Codeine

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Skeletal formula
Ball-and-stick model
Codeine
Systematic (IUPAC) name
(5α,6α)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol
Identifiers
CAS number 76-57-3
ATC code R05DA04 Combinations: N02AA59, N02AA79, N02AJ08, N02AJ06, N02AJ07
PubChem 5284371
DrugBank DB00318
ChemSpider 4447447
Chemical data
Formula C18H21Template:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxNTemplate:OrganicBoxO3Template:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBox 
Mol. mass ?
Synonyms 3-Methylmorphine
Pharmacokinetic data
Bioavailability c. 60% (by mouth)[1]
Metabolism Liver: CYP2D6 (to morphine), CYP3A4 (to norcodeine), UGT2B7 (to 3- and 6-glucuronides of codeine, norcodeine, and morphine)[2]
Half life 2.5–3 hours
Excretion ?
Therapeutic considerations
Licence data

US Daily Med:link

Pregnancy cat.

A(AU)

Legal status

Controlled (S8)(AU) Schedule I(CA) Class B(UK) Schedule II(US)

Dependence Liability High
Routes By mouth, rectal, subcutaneous, intramuscular

Codeine is an opiate drug. In the human body, it is made into morphine by the liver (a prodrug). It is the morphine that gives codeine its effects. It is mainly used to treat pain, coughing, and diarrhea. It is also commonly used as a recreational drug. It is found in the sap of the opium poppy, Papaver somniferum.[3][4]

It is usually used to treat lower amounts of pain than morphine is used for.[3] It might work better if mixed with paracetamol (acetaminophen) as codeine/paracetamol or a nonsteroidal anti-inflammatory drug (NSAID) such as aspirin or ibuprofen.[3] It should not be used for coughs in children.[5][6] It is usually taken by mouth.[3] It typically starts working after half an hour, working best two hours after taking.[3] It lasts for about four to six hours overall. Codeine can be addictive and too much can cause overdose.[3]

Common side effects are nausea, vomiting, constipation, itchiness, lightheadedness, and sleepiness.[3] Codeine was first found in 1832 by Pierre Jean Robiquet.[7] It is on the World Health Organization's List of Essential Medicines.[8] Codeine makes up about 2% of opium.[7]

Codeine Media

  • The recreational drug lean can be created with codeine syrup (pictured).

References

  1. ↑ Kelley and Firestein's Textbook of Rheumatology (21 June 2016)Elsevier Health Sciences. p. 1081–. ISBN 978-0-323-41494-4.
  2. ↑ Comparative metabolic capabilities and inhibitory profiles of CYP2D6.1, CYP2D6.10, and CYP2D6.17. Drug Metabolism and Disposition 35 (8) (August 2007). p. 1292–1300. doi:10.1124/dmd.107.015354.
  3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 3.6 CodeineThe American Society of Health-System Pharmacists. Retrieved 5 January 2016.
  4. ↑ Role of codeine in palliative care. Journal of Opioid Management 7 (5) (2010). p. 401–406. doi:10.5055/jom.2011.0081.
  5. ↑ Therapeutic options for acute cough due to upper respiratory infections in children. Lung 190 (1) (February 2012). p. 41–44. doi:10.1007/s00408-011-9319-y.
  6. ↑ Over-the-counter (OTC) medications for acute cough in children and adults in community settings. The Cochrane Database of Systematic Reviews 2014 (11) (November 2014). p. CD001831. doi:10.1002/14651858.CD001831.pub5.
  7. ↑ 7.0 7.1 Prescription Drug Abuse: A Reference Handbook (2015)ABC-CLIO. p. 20. ISBN 978-1-4408-3979-5.
  8. ↑ World Health Organization model list of essential medicines: 22nd list (2021) (2021). Geneva: World Health Organization.

Notes



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