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Merck

C5901

Codeine monohydrate

analytical standard

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About This Item

Empirical Formula (Hill Notation):
C18H21NO3 · H2O
CAS Number:
6059-47-8
Molecular Weight:
317.38
NACRES:
NA.24
PubChem Substance ID:
329775106
UNSPSC Code:
41116107
MDL number:
MFCD01940504

Product Name

Codeine monohydrate, analytical standard

InChI

1S/C18H21NO3.H2O/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;1H2/t11-,12+,13-,17-,18-;/m0./s1

SMILES string

CN1[C@H](C2)[C@@]3([H])[C@@]4(CC1)C5=C2C=CC(OC)=C5O[C@@]4([H])[C@@H](O)C=C3.O

InChI key

WRRSFOZOETZUPG-FFHNEAJVSA-N

grade

analytical standard

agency

EPA 1694

drug control

USDEA Schedule II; Home Office Schedule 2; stupéfiant (France); kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada; estupefaciente (Spain); Decreto Lei 15/93: Tabela IA (Portugal)
kontrollierte Droge in Deutschland

Quality Level

200

Gene Information

human ... CYP2D6(1565), OPRD1(4985), OPRK1(4986), OPRM1(4988)
rat ... Cyp2d1(266684), Cyp2d2(25053), Cyp2d3(24303), Cyp2d4v1(171522)

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

clinical testing

format

neat

storage temp.

2-8°C

Related Categories

Application

Codeine monohydrate has been used as a standard in the quantitative analysis of codeine by using different types of protein assays like biuret, bicinchoninic acid (BCA), coomassie brilliant blue (CBB) , pyrogallol red–molybdate (PRM) assay, Lowry assay and benzethonium chloride (BEC) assay, while relating the effective response of the drug with the type of assay.
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

Weak narcotic analgesic, perhaps due to conversion to morphine, with minimal hypnotic properties; potent antitussive

Legal Information

German
Dieses Produkt fällt unter das Betäubungsmittelgesetz (BtMG). Für eine Bestellung dieses Produktes ist eine Erlaubnis nach § 3 BtMG zwingend erforderlich, es sei denn, es greift eine Ausnahme von der Erlaubnispflicht nach § 4 oder § 26 BtMG.

English
This product is subject to the German Narcotics Act. A permit under Section 3 of the German Narcotics Act is mandatory for ordering this product unless an exemption from the permit requirement under Section 4 or Section 26 of the German Narcotics Act applies.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SLBP3955V
SLBM7029V
SLBH9849V
SLBF7351V
SLBD2068V

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An evaluation of protein assays for quantitative determination of drugs.
Williams K M, et al.
Journal of Biochemical and Biophysical Methods, 57(1), 45-55 (2003)
Is it farewell to codeine?
Brian J Anderson
Archives of disease in childhood, 98(12), 986-988 (2013-08-27)
Parvaz Madadi et al.
Pharmacogenomics, 9(9), 1267-1284 (2008-09-11)
Codeine has been used medicinally since the 1800s as an analgesic and antitussive agent. Although very few studies have methodically examined the safety of codeine use in the pediatric age group, it is nonetheless commonly prescribed to children and breastfeeding
Marieke Nauta et al.
American journal of surgery, 198(2), 256-261 (2009-07-25)
Cesarean section, episiotomy, and third and perineal tears are associated with significant tissue damage, causing pain in the immediate postpartum period. The current standard in North America is to prescribe oral acetaminophen/codeine (A + C) for postpartum pain. Codeine has
Lauren E Kelly et al.
Therapeutic drug monitoring, 34(3), 249-256 (2012-05-10)
Codeine is an old and commonly used analgesic agent for mild to moderate pain. It is the prototypical "prodrug" in that its analgesic effect is almost wholly dependent on its biotransformation to morphine, a process that is mediated by the
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