codeine

Also known as Codicept®, methylmorphine, morphine 3-methyl ether, morphine monomethyl ether, morphine-3-methyl ether, O(3)-methylmorphine, l-codeine, codeine anhydrous

AI overview

Codeine is an opiate derived from the opium poppy plant that doctors use to treat mild to moderate pain, coughing, and diarrhea, often in combination with other medications like paracetamol or ibuprofen. Because it is an opiate, codeine carries risks of recreational misuse and addiction, which is why its use—particularly for cough suppression in children—is increasingly restricted in many countries.

AI-generated from the Wikipedia summary — may contain errors.

Key facts

Drug.image: Codeine Structure.svg
Drug.image_class: skin-invert-image
Drug.width: 175
Drug.alt: Skeletal formula
Drug.image2: Codeine molecule ball.png
Drug.image_class2: bg-transparent
Drug.alt2: Ball-and-stick model
Drug.MedlinePlus: a682065
Drug.DailyMedID: Codeine
Drug.pregnancy_AU: A
Drug.dependency_liability: High
Drug.addiction_liability: High
Drug.routes_of_administration: By mouth, rectal, subcutaneous, intramuscular
Drug.ATC_prefix: R05
Drug.ATC_suffix: DA04
Drug.ATC_supplemental: Combinations: , , , ,
Drug.legal_AU: S8
Drug.legal_AU_comment: / S4 (Prescription only)

via Wikipedia infobox

Chemical data

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
SMILES: CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)O
InChIKey: OROGSEYTTFOCAN-DNJOTXNNSA-N
XLogP: 1.1
Polar surface area: 41.9 Å²
H-bond donors: 1
H-bond acceptors: 4
Formal charge: 0

via PubChem

Research

11,315 papers

A Review of Analytical Methods for Codeine Determination.ReviewMolecules (Basel, Switzerland) · 2021Pratiwi R, Noviana E, Fauziati R et al.DOI: 10.3390/molecules26040800
Codeine, cough and upper respiratory infection.ReviewPulmonary pharmacology · 1996Eccles RDOI: 10.1006/pulp.1996.0038
Concise Total Synthesis of (-)-Codeine.The Journal of organic chemistry · 2024Mondal A, Pal S, Khatua A et al.DOI: 10.1021/acs.joc.4c01452
Codeine sensitivity.British medical journal · 1951MACKENZIE GKDOI: 10.1136/bmj.1.4701.281
Identifying and treating codeine dependence: a systematic review.The Medical journal of Australia · 2018Nielsen S, MacDonald T, Johnson JLDOI: 10.5694/mja17.00749
Codeine analgesia is due to codeine-6-glucuronide, not morphine.ReviewInternational journal of clinical practice · 2000Vree TB, van Dongen RT, Koopman-Kimenai PM
A software tool to adjust codeine dose based on CYP2D6 gene-pair polymorphisms and drug-drug interactions.ReviewThe pharmacogenomics journal · 2023Saab Y, Nakad ZDOI: 10.1038/s41397-023-00318-7
The pharmacogenetics of codeine hypoalgesia.ReviewPharmacogenetics · 1995Sindrup SH, Brøsen KDOI: 10.1097/00008571-199512000-00001

via PubMed

Wikidata facts

Mass: 299.152

Show 6 more facts

chemical formula: C₁₈H₂₁NO₃
Commons category: Codeine
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
World Health Organisation international non-proprietary name: codeine
defined daily dose: 0.1

Sources (6)

via Wikidata · CC0

~30 min read

Article

44 sections

Contents

Medical uses
Pain
Cough
Diarrhea
Formulations
Side effects
Breastfeeding
Withdrawal and dependence
Pharmacology
Pharmacodynamics
Mechanism of action
Pharmacokinetics
Chemistry
Relation to other opioids
History
Society and culture
Names
Recreational use
Detection
Legal status
Australia
Canada
Denmark
Estonia
Ethiopia
France
Greece
Hong Kong
India
Ireland
Italy
Japan
Latvia
Nigeria
South Africa
United Arab Emirates
United Kingdom
United States
Schedule V controlled substances
Veterinary use
References
Notes
Further reading
External links

Codeine is an opiate and prodrug of morphine mainly used to treat pain, coughing, and diarrhea. It is commonly used as a recreational drug. It is found naturally in the sap of the opium poppy, Papaver somniferum. It is typically used to treat mild to moderate degrees of pain. Greater benefit may occur when combined with paracetamol (acetaminophen) as codeine/paracetamol or a nonsteroidal anti-inflammatory drug (NSAID) such as aspirin or ibuprofen. Evidence does not support its use for acute cough suppression in children. In Europe, it is not recommended as a cough medicine for those under 12 years of age. It is generally taken orally. It usually starts working after half an hour, with maximum effect at two hours. Its effects last for about four to six hours. Codeine exhibits abuse potential similar to other opioid medications, including a risk of addiction and overdose.

Common side effects include nausea, vomiting, constipation, itchiness, lightheadedness, and drowsiness. Serious side effects may include breathing difficulties and addiction. Whether it can be used safely during pregnancy is unclear. Care should be used during breastfeeding, as it may result in opiate toxicity in the baby. Its use as of 2016 is not recommended for children. Codeine works by being broken down by the liver into morphine; how quickly this occurs depends on a person's genetics.