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Hydromorphinol
Systematic (IUPAC) name
3,6,14-trihydroxy- (5α,6α)- 4,5- epoxy- 17-methylmorphinan
Identifiers
CAS number  ?
ATC code none
PubChem 5463858
Chemical data
Formula C 17H21NO4  
Mol. mass 303.35 g/mol
SMILES eMolecules & PubChem
Synonyms Hydromorphinol,
14-hydroxy- 7,8-dihydromorphine
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status Schedule I (US)
Routes  ?

Hydromorphinol (14-Hydroxydihydromorphine) is an opiate analogue that is a derivative of morphine, where the 14-position has been hydroxylated and the 7,8- double bond saturated.[1] 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.[2] 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.

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.

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 and the laws governing habit-forming substances in each country, such as the Controlled Substances Act of 1970 of the United States (Schedule I/Narcotic), the Betäubungsmittelgesetz (BtMG) of Germany, UK Misuse of Drugs Act, the Suchtgiftverordnung of Austria and others.

References

  1. ^ Weiss U, Daum SJ. Derivatives of Morphine. IV. 14-Hydroxymorphine and 14-Hydroxydihydromorphine. Journal of Medicinal Chemistry. 1965 Jan;8:123-5. PMID 14287245
  2. ^ Plummer JL, Cmielewski PL, Reynolds GD, Gourlay GK, Cherry DA. Influence of polarity on dose-response relationships of intrathecal opioids in rats. Pain. 1990 Mar;40(3):339-47. PMID 2326098







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