CODEINE HYDROCHLORIDE

US Approved OTC

First marketed in 1921

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H21NO3.ClH.2H2O
Molecular Weight	371.856
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=AWFZELCPUGEQGQ-NLMNJOOOSA-N

InChI=1S/C18H21NO3.ClH.2H2O/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;1H;2*1H2/t11-,12+,13-,17-,18-;;;/m0.../s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://online.lexi.com/lco/medguides/622452.pdf | https://www.ncbi.nlm.nih.gov/pubmed/7885194

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

Targets

Primary Target	Pharmacology	Potency
Mu opioid receptor 221 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7885194 \| \|https://adisinsight.springer.com/drugs/800042774	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) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7885194	Agonist 2678
Delta-type opioid receptor 45 Target ID: P41143 Gene ID: 4985.0 Gene Symbol: OPRD1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7885194	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://online.lexi.com/lco/medguides/622452.pdf	Primary		Approved 8429	CAPITAL AND CODEINE Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Over-the-counter medications for acute cough in children and adults in ambulatory settings.	2001	11686998
Dystonia as acute adverse reaction to cough suppressant in a 3-year-old girl.	2001	11587381
[Guillain-Barre syndrome as a result of poisoning with a mixture of "kompot"(Polish heroin) and drugs].	2001	11450369
Determination of opiates in serum, saliva and hair addicted persons.	2001	11450354
Results of a phase-I/II randomized, masked, placebo-controlled trial of recombinant human interleukin-11 (rhIL-11) in the treatment of subjects with active rheumatoid arthritis.	2001	11438043
Pharmacological control of cough.	2001 Apr	11411376
Sticky business: patterns of procurement and misuse of prescription cough syrup in Houston.	2001 Apr-Jun	11476259
Simultaneous determination of codeine and ethyl morphine HCL in tablet formulations using LC.	2001 Aug	11451638
Precipitated withdrawal following codeine administration is dependent on CYP genotype.	2001 Aug 17	11513833
[Paracetamol-codeine induced hepatic colic].	2001 Aug-Sep	11481075
LC method for the analysis of paracetamol, caffeine and codeine phosphate in pharmaceutical preparations.	2001 Dec	11600297
Effect of prophylactic amoxicillin on endodontic flare-up in asymptomatic, necrotic teeth.	2001 Jan	11487166
Are cannabinoids an effective and safe treatment option in the management of pain? A qualitative systematic review.	2001 Jul 7	11440935
[Chronic pain in geriatrics].	2001 Jun	11488082
Effect of apical trephination on postoperative pain and swelling in symptomatic necrotic teeth.	2001 Jun	11487138
Successful withdrawal from analgesic abuse in a group of youngsters with chronic daily headache.	2001 Jun	11417614
Analysis of cocaine, benzoylecgonine, codeine, and morphine in hair by supercritical fluid extraction with carbon dioxide modified with methanol.	2001 Jun 1	11403274
[Information on preparations containing codeine].	2001 Jun 20	11488191
Codeine phosphate in paediatric medicine.	2001 Mar	11573533
Codeine phosphate in children: time for re-evaluation?	2001 Mar	11573519
Expression and activity of cell-wall-degrading enzymes in the latex of opium poppy, Papaver somniferum L.	2001 Mar	11414615
Dextromethorphan is an effective cough suppressant.	2001 May	11394377
[Analgesics-induced chronic renal failure in patients on dialysis therapy in Hungary].	2001 May 13	11419294
Capillary electrophoresis-electrospray ionization ion trap mass spectrometry for analysis and confirmation testing of morphine and related compounds in urine.	2001 May 4	11382295
Application of liquid chromatography to the simultaneous determination of acetylsalicylic acid, caffeine, codeine, paracetamol, pyridoxine, and thiamine in pharmaceutical preparations.	2001 May-Jun	11417630
Scalp nerve blocks decrease the severity of pain after craniotomy.	2001 Nov	11682413
Concentration ratios of morphine to codeine in blood of impaired drivers as evidence of heroin use and not medication with codeine.	2001 Nov	11673366
The role of adrenal corticosteroids in induction of micronuclei by morphine.	2001 Nov 15	11673078
Nutritional effects of surgical and medical treatment for short bowel syndrome.	2001 Nov-Dec	11688937
Novel dynamic polymer coating for capillary electrophoresis in nonaqueous methanolic background electrolytes.	2001 Oct	11699922
Seizures with intravenous codeine phosphate.	2001 Oct	11675848
Incorporation of selegiline metabolites into hair after oral selegiline intake.	2001 Oct	11599606
Analysis of morphine and codeine in samples adulterated with Stealth.	2001 Oct	11599602
Detection of opiate use in a methadone maintenance treatment population with the CEDIA 6-acetylmorphine and CEDIA DAU opiate assays.	2001 Oct	11599593
Ropivacaine with or without clonidine improves pediatric tonsillectomy pain.	2001 Oct	11587610
Drug contamination of US paper currency.	2001 Oct 1	11566423
Predictors for completing an inpatient detoxification program among intravenous heroin users, methadone substituted and codeine substituted patients.	2001 Oct 1	11543987
Endogenous morphine and codeine. Possible role as endogenous anticonvulsants.	2001 Oct 12	11595204
Spontaneous reports on drug-induced pancreatitis in Denmark from 1968 to 1999.	2001 Sep	11699619
Community pharmacists' experience of over-the-counter medicine misuse in Scotland.	2001 Sep	11688306
Cetirizine inhibits skin reactions but not mediator release in immediate and developing late-phase allergic cutaneous reactions. A double-blind, placebo-controlled study.	2001 Sep	11591187
Rofecoxib versus codeine/acetaminophen in postoperative dental pain: a double-blind, randomized, placebo- and active comparator-controlled clinical trial.	2001 Sep	11589259
Tramadol/acetaminophen combination tablets and codeine/acetaminophen combination capsules for the management of chronic pain: a comparative trial.	2001 Sep	11589258
Blind trials of an onsite saliva drug test for marijuana and opiates.	2001 Sep	11569567
[Weak opioids].	2001 Sep	11554054
[Strong opioids].	2001 Sep	11554052
Concentration ratios of codeine-to-morphine in plasma after a single oral dose (100 mg) of codeine phosphate.	2001 Sep	11550826
Detection of non-prescription heroin markers in urine with liquid chromatography-atmospheric pressure chemical ionization mass spectrometry.	2001 Sep	11550816
Pain control in medical abortion.	2001 Sep	11543752
Engineering novel biocatalytic routes for production of semisynthetic opiate drugs.	2001 Sep	11535415

