kodein

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

opioid använd för smärtlindring

OverviewAI-generated

Codeine is a chemical compound with the formula C₁₈H₂₁NO₃. Its IUPAC name is (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. The substance has a mass of 299.152 and a weight of 299.4. It carries a defined daily dose of 0.1.

Chemical properties include an xlogp of 1.1 and a tpsa of 41.9. The molecule contains one hydrogen bond donor and four hydrogen bond acceptors, with a charge of 0. It is referenced by 1,577 other encyclopedia articles.

Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still 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

Article · Svenska

Kodein, C18H21NO3, är ett smärtstillande ämne, ett morfinderivat, tillhörande gruppen opiater. Kodein är en av de naturliga opiaterna i opiumvallmo. Jämfört med de besläktade ämnena heroin och morfin, har kodein lägre potens. Den biokemiska förklaringen till att kodeins verkan är densamma som den för morfin, är att kodein omvandlas till morfin i kroppen.

Abstract from DBpedia / Wikipedia · CC BY-SA

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kodein