Dihydromorphine

Title: Dihydromorphine
CAS Registry Number: 509-60-4
CAS Name: (5a,6a)-4,5-Epoxy-17-methylmorphinan-3,6-diol
Molecular Formula: C17H21NO3
Molecular Weight: 287.35
Percent Composition: C 71.06%, H 7.37%, N 4.87%, O 16.70%
Literature References: Prepd by hydrogenation of morphine or opium; by demethylation of tetrahydrothebaine; from dihydrocodeine. Ref: Small, Lutz, "Chemistry of the Opium Alkaloids" in U.S. Public Health Reports Suppl. No. 103 (Washington, 1932); Eddy, Reid J. Pharmacol. 52, 468 (1934); K. W. Bentley, The Chemistry of the Morphine Alkaloids (Oxford, 1954).
Derivative Type: Monohydrate
Properties: Prisms from chloroform, mp (dry) 157° (dec). Insoluble in water. Sol in acetone, alcohol, chloroform, dil acids.
Melting point: mp (dry) 157° (dec)
Derivative Type: Hydrochloride
Additional Names: Paramorphan; paramorfan
Molecular Formula: C17H21NO3.HCl
Molecular Weight: 323.81
Percent Composition: C 63.06%, H 6.85%, N 4.33%, O 14.82%, Cl 10.95%
Properties: Prismatic crystals, unmelted at 280° in vacuo. [a]D25 -112° (c = 1.6). Very sol in water; sparingly sol in abs alcohol.
Optical Rotation: [a]D25 -112° (c = 1.6)
Derivative Type: Hydriodide
Molecular Formula: C17H21NO3.HI
Molecular Weight: 415.27
Percent Composition: C 49.17%, H 5.34%, N 3.37%, O 11.56%, I 30.56%
Properties: Crystals, soften at 270°. mp 275°.
Melting point: mp 275°
NOTE: This is a controlled substance (opium derivative): 21 CFR, 1308.11.
Therap-Cat: Analgesic (narcotic).
Keywords: Analgesic (Narcotic).
Dihydroresorcinol Dihydrostreptomycin Dihydrotachysterol Dihydrothebaine Dihydroxyaluminum Acetylsalicylate

Dihydromorphine
Systematic (IUPAC) name
3,6-Dihydroxy-(5α,6α)-4,5-epoxy-17-methylmorphinan
Clinical data
Legal status Schedule I (US)
Routes Oral, Intravenous, Intranasally, Sublingually
Identifiers
CAS number 509-60-4 N
ATC code None
PubChem CID 5359421
IUPHAR ligand 1616
DrugBank DB01565
ChemSpider 4514282 YesY
KEGG C11782 YesY
ChEMBL CHEMBL1500 YesY
Synonyms Dihydromorphine, Paramorphan
Chemical data
Formula C17H21NO3 
Mol. mass 287.354 g/mol
 N (what is this?)  (verify)

Dihydromorphine (Paramorfan, Paramorphan) is a semi-synthetic opioid structurally related to and derived from morphine. The 7,8-double bond in morphine is reduced to a single bond to get dihydromorphine.[1] Dihydromorphine is a moderately strong analgesic and is used clinically in the treatment of pain and also is an active metabolite of the analgesic opioid drug dihydrocodeine.[2][3][4]