1421-28-9

Basic information

• Product Name: Dihydromorphine hydrochloride
• Synonyms: Morphinan-3,6.alpha.-diol, 4,5.alpha.-epoxy-17-methyl-, hydrochloride;Morphinan-3,6-diol, 4,5-epoxy-17-methyl-, hydrochloride, (5.alpha.,6.alpha.)-;Morphine, dihydro, hydrochloride;Morphine, dihydro-, hydrochloride;Nsc404353
• CAS NO: 1421-28-9
• Molecular Formula: C₁₇H₂₁NO₃*ClH
• Molecular Weight: 323.85
• Mol File: 1421-28-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: >280 °C
• Boiling Point: 475.4°Cat760mmHg
• Flash Point: 241.3°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 7.65E-10mmHg at 25°C
• CAS DataBase Reference: Dihydromorphine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Dihydromorphine hydrochloride(1421-28-9)
• EPA Substance Registry System: Dihydromorphine hydrochloride(1421-28-9)

Safety Data

• Hazardous Substances Data: 1421-28-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C17H21NO3.ClH/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18;/h2,4,10-11,13,16,19-20H,3,5-8H2,1H3;1H/t10-,11+,13-,16-,17-;/m0./s1

Upstream product

• 33049-61-5 (-)-tetrahydrothebaine 
• 52-26-6 morphine hydrochloride 
• 57-27-2 MORPHIN 

Downstream Products

• 58752-60-6 3-O-acetyldihydromorphine 
• 71-68-1 hydromorphone hydrochloride 
• 466-99-9 hydromorphone 
• 14696-23-2 Norhydromorphone 

Relevant articles and documents

Towards an efficient preparation of hydromorphone

Dihydromorphone was prepared from morphine in high yield, excellent purity, and low residual metal content. The key steps used palladium on porous glass and a modified Oppenauer oxidation, or Wilkinson's catalyst. Georg Thieme Verlag Stuttgart ? New York.

Oxidative metabolism of dihydrocodeine in Dark-Agouti and Sprague-Dawley rat liver microsomes

The oxidative metabolism of dihydrocodeine to nordihydrocodeine and dihydromorphine was studied in liver microsomes of female Dark-Agouti (cytochrome P450 2D1 (CYP2D1) deficient) and Sprague-Dawley rats. Evaluation of microsomal metabolism in these two rat strains is a useful in-vitro model to test possible substrates of polymorphic human cytochrome P450 2D6 (CYP2D6). Nordihydrocodeine formation rates were similar in both strains. Analysis of the Michaelis-Menten kinetics of dihydromorphine formation showed a significant difference (P -1 g-1) and intrinsic clearance (0.986; 19.5 mL min-1 g-1). In Sprague-Dawley liver microsomes, dihydromorphine formation was suppressed by the CYP2D1 inhibitors, quinine and quinidine, at concentrations which had no effect on nordihydrocodeine formation. These in-vitro findings indicate that in rat liver microsomes the cytochrome P450 system is involved in dihydrocodeine metabolism to dihydromorphine and nordihydrocodeine and that CYP2D1 is involved in the O-demethylation to dihydromorphine but not the N-demethylation to nordihydrocodeine. The results of this study are in agreement with recent in-vivo studies of dihydrocodeine metabolism in man which indicate CYP2D6 is the predominant enzyme catalysing dihydromorphine formation.