|CompTox Dashboard (EPA)|
|Chemical and physical data|
|Molar mass||303.35 g/mol g·mol−1|
|3D model (JSmol)|
|(what is this?)|
Hydromorphinol (RAM-320, 14-Hydroxydihydromorphine), 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. It has similar effects to morphine such as sedation, analgesia and respiratory depression, but is twice as potent as morphine and has a steeper dose-response curve and longer half-life. 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)
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.
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.
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.
- 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.
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