U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H21NO3
Molecular Weight 299.3642
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CODEINE ANHYDROUS

SMILES

[H][C@@]12OC3=C4C(C[C@H]5N(C)CC[C@@]14[C@@]5([H])C=C[C@@H]2O)=CC=C3OC

InChI

InChIKey=OROGSEYTTFOCAN-DNJOTXNNSA-N
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

HIDE SMILES / InChI
Molecular Formula C18H21NO3
Molecular Weight 299.3642
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Codeine is an opiate used to manage mild to moderate pain severe enough to require an opioid. Codeine is a selective agonist for the mu opioid receptor and has an affinity to delta and kappa-opioid receptors. In some countries, this drug is regulated under various narcotic control laws, because its chronic use can cause physical dependence. In others, it is available without a medical prescription in combination with paracetamol.

CNS Activity

Approval Year

1921
1467
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 6.1 µM [EC50]
Kappa-type opioid receptor
60
Target ID: P41145
Gene ID: 4986.0
Gene Symbol: OPRK1
Target Organism: Homo sapiens (Human)
Agonist
2678
Delta-type opioid receptor
45
Target ID: P41143
Gene ID: 4985.0
Gene Symbol: OPRD1
Target Organism: Homo sapiens (Human)
Agonist
2678
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
CAPITAL AND CODEINE

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
ABI Chem
AC1Q4DTD
AN PharmaTech
AN-23899
Alfa Chemistry
170301
Alfa Chemistry
ACM52453040
Angene
AGN-PC-0U9ZUU
Aurora Fine Chemicals LLC
A17.876.233
http://online.aurorafinechemicals.com/info?ID=A17.876.233
Avantor Inc
75835-236
https://us.vwr.com/store/product/21998648/exempted-drug-of-abuse-reference-standards-restek
Changzhou Highassay Chemical Co., Ltd
my_sub1415
ChemMol
30101025
http://www.chemmol.com/chemmol/30101025.html
ChemMol
49416695
http://www.chemmol.com/chemmol/49416695.html
ChemMol
99138769
http://www.chemmol.com/chemmol/99138769.html
Chemieliva Pharmaceutical Co., Ltd
PBCM0821173
Clearsynth
CS-T-56966
http://www.clearsynth.com/en/CST56966.html
Compound Cloud
21155870
Compound Cloud
24892867
Compound Cloud
5284371
Compound Cloud
5362471
Compound Cloud
6321303
Hangzhou APIChem Technology
AC-11114
HongKong Chemhere
SCA54117
IBScreen
BB_NC-00138
IBScreen
STOCK1N-42851
LGC Standards
LGCAMP0004.10-01
https://www.lgcstandards.com/US/en/p/LGCAMP0004.10-01
LGC Standards
LGCAMP0004.10-02
https://www.lgcstandards.com/US/en/p/LGCAMP0004.10-02
LGC Standards
LGCFOR0004.10
https://www.lgcstandards.com/US/en/p/LGCFOR0004.10
LGC Standards
MM0004.10
https://www.lgcstandards.com/US/en/p/MM0004.10
Parchem
87121
https://www.parchem.com/chemical-supplier-distributor/Codeine-Alkaloid-087121.aspx
Parchem
87123
https://www.parchem.com/chemical-supplier-distributor/Codeine-USP-087123.aspx
Sigma Aldrich
C1653|SIAL
Sigma Aldrich
C3539|SIAL
Sigma Aldrich
C5901|SIAL
Sigma Aldrich
Y0000722
Sigma Aldrich
Y0000722|SIAL
Sigma-Aldrich
C-006_CERILLIAN
https://www.sigmaaldrich.com/catalog/product/cerillian/c006?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich
C1653_SIAL
https://www.sigmaaldrich.com/catalog/product/sial/c1653?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich
Y0000722_SIAL
https://www.sigmaaldrich.com/catalog/product/sial/y0000722?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule
S627560
https://www.smolecule.com/products/s627560
Tetrahedron
TS63993
Tetrahedron
TS80953
Toronto Research Chemicals
C634075
Toronto Research Chemicals
C634080
Toronto Research Chemicals
KIT0410
Toronto Research Chemicals
KIT2460
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.
PH-1498A
ZINC
ZINC000003806721
http://zinc15.docking.org/substances/ZINC000003806721
eMolecules
193733897
mcule
MCULE-4129237460
mcule
MCULE-6243921692
PubMed

