Codeine monohydrate

Cat. No.: B1239579

CAS No.: 6059-47-8

M. Wt: 299.4 g/mol

InChI Key: OROGSEYTTFOCAN-DNJOTXNNSA-N

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Overview

1. Description

6. Properties

2. Preparation methods

7. Retrosynthesis analysis

3. Scientific research applications

8. Q & A

4. Mechanism of action

9. Disclaimer

5. Comparison with similar compounds

Description

Codeine is a naturally occurring alkaloid found in the sap of the opium poppy, Papaver somniferum. It is an opiate and a prodrug of morphine, primarily used to treat pain, coughing, and diarrhea . Codeine is commonly used in medicine due to its analgesic, antitussive, and antidiarrheal properties .

Preparation Methods

Synthetic Routes and Reaction Conditions: This involves reacting morphine with trimethyl phenyl ammonium chloride in the presence of an alkali metal carbonate and a hydrocarbon solvent at temperatures ranging from 40°C to 120°C .

Industrial Production Methods: In industrial settings, codeine is often extracted from opium or synthesized from morphine. The extraction process involves isolating morphine from opium and then converting it to codeine through methylation .

Types of Reactions:

Oxidation: Codeine can undergo oxidation to form codeinone.

Reduction: Codeine can be reduced to dihydrocodeine.

Substitution: Codeine can undergo substitution reactions, such as N-demethylation to form norcodeine.

Common Reagents and Conditions:

Oxidation: Reagents like potassium permanganate or chromium trioxide.

Reduction: Reagents like hydrogen in the presence of a palladium catalyst.

Substitution: Reagents like sodium hydroxide for N-demethylation.

Major Products:

Oxidation: Codeinone.

Reduction: Dihydrocodeine.

Substitution: Norcodeine.

Scientific Research Applications

Codeine has a wide range of applications in scientific research:

Chemistry: Used as a reference compound in the synthesis of other opioids.

Biology: Studied for its effects on the central nervous system.

Medicine: Used in pain management, cough suppression, and treatment of diarrhea.

Industry: Utilized in the production of various pharmaceutical formulations.

Mechanism of Action

Codeine exerts its effects by binding to the mu-opioid receptors in the brain and spinal cord. This binding results in the inhibition of nociceptive neurotransmitter release, leading to analgesia and increased pain tolerance . Codeine is metabolized in the liver by the enzyme cytochrome P450 2D6 to form morphine, which is responsible for its analgesic effects .

Comparison with Similar Compounds

Morphine: A more potent analgesic with a higher risk of addiction.

Hydrocodone: Similar to codeine but more potent and often used for severe pain.

Oxycodone: Another potent opioid used for managing moderate to severe pain.

Uniqueness of Codeine: Codeine is unique in its relatively mild potency and lower risk of addiction compared to other opioids like morphine and oxycodone. It is often preferred for treating mild to moderate pain and cough due to its favorable safety profile .

Properties

CAS No.	6059-47-8
Molecular Formula	C18H21NO3
Molecular Weight	299.4 g/mol
IUPAC Name	(4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol
InChI	InChI=1S/C18H21NO3/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,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1
InChI Key	OROGSEYTTFOCAN-DNJOTXNNSA-N
SMILES	CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)O.O
Isomeric SMILES	CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)O
Canonical SMILES	CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)O
boiling_point	482 °F at 22 mmHg (sublimes) (NTP, 1992) BP: 250 °C at 22 mm Hg
Color/Form	Orthorhombic crystals from water, dilute alcohol, ether Colorless or white crystals or powde
density	1.32 at 68 °F (NTP, 1992) - Denser than water; will sink
flash_point	167 °F (NTP, 1992)
melting_point	309 to 313 °F (after drying at 176 °F) (NTP, 1992) 154-156 157.5 °C
	6059-47-8
physical_description	Codeine appears as colorless to white crystalline solid or white powder. Sublimes at 284 °F. Odorless. Bitter taste. pH (saturated aqueous solution) 9.8. (NTP, 1992) Solid
Pictograms	Acute Toxic; Irritant; Health Hazard
Related CAS	41444-62-6 (PO4)
solubility	less than 1 mg/mL at 70 °F (NTP, 1992) soluble in water Soluble in water Slightly soluble in water Soluble in ethyl ether, benzene, chloroform, toluene; very soluble in ethanol; insoluble in petroleum ether Soluble in alcohol and chloroform 0.577 g/L
Synonyms	Ardinex Codeine Codeine Phosphate Isocodeine N Methylmorphine N-Methylmorphine
Origin of Product	United States

Retrosynthesis Analysis

AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.

One-Step Synthesis Focus: Specifically designed for one-step synthesis, it provides concise and direct routes for your target compounds, streamlining the synthesis process.

Accurate Predictions: Utilizing the extensive PISTACHIO, BKMS_METABOLIC, PISTACHIO_RINGBREAKER, REAXYS, REAXYS_BIOCATALYSIS database, our tool offers high-accuracy predictions, reflecting the latest in chemical research and data.

Strategy Settings

Precursor scoring	Relevance Heuristic
Min. plausibility	0.01
Model	Template_relevance
Template Set	Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis
Top-N result to add to graph	6

Feasible Synthetic Routes

Reactant of Route 1

Codeine monohydrate

Reactant of Route 2

Codeine monohydrate

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Codeine monohydrate

Reactant of Route 4

Codeine monohydrate

Reactant of Route 5

Codeine monohydrate

Reactant of Route 6

Codeine monohydrate

Customer

Q & A

Q1: What structural information about codeine monohydrate, codeine (anhydrous), and dihydrocodeinone is available from the research paper?

A1: The research paper titled "UNIT CELL, SPACE GROUP, AND INDEXED X-RAY DIFFRACTION POWDER DATA FOR CERTAIN NARCOTICS: I. This compound, CODEINE (ANHYDROUS), DIHYDROCODEINONE" [] investigates the crystallographic properties of these compounds. This includes determining the unit cell parameters, space group, and indexed X-ray diffraction powder data. This information is crucial for understanding the arrangement of molecules within the crystal lattice, which can influence properties such as stability, solubility, and bioavailability.

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Please be aware that all articles and product information presented on BenchChem are intended solely for informational purposes. The products available for purchase on BenchChem are specifically designed for in-vitro studies, which are conducted outside of living organisms. In-vitro studies, derived from the Latin term "in glass," involve experiments performed in controlled laboratory settings using cells or tissues. It is important to note that these products are not categorized as medicines or drugs, and they have not received approval from the FDA for the prevention, treatment, or cure of any medical condition, ailment, or disease. We must emphasize that any form of bodily introduction of these products into humans or animals is strictly prohibited by law. It is essential to adhere to these guidelines to ensure compliance with legal and ethical standards in research and experimentation.

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