Codeine

Base Information Edit

Chemical Name:Codeine
CAS No.:76-57-3
Molecular Formula:C18H21 N O3
Molecular Weight:299.37
Hs Code.:2939110012
European Community (EC) Number:200-969-1
UNII:UX6OWY2V7J
DSSTox Substance ID:DTXSID2020341
Nikkaji Number:J4.178E
Wikipedia:Codeine
Wikidata:Q174723
NCI Thesaurus Code:C383,C77284
RXCUI:2670,1545976
Pharos Ligand ID:MFTT55MXH58M
Metabolomics Workbench ID:42703
ChEMBL ID:CHEMBL485
Mol file:76-57-3.mol

Synonyms:Ardinex;Codeine;Codeine Phosphate;Isocodeine;Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5alpha,6alpha)-;N Methylmorphine;N-Methylmorphine

This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Codeine Edit

Chemical Property:

Appearance/Colour:white crystalline powder
Vapor Pressure:2.47E-09mmHg at 25°C
Melting Point:154 - 156 C
Refractive Index:1.5500 (estimate)
Boiling Point:462°C at 760 mmHg
PKA:8.21(at 25℃)
Flash Point:75 C
PSA：41.93000
Density:1.34g/cm³
LogP:1.43900
Storage Temp.:2-8°C
Solubility.:Soluble in boiling water, freely soluble in ethanol (96 per cent).
Water Solubility.:47.62g/L(25 oC)
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:299.15214353
Heavy Atom Count:22
Complexity:509

Purity/Quality:

Safty Information:

Pictogram(s): Habit-forming narcotic, sale legally restricted.
Hazard Codes:F,T
Statements: 11-23/24/25-39/23/24/25
Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

Chemical Classes:Biological Agents -> Plant Toxins
Drug Classes:Opioids
Canonical SMILES:CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)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
Recent ClinicalTrials:Paracetamol Vs Caffeine Vs Codeine in the Management of Post Traumatic Pain in Emergencies
Recent EU Clinical Trials:PREemptive Pharmacogenomic testing for Preventing Adverse drug REactions
Description Codein phosphate and hydrochloride caused contact dermatitis in a worker in the production of opium alkaloids. Codeine bitartrate caused contact dermatitis in a worker in the production of concentrated poppy straw. Codeine was a sensitizer in a laboratory worker at an opiate-manufacturing pharmaceutical company, also sensitive to the baine. Codeine (CRM) (Item No. ISO60140) is a certified reference material categorized as an opioid. Like other opioid analgesics, codeine is commonly abused. Codeine is regulated as a Schedule II compound in the United States. Codeine (CRM) (Item No. ISO60140) is provided as a DEA exempt preparation. This product is intended for research and forensic applications.
Uses Codeine is derived from opium by extraction or by the methylation of morphine. For medical use, codeine is usually offered as the dichloride, phosphate, or sulfate. Codeine is habit forming. Codeine is known to exacerbate urticaria (familiarly known as hives). Since codeine is incorporated in numerous prescription medicines for headache, heartburn, fatigue, coughing, and relief of aches and pains, persons with a history of urticaria should make this fact known to their physician. Codeine is sometimes used in cases of acute pericarditis to relieve severe chest pains in early phases of disease. Codeine is sometimes used in drug therapy of renal (kidney) diseases. Codeine is used in medicine for its narcoticanalgesic action. It is used as a sedative incough mixtures. Codeine occurs in opiumfrom 0.7% to 2.5%. It is prepared frommorphine by methylating the phenolic OHgroup of the morphine. It is also obtained byextraction of opium.
Biological Functions Like morphine, codeine is a naturally occurring opioid found in the poppy plant. Codeine is indicated for the treatment of mild to moderate pain and for its antitussive effects. It is widely used as an opioid antitussive because at antitussive doses it has few side effects and has excellent oral bioavailability. Codeine is metabolized in part to morphine, which is believed to account for its analgesic effect. It is one of the most commonly used opioids in combination with nonopioids for the relief of pain. The administration of 30 mg of codeine in combination with aspirin is equivalent in analgesic effect to the administration of 65 mg of codeine. The combination of the drugs has the advantage of reducing the amount of opioid required for pain relief and abolition of the pain via two distinct mechanisms, inhibition of prostanoid synthesis and opioid inhibition of nociceptive transmission. When given alone, orally administered codeine has about one-tenth to one-fifth the potency of morphine for the relief of pain. In addition, IV codeine has a greater tendency to release histamine and produce vasodilation and hypotension than does morphine. Thus, the use of IV codeine is rare. Codeine is rarely addictive and produces little euphoria.

Technology Process of Codeine

There total 59 articles about Codeine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%