58077-68-2

Basic information

• Product Name: 4-(4-Methyl-1-piperazinyl)butanoic Acid
• Synonyms: 4-(4-Methyl-1-piperazinyl)butanoic Acid;4-methyl-1-Piperazinebutanoic acid;4-(4-Methylpiperazin-1-yl);4-(4-methylpiperazin-1-ium-1-yl)butanoate
• CAS NO: 58077-68-2
• Molecular Formula: C₉H₁₈N₂O₂
• Molecular Weight: 186.25142
• Mol File: 58077-68-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 327.2±27.0 °C(Predicted)
• Appearance: /
• Density: 1.071±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.74±0.10(Predicted)
• CAS DataBase Reference: 4-(4-Methyl-1-piperazinyl)butanoic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-Methyl-1-piperazinyl)butanoic Acid(58077-68-2)
• EPA Substance Registry System: 4-(4-Methyl-1-piperazinyl)butanoic Acid(58077-68-2)

Safety Data

• Hazardous Substances Data: 58077-68-2(Hazardous Substances Data)

Usage

General Description

4-(4-Methyl-1-piperazinyl)butanoic acid is a chemical compound with molecular formula C11H22N2O2. It is also known as Gabapentin, and it is used as a medication to treat epilepsy, neuropathic pain, and restless leg syndrome. It belongs to the class of anticonvulsant medications, and it works by affecting the chemicals and nerves in the body that are involved in seizures and in the symptoms of neuropathic pain. Gabapentin is often prescribed in tablet or capsule form and is typically taken orally. It is important to follow the directions of a healthcare professional when taking this medication, as it can have potential side effects and interactions with other drugs.

Upstream product

• 487008-51-5 ethyl 4-(4-methylpiperazin-1-yl)butanoate 
• 109-01-3 1-methyl-piperazine 

Relevant articles and documents

Synthesis and in vitro evaluation of novel morpholinyl- and methylpiperazinylacyloxyalkyl prodrugs of 2-(6-methoxy,2-naphthyl)propionic acid (naproxen) for topical drug delivery

Various novel morpholinyl- (3a,b) and methylpiperazinylacyloxyalkyl (3c- f) esters of 2-(6-methoxy-2-naphthyl)propionic acid were synthesized and evaluated in vitro for topical drug delivery as potential prodrugs of naproxen (1). Compounds 3a-f were prepared by coupling the corresponding naproxen hydroxyalkyl ester with the morpholinyl- or (4-methyl-1- piperazinyl)acyl acid in the presence of dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino)-pyridine (DMAP) and quantitatively hydrolyzed (t(1/2) = 1- 26 min) to naproxen in human serum. Compounds 3c-f showed higher aqueous solubility and similar lipophilicity, determined by their octanol-buffer partition coefficients (log P(app)), at pH 5.0 when compared to naproxen. At pH 7.4 they were significantly more lipophilic than naproxen. The best prodrug 3c led to a 4-and 1.5-fold enhancement of skin permeation when compared to naproxen at pH 7.4 and 5.0, respectively. The present study indicates using a methylpiperazinyl group yields prodrugs that are partially un-ionized under neutral and slightly acidic conditions, and thus, a desirable combination is achieved in terms of aqueous solubility and lipophilicity. Moreover, the resulting combination of biphasic solubility and fast enzymatic hydrolysis of the methylpiperazinylacyloxyalkyl derivatives gave improved topical delivery of naproxen.