Hydralazine

Base Information

• Chemical Name: Hydralazine
• CAS No.: 86-54-4
• Molecular Formula: C₈H₈N₄
• Molecular Weight: 160.178
• European Community (EC) Number: 201-680-3
• NSC Number: 126699
• UNII: 26NAK24LS8
• DSSTox Substance ID: DTXSID4023129
• Nikkaji Number: J4.262E
• Wikipedia: Hydralazine
• Wikidata: Q419987
• NCI Thesaurus Code: C62032
• RXCUI: 5470
• Pharos Ligand ID: 83Y6N4M6S79Z
• Metabolomics Workbench ID: 43476
• ChEMBL ID: CHEMBL276832
• Mol file: 86-54-4.mol

Synonyms:Apresoline;Apressin;Apressoline;Hydralazine;Hydralazine Hydrochloride;Hydralazine mono Hydrochloride;Hydralazine mono-Hydrochloride;Hydrallazin;Hydrazinophthalazine;Hydrochloride, Hydralazine;mono-Hydrochloride, Hydralazine;Nepresol

Chemical Property of Hydralazine

Chemical Property:

• Appearance/Colour: Yellow needles from methanol.
• Melting Point: 172 ºC
• Refractive Index: 1.5872 (estimate)
• Boiling Point: 276.07°C (rough estimate)
• PKA: pKa 6.820± 0.005(H2O,t = 25.0,Iundefined) (Uncertain)
• PSA: 63.83000
• Density: 1.2583 (rough estimate)
• LogP: 1.68870
• Water Solubility.: 4.8mg/L(22.5 oC)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 160.074896272
• Heavy Atom Count: 12
• Complexity: 150

Purity/Quality:

99%, ^*data from raw suppliers

1-Hydrazinylphthalazine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Drug Classes: Antihypertensive Agents
• Canonical SMILES: C1=CC=C2C(=C1)C=NN=C2NN
• Recent ClinicalTrials: Blood Pressure Management in Stroke Following Endovascular Treatment
• Recent EU Clinical Trials: Improving Treatment Options for Somatostatin Type 2 Receptor Negative Neuroendocrine Tumor Patients
• Description: Cross-reactions between hydrazine derivatives occur. Hydralazine may sometimes cause flushing and reversible Lupus erythematosis
• Uses: Hydralazine is widely used cardiovascular drug dilating arterioies by relaxation of artetiolar smooth muscles. Inhibits DNA methyltransferase and modulates epigenetic regulation of gene expression. Non-selective MAO-A/B inhibitor; semicarbazide-sensitive amine oxidase inhibitor. Antihypertensive
• Therapeutic Function: Antihypertensive
• Biological Functions: The vasodilation produced by hydralazine (Apresoline) depends in part on the presence of an intact blood vessel endothelium. This implies that hydralazine causes the release of nitric oxide, which acts on the vascular smooth muscle to cause relaxation. In addition, hydralazine may produce vasodilation by activating K+ channels.
• Clinical Use: Hydralazine is generally reserved for moderately hypertensive ambulatory patients whose blood pressure is not well controlled either by diuretics or by drugs that interfere with the sympathetic nervous system. It is almost always administered in combination with a diuretic (to prevent Na+ retention) and a β-blocker, such as propranolol (to attenuate the effects of reflex cardiac stimulation and hyperreninemia). The triple combination of a diuretic, β-blocker, and hydralazine constitutes a unique hemodynamic approach to the treatment of hypertension, since three of the chief determinants of blood pressure are affected: cardiac output (β-blocker),plasma volume (diuretic), and peripheral vascular resistance (hydralazine). Although hydralazine is available for intravenous administration and has been used in the past for hypertensive emergencies, it is not generally employed for this purpose. The onset of action after intravenous injection is relatively slow, and its actions are somewhat unpredictable in comparison with those of several other vasodilators.

Technology Process of Hydralazine

There total 1 articles about Hydralazine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ hydralazine (86-54-4,59275-69-3,1044569-46-1)

Guidance literature:

DOI:10.1007/BF00479580

Reference yield: 55.0%

(Z)-ethyl 2-hydroxy-4-(4-methoxyphenyl)-4-oxo-2-butenoate (63913-14-4) + 1-hydrazinophthalazine (86-54-4,59275-69-3,1044569-46-1) → 1-(phthalazin-1-yl)-3-ethoxycarbonyl-5-(4-methoxyphenyl)pyrazole (110829-65-7)

Guidance literature:

With PPA; Polyphosphoric acid (PPA); for 0.333333h; Heating;

DOI:10.3987/R-1987-05-1177

Reference yield: 50.0%

ethyl-(Z)-2-hydroxy-4-oxo-4-phenyl-but-2-enoate (88330-79-4,244277-46-1) + 1-hydrazinophthalazine (86-54-4,59275-69-3,1044569-46-1) → 1-(phthalazin-1-yl)-3-ethoxycarbonyl-5-phenylpyrazole (110854-00-7)

Guidance literature:

With PPA; Polyphosphoric acid (PPA); for 0.333333h; Heating;

DOI:10.3987/R-1987-05-1177

Downstream raw materials:

1-(phthalazin-1-yl)-3-ethoxycarbonyl-5-phenylpyrazole

1-(phthalazin-1-yl)-3-ethoxycarbonyl-5-(4-methoxyphenyl)pyrazole