Hydralazine hydrochloride

Base Information

• Chemical Name: Hydralazine hydrochloride
• CAS No.: 304-20-1
• Deprecated CAS: 40671-54-3,1202866-95-2,1202866-95-2
• Molecular Formula: C8H9ClN4
• Molecular Weight: 196.639
• Hs Code.: 29339900
• European Community (EC) Number: 206-151-0
• NSC Number: 757058,89394
• UNII: FD171B778Y
• DSSTox Substance ID: DTXSID1044645
• Wikidata: Q27114606
• NCI Thesaurus Code: C551
• RXCUI: 82027
• ChEMBL ID: CHEMBL542541
• Mol file: 304-20-1.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 hydrochloride

Chemical Property:

• Appearance/Colour: white crystalline solid
• Melting Point: 273 °C
• Refractive Index: 1.6110 (estimate)
• Boiling Point: 491.9 °C at 760 mmHg
• Flash Point: 251.3 °C
• PSA: 63.10000
• Density: 1.2961 (rough estimate)
• LogP: 1.72400
• Storage Temp.: -20?C Freezer
• Solubility.: Soluble in water, slightly soluble in ethanol (96 per cent), very slightly soluble in methylene chloride
• Water Solubility.: Soluble in water. Slightly soluble in diethyl ether and alcohol.
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 196.0515740
• Heavy Atom Count: 13
• Complexity: 150

Purity/Quality:

98%min ^*data from raw suppliers

Hydralazine hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=NN=C2NN.Cl
• Recent ClinicalTrials: Effect of Hydralazine on Alzheimer's Disease
• Recent EU Clinical Trials: Efficacy and safety of hydralazine in combination with valproate to treat hypocretin deficiency in recent onset narcolepsy: a pilot study
• Description: Hydralazine is an orally bioavailable vasodilator and antihypertensive agent. It decreases DNA methylation in Jurkat cells at a concentration of 10 μM and inhibits extracellular and intracellular production of reactive oxygen species (ROS) in rat macrophages activated by phorbol 12-myristate 13-acetate (PMA; ) at a concentration of 100 μM. Hydralazine (100 μM) also decreases nitric oxide production and mRNA expression of inducible nitric oxide synthase (iNOS) in rat macrophages activated by LPS (Item Nos. 19660| 19661| 19662) and interferon-γ (IFN-γ). It reduces contraction of rat aortic arterial strips induced by potassium and norepinephrine (; IC50s = 2.2 and 3.06 mM, respectively). Hydralazine (2.6 mg/kg) lowers mean arterial blood pressure (MAP) by 41.76% in conscious rats. Formulations containing hydralazine have been used in the treatment of high blood pressure and heart failure.
• Uses: Hydralazine hydrochloride has been used:as a vasodilator to study its effects on hypertension in T-cell frequencies in juvenile ratsas a semicarbazide-sensitive amine oxidase (SSAO) inhibitor to study its effects on myocardial ischemia-reperfusion (I/R) injuryas a vasodilator to study its effects on insulin secretion and glucose tolerance Inhibits DNA methyltransferase and modulates epigenetic regulation of gene expression. Non-selective MAO-A/B inhibitor; semicarbazide sensitive amine oxidase inhibitor. Antihypertensive Hydralazine is a non-nucleoside analog that inhibits DNA methylation and reactivates the expression of tumor suppressor genes. Non-selective MAO-A/B inhibitor; semicarbazide-sensitive amine oxidase inhibitor. Antihypertensive.
• Therapeutic Function: Antihypertensive
• Clinical Use: Hydralazine hydrochloride is useful in the treatment ofmoderate-to-severe hypertension. It is often used in conjunctionwith less potent antihypertensive agents, becauseside effects occur frequently when it is used alone in adequatedoses. In combinations, it can be used in lower andsafer doses. Its action appears to be centered on the smoothmuscle of the vascular walls, with a decrease in peripheralresistance to blood flow. This results in increased bloodflow through the peripheral blood vessels. It also has theunique property of increasing renal blood flow, an importantconsideration in patients with renal insufficiency.Hydralazine hydrochloride acts on vascular smooth muscleto cause relaxation. Its mechanism of action is unclear. Itinterferes with Ca2+ entry andCa2+release from intracellularstores and reportedly causes activation of guanylate cyclase,resulting in increased levels of cGMP. All of thesebiochemical events can cause vasodilation.
• Drug interactions: The coadministration of diuretics and other hypotensive drugs may have a synergistic effect, resulting in a marked decrease in blood pressure.

Technology Process of Hydralazine hydrochloride

There total 6 articles about Hydralazine hydrochloride 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: 95.0%

→ hydralazine hydrochloride (304-20-1)

Guidance literature:

With ethylenediaminetetraacetic acid; In water; at 75 - 80 ℃; for 0.5h; Activated carbon;

With sodium hydrogencarbonate; In methanol; water; at -20 - 20 ℃; pH=3 - 4.5; Purification / work up;

Reference yield: 80.0%

1-hydrazinophthalazine (1044569-46-1) → hydralazine hydrochloride (304-20-1)

Guidance literature:

With hydrogenchloride; In water; at 70 - 80 ℃; Product distribution / selectivity;

Reference yield: 65.0%

phthalazone (119-39-1) → hydralazine hydrochloride (304-20-1)

Guidance literature:

phthalazone; With trichlorophosphate; at 75 ℃; for 0.5h;

With hydrazine hydrate; In ethanol; water; at 60 - 70 ℃; for 2h;

With hydrogenchloride; In ethanol; water; pH=3;

DOI:10.1016/j.tet.2016.10.065

upstream raw materials:

1-hydrazinophthalazine

2-formylphenyl tosylate

phthalazone

salicylaldehyde

Downstream raw materials:

4-hydroxy-benzaldehyde-phthalazin-1-ylhydrazone

N-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-N'-phthalazin-1-yl-hydrazine

Dimethyl-[4-(phthalazin-1-yl-hydrazonomethyl)-phenyl]-amine

phthalazone

Refernces

• 1、 Liu, Bin,Zhang, Chunlei,Zhou, Xigeng. "Access to phthalazinones via palladium-catalyzed three-component cycloamino-carbonylation of 2-formylaryl tosylates, hydrazines and CO". . p. 8282 - 8286. Retrieved 2016/12/02.
• 2、 -. "Synthesis of hydrazine derivatives of pyridazine". Page/Page column 7. . Retrieved 2008/06/13.