20062-41-3

Usage

Uses

Used in Pharmaceutical Industry:
3-METHYL-1,2,4-TRIAZOLO[3,4-A]PHTHALAZINE is used as an intermediate compound for the synthesis of various pharmaceutical products. Its role in the metabolism of Hydralazine makes it a significant compound for further research and development in drug design and modification.
Used in Chemical Research:
As a unique chemical entity, 3-METHYL-1,2,4-TRIAZOLO[3,4-A]PHTHALAZINE is used as a subject of study in chemical research. Its properties and behavior in different reactions can provide valuable insights into the development of new chemical processes and the creation of novel compounds.
Used in Toxicology Studies:
Given its connection to Hydralazine, a well-known drug, 3-METHYL-1,2,4-TRIAZOLO[3,4-A]PHTHALAZINE is used in toxicology studies to understand its potential effects on biological systems. This information can be crucial for assessing the safety and side effects of related pharmaceutical compounds.
Used in Material Science:
The yellow solid nature of 3-METHYL-1,2,4-TRIAZOLO[3,4-A]PHTHALAZINE may find applications in material science, particularly in the development of pigments or dyes for various industries, such as textiles, plastics, and printing.

InChI:InChI=1/C10H8N4/c1-7-12-13-10-9-5-3-2-4-8(9)6-11-14(7)10/h2-6H,1H3

Upstream product

• 1044569-46-1 1-hydrazinophthalazine 
• 141-97-9 ethyl acetoacetate 
• 87100-61-6 1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)butane-1,3-dione 
• 88330-84-1 (Z)-1-Phenyl-3-(N'-phthalazin-1-yl-hydrazino)-but-2-en-1-one 
• 304-20-1 hydralazine hydrochloride 

Relevant academic research and scientific papers

A convenient synthesis of 4-acetyl-5-hydroxy-3-methyl-1-substituted pyrazoles

Reaction of 1-(5-hydroxy-3-methyl-1-substituted-4-pyrazolyl)-1,3-butanediones (1a-d) with 1-hydrazinophthalazine hydrochloride leads to the formation of 4-acetyl-5-hydroxy-3-methyl-1-substituted pyrazoles (3a-d) along with 3-methyl-s-triazolo[3,4-a]phthalazine (4) in good yields.

Ring closure reactions involving 1-hydrazinophthalazine [1]. Reactions with 1,2,4-tricarbonyl and 1,3-dicarbonyl compounds

Annelation reactions of six-membered rings to 1-hydrazinophthalazine, 1, were investigated. With aroyl(acyl)pyruvates, 2, the desired system was obtained. It was found that the course of the reaction depends on the reaction condition as well as the substituted pyruvates. Thus, 3-(2-oxo-2-substituted ethyl)-4H-as-triazino-[3,4-a]phthalazin-4-one, 4, was the product when 1 reacted with 2 in alcoholic medium. The side chain tautomerism of 4 was studied by using ir, 1H-nmr, and ms spectral methods. When 1 hydrochloride instead of 1 was reacted with 2, 3-ethoxycarbonyl-s-triazolol[3,4-a]phthalazine, 6, was the major product. The reaction of 1 with benzoylacetone in ethanol afforded the hydrazolone, 9. By ir, 1H-nmr, and 13C-nmr methods it was shown that in solution it is involved in an enhydrazine-hydrazone as well as a ring-chain tautomerism. Compound 9 upon the action of PPA underwent dehydrative cyclization to 3-methyl-s-triazolol[3,4-a]phthalazine, 10, and 3-methyl-5-phenyl-1-(1-phthalazinyl)pyrazole, 7. The reaction of 1 with ethyl phenylpropiolate in ethanol was reported by others to give 1-(1-phthalazinyl)-3-phenyl-5-pyrazolone, 8. Upon reinvestigation of this reaction it is shown that the product actually is ethyl β-(1-phthalazinylhydrazono)benzenepropanoate, 11. Attempts to synthesize 8 were unsuccessful by this method. In the reaction of 1 with ethyl benzoylacetate the expected hydralazone 11 was easily formed which upon reaction with PPA yielded the desired species 8.

Metabolism of hydralazine in man. Investigation of features relevant to drug safety, Part I

The metabolite pattern of 1-hydrazinophthalazine hydrochloride (hydralazine hydrochloride, Apresoline) in the 0-24-h urine of hypertensive patients of both slow and fast acetylator phenotype, was studied after administration of an intercurrent oral dose of 14C-labelled hydralazine hydrochloride during chronic treatment with daily doses of either 50 mg b.i.d. or 100 mg b.i.d. hydralazine hydrochloride. Within either group of acetylator phenotype no statistically significant difference of the percentage yields of the individual metabolites between the low- and high-dose regimen could be found. The dominant urinary metabolite in both acetylator phenotypes was found to be 4-(2-acetylhydrazino)-phthalazinone (NAc-HPZ). In slow acetylators 18% and in fast acetylators 33% of the total radioactivity recovered in the urine was identified as NAc-HPZ. Another important metabolite assigned to the acetylation pathway is 3-hydroxymethyl-s-triazolo-[3,4-α] phthalazine (30H-MTP), excreted in conjugated form. Again in the urine of fast acetylators this metabolite was present in higher amounts (19%) than in slow acetylators (8.3%). A possible precursor of 30H-MTP, methyl-s-triazolo-[3,4-α]phthalazine (MTP) was found in low, but about equal, amounts in both acetylator phenotypes (slow: 3.3%; fast: 2.7%). An increased amount of MTP detected after enzymatic hydrolysis is probably due to conversion of hydralazine pyruvic acid hydrazone (HPPAH) into MTP under the applied reaction conditions. An acetylator phenotype related difference was also found for metabolites arising from pathways other than acetylation. s-Triazolo-[3,4-α]phthalazine (TP) was found to represent 0.9% of urinary radioactivity in slow acetylators and 6% in fast acetylators. Conditions of enzymatic hydrolysis reversed the pattern, there being higher amounts of TP in the urine of slow acetylators (10.9%) than in fast acetylators (8.4%). Also higher amounts of phthalazin-1-one (PZ) appeared in the urine of slow acetylators (4.3%) than in the urine of fast acetylators (1.8%). The assay of NAc-HPZ in urine of hypertensive patients will allow to determine their acetylation phenotypes more relevantly to hydralazine treatment than the conventional phenotyping tests can do.