Category: 75907-74-3

Synthesis of tetramethylpyrazine derivatives and screening for 5-HT₃ receptor antagonistic activity was written by Jiang, Xiang-Qing;Huang, Chuan-Man;Zhu, Li-Ping;Ye, De-Yong. And the article was included in Gaodeng Xuexiao Huaxue Xuebao in 2005.Quality Control of (3,5,6-Trimethylpyrazin-2-yl)methanol This article mentions the following:

According to the principle of bioisosterism and the Evans’ pharmacophore model of 5-HT₃ receptor antagonists, twelve tetramethylpyrazine derivatives were synthesized. The structures of the compounds were confirmed by MS, ¹H NMR and HRMS. All the target compounds are unreported. The preliminary activity test showed that most of the compounds had fairly potent 5-HT₃ receptor antagonistic activities, especially compound I. The conformational anal. showed that the active conformation of the compounds was quite fitted to the Evans model. This indicates that besides the three pharmacophoric elements, the aromatic ring and the substituents attached may affect the bioactivities of the compounds In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Quality Control of (3,5,6-Trimethylpyrazin-2-yl)methanol).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) belongs to pyrazine derivatives. Pyrazine heterocycles and their benzo derivatives possess many interesting properties, including chemical reactivity profiles, and have diverse applications in total synthesis, medicine, chemical biology, materials, dyes, and imaging. A large number of pyrazine derivatives are known for their antitumor, antibiotic, anticonvulsant, antituberculosis, and diuretic activities.Quality Control of (3,5,6-Trimethylpyrazin-2-yl)methanol

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Design, synthesis, and biological evaluation of novel tetramethylpyrazine derivatives as potential neuroprotective agents was written by Chen, Haiyun;Tan, Guolian;Cao, Jie;Zhang, Gaoxiao;Yi, Peng;Yu, Pei;Sun, Yewei;Zhang, Zaijun;Wang, Yuqiang. And the article was included in Chemical & Pharmaceutical Bulletin in 2017.Recommanded Product: 75907-74-3 This article mentions the following:

A series of tetramethylpyrazine (TMP) derivatives, e.g., I were designed, synthesized and investigated their abilities for scavenging free radicals and preventing against oxidative stress-induced neuronal damage in vitro. Among them, compound, I consisting of TMP, caffeic acid and a nitrone group, showed potent radical-scavenging activity. Compound, I had broad neuroprotective effects, including rescuing iodoacetic acid-induced neuronal loss and, preventing from tert-butylhydroperoxide (t-BHP)-induced neuronal injury. Compound, I exerted its neuroprotective effect against t-BHP injury via activation of the phosphatidyl inositol 3-kinase (P13K)/Akt signaling pathway. Furthermore, in a rat model of permanent middle cerebral artery occlusion, compound, e.g., I significantly improved neurol. deficits, and alleviated the infarct area and brain edema. Thus, the results suggest that compound I could be a potential neuroprotective agent for the treatment of neurol. disease, particularly ischemic stroke. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Recommanded Product: 75907-74-3).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) belongs to pyrazine derivatives. Pyrazines are part of several biologically active polycyclic compounds; examples are quinoxalines, phenazines; and the bio-luminescent natural products pteridines, flavins, and their derivatives. Pyrazine and a variety of alkylpyrazines are flavor and aroma compounds found in baked and roasted goods. Tetramethylpyrazine (also known as ligustrazine) is reported to scavenge superoxide anion and decrease nitric oxide production in human Granulocytes.Recommanded Product: 75907-74-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthesis of tetramethylpyrazine derivatives by Mitsunobu reaction was written by Wang, Hui-ying;Sun, Ping-hua;Chen, Wei-min. And the article was included in Hecheng Huaxue in 2011.Application of 75907-74-3 This article mentions the following:

Three tetramethylpyrazine derivatives I(R = H, MeO), and II in yields of 87%∼92% were synthesized by Mitsunobu reaction from tetramethylpyrazine. The structures were characterized by ¹H NMR, ¹³C NMR and ESI-MS. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Application of 75907-74-3).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) belongs to pyrazine derivatives. Pyrazine heterocycles and their benzo derivatives possess many interesting properties, including chemical reactivity profiles, and have diverse applications in total synthesis, medicine, chemical biology, materials, dyes, and imaging. Pyrazine heterocycles and their benzo derivatives possess many interesting properties, including chemical reactivity profiles, and have diverse applications in total synthesis, medicine, chemical biology, materials, dyes, and imaging.Application of 75907-74-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Research of metabolic kinetics and reaction phenotyping of ligustrazin by using liver microsomes and recombinant human enzymes was written by Tan, Yan;Zhuang, Xiao-mei;Shen, Guo-lin;Li, Hua;Gao, Yue. And the article was included in Yaoxue Xuebao in 2014.Synthetic Route of C8H12N2O This article mentions the following:

