Hydromorphone

Title: Hydromorphone
CAS Registry Number: 466-99-9
CAS Name: 4,5-Epoxy-3-hydroxy-17-methylmorphinan-6-one
Additional Names: dihydromorphinone
Trademarks: Dimorphone; Novolaudon
Molecular Formula: C17H19NO3
Molecular Weight: 285.34
Percent Composition: C 71.56%, H 6.71%, N 4.91%, O 16.82%
Literature References: Prepn by electrolytic reduction of morphine: Takagi, Ueda, J. Pharm. Soc. Jpn. 56, 44 (1936); Nakamura, ibid. 62, 347 (1942); by oxidation of dihydromorphine: Rapoport et al., J. Org. Chem. 15, 1103 (1950); Homeyer, De la Mater, US 2628962 and US 2654756 (both 1953 to Mallinckrodt); Rapoport, US 2649454 (1953 to Univ. of California). Crystal structure: Steinmetz, Z. Kristallogr. 67, 434 (1928). Toxicity data: M. E. Buchwald, G. S. Eadie, J. Pharmacol. Exp. Ther. 71, 197 (1941). Review: King et al., U.S. Public Health Reports Suppl. no. 113, 38 pp (1935).
Properties: Crystals from ethanol, mp 266-267°. [a]D25 -194° (c = 0.98 in dioxane).
Melting point: mp 266-267°
Optical Rotation: [a]D25 -194° (c = 0.98 in dioxane)
Derivative Type: Hydrochloride
CAS Registry Number: 71-68-1
Trademarks: Dilaudid (Knoll); Laudicon; Hymorphan (Endo); Palladone (Napp)
Molecular Formula: C17H19NO3.HCl
Molecular Weight: 321.80
Percent Composition: C 63.45%, H 6.26%, N 4.35%, O 14.92%, Cl 11.02%
Properties: Crystals, dec 305-315° (evacuated tube). [a]D25 -133°. Sol in 3 parts water; sparingly sol in alc. LD50 in mice (mg/kg): 61-96 i.v. (Buchwald, Eadie).
Optical Rotation: [a]D25 -133°
Toxicity data: LD50 in mice (mg/kg): 61-96 i.v. (Buchwald, Eadie)
NOTE: This is a controlled substance (opiate): 21 CFR, 1308.12.
Therap-Cat: Analgesic (narcotic).
Keywords: Analgesic (Narcotic).
Hydrone? Hydroorotic Acid Hydroprene Hydroquinidine Hydroquinine

Hydromorphone
Hydromorphone - Hydromorphon.svg
Hydromorphone 27feb.gif
Systematic (IUPAC) name
4,5-α-epoxy-3-hydroxy-17-methyl morphinan-6-one
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a682013
Pregnancy cat. C
Legal status Controlled (S8) (AU) Class A—Non-Clinical use—and Schedule II—Clinical use (UK),
DEA Schedule II (USA)
Routes oral, intramuscular, intravenous, subcutaneous, intranasal, rectal, sublingual, transmucosal, buccal, transdermal (experimental)
Pharmacokinetic data
Bioavailability Oral: 30–35%, Intranasal: 52–58%[1]
Protein binding 20%
Metabolism Hepatic
Half-life 2–3 hours[2]
Excretion Renal
Identifiers
CAS number 466-99-9 YesY
ATC code N02AA03
PubChem CID 5284570
DrugBank DB00327
ChemSpider 4447624 YesY
UNII Q812464R06 YesY
KEGG D08047 YesY
ChEBI CHEBI:5790 YesY
ChEMBL CHEMBL398707 YesY
Synonyms dihydromorphinone
Chemical data
Formula C17H19NO3 - HCL 
Mol. mass 321.8g/mol
Physical data
Solubility in water HCl: 333 mg/mL (20 °C)
 YesY (what is this?)  (verify)

Hydromorphone, a more common synonym for dihydromorphinone (not to be confused by dihydromorphine, which is a different derivative of the morphine family), commonly a hydrochloride (brand names Palladone, Dilaudid, and numerous others) is a very potent centrally acting analgesic drug of the opioid class. It is a derivative of morphine; to be specific, a hydrogenated ketone thereof, and it can be said that hydromorphone is to morphine as hydrocodone is to codeine and, therefore, a semi-synthetic drug. It is in medical terms an opioid analgesic and in legal terms a narcotic. Hydromorphone is commonly used in the hospital setting, mostly intravenously (IV) because its bioavailability orally, rectally, and intranasally is very low. Sublingual administration is usually superior to swallowing for bioavailability and effects.

Hydromorphone is much more soluble in water than morphine and therefore hydromorphone solutions can be produced to deliver the drug in a smaller volume of water. The hydrochloride salt is soluble in three parts of water whereas a gramme of morphine hydrochloride dissolves in 16 ml of water; for all common purposes the pure powder for hospital use can be used to produce solutions of virtually arbitrary concentration. When the powder has appeared on the street, this very small volume of powder needed for a dose means that overdoses are likely for those who mistake it for heroin or other powdered narcotics, especially those that have been cut or stepped on already.

Very small quantities of hydromorphone are detected in assays of opium on rare occasions; it appears to be produced by the plant under circumstances and by processes which are not understood at this time and may include the action of bacteria. A similar process and/or other metabolic processes in the plant may very well be responsible for the very low quantities of hydrocodone also found on rare occasions in opium and alkaloid mixtures derived therefrom; dihydrocodeine, oxymorphol, oxycodone, oxymorphone, metopon and possibly other derivatives of morphine and/or hydromorphone also are found in trace amounts in opium.