795-38-0

Basic information

• Product Name: (-)-Dihydroisocodeine
• Synonyms: (-)-Dihydroisocodeine;(5R,6R)-4,5-Epoxy-3-methoxy-17-methylmorphinan-6-ol;4,5α-Epoxy-3-methoxy-17-methylmorphinan-6β-ol;DHIC;Dihydroisocodeine;6-Hydrocodol (CRM)
• CAS NO: 795-38-0
• Molecular Formula: C₁₈H₂₃NO₃
• Molecular Weight: 301.38012
• Mol File: 795-38-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 199-200°
• Boiling Point: 462°Cat760mmHg
• Flash Point: 233.2°C
• Appearance: /
• Density: 1.31g/cm³
• Vapor Pressure: 2.48E-09mmHg at 25°C
• Refractive Index: 1.643
• CAS DataBase Reference: (-)-Dihydroisocodeine(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Dihydroisocodeine(795-38-0)
• EPA Substance Registry System: (-)-Dihydroisocodeine(795-38-0)

Safety Data

• Hazardous Substances Data: 795-38-0(Hazardous Substances Data)

Usage

General Description

(-)-Dihydroisocodeine is a chemical compound that belongs to the class of isoquinoline alkaloids and is a derivative of codeine. It is a potent opioid analgesic and has been used in the treatment of moderate to severe pain. In addition to its analgesic properties, (-)-Dihydroisocodeine also exhibits sedative and antitussive effects, making it useful in the treatment of cough. The compound works by binding to opioid receptors in the central nervous system, ultimately leading to the modulation of pain perception and the suppression of cough reflex. However, (-)-Dihydroisocodeine also carries a risk of addiction, tolerance, and dependence, and should be used with caution under medical supervision.

InChI:InChI=1/C18H23NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3/t11-,12+,13+,17-,18-/m0/s1

Upstream product

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• 144318-26-3 N-[2-(3-Hydroxy-cyclohex-1-enyl)-ethyl]-4,N-dimethyl-benzenesulfonamide 
• 144318-24-1 4-Methyl-N-[2-(3-oxo-cyclohex-1-enyl)-ethyl]-benzenesulfonamide 
• 144318-28-5 N-[2-((5R,6S)-5,6-Dihydroxy-cyclohex-1-enyl)-ethyl]-4,N-dimethyl-benzenesulfonamide 
• 144318-25-2 4,N-Dimethyl-N-[2-(3-oxo-cyclohex-1-enyl)-ethyl]-benzenesulfonamide 
• 144318-32-1 N-{2-[(5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxy-cyclohex-1-enyl]-ethyl}-4,N-dimethyl-benzenesulfonamide 

Downstream Products

• 125-29-1 Hydrocodone 

Relevant articles and documents

Programmed serial stereochemical relay and its application in the synthesis of morphinans

Herein we report a rationally designed, serial point-to-axial and axial-to-point stereoinduction and its integration into multi-step and target-oriented organic synthesis. In this proof-of-concept study, the configurational stability of several carefully designed atropisomeric intermediates and the fidelity of their unconventional stereoinductions were systematically investigated. The highly functionalized prepared synthetic intermediate was further applied in a novel chemical method to access the morphinans and it is potentially applicable to other structurally related alkaloids.

Enantioselective synthesis of (-)-dihydrocodeinone: A short formal synthesis of (-)-morphine

The radical cyclization approach to the morphine alkaloids has been applied in an asymmetric synthesis of (-)-dihydrocodeinone. A chiral cyclohexenol (R-32), from the CBS reduction of the enone, is the source of chirality. The first key step, tandem closure in which stereochemistry is controlled by geometric constraints, (-)-15b → (+)-16, was followed by an unprecedented reductive hydroamination, completing the synthesis of (-)-dihydroisocodeine ((-)-17) in 13 steps from commercially available materials.