Hydromorphinol

Hydromorphinol
Clinical data
Other names	Hydromorphinol,; 14-hydroxy-7,8-dihydromorphine,; RAM-320
ATC code	none;
Legal status
Legal status	US: Schedule I;
Identifiers
	IUPAC name 3,6,14-trihydroxy- (5α,6α)- 4,5- epoxy- 17-methylmorphinan;
CAS Number	2183-56-4 ; 2190-27-4;
PubChem CID	5463858;
UNII	1O00P9X5C1;
CompTox Dashboard (EPA)	DTXSID30176242 ;
ECHA InfoCard	100.016.878
Chemical and physical data
Formula	C17H21NO4
Molar mass	303.35 g/mol 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;
	(what is this?) (verify)

Hydromorphinol (RAM-320, 14-Hydroxydihydromorphine)^[1] 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 more potent and has a steeper dose-response curve and longer half-life.^[3] 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 was developed in Austria in 1932. It is available, and commonly used, as a medicine in Sweden; in the United States, it was never available and is classified as a Schedule I drug.

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 also therefore an active metabolite too of a first order active metabolite of oxycodone).

It is distributed under the trade name Numorphan in some countries, whereas this trade name is used for oxymorphone much more commonly. It is controlled under the Single Convention On Narcotic Drugs.

References

^ US 2960505, Weiss U., published 11/15/1960
^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 14287245, please use {{cite journal}} with |pmid=14287245 instead.
^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 2326098, please use {{cite journal}} with |pmid=2326098 instead.

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[1] US 2960505, Weiss U., published 11/15/1960

[2] Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 14287245, please use {{cite journal}} with |pmid=14287245 instead.

[3] Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 2326098, please use {{cite journal}} with |pmid=2326098 instead.

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See also

References