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D2531

Sigma-Aldrich

Dextromethorphan hydrobromide monohydrate

≥99% (TLC)

Synonym(s):

d-3-Methoxy-N-methylmorphinan hydrobromide monohydrate, (9S,13S,14S)-3-Methoxy-17-methylmorphinan hydrobromide

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About This Item

Empirical Formula (Hill Notation):
C18H25NO · HBr · H2O
CAS Number:
6700-34-1
Molecular Weight:
370.32
Beilstein/REAXYS Number:
6453793
MDL number:
MFCD02173901
UNSPSC Code:
12352200
PubChem Substance ID:
57654086
NACRES:
NA.77

Quality Level

200

assay

≥99% (TLC)

form

powder

SMILES string

Br[H].[H]O[H].[H][C@]12CCCC[C@]13CCN(C)[C@H]2Cc4ccc(OC)cc34

InChI

1S/C18H25NO.BrH.H2O/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18;;/h6-7,12,15,17H,3-5,8-11H2,1-2H3;1H;1H2/t15-,17+,18+;;/m1../s1

InChI key

STTADZBLEUMJRG-IKNOHUQMSA-N

Gene Information

human ... GRIN1(2902) , GRIN2A(2903) , GRIN2B(2904) , GRIN2C(2905) , GRIN2D(2906) , GRIN3A(116443) , GRIN3B(116444) , SIGMAR1(10280)

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Application

Dextromethorphan hydrobromide monohydrate has been used as a substrate for cytochrome P450 2D6 enzyme action, in potassium phosphate buffer for measuring P450 activity and is used in enzyme inhibition studies.

Biochem/physiol Actions

Dextromethorphan hydrobromide is an allosteric antagonist at N-methyl D- aspartate (NMDA)-controlled ion channels and antagonist at voltage-dependent channels. Dextromethorphan hydrobromide is useful in treating dry cough.

pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 2

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The effect of prototypic sigma ligands on the binding of [3H]dextromethorphan to guinea pig brain.
Klein, et al.
Neuroscience Letters, 91, 175-175 (1989)
Dependence on dextromethorphan hydrobromide.
Fleming Philip M
British Medical Journal (Clinical Research ed.), 293(6547), 597-597 (1986)
J M Musacchio et al.
Life sciences, 45(19), 1721-1732 (1989-01-01)
There is increasing evidence that sigma ligands and dextromethorphan (DM) bind to at least one common high-affinity site. DM and other antitussives do not produce psychotomimetic effects. This suggested that sigma ligands may produce their characteristic effects through another site
T Zimmermann et al.
Arzneimittel-Forschung, 45(1), 41-43 (1995-01-01)
The polymorphism of dextromethorphan (CAS 125-71-3) metabolism is dependent on hepatic cytochrom P4502D6 (CYP2D6) activity. The relationship between the CYP2D6 genotype and the dextromethorphan phenotype was studied in 83 healthy unrelated subjects. Genotype was determined by allele-specific polymerase chain reaction
In Vitro Inhibition and Induction of Human Liver Cytochrome P450 Enzymes by Gentiopicroside: Potent Effect on CYP2A6
Deng Y, et al.
Drug Metabolism and Pharmacokinetics, 28(4), 339-344 (2013)
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