PubMed

TitleDatePubMed
Over-the-counter medications for acute cough in children and adults in ambulatory settings.
2001
Dystonia as acute adverse reaction to cough suppressant in a 3-year-old girl.
2001
Angle closure risk from proprietary medicines.
2001 Apr
LC method for the analysis of acetylsalicylic acid, caffeine and codeine phosphate in pharmaceutical preparations.
2001 Apr
Randomized placebo controlled trial of lofexidine hydrochloride for chronic pelvic pain in women.
2001 Aug
Precipitated withdrawal following codeine administration is dependent on CYP genotype.
2001 Aug 17
[Paracetamol-codeine induced hepatic colic].
2001 Aug-Sep
LC method for the analysis of paracetamol, caffeine and codeine phosphate in pharmaceutical preparations.
2001 Dec
Effect of penicillin on postoperative endodontic pain and swelling in symptomatic necrotic teeth.
2001 Feb
Opiate-sensitivity: clinical characteristics and the role of skin prick testing.
2001 Jul
Use of beta-cyclodextrin in the capillary zone electrophoretic separation of the components of clandestine heroin preparations.
2001 Jul 27
Are cannabinoids an effective and safe treatment option in the management of pain? A qualitative systematic review.
2001 Jul 7
Heroin use by motorists in Sweden confirmed by analysis of 6-acetylmorphine in urine.
2001 Jul-Aug
Laboratory analysis of remotely collected oral fluid specimens for opiates by immunoassay.
2001 Jul-Aug
[Chronic pain in geriatrics].
2001 Jun
Myth: codeine is a powerful and effective analgesic.
2001 Jun
Oral ibuprofen versus paracetamol plus codeine for analgesia after ambulatory surgery.
2001 Jun
Ulcerated hemangiomas: clinical characteristics and response to therapy.
2001 Jun
Time of drug elimination in chronic drug abusers. Case study of 52 patients in a "low-step" detoxification ward.
2001 Jun 15
[Information on preparations containing codeine].
2001 Jun 20
Codeine phosphate in paediatric medicine.
2001 Mar
Codeine phosphate in children: time for re-evaluation?
2001 Mar
Myocardial Infarction associated with methadone and/or dihydrocodeine.
2001 Mar
Acetylcodeine as a marker of illicit heroin in human hair: method validation and results of a pilot study.
2001 Mar
Opiate use to control bowel motility may induce chronic daily headache in patients with migraine.
2001 Mar
Audit of pain management at home following tonsillectomy in children.
2001 Mar
Treatment of severe pain from osteoarthritis with slow-release tramadol or dihydrocodeine in combination with NSAID's: a randomised study comparing analgesia, antinociception and gastrointestinal effects.
2001 Mar
Dextromethorphan is an effective cough suppressant.
2001 May
Effect of an enteric-release formulation of naloxone on intestinal transit in volunteers taking codeine.
2001 May
The analgesic effect of codeine as compared to imipramine in different human experimental pain models.
2001 May
From codeine to transdermal fentanyl for cancer pain control: a safety and efficacy clinical trial.
2001 May-Jun
Application of liquid chromatography to the simultaneous determination of acetylsalicylic acid, caffeine, codeine, paracetamol, pyridoxine, and thiamine in pharmaceutical preparations.
2001 May-Jun
Scalp nerve blocks decrease the severity of pain after craniotomy.
2001 Nov
Concentration ratios of morphine to codeine in blood of impaired drivers as evidence of heroin use and not medication with codeine.
2001 Nov
The role of adrenal corticosteroids in induction of micronuclei by morphine.
2001 Nov 15
Nutritional effects of surgical and medical treatment for short bowel syndrome.
2001 Nov-Dec
Novel dynamic polymer coating for capillary electrophoresis in nonaqueous methanolic background electrolytes.
2001 Oct
Seizures with intravenous codeine phosphate.
2001 Oct
Incorporation of selegiline metabolites into hair after oral selegiline intake.
2001 Oct
Ropivacaine with or without clonidine improves pediatric tonsillectomy pain.
2001 Oct
Drug contamination of US paper currency.
2001 Oct 1
Spontaneous reports on drug-induced pancreatitis in Denmark from 1968 to 1999.
2001 Sep
Community pharmacists' experience of over-the-counter medicine misuse in Scotland.
2001 Sep
Blind trials of an onsite saliva drug test for marijuana and opiates.
2001 Sep
[Weak opioids].
2001 Sep
[Strong opioids].
2001 Sep
Concentration ratios of codeine-to-morphine in plasma after a single oral dose (100 mg) of codeine phosphate.
2001 Sep
Detection of non-prescription heroin markers in urine with liquid chromatography-atmospheric pressure chemical ionization mass spectrometry.
2001 Sep
Can standard open pediatric urological procedures be performed on an outpatient basis?
2001 Sep
Experience with urine drug testing by the Correctional Service of Canada.
2001 Sep 15
Patents

