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H1753

Sigma-Aldrich

Hydralazine hydrochloride

Synonym(s):

1-Hydrazinophthalazine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C8H8N4 · HCl
CAS Number:
304-20-1
Molecular Weight:
196.64
EC Number:
206-151-0
MDL number:
MFCD00135998
UNSPSC Code:
12352200
PubChem Substance ID:
24278461
NACRES:
NA.77

biological source

synthetic (organic)

Assay

≥99% (TLC)

form

powder

mp

273 °C

solubility

water: 50 mg/mL

SMILES string

Cl[H].N\N=C1/N=NC=C2C=CC=CC12

InChI

1S/C8H8N4.ClH/c9-11-8-7-4-2-1-3-6(7)5-10-12-8;/h1-5,7H,9H2;1H/b11-8-;

InChI key

SECXUXOCDLQOBI-MKFZHGHUSA-N

Gene Information

human ... MAOA(4128) , MAOB(4129)

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Application

Hydralazine hydrochloride has been used:
  • as a vasodilator to study its effects on hypertension in T-cell frequencies in juvenile rats
  • as a semicarbazide-sensitive amine oxidase (SSAO) inhibitor to study its effects on myocardial ischemia-reperfusion (I/R) injury
  • as a vasodilator to study its effects on insulin secretion and glucose tolerance

Biochem/physiol Actions

Hydralazine hydrochloride has therapeutic effects against heart failure and high blood pressure.
Inhibits DNA methyltransferase and modulates epigenetic regulation of gene expression. Non-selective MAO-A/B inhibitor; antihypertensive; semicarbazide-sensitive amine oxidase inhibitor.

Features and Benefits

This compound is featured on the Dopamine and Norepinephrine Metabolism page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

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

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)

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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Mahesh P Kate et al.
Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism, 34(1), 81-86 (2013-09-21)
Blood pressure (BP) reduction after intracerebral hemorrhage (ICH) is controversial, because of concerns that this may cause critical reductions in perihematoma perfusion and thereby precipitate tissue damage. We tested the hypothesis that BP reduction reduces perihematoma tissue oxygenation.Acute ICH patients
Philip C Burcham et al.
Molecular pharmacology, 82(5), 876-886 (2012-08-08)
Toxic carbonyls such as acrolein participate in many degenerative diseases. Although the nucleophilic vasodilatory drug hydralazine readily traps such species under "test-tube" conditions, whether these reactions adequately explain its efficacy in animal models of carbonyl-mediated disease is uncertain. We have
Ashley D Hunt et al.
The Journal of organic chemistry, 78(17), 8847-8852 (2013-07-31)
Azomethine imines can be accessed upon heating appropriate alkynylhydrazide precursors. This simple thermal hydroamination approach allows the formation of five- and six-membered dipoles in modest to excellent yields. The structure of the acyl group is important to minimize side reactions
Dirk Westermann et al.
Basic research in cardiology, 107(6), 308-308 (2012-11-03)
Sildenafil inhibits cyclic GMP-specific phosphodiesterase type-5A (PDE5A) and can prevent cardiac hypertrophy and left ventricular (LV) dysfunction in mice subjected to severe pressure-overload. The pathophysiological role of sildenafil in adverse remodeling in the hypertensive heart after chronic renin-angiotensin aldosterone system
Nadine S Sauter et al.
Diabetes, 64(4), 1273-1283 (2014-10-30)
Pathological activation of the renin-angiotensin system (RAS) is associated with the metabolic syndrome, and the new onset of type 2 diabetes can be delayed by RAS inhibition. In animal models of type 2 diabetes, inhibition of the RAS improves insulin
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