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D1306

Sigma-Aldrich

Debrisoquine sulfate

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Synonym(s):
3,4-Dihydro-2(1H)-isoquinolinecarboximidamide, Debrisoquin sulfate, Ro 5-33071
Linear Formula:
C20H26N6 · H2SO4
CAS Number:
Molecular Weight:
448.54
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Assay

≥98% (TLC)

Quality Level

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
BP103UC261F6627
Debrisoquine sulfate

Sigma-Aldrich

D1306

Debrisoquine sulfate

Debrisoquine sulfate British Pharmacopoeia (BP) Reference Standard

BP103

Debrisoquine sulfate

5-Fluorouracil ≥99% (HPLC), powder

Sigma-Aldrich

F6627

5-Fluorouracil

form

powder

form

-

form

solid

form

powder

mp

285 °C

mp

-

mp

267 °C

mp

282-286 °C (dec.) (lit.)

solubility

H2O: 20 mg/mL (with heat)

solubility

-

solubility

-

solubility

1 M NH4OH: soluble, DMSO/DMF: soluble, methanol: soluble

storage temp.

room temp

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

room temp

Quality Level

200

Quality Level

-

Quality Level

200

Quality Level

200

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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J W Ho et al.
Analytical biochemistry, 203(2), 348-351 (1992-06-01)
Debrisoquine and sparteine are prototype substrates of a genetic deficiency in cytochrome P450-dependent drug metabolism. Sensitive assays of in vitro oxidation of sparteine and debrisoquine are required for evaluation of this polymorphism. The activities were measured by quantitative analysis of
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
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
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.
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)

Articles

Phase I Drug Metabolism

Phase I biotransformation reactions introduce or expose functional groups on the drug with the goal of increasing the polarity of the compound. Although Phase I drug metabolism occurs in most tissues, the primary and first pass site of metabolism occurs during hepatic circulation.

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