467-13-0

Basic information

• Product Name: CODEINONE
• Synonyms: CODEINONE;OXYCODONE BASE;6-codeinone;7,8-didehydro-4,5-alpha-epoxy-3-methoxy-17-methyl-morphinan-6-on;(5alpha)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-one;(5a)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methyl-morphinan-6-one;6-Oxocodeine;7,8-Didehydro-4,5a-epoxy-3-methoxy-17-methyl-morphinan-6-one
• CAS NO: 467-13-0
• Molecular Formula: C₁₈H₁₉NO₃
• Molecular Weight: 297.35
• EINECS: 207-386-1
• Product Categories: Glucuronides;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 467-13-0.mol
• Article Data: 22

Chemical Properties

• Melting Point: 182-183°C
• Boiling Point: 466.9 °C at 760 mmHg
• Flash Point: 236.1 °C
• Appearance: /
• Density: 1.34 g/cm³
• Vapor Pressure: 6.84E-09mmHg at 25°C
• Refractive Index: 1.656
• Storage Temp.: Controlled Substance, -20°C Freezer
• PKA: 8.10±0.20(Predicted)
• CAS DataBase Reference: CODEINONE(CAS DataBase Reference)
• NIST Chemistry Reference: CODEINONE(467-13-0)
• EPA Substance Registry System: CODEINONE(467-13-0)

Safety Data

• Statements: 22
• Hazardous Substances Data: 467-13-0(Hazardous Substances Data)

Usage

Description

CODEINONE is a metabolite of Codeine, which is a naturally occurring opiate alkaloid found in the opium poppy plant. It is a controlled substance and is known for its brown solid appearance. CODEINONE is used in various applications due to its chemical properties and pharmacological effects.

Uses

Used in Pharmaceutical Industry:
CODEINONE is used as an active pharmaceutical ingredient for its pain-relieving and cough-suppressing properties. It is particularly useful in the development of medications aimed at treating moderate to severe pain and persistent coughing.
Used in Research and Development:
In the field of research and development, CODEINONE serves as a valuable compound for studying the effects of opiate alkaloids on the human body. Its controlled substance status allows for the exploration of its potential therapeutic applications and the development of new drugs with similar properties.
Used in Regulatory Compliance:
As a controlled substance, CODEINONE is subject to strict regulations and monitoring. It is used in the enforcement of drug control policies and the prevention of drug abuse and diversion. This application helps maintain public health and safety by ensuring the responsible use and distribution of the substance.
Used in Toxicology and Forensic Analysis:
CODEINONE is utilized in toxicology and forensic analysis to detect and identify the presence of Codeine and its metabolites in biological samples. This application is crucial in cases involving drug overdose, drug-facilitated crimes, and the investigation of suspicious deaths.

InChI:InChI=1/C18H19NO3/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/h3-6,11-12,17H,7-9H2,1-2H3/t11-,12+,17-,18-/m0/s1

Upstream product

• 115-37-7 thebaine 
• 76-57-3 codeine 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 79-37-8 oxalyl dichloride 
• 121-44-8 triethylamine 
• 555-31-7 aluminum isopropoxide 
• 497-19-8 sodium carbonate 
• 110-89-4 piperidine 
• 865-47-4 potassium tert-butylate 
• 67-68-5 dimethyl sulfoxide 
• 52-28-8 codeine phosphate 
• 20736-11-2 codeine 6-glucuronide 

Downstream Products

• 467-98-1 thebainone 
• 476-68-6 6-methoxy-4-(2-methylamino-ethyl)-phenanthrene-1,5-diol 
• 510-66-7 4-hydroxy-3-methoxy-17-methyl-14,15-cyclo-13,15-seco-morphin-5⁽¹³⁾-en-6-one 
• 76-57-3 codeine 
• 86537-89-5 C₂₇H₃₃NO₄ 
• 86537-84-0 C₂₉H₃₃NO₄ 
• 115-37-7 thebaine 
• 57-27-2 MORPHIN 
• 125-29-1 Hydrocodone 
• 6703-27-1 6-acetylcodeine 
• 478-53-5 Morphothebaine 
• 125-29-1 4,5α-epoxy-3-methoxy-17-methyl-morphinan-6-one 
• 508-54-3 14-hydroxycodeinone 
• 72707-00-7 8β-phenyldihydrocodeinone 

Relevant articles and documents

Combined biological and chemical catalysis in the preparation of oxycodone

The opioid oxycodone was produced from codeine, using a combination of chemical and biological catalysis. The use of novel functionalized ionic liquids permitted this reaction to be performed in a single solvent.

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Transformation of codeine and codeine-6-glucuronide to opioid analogues by urine adulteration with pyridinium chlorochromate: Potential issue for urine drug testing

Rationale: Pyridinium chlorochromate (PCC) is the active ingredient of 'Urine Luck', a commercially available in vitro adulterating agent used to conceal the presence of drugs in a urine specimen. The exposure of codeine and its major glucuronide metabolite codeine-6-glucuronide (C6G) to PCC was investigated to determine whether PCC is an effective masking agent for these opiate compounds. Methods: Following the addition of PCC to both spiked and authentic codeine and C6G-positive urine specimens, the samples were monitored using liquid chromatography/mass spectrometry (LC/MS). Stable reaction products were identified and characterized using high-resolution MS analysis and, where possible, nuclear magnetic resonance (NMR) analysis. Results: It was determined that PCC effectively oxidizes codeine and C6G, thus altering the original codeine-to-C6G ratio in the urine specimen. Four reaction products were identified for codeine: codeinone, 14-hydroxycodeinone, 6-O-methylcodeine and 8-hydroxy-7,8-dihydrocodeinone. Similarly, three reaction products were identified for C6G: codeinone, codeine and a lactone of C6G (tentative assignment). Conclusions: Besides addressing the complications added to interpretation, more investigation is warranted to further determine their potential for use as markers for monitoring the presence of codeine and C6G in urine specimens adulterated with PCC. Copyright

Compositions and Methods For Making Alkaloid Morphinans

Methods that may be used for the manufacture of a class of chemical compounds known as morphinans, including neopine, are provided. Compositions useful for the synthesis of morphinans, including neopine, are also provided.