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D1306

Sigma-Aldrich

Debrisoquine sulfate

powder, ≥98% (TLC)

Synonym(s):

3,4-Dihydro-2(1H)-isoquinolinecarboximidamide, Debrisoquin sulfate, Ro 5-33071

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About This Item

Linear Formula:
C20H26N6 · H2SO4
CAS Number:
581-88-4
Molecular Weight:
448.54
EC Number:
209-472-4
MDL number:
MFCD00153791
UNSPSC Code:
12352204
PubChem Substance ID:
24277710
NACRES:
NA.32

product name

Debrisoquine sulfate,

assay

≥98% (TLC)

Quality Level

200

form

powder

mp

285 °C

solubility

H2O: 20 mg/mL (with heat)

storage temp.

room temp

SMILES string

OS(O)(=O)=O.NC(=N)N1CCc2ccccc2C1.NC(=N)N3CCc4ccccc4C3

InChI

1S/2C10H13N3.H2O4S/c2*11-10(12)13-6-5-8-3-1-2-4-9(8)7-13;1-5(2,3)4/h2*1-4H,5-7H2,(H3,11,12);(H2,1,2,3,4)

InChI key

CAYGYVYWRIHZCQ-UHFFFAOYSA-N

Gene Information

human ... SLC6A2(6530)

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Biochem/physiol Actions

Debrisoquine is an anti-hypertensive agent. It is metabolized by cytochrome P4502D6.

Substrates

A substrate for cytochrome P450 CYP2D6; an indicator for genetic polymorphism in cytochrome P450.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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E Jacqz-Aigrain et al.
Biochemical pharmacology, 41(11), 1657-1663 (1991-06-01)
Interindividual variations of debrisoquine metabolism was recently identified in non-human primates tested in vivo. The catalytical and immunological characterization of cytochrome P450IID subfamily was undertaken in hepatic microsomes from extensive metabolizer primates. The NADPH/O2 mediated metabolism of debrisoquine, dextromethorphan and
N E Caporaso et al.
Environmental health perspectives, 98, 101-105 (1992-11-01)
Debrisoquine is an antihypertensive drug that is metabolized by cytochrome P4502D6. Deficient metabolism is inherited as an autosomal recessive condition. We previously reported in a case-control study that extensive metabolizers of debrisoquine were at greater risk of lung cancer compared
The debrisoquine metabolic phenotype and DNA-based assays: implications of misclassification for the association of lung cancer and the debrisoquine metabolic phenotype.
Caporaso N E, et al.
Environmental Health Perspectives, 98, 101-105 (1992)
B Clement et al.
Biochemical pharmacology, 46(12), 2249-2267 (1993-12-14)
The microsomal N-hydroxylation of the strongly basic guanidinium group (debrisoquine) to N-hydroxyguanidine (N-hydroxydebrisoquine) and the retroreduction of the N-hydroxyguanidine are demonstrated for the first time. The reduction of the N-hydroxyguanidine by liver homogenates and hepatocytes is catalysed by a microsomal
Ping-Ching Hsu et al.
Molecular carcinogenesis, 56(2), 594-606 (2016-06-25)
Smoking-related biomarkers for lung cancer and other diseases are needed to enhance early detection strategies and to provide a science base for tobacco product regulation. An untargeted metabolomics approach by ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry (UHPLC-Q-TOF MS) totaling
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