Hydromorphinol

Hydromorphinol (RAM-320, 14-hydroxydihydromorphine),^[2] is an opiate analogue that is a derivative of morphine, where the 14-position has been hydroxylated and the 7,8- double bond saturated.^[3] It has similar effects to morphine such as sedation, analgesia and respiratory 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)

Trade namesNumorphan

Other namesHydromorphinol,
14-hydroxy-7,8-dihydromorphine,
RAM-320

ATC code

• none

Legal status

• AU: S8 (Controlled drug)
• BR: Class A1 (Narcotic drugs)^[1]
• CA: Schedule I
• DE: Anlage I (Authorized scientific use only)
• US: Schedule I

Quick facts Clinical data, Trade names ...

Hydromorphinol

Clinical data
Trade names	Numorphan
Other names	Hydromorphinol, 14-hydroxy-7,8-dihydromorphine, RAM-320
ATC code	none
Legal status
Legal status	AU: S8 (Controlled drug) BR: Class A1 (Narcotic drugs)[1] CA: Schedule I DE: Anlage I (Authorized scientific use only) US: Schedule I
Identifiers
IUPAC name (5α,6α)-3,6,14-Trihydroxy-4,5-epoxy-17-methylmorphinan
CAS Number	2183-56-4 Y 2190-27-4
PubChem CID	5463858
DrugBank	DB01512 Y
ChemSpider	4576407 N
UNII	1O00P9X5C1
KEGG	D12686 Y
ChEMBL	ChEMBL1951706 N
CompTox Dashboard (EPA)	DTXSID30176242
ECHA InfoCard	100.016.878
Chemical and physical data
Formula	C17H21NO4
Molar mass	303.358 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN1CC[C@]23[C@@H]4[C@H](CC[C@]2([C@H]1CC5=C3C(=C(C=C5)O)O4)O)O
InChI InChI=1S/C17H21NO4/c1-18-7-6-16-13-9-2-3-10(19)14(13)22-15(16)11(20)4-5-17(16,21)12(18)8-9/h2-3,11-12,15,19-21H,4-8H2,1H3/t11-,12+,15-,16-,17+/m0/s1 N Key:AABLHGPVOULICI-BRJGLHKUSA-N N
NY (what is this?)  (verify)

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Hydromorphinol has also been discovered to occur naturally in trace amounts within opium, although this is a very rare occurrence.^[5]

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.^[6]

Hydromorphinol is metabolized 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.