The metabolic characteristics of ligustrazin (TMPz) in liver microsomes were studied. The reaction phenotyping of TMPz metabolism was also identified by in vitro assessment using recombinant human cytochrome P 450 enzymes (CYP) and UDP glucuronosyltransferases (UGT). TMPz was incubated at 37°C with human (HLM) and rat liver microsomes (RLM) in the presence of different co-factors. The metabolic stability and enzyme kinetics of TMPz were studied by determining its remaining concentrations with a LC-MS/MS method. TMPz was only metabolically eliminated in the microsomes with NADPH or NADPH+UDPGA. In the HLM and RLM with NADPH+UDPGA, t_1/2, K_m, and V_max of TMPz were 94.24±4.53 and 105.07±9.44 min, 22.74±1.89 and 33.09±2.74μmol·L^-1, 253.50±10.06 and 190.40±8.35 nmol·min^-1·mg^-1 (protein), resp. TMPz showed a slightly higher metabolic rate in HLM than that in RLM. Its primary oxidative metabolites, 2-hydroxymethyl-3,5,6-trimethylpyrazine (HTMP), could undergo glucuronide conjugation. The CYP reaction phenotyping of TMPz metabolism was identified using a panel of recombinant CYP isoforms (rCYP) and specific CYP inhibitors in HLM. CYP1A2, 2C9, and 3A4 were the major CYP isoforms involved in TMPz metabolism Their individual contributions were assessed by using the method of the total normalized rate to be 19.32, 27.79, and 52.90%, resp. It was observed that these CYP isoforms mediated the formation of HTMP in rCYP incubation. The UGT reaction phenotyping of HTMP glucuronidation was also studied preliminarily by using a panel of 6 UGT isoforms (rUGT). UGT1A1, 1A4, and 1A6 were the predominant isoforms mediated the HTMP glucuronidation. The results above indicated that the metabolism of TMPz involves multiple enzymes mediated phase I and phase II reactions. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Synthetic Route of C8H12N2O).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) belongs to pyrazine derivatives. Pyrazine has the elements of symmetry for the point group D2h. It has three mutually perpendicular two-fold axes. It also has three mutually perpendicular planes of symmetry. As a result, pyrazine also has a centre of symmetry. Substituted pyrazines have been found as subunits of multiple synthetically constructed therapeutic agents, as well as several natural products.Synthetic Route of C8H12N2O

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

A Specific Blend of Drakolide and Hydroxymethylpyrazines: An Unusual Pollinator Sexual Attractant Used by the Endangered Orchid Drakaea micrantha was written by Bohman, Bjoern;Tan, Monica M. Y.;Phillips, Ryan D.;Scaffidi, Adrian;Sobolev, Alexandre N.;Moggach, Stephen A.;Flematti, Gavin R.;Peakall, Rod. And the article was included in Angewandte Chemie, International Edition in 2020.COA of Formula: C8H12N2O This article mentions the following:

Bioactive natural products underpin the intriguing pollination strategy used by sexually deceptive orchids. These compounds, which mimic the sex pheromones of the female insect, are emitted in particular blends to lure male insect pollinators of specific species. By combining methods from field biol., anal. chem., electrophysiol., crystallog., and organic synthesis, we report that an undescribed β-hydroxylactone, in combination with two specific hydroxymethylpyrazines, act as pollinator attractants in the rare hammer orchid Drakaea micrantha. This discovery represents an unusual case of chem. unrelated compounds being used together as a sexual attractant. Furthermore, this is the first example of the identification of pollinator attractants in an endangered orchid, enabling the use of chem. in orchid conservation. Our synthetic blend is now available to be used in pollinator surveys to locate suitable sites for plant conservation translocations. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3COA of Formula: C8H12N2O).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) belongs to pyrazine derivatives. Pyrazine is an N-heterocyclic moiety, and it can be easily prepared from ethylenediamine and 1,2-diketone, α-hydroxyketone, α-methyl ketone. Pyrazine and a variety of alkylpyrazines are flavor and aroma compounds found in baked and roasted goods. Tetramethylpyrazine (also known as ligustrazine) is reported to scavenge superoxide anion and decrease nitric oxide production in human Granulocytes.COA of Formula: C8H12N2O

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Development of 2-hydroxymethyl-3,5,6-trimethylpyrazine palmitate-loaded lipid emulsion: formulation, optimization, characterization, pharmacokinetics, biodistribution and pharmacodynamics was written by Cao, Ran;Li, Qian;Li, Hui;Chu, Ting;Jin, Hui;Mao, Sheng-jun. And the article was included in Journal of Drug Targeting in 2013.SDS of cas: 75907-74-3 This article mentions the following:

