Piperazine
Title: Piperazine
CAS Registry Number: 110-85-0
Additional Names: Hexahydropyrazine; piperazidine; diethylenediamine
Molecular Formula: C4H10N2
Molecular Weight: 86.14
Percent Composition: C 55.77%, H 11.70%, N 32.52%
Literature References: Prepn: Cloez, Jahresber. 1853, 468; Wolff, Ber. 26, 724 (1893); Kyrides, US 2267686 (1941); Martin, Martell, J. Am. Chem. Soc. 70, 1817 (1948); MacKenzie, Turbin, US 2901482 (1959 to Dow); Moss, Godfrey, US 3037023 (1962 to Jefferson Chem.). Prepn of salts: Hefferren et al., J. Am. Pharm. Assoc. 44, 678 (1955). Determn in animal feeds: J. D. McLean, O. L. Daniels, J. Assoc. Off. Anal. Chem. 54, 555 (1971). Veterinary trial in combination with levamisole: J. H. Drudge et al., Am. J. Vet. Res. 35, 67 (1974). Clinical efficacy in roundworm infection: A. S. Nanivadekar et al., J. Postgrad. Med. 30, 144 (1984).
Properties: Leaflets from alc, mp 106°. Salty taste. bp760 146°. Strong base: pKa: 4.19, absorbs water and CO2 from air. Absorption spectrum: Purvis, J. Chem. Soc. 103, 2286, 2293 (1913). Freely sol in water, glycerol, glycols; one gram dissolves in 2 ml of 95% alcohol. Insol in ether. pH of a 10% aq soln 10.8-11.8. Forms a sol compd with theophylline. Keep tightly closed and protect from light.
Melting point: mp 106°
Boiling point: bp760 146°
pKa: pKa: 4.19, absorbs water and CO2 from air
 
Derivative Type: Hexahydrate
Trademarks: Dietelmin; Helmifren; Parid (Cooper); Paravermin; Tasnon (elixir) (Tropon); Upixon (Bayer); Uvilon (Bayer)
Molecular Formula: C4H10N2.6H2O
Molecular Weight: 194.23
Percent Composition: C 24.74%, H 11.42%, N 14.42%, O 49.42%
Properties: Crystals from water (contg 44.34% anhydr piperazine), mp 44°. bp 125-130°. The piperazine of commerce is usually this hydrate. Freely sol in water; sol in alc (~1:2). Practically insol in ether. pH of a 10% aq soln 10.8-11.8.
Melting point: mp 44°
Boiling point: bp 125-130°
 
Derivative Type: Citrate
CAS Registry Number: 144-29-6
Additional Names: Tripiperazine dicitrate
Trademarks: Helmezine (Allen & Hanburys); Oxucide; Parazine; Pinozan; Pipizan Citrate (Merck & Co.); Pipracid (syrup) (Universal Drug); Rhomex; Ta-Verm; Worm Away (Robins)
Molecular Formula: 3C4H10N2.2C6H8O7
Molecular Weight: 642.65
Percent Composition: C 44.85%, H 7.21%, N 13.08%, O 34.85%
Properties: Crystals, dec 182-187°. Freely sol in water. Practically insol in alcohol, ether, chloroform. pH of a 10% aq soln 5.0-6.0.
 
Derivative Type: Edetate calcium
CAS Registry Number: 12002-30-1
Additional Names: Piperazine calcium edathamil
Trademarks: Perin (Endo)
Molecular Formula: C14H24CaN4O8
Molecular Weight: 416.44
Percent Composition: C 40.38%, H 5.81%, Ca 9.62%, N 13.45%, O 30.74%
Literature References: Prepn: Schlesinger et al., US 2834782 (1958 to Endo).
Properties: Occurs as the dihydrate. Crystals; slightly salty taste. Freely sol in water. Very slightly sol in alcohol, chloroform. Practically insol in ether. pH of 20% aq soln 4.3-5.4.
 
Derivative Type: Phosphate
