314728-85-3

Basic information

• Product Name: Piperazine, 1-benzoyl-4-(1-oxopropyl)-
• Synonyms: Piperazine, 1-benzoyl-4-(1-oxopropyl)-;SunifiraM;1-(4-Benzoyl-1-piperazinyl)-1-propanone;1-Benzoyl-4-(1-oxopropyl)-piperazine;1-(4-Benzoylpiperazin-1-yl)propan-1-one;1-Benzoyl-4-propanoylpiperazine;Sunifiram DM235
• CAS NO: 314728-85-3
• Molecular Formula: C14H18N2O2
• Molecular Weight: 246.30492
• EINECS: 1312995-182-4
• Product Categories: pharmaceutical
• Mol File: 314728-85-3.mol

Chemical Properties

• Boiling Point: 442.0±38.0 °C(Predicted)
• Appearance: white/
• Density: 1.154±0.06 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble24mg/mL
• PKA: 0.08±0.70(Predicted)
• CAS DataBase Reference: Piperazine, 1-benzoyl-4-(1-oxopropyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Piperazine, 1-benzoyl-4-(1-oxopropyl)-(314728-85-3)
• EPA Substance Registry System: Piperazine, 1-benzoyl-4-(1-oxopropyl)-(314728-85-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 314728-85-3(Hazardous Substances Data)

Usage

Uses

Sunifiram is a potent nootropic agent.

Side effects

While initial research suggests that sunifiram is virtually non-toxic and doesn’t produce any notable side effects, it’s important to note how little research has been conducted on this compound. For this reason, it’s incredibly important that you begin with a low dosage before ramping up to a higher one, and pay close attention to any noted side effects you experience.Based on anecdotal evidence, some sunifiram users have experienced side effects such as:HeadacheHot flashesDifficulty sleepingManic feelingsThese side effects seem only to be mentioned with dosages outside of the 5-10mg range, with higher doses producing more pronounced side effects. If you find that you’re experiencing side effects as you up your dosage, ramp down your dosage to a level where no side effects are present.

Mode of action

Sunifiram enhances NMDA-dependent signaling by increasing PKCα phosphorylation, at a dosage range of 10-100nM. This mechanism of action is dependent on the availability of the glycine binding site and Sunifiram has been shown to act as an antagonist to glycine at a concentration of 300μM.Furthermore, the increased activity of AMPA receptor activation has been associated with increased CAMKII and PKCα phosphorylation. Although studies have confirmed that intracellular proteins like CAMKII and PKCα are activated after Sunifiram administration, other proteins like CaMKIV and ERK remain unaffected.A brief summary of the mechanism of action, as it is currently understood, is that Sunifiram acts on the NMDA receptor’s glycine binding site, which results in increased signaling and activation of CAMKII and PKCα proteins and the subsequent positive regulation of AMPA receptors.Furthermore, animal studies have indicated that a dosage of 0.01mg/kg increases acetylcholine release by up to 200% within one hour of injection, in rat prefrontal cortex. This effect is not seen at a higher dosage of 1mg/kg.

Upstream product

• 76816-54-1 1-(piperazin-1-yl)propan-1-one 
• 98-88-4 benzoyl chloride 
• 314728-80-8 1-(4-benzyl-piperazin-1-yl)-propan-1-one 
• 79-03-8 propionyl chloride 
• 13754-38-6 N-Benzoylpiperazine 
• 54264-50-5 1-(1H-benzo[d][1,2,3]triazol-1-yl)propan-1-one 

Relevant articles and documents

Novel Sunifiram-carbamate hybrids as potential dual acetylcholinesterase inhibitor and NMDAR co-agonist: simulation-guided analogue design and pharmacological screening

An efficient method for synthesising NMDAR co-agonist Sunifiram (DM235), in addition to Sunifram-carbamate and anthranilamide hybrids, has been developed in high yields via protecting group-free stepwise unsymmetric diacylation of piperazine using N-acylb

Meta-Selective C-H Borylation of Benzamides and Pyridines by an Iridium-Lewis Acid Bifunctional Catalyst

We report herein the iridium-catalyzed meta-selective C-H borylation of benzamides by using a newly designed 2,2′-bipyridine (bpy) ligand bearing an alkylaluminum biphenoxide moiety. We also demonstrate the iridium-catalyzed C3-selective C-H borylation of pyridine with a 1,10-phenanthroline (Phen) ligand bearing an alkylborane moiety. It is proposed that the Lewis acid-base interaction between the Lewis acid moiety and the aminocarbonyl group or the sp2-hybridized nitrogen atom accelerates the reaction and controls the site-selectivity.

Molecular simplification of 1,4-diazabicyclo[4.3.0]nonan-9-ones gives piperazine derivatives that maintain high nootropic activity

Several 4-substituted 1-acylpiperazines, obtained by molecular simplification of 4-substituted 1,4-diazabicyclo[4.3.0]nonan-9-ones, have been synthesized and tested in vivo on the mouse passive avoidance test, to evaluate their nootropic activity. The results show that, apparently, an N-acylpiperazine group can mimic the 2-pyrrolidinone ring of 1,4-diazabicyclo[4.3.0]nonan-9-one, as the compounds of the new series maintain high nootropic activity. Moreover molecular simplification produces more clear-cut structure-activity relationships with respect to the parent series. The mechanism of action also appears to be similar in the two series. In fact, although the molecular mechanism remains to be elucidated, the most potent compound of each class (DM232 and 13, DM235) is able to increase acetylcholine release in rat brain. Piperazine derivatives represent a new class of nootropic drugs with an in vivo pharmacological profile very similar to that of piracetam, showing much higher potency with respect to the reference compound. Among the compounds studied, 13 (DM235) shows outstanding potency, being active at a dose of 0.001 mg kg-1 sc.