with a DEA ACSCN of 9301. The salts in use are the bitartrate (free base conversion ratio 0.643) and hydrochloride (0.770). The 2014 national aggregate manufacturing quota was 2 grams, unchanged from prior years.[6]
Hydromorphinol is metabolised mainly in the liver in the same fashion as many other opioids and is itself a minor active metabolite of 14-Hydroxydihydrocodeine, an uncommonly used opiate (but is therefore also an active metabolite of a first-order active metabolite of oxycodone).
It is distributed under the trade name Numorphan in some countries. It is controlled under the Single Convention On Narcotic Drugs.
See also
- Oxymorphol
- N-Phenethylhydromorphinol (RAM-378)
References
- US 2960505, Weiss U., published 11/15/1960
- Weiss, U.; Daum, S. J. (1965). "Derivatives of Morphine. Iv. 14-Hydroxymorphine and 14-Hydroxydihydromorphine". Journal of Medicinal Chemistry. 8: 123–125. doi:10.1021/jm00325a028. PMID 14287245.
- US Patent 2960505 - Morphine Derivatives'
- Plummer, J. L.; Cmielewski, P. L.; Reynolds, G. D.; Gourlay, G. K.; Cherry, D. A. (1990). "Influence of polarity on dose-response relationships of intrathecal opioids in rats". Pain. 40 (3): 339–347. doi:10.1016/0304-3959(90)91131-2. PMID 2326098.
- http://www.chemicalbook.com/ProductChemicalPropertiesCB0933076_EN.htm
- http://www.deadiversion.usdoj.gov/fed_regs/quotas/2014/fr0825.htm