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466-99-9

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Basic Information
CAS No.: 466-99-9
Name: HYDROMORPHONE
Article Data: 39
Molecular Structure:
Molecular Structure of 466-99-9 (HYDROMORPHONE)
Formula: C17H19 N O3
Molecular Weight: 285.343
Synonyms: Morphinan-6-one,4,5a-epoxy-3-hydroxy-17-methyl-(8CI); Morphinone, dihydro- (5CI); (-)-Hydromorphone; DiMo; Dihydromorphinone;Dihydromorphone; Dimorphone; Hydromorphon; Hydromorphone; NSC 19046;Novolaudon; OROS hydromorphone
Density: 1.4g/cm3
Melting Point: 266-267°
Boiling Point: 475.6°Cat760mmHg
Flash Point: 241.4°C
Solubility: 1.931g/L(25 oC)
Hazard Symbols: F,T
Risk Codes: 11-23/24/25-39/23/24/25
Safety: A deadly human poison by ingestion. An experimental poison by ingestion and subcutaneous routes. When heated to decomposition it emits toxic fumes of NOx. See also (−)-MORPHINE.
PSA: 49.77000
LogP: 1.56820
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Chemistry

Chemical Name: Hydromorphone
CAS No.: 466-99-9
EINECS: 207-383-5
Molecular Formula: C17H19NO3
Molecular Weight: 285.34 g/mol
Density: 1.4 g/cm3 
Flash Point: 241.4 °C
Boiling Point: 475.6 °C at 760 mmHg
Following is the structure of Dihydromorphinone (466-99-9):

History

 Dihydromorphinone (466-99-9) was first synthesized and researched in Germany in 1924 and introduced to the mass market by Knoll in 1926 under the brand name Dilaudid indicating its derivation and degree of similarity to morphine (by way of laudanum)—Cf. Dicodid (hydrocodone), Dihydrin (dihydrocodeine) and Dinarkon (oxycodone). Some authorities and publications use the name dilaudid as a synecdoche (e.g. like Kleenex for tissues, Xerox for copies &c.) for hydromorphone. Hydromorphone may also be known by the brand name Morphodid.

Uses

 Dihydromorphinone (466-99-9) is used in medicine as an alternative to morphine and diacetylmorphine for analgesia, and as a second- or third-line narcotic antitussive (cough suppressant) for cases of dry, painful, paroxysmal coughing resulting from continuing bronchial irritation after influenza and other ailments, inhalation of fungus, and other causes. It is generally considered the strongest of the antitussive drugs, and was developed shortly after another powerful antitussive, heroin, was removed from clinical use for this purpose in most of the world and banned outright in many countries. The effectiveness of hydrocodone as an antitussive may be partly due its being partially converted to hydromorphone in the liver.

Production

 Dihydromorphinone (466-99-9) is made from morphine via catalytic hydrogenation and is also produced in trace amounts by human and other mammalian metabolism of morphine and occasionally appears in assays of opium latex in very small quantities, apparently forming in the plant in an unknown percentage of cases under poorly-understood conditions.

Toxicity Data With Reference

1.    

orl-hmn LDLo:1428 µg/kg

    34ZIAG    Toxicology of Drugs and Chemicals ,Deichmann, W.B.,New York, NY.: Academic Press, Inc.,1969,223.
2.    

scu-mus LD50:84 mg/kg

    JPETAB    Journal of Pharmacology and Experimental Therapeutics. 52 (1934),468.
3.    

ivn-mus LD50:104 mg/kg

    YKKZAJ    Yakugaku Zasshi. Journal of Pharmacy. 84 (1964),268.

Safety Profile

A deadly human poison by ingestion. An experimental poison by ingestion and subcutaneous routes. When heated to decomposition it emits toxic fumes of NOx. See also (−)-MORPHINE.

Specification

 Dihydromorphinone (466-99-9) is a potent centrally-acting analgesic drug of the opioid class. It is a derivative of morphine, specifically a hydrogenated ketone thereof and therefore a semi-synthetic drug. It is both medically an opiate analgesic and legally a narcotic. It should not be confused with hydromorphinol, also known as 14-hydroxydihydromorphine and RAM-320 nor dihydromorphine (Paramorfan). While all of these are strong opioids, they are indeed different drugs. Additional confusion arises from the fact that in a handful of countries hydromorphinol is distributed under the trade name Numorphan, which is the trade name for oxymorphone in the rest of the world according to the current version of The A-Z Encyclopaedia of Alcohol & Drug Abuse and other references.It is known in various countries around the world by the trade names Hydal, Sophidone, Hydrostat Hydromorfan, Hydromorphan, Laudicon, Hymorphan, Opidol, Palladone and others (warning: the brand names are inconsistent from country to country). An extended-release version of hydromorphone called Palladone was available for a short time in the United States before being voluntarily withdrawn from the market after a July 2005 FDA advisory warned of a high overdose potential when taken with alcohol. As of March 2007 it is still available in the United Kingdom under the brand name Palladone SR, and in most other European countries. Another extended-release version called Hydromorph Contin, manufactured as controlled release capsules, continues to be produced and distributed in Canada by Purdue Pharma Inc. of Pickering, Ontario. In addition to Purdue-Frederick, manufacturers of hydromorphone products include Ethex, Knoll, Abbott, Endo, Mallinkroft, Merck, Mundipharma, and Lannacher, amongst others.