Patents

05869669
14
08337890
16
08710069
12
08790700
16
JP2002104963A
12
JP2002511777A
414
JP2006520379A
72
JP2009520033A
20
JP2011507842A
17
JP4804361B2
32
JPH00286794A
24
JPS5323998A
14
JPS572288A
16

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:30:15 GMT 2023
Edited
by admin
on Fri Dec 15 16:30:15 GMT 2023
Record UNII
UX6OWY2V7J
Record Status Validated (UNII)
Record Version
  • Download
Related Record Type
Name Type Language
CODEINE ANHYDROUS
Common Name English
MYTUSSIN
Common Name English
ETHYLMORPHINE HYDROCHLORIDE IMPURITY C [EP IMPURITY]
Common Name English
IDS-NC-005(SECT.-2)
Code English
CODEINE [HSDB]
Common Name English
CODEINE [MI]
Common Name English
SS85U8K5ZN
Common Name English
KODELAK FITO
Common Name English
MORPHINE MONOMETHYL ETHER
Common Name English
HYDROCODONE HYDROGEN TARTRATE 2.5-HYDRATE IMPURITY C [EP IMPURITY]
Common Name English
7,8-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan-6α-ol
Systematic Name English
O3-METHYLMORPHINE
Common Name English
CODICEPT
Common Name English
DIHYDROCODEINE HYDROGEN TARTRATE IMPURITY A [EP IMPURITY]
Common Name English
Codeine [WHO-DD]
Common Name English
METHYLMORPHINE
Common Name English
CODUCEPT
Common Name English
MORPHINAN-6-OL, 7,8-DIDEHYDRO-4,5-EPOXY-3-METHOXY-17-METHYL-, (5.ALPHA.,6.ALPHA.)-
Systematic Name English
MORPHINE SULFATE IMPURITY A [EP IMPURITY]
Common Name English
MORPHINE HYDROCHLORIDE IMPURITY A [EP IMPURITY]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175690
Created by admin on Fri Dec 15 16:30:16 GMT 2023 , Edited by admin on Fri Dec 15 16:30:16 GMT 2023
NDF-RT N0000175684
Created by admin on Fri Dec 15 16:30:16 GMT 2023 , Edited by admin on Fri Dec 15 16:30:16 GMT 2023
CFR 21 CFR 862.3270
Created by admin on Fri Dec 15 16:30:16 GMT 2023 , Edited by admin on Fri Dec 15 16:30:16 GMT 2023
DEA NO. 9050
Created by admin on Fri Dec 15 16:30:16 GMT 2023 , Edited by admin on Fri Dec 15 16:30:16 GMT 2023
WHO-ATC N02AJ09
Created by admin on Fri Dec 15 16:30:16 GMT 2023 , Edited by admin on Fri Dec 15 16:30:16 GMT 2023
Code System Code Type Description
DRUG BANK
DB00318
Created by admin on Fri Dec 15 16:30:16 GMT 2023 , Edited by admin on Fri Dec 15 16:30:16 GMT 2023
PRIMARY
SMS_ID
100000079790
Created by admin on Fri Dec 15 16:30:16 GMT 2023 , Edited by admin on Fri Dec 15 16:30:16 GMT 2023
PRIMARY
CAS
76-57-3
Created by admin on Fri Dec 15 16:30:16 GMT 2023 , Edited by admin on Fri Dec 15 16:30:16 GMT 2023
PRIMARY
NCI_THESAURUS
C171855
Created by admin on Fri Dec 15 16:30:16 GMT 2023 , Edited by admin on Fri Dec 15 16:30:16 GMT 2023
ALTERNATIVE
ECHA (EC/EINECS)
200-969-1
Created by admin on Fri Dec 15 16:30:16 GMT 2023 , Edited by admin on Fri Dec 15 16:30:16 GMT 2023
PRIMARY
PUBCHEM
5284371
Created by admin on Fri Dec 15 16:30:16 GMT 2023 , Edited by admin on Fri Dec 15 16:30:16 GMT 2023
PRIMARY
MERCK INDEX
m3718
Created by admin on Fri Dec 15 16:30:16 GMT 2023 , Edited by admin on Fri Dec 15 16:30:16 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C77284
