1-Cyclohexylpiperazine is a synthetic chemical compound derived from piperazine. As a substituted piperazine, 1-cyclohexylpiperazine serves as a precursor and intermediate for several experimental antineoplastics and substances, including PB-28 and phenoxyalkylpiperazine derivatives.
1-cyclohexylpiperazine is also recognized as an eye and respiratory irritant, and is potentially corrosive to human skin.
In pharmacology, 1-cyclohexylpiperazine, unlike some derived piperazines, is not considered a drug. It is instead classified as a ligand with an affinity for sigma receptors (σ-receptors). In unsubstituted variants, 1-cyclohexylpiperazine has a weak affinity for sigma-1 and sigma-2 receptors (σ-receptors), though its derivatives have some form of nanomolar affinity.
Characteristics Properties and molecular structure
At standard temperature and pressure, 1-cyclohexylpiperazine is a solid powder with variable color ranging between white, yellow, and brown. 1-cyclohexylpiperazine has a molecular formula of C10H20N2 and a molar mass of 168.28 g/mol, or 168.162648646 Da.
1-cyclohexylpiperazine is composed of a piperazine ring, a cyclohexyl group, and aliphatic nitrogen amines. As nitrogen possesses lone pairs of electrons, this leads to the compound's high molecular nucleophilicity and a potential to transfer electrons. As such, 1-cyclohexylpiperazine may react strongly with oxidizing agents during N-oxidation. Its nitrogen atoms may also exist in protonated forms, which supplement the formation of an ionic salt if counterions are present.
Physical properties At 25°C (77°F) and 1 standard atmosphere (101.325 kPa) in air, 1-cyclohexylpiperazine possesses a density of 0.9725 g/cm. Furthermore, it retains a low melting point of 28°C (88.2°F) to 37°C (98.6°F), a flash point of 103.3°C (217.94°F) and a boiling point of 255.7 (492.26°F) to 287.25°C (549.05°F), assuming 760 mmHg.
As 1-cyclohexylpiperazine is moderately hydrophobic, it is only slightly soluble in water. It is soluble in methanol and chloroform.
Safety and precautions
Toxicity 1-cyclohexylpiperazine is considered toxic to the human body, specifically the respiratory system. In vaporous forms, it is advised to use in a well-ventilated area, or outdoors. In solid forms, it is ill-advised for consumption.
Applications 1-cyclohexylpiperazine serves as a fundamental intermediate, e.g. neuropharmacological derivatives used for the treatment of cranial nerve disorders, or for the synthesis of active pharmaceutical ingredients like Avatrombopag. It may also serve as a negative control and reference standard for nuclear magnetic resonance spectroscopy.
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