467-02-7

Basic information

• Product Name: Morphinone
• Synonyms: (5α)-7,8-didehydro-4,5-epoxy-3-hydroxy-17-methylmorphinan-6-one; BRN 0042464; Didehydro-4,5-alpha-epoxy-3-hydroxy-17-methylmorphinan-6-one; (5alpha)-7,8-Didehydro-4,5-epoxy-3-hydroxy-17-methylmorphinan-6-one; Morphinan-6-one, 7,8-didehydro-4,5-epoxy-3-hydroxy-17-methyl-, (5-alpha)-; (5alpha)-3-hydroxy-17-methyl-7,8-didehydro-4,5-epoxymorphinan-6-one; (5α,6α)-3,6-dihydroxy-17-methyl-7,8-didehydro-4,5-epoxymorphinan-10-one
• CAS NO: 467-02-7
• Molecular Formula: C₁₇H₁₇NO₃
• Molecular Weight: 299.3212
• EINECS: 207-384-0
• Mol File: 467-02-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 557°C at 760 mmHg
• Flash Point: 290.6°C
• Density: 1.53g/cm³
• Vapor Pressure: 3.06E-13mmHg at 25°C
• Refractive Index: 1.735
• CAS DataBase Reference: Morphinone(CAS DataBase Reference)
• NIST Chemistry Reference: Morphinone(467-02-7)
• EPA Substance Registry System: Morphinone(467-02-7)

Safety Data

• Hazardous Substances Data: 467-02-7(Hazardous Substances Data)

Usage

General Description

Morphinone, also known as 3-hydroxy morphine or as the related compounds 9β, 10α-morphinan-3,6α-diol, is an opioid agonist that is the active metabolite of the drug morphine. It is formed in the liver through the process of O-demethylation of morphine. Morphinone is a potent analgesic and can produce effects similar to morphine, including pain relief and sedation. It has a high affinity for the mu-opioid receptor and is thought to contribute to the overall effects of morphine in the body. Additionally, morphinone is a precursor in the synthesis of a variety of semi-synthetic opiates, including hydromorphone and oxymorphone. Due to its pharmacological properties, morphinone is a controlled substance and has potential for abuse and dependence.

Upstream product

• 50291-32-2 morphine sodium salt 
• 91265-70-2 3-(_tbutyldimethylsilyl)morphine 
• 57-27-2 MORPHIN 
• 91265-75-7 3-(_tbutyldimethylsilyl)morphinone 

Downstream Products

• 91265-75-7 3-(_tbutyldimethylsilyl)morphinone 

Relevant articles and documents

In vivo and in vitro formation of morphinone from morphine in rat

1. Morphinone, a toxic metabolite, and its glutathione adduct (MO-GSH) were identified in the bile of rat after subcutaneous injection of morphine (25 mg/kg) by hplc procedures. The amounts of morphinone and MO-GSH excreted in the 12-h bile were 0.8 ± 0 3 and 8.4 ± 4.3% respectively. 2. The 9000 g supernatants of rat, guinea pig, rabbit, mouse, hamster and bovine livers produced morphinone from morphine in the presence of either NAD+ or NADP+. NAD+ was a more efficient cofactor than NADP+ except in the guinea pig which equally utilized both cofactors. With NAD+ as cofactor, the amounts of morphinone formed in rat and guinea pig were 5.70 and 5.82 μmol/g liver/30 min respectively and were three-to-four times those in other species. 3. The enzyme activity responsible for formation of morphinone from morphine in the rat was almost exclusively distributed in the microsomal fraction, whereas guinea pig, hamster and bovine expressed the enzyme activity mainly in the cytosolic fraction. Rabbit and mouse gave higher activity in the cytosolic and microsomal fractions respectively, but other fractions of both species contained considerable activity. 4. The enzyme activities in male and female rat microsomes were characterized with respect to developmental pattern, kinetic parameters, pH dependency and susceptibility to inhibitors. 5. In conclusion the metabolism of morphine to morphinone in rat was confirmed by in vivo and in vitro experiments. It is also suggested that this pathway is a common route in morphine metabolism in several mammalian species.

Activities of morphinone and N-(cyclopropylmethyl)normorphinone at opioid receptors

Morphinone (3) and N-(cyclopropylmethyl)normorphinone (4) were synthesized and tested on electrically stimulated smooth muscle preparations (guinea pig ileum and mouse vas deferens) and in mice. Compound 3 behaved as an agonist and 4 as an antagonist in vitro and in vivo. No pronounced nonequilibrium agonist or antagonist activity was observed with either compound.