Created by admin on Fri Dec 15 16:30:16 GMT 2023 , Edited by admin on Fri Dec 15 16:30:16 GMT 2023
PRIMARY
CHEBI
16714
Created by admin on Fri Dec 15 16:30:16 GMT 2023 , Edited by admin on Fri Dec 15 16:30:16 GMT 2023
PRIMARY
EPA CompTox
DTXSID2020341
Created by admin on Fri Dec 15 16:30:16 GMT 2023 , Edited by admin on Fri Dec 15 16:30:16 GMT 2023
PRIMARY
DAILYMED
UX6OWY2V7J
Created by admin on Fri Dec 15 16:30:16 GMT 2023 , Edited by admin on Fri Dec 15 16:30:16 GMT 2023
PRIMARY
RXCUI
236131
Created by admin on Fri Dec 15 16:30:16 GMT 2023 , Edited by admin on Fri Dec 15 16:30:16 GMT 2023
ALTERNATIVE
RXCUI
1545976
Created by admin on Fri Dec 15 16:30:16 GMT 2023 , Edited by admin on Fri Dec 15 16:30:16 GMT 2023
PRIMARY
HSDB
3043
Created by admin on Fri Dec 15 16:30:16 GMT 2023 , Edited by admin on Fri Dec 15 16:30:16 GMT 2023
PRIMARY
EVMPD
SUB127261
Created by admin on Fri Dec 15 16:30:16 GMT 2023 , Edited by admin on Fri Dec 15 16:30:16 GMT 2023
PRIMARY
EVMPD
SUB13424MIG
Created by admin on Fri Dec 15 16:30:16 GMT 2023 , Edited by admin on Fri Dec 15 16:30:16 GMT 2023
PRIMARY
FDA UNII
UX6OWY2V7J
Created by admin on Fri Dec 15 16:30:16 GMT 2023 , Edited by admin on Fri Dec 15 16:30:16 GMT 2023
PRIMARY
Related Record Type Details
Structure of CODEINE HYDROBROMIDE
SALT/SOLVATE -> PARENT
Structure of CODEINE PHOSPHATE ANHYDROUS
SALT/SOLVATE -> PARENT
Structure of CODEINE SULFATE
SALT/SOLVATE -> PARENT
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Structure of CODEINE PHOSPHATE
SALT/SOLVATE -> PARENT
Structure of CODEINE
SOLVATE->ANHYDROUS
Structure of CODEINE SULFATE ANHYDROUS
SALT/SOLVATE -> PARENT
Structure of CODEINE METHYL BROMIDE
SALT/SOLVATE -> PARENT
URIDINE DIPHOSPHATE GLUCURONOSYLTRANSFERASE 2B4
METABOLIC ENZYME -> SUBSTRATE
CODEINE POLISTIREX
SUB_CONCEPT->SUBSTANCE
Structure of CODEINE
SALT/SOLVATE -> PARENT
Structure of CODEINE PHOSPHATE SESQUIHYDRATE
SALT/SOLVATE -> PARENT
URIDINE DIPHOSPHATE GLUCURONOSYLTRANSFERASE 2B7
METABOLIC ENZYME -> SUBSTRATE
Structure of CODEINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
CYTOCHROME P450 2D6
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
Structure of CODEINONE
METABOLITE -> PARENT
Structure of NORCODEINE
METABOLITE INACTIVE -> PARENT
Metabolic Enzyme - cytochrome P-450 3A4
Structure of CODEINE-6-GLUCURONIDE
METABOLITE ACTIVE -> PRODRUG
MAJOR METABOLITE MAY BE RESPONSIBLE FOR ANALGESIC EFFECT
MAJOR
Structure of MORPHINE
METABOLITE ACTIVE -> PRODRUG
MINOR METABOLITE
MINOR
Related Record Type Details
Structure of ETHYLMORPHINE HYDROCHLORIDE
PARENT -> IMPURITY
Structure of ETHYLMORPHINE HYDROCHLORIDE DIHYDRATE
PARENT -> IMPURITY
Structure of DIHYDROCODEINE BITARTRATE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of HYDROCODONE BITARTRATE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of MORPHINE SULFATE
PARENT -> IMPURITY
UNSPECIFIED
EP
Structure of MORPHINE HYDROCHLORIDE
PARENT -> IMPURITY
Related Record Type Details
Structure of CODEINE ANHYDROUS
ACTIVE MOIETY
NIH
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