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| Trade names | Numorphan |
| Other names | Hydromorphinol, 14-hydroxy-7,8-dihydromorphine, RAM-320 |
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| ECHA InfoCard | 100.016.878 |
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| Formula | C17H21NO4 |
| Molar mass | 303.358 g·mol−1 |
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Hydromorphinol (RAM-320,14-hydroxydihydromorphine),[2] is anopiate analogue that is a derivative ofmorphine, where the 14-position has been hydroxylated and the 7,8- double bond saturated.[3] It has similar effects to morphine such assedation,analgesia andrespiratory depression, but is twice as potent as morphine[2] 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)
Hydromorphinol has also been discovered to occur naturally in trace amounts withinopium, although this is a very rare occurrence.[5]
It is also called α-oxymorphol, andoxymorphol 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 theUnited States, it was never available and is classified as a Schedule I drug with a DEAACSCN 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 ismetabolized mainly in the liver in the same fashion as many other opioids and is itself a minor active metabolite of14-hydroxydihydrocodeine, an uncommonly used opiate (but is therefore also an active metabolite of a first-order active metabolite ofoxycodone).
It is distributed under the trade name Numorphan in some countries. It is controlled under theSingle Convention On Narcotic Drugs.