Hydromorphinol

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IUPAC_name = 3,6,14-trihydroxy-(5α,6α)-7,8-didehydro-4,5-epoxy-17-methylmorphinan

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synonyms = Hydromorphinol, 14-hydroxy-7,8-dihydromorphine
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PubChem = 5463858
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C = 17 | H = 21 | N = 1 | O = 4
molecular_weight = 303.35 g/mol
smiles = CN1CC [C@] 23 [C@@H] 4 [C@H] (CC [C@] 2( [C@H] 1CC5=C3C(=C(C=C5)O)O4)O)O
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legal_US = Schedule I
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Hydromorphinol (14-Hydroxydihydromorphine) is an opiate analogue that is an derivative of morphine, where the 14-position has been hydroxylated and the 7,8- double bond saturated. [Weiss U, Daum SJ. Derivatives of Morphine. IV. 14-Hydroxymorphine and 14-Hydroxydihydromorphine. "Journal of Medicinal Chemistry". 1965 Jan;8:123-5. PMID 14287245] 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. [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] 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 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 which is related to oxycodone as codeine is to morphine and could therefore be called oxycodeine.

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. Hydromorphinol is not the same thing as hydromorphone, although they are both strong semi-synthetic opioids. In fact hydromorphinol is to oxymorphone as dihydromorphine is to hydromorphone.

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