D1306

Debrisoquine sulfate

Name: Debrisoquine sulfate
Brand: SIGMA

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

Key Documents

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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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This Item	UC261	SML0140	N0165
Sigma-Aldrich D1306 Debrisoquine sulfate	Sigma-Aldrich UC261 (±)-4-Hydroxydebrisoquin sulfate	Sigma-Aldrich SML0140 BV02	Sigma-Aldrich N0165 Nisoldipine
assay ≥98% (TLC)	assay -	assay ≥98% (HPLC)	assay ≥98% (HPLC)
Gene Information human ... SLC6A2(6530)	Gene Information -	Gene Information -	Gene Information human ... CACNA1C(775), CACNA1D(776), CACNA1F(778), CACNA1S(779)
Quality Level 200	Quality Level 200	Quality Level 100	Quality Level 100
form powder	form solid	form powder	form powder
solubility H₂O: 20 mg/mL (with heat)	solubility -	solubility DMSO: >5 mg/mL	solubility DMSO: >10 mg/mL
storage temp. room temp	storage temp. 2-8°C	storage temp. room temp	storage temp. room temp

General description

A substrate for cytochrome P450 CYP2D6;[1][2] an indicator for genetic polymorphism in cytochrome P450.[3]

Biochem/physiol Actions

Debrisoquine is an anti-hypertensive agent. It is metabolized by cytochrome P4502D6.[4]

pictograms

GHS07

signalword

Warning

hcodes

H302

pcodes

P301 + P312 + P330

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

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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)

Cytochrome P450 dependent N-hydroxylation of a guanidine (debrisoquine), microsomal catalysed reduction and further oxidation of the N-hydroxy-guanidine metabolite to the urea derivative. Similarity with the oxidation of arginine to citrulline and nitric oxide.

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

Studies on the properties of some peripheral MAO inhibitors.

E Scarr et al.

Progress in neuro-psychopharmacology & biological psychiatry, 15(2), 297-301 (1991-01-01)

1. Studies were carried out on three monoamine oxidase (MAO) inhibitors, two of which, debrisoquine and para- hydroxyphenelzine, are purported to be peripheral inhibitors and one, phenelzine, is a peripherally acting inhibitor, which has been included for comparitive purposes. 2.

Metabolomic profiles of current cigarette smokers.

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

The debrisoquine metabolic phenotype and DNA-based assays: implications of misclassification for the association of lung cancer and the debrisoquine metabolic phenotype.

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

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