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

Description

(-)-Dihydroisocodeine is a potent opioid analgesic and a derivative of codeine, belonging to the class of isoquinoline alkaloids. It is known for its effectiveness in treating moderate to severe pain, as well as its sedative and antitussive properties, which make it useful for managing cough. (-)-Dihydroisocodeine acts by binding to opioid receptors in the central nervous system, modulating pain perception and suppressing the cough reflex. However, due to its potential for addiction, tolerance, and dependence, it should be used with caution and under medical supervision.

Uses

Used in Pharmaceutical Industry:
(-)-Dihydroisocodeine is used as an analgesic for the treatment of moderate to severe pain. Its potent pain-relieving effects make it a valuable component in pain management therapies.
(-)-Dihydroisocodeine is also used as a sedative to help alleviate anxiety and promote relaxation in patients experiencing discomfort or distress due to pain.
Additionally, (-)-Dihydroisocodeine is used as an antitussive agent for the treatment of cough, effectively suppressing the cough reflex and providing relief from persistent coughing.

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

• 144318-30-9 N-{2-[(5R,6R)-6-[2-Bromo-6-methoxy-3-((E)-2-phenylsulfanyl-vinyl)-phenoxy]-5-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-ethyl}-4,N-dimethyl-benzenesulfonamide 
• 144318-22-9 N-(2-{(5S,6S)-6-[2-Bromo-6-methoxy-3-((E)-2-phenylsulfanyl-vinyl)-phenoxy]-5-hydroxy-cyclohex-1-enyl}-ethyl)-4,N-dimethyl-benzenesulfonamide 
• 144318-32-1 N-{2-[(5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxy-cyclohex-1-enyl]-ethyl}-4,N-dimethyl-benzenesulfonamide 
• 144318-25-2 4,N-Dimethyl-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 
• 144318-24-1 4-Methyl-N-[2-(3-oxo-cyclohex-1-enyl)-ethyl]-benzenesulfonamide 
• 144318-26-3 N-[2-(3-Hydroxy-cyclohex-1-enyl)-ethyl]-4,N-dimethyl-benzenesulfonamide 
• 144318-27-4 N-[2-((1S,5S,6S)-5-Hydroxy-7-oxa-bicyclo[4.1.0]hept-1-yl)-ethyl]-4,N-dimethyl-benzenesulfonamide 
• 61273-80-1 2-(5-methoxy-cyclohexa-1,4-dienyl)-ethylamine 
• 28165-49-3 6-bromoguaiacol 
• 871951-77-8 2-Bromo-6-methoxy-3-((E)-2-phenylsulfanyl-vinyl)-phenol 
• 144318-23-0 N-[2-((3R,3aR,9aS,9bS)-3-Hydroxy-5-methoxy-1,3,3a,9a-tetrahydro-2H-phenanthro[4,5-bcd]furan-9b-yl)-ethyl]-4,N-dimethyl-benzenesulfonamide 
• 74035-75-9 (+/-)-dihydrocodeinone 

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.