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:00:50 GMT 2023` Edited by `admin` on `Fri Dec 15 17:00:50 GMT 2023`
Record UNII	NTZ53GG7XN
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CODEINE HYDROCHLORIDE

Common Name

English

CODEINE HYDROCHLORIDE DIHYDRATE

Common Name

English

MORPHINAN-6-OL, 7,8-DIDEHYDRO-4,5-EPOXY-3-METHOXY-17-METHYL-, HYDROCHLORIDE, DIHYDRATE, (5.ALPHA.,6.ALPHA.)-

Systematic Name

English

CODEINE HYDROCHLORIDE DIHYDRATE [EP IMPURITY]

Common Name

English

CODEINE HCL

Common Name

English

CODEINE HYDROCHLORIDE DIHYDRATE [EP MONOGRAPH]

Common Name

English

Classification Tree Code System Code

DEA NO.

9050

Created by admin on Fri Dec 15 17:00:50 GMT 2023 , Edited by admin on Fri Dec 15 17:00:50 GMT 2023

Code System Code Type Description

FDA UNII

NTZ53GG7XN

Created by admin on Fri Dec 15 17:00:50 GMT 2023 , Edited by admin on Fri Dec 15 17:00:50 GMT 2023

PRIMARY

DRUG BANK

DBSALT001068

Created by admin on Fri Dec 15 17:00:50 GMT 2023 , Edited by admin on Fri Dec 15 17:00:50 GMT 2023

PRIMARY

WIKIPEDIA

Codeine hydrochloride

Created by admin on Fri Dec 15 17:00:50 GMT 2023 , Edited by admin on Fri Dec 15 17:00:50 GMT 2023

PRIMARY

EPA CompTox

DTXSID10207886

Created by admin on Fri Dec 15 17:00:50 GMT 2023 , Edited by admin on Fri Dec 15 17:00:50 GMT 2023

PRIMARY

EVMPD

SUB01405MIG

Created by admin on Fri Dec 15 17:00:50 GMT 2023 , Edited by admin on Fri Dec 15 17:00:50 GMT 2023

PRIMARY

RXCUI

1115966

Created by admin on Fri Dec 15 17:00:50 GMT 2023 , Edited by admin on Fri Dec 15 17:00:50 GMT 2023

PRIMARY

RxNorm

PUBCHEM

44146477

Created by admin on Fri Dec 15 17:00:50 GMT 2023 , Edited by admin on Fri Dec 15 17:00:50 GMT 2023

PRIMARY

EVMPD

SUB11840MIG

Created by admin on Fri Dec 15 17:00:50 GMT 2023 , Edited by admin on Fri Dec 15 17:00:50 GMT 2023

PRIMARY

CAS

5916-29-0

Created by admin on Fri Dec 15 17:00:50 GMT 2023 , Edited by admin on Fri Dec 15 17:00:50 GMT 2023

PRIMARY

SMS_ID

100000076636

Created by admin on Fri Dec 15 17:00:50 GMT 2023 , Edited by admin on Fri Dec 15 17:00:50 GMT 2023

PRIMARY

Related Record Type Details


					406LPJ779Q

CODEINE HYDROCHLORIDE ANHYDROUS

ANHYDROUS->SOLVATE


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CODEINE ANHYDROUS

PARENT -> SALT/SOLVATE

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					22B5AW0ANN

CODEINONE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

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Amount:


					22O8BJ3GKX

7,7-OXYBIS(4,5.ALPHA.-EPOXY-3-METHOXY-17-METHYL-6,7,8,14-TETRADEHYDROMORPHINAN-6-OL)

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					76I7G6D29C

MORPHINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

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Amount:


					Z32OFX7V17

CODEINE N-OXIDE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

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Amount:


					LG15ICI5H5

10-HYDROXYCODEINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					2P9MKG8GX7

THEBAINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					332OI8E5Z4

14-HYDROXYCODEINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					575AOU51CR

ORIPAVINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					91138F771G

HYDROXYCODEINONE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					9B0ATL3Q9A

2,2'-BISCODEINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					SC6N3ZX5FG

3-O-(CODEIN-2-YL)MORPHINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					32W9P3T4ML

NORCODEINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					15M9MY9A04

METHYLCODEINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

Related Record Type Details


					UX6OWY2V7J

CODEINE ANHYDROUS

ACTIVE MOIETY

Details

SMILES

InChI

DescriptionSources: https://online.lexi.com/lco/medguides/622452.pdf | https://www.ncbi.nlm.nih.gov/pubmed/7885194

CNS Activity

Approval Year

Targets

Conditions

Approved Use

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://online.lexi.com/lco/medguides/622452.pdf | https://www.ncbi.nlm.nih.gov/pubmed/7885194