Tetramethylpyrazine (TMP) is used to treat cerebrovascular and cardiovascular diseases. However, it displays a short half-life that restricts clin. applications. 2-Hydroxymethyl-3,5,6-trimethylpyrazine (HTMP) is the principal active metabolite of TMP, with similar activity of TMP. Therefore, it makes sense to improve the biopharmaceutical characteristics via HTMP bypassing TMP. Purpose: To prolong the half-life of HTMP and achieve improved bioavailability and efficacy compared to com. available product of tetramethylpyrazine phosphate injection (TMPP-I). A lipophilic prodrug of HTMP, palmitate of HTMP (HTMPP) was synthesized, and then the lipid emulsion of HTMPP was developed. The middle cerebral artery occlusion (MCAO) model was applied to evaluate the efficacy in different administration group. The optimized formulation consisted of 1.5% (w/v) HTMPP, 15% (w/v) soybean oil, 1.2% (w/v) soybean lecithin and 0.3% (w/v) poloxamer 188. The AUC_0-180 min and the half-life of HTMP in HTMPP-LE was 2.05-fold and 1.48-fold greater than that in TMPP-I. The brain AUC_0-120 min of HTMP in HTMPP-LE group increased by 145.6% compared to that in TMPP-I group. These differences could be primarily attributed to dissimilar metabolism between HTMPP and TMP. Consistently, HTMPP-LE exhibited better efficacy on ischemia/reperfusion model than TMPP-I. The developed HTMPP-LE suggests a great therapeutic potential for clin. applications. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3SDS of cas: 75907-74-3).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) belongs to pyrazine derivatives. Pyrazinesare six-membered aromatic heterocyclic organic compounds with two nitrogen atoms at 1,4-positions. Pyrazine is a weaker base (pKb = 13.4) than pyridine (pKb = 8.8), pyrimidine (pKb = 12.7). Pyrazines are chemical compounds (technically called “methoxypyrazines”) found in grape skin and stems that are responsible for many “green” flavors in wine. Levels of pyrazines are dependent on viticultural practices, climate, and grape variety.SDS of cas: 75907-74-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Determination of tetramethylpyrazine and its active metabolite in rat plasma by HPLC was written by Yuan, Fang;Chen, Zhuojia;Chen, Jie. And the article was included in Zhongguo Xiandai Yingyong Yaoxue in 2012.Application of 75907-74-3 This article mentions the following:

An HPLC method for the determination of concentration of tetramethylpyrazine (TMP) and its active metabolite, 2-hydroxymethyl-3,5,6-trimethylpyrazine (HTMP) in rat plasma was established, and applied this method to the pharmacokinetic study of TMP. 2-Methylpyrazine was used as internal standard The alkalified serum samples were extracted with a chloroform-1-chloro-butane (3:1) induced liquid-liquid extraction The target analytes were quant. determined by HPLC. Hypersil BDS C₁₈ column (4.6 mm×250 mm, 5 μm) was used. The mobile phase consisted of 20 mmol · L^-1 potassium dihydrogen phosphate buffer (pH 5.6)-methanol (72:28). The flow rate was 1.0 mL · min^-1, 15 μL sample was injected and detected by the ultra-violet detector at 285 nm. The linearity was obtained over the concentration ranges of 0.03125-50 μg · mL^-1 for TMP (γ=0.9995) and 0.03125-5 μg · mL^-1 for HTMP (γ=0.9998). The lower limit of quantitation (LLOQ) was 0.03125 μg · mL^-1 for TMP and HTMP. The inter- and intra-batch precisions (RSD%) were less than 9% for both analyses. The accuracies and extracted recoveries were 86.2%-93.0% for TMP and 73.8%-95.1% for HTMP. The relative recoveries were 96.9%-117.7% for TMP and 97.5%-104.9% for HTMP. The method has good selectivity, acceptable accuracy, precision and sensitivity. It can be applied to pharmacokinetic study of TMP in rats. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Application of 75907-74-3).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) belongs to pyrazine derivatives. Pyrazine is an N-heterocyclic moiety, and it can be easily prepared from ethylenediamine and 1,2-diketone, α-hydroxyketone, α-methyl ketone. A number of pyrazine-based derivatives were used as dyes or fluorescent probes.Application of 75907-74-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Discovery of a new tetramethylpyrazine based chalcone with α, β-Unsaturated ketone moiety as a potential anticancer agent was written by Bukhari, Syed Nasir Abbas. And the article was included in International Journal of Research in Pharmaceutical Sciences (Madurai, India) in 2020.Related Products of 75907-74-3 This article mentions the following:

In this study, a new ligustrazine-based chalcone mol. has been synthesized that contains an extra alpha, beta-Unsaturated ketone moiety along with alpha, the beta-Unsaturated carbonyl group of chalone. A new tetramethylpyrazine (TMP) based aldehyde was synthesized to make the TMP (ligustrazine) as part of chalcone and then it was reacted with newly synthesized ketone containing addnl. alpha, beta-Unsaturated ketone moiety. After characterization, this new compound was evaluated for its effect on different types of cancer cell lines and very promising results were obtained. The growth of these cancer cells was inhibited by newly designed and synthesized compounds, especially for colon and pancreatic cancer cells with IC50 0.04 – 0.05 μM. In the experiment, the researchers used many compounds, for example, (3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3Related Products of 75907-74-3).

(3,5,6-Trimethylpyrazin-2-yl)methanol (cas: 75907-74-3) belongs to pyrazine derivatives. Pyrazine has the elements of symmetry for the point group D2h. It has three mutually perpendicular two-fold axes. It also has three mutually perpendicular planes of symmetry. As a result, pyrazine also has a centre of symmetry. A number of pyrazine-based derivatives were used as dyes or fluorescent probes.Related Products of 75907-74-3

Referemce:
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem