Hydromorphinol

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Hydromorphinol
Hydromorphinol.svg
Clinical data
Synonyms Hydromorphinol,
14-hydroxy-7,8-dihydromorphine,
RAM-320
ATC code
  • none
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
ECHA InfoCard 100.016.878 Edit this at Wikidata
Chemical and physical data
Formula C17H21NO4
Molar mass 303.35 g/mol
3D model (JSmol)
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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)

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[edit]

References[edit]

  1. ^ US 2960505, Weiss U., published 11/15/1960 
  2. ^ 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. 
  3. ^ US Patent 2960505 - Morphine Derivatives'
  4. ^ 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. 
  5. ^ http://www.chemicalbook.com/ProductChemicalPropertiesCB0933076_EN.htm
  6. ^ http://www.deadiversion.usdoj.gov/fed_regs/quotas/2014/fr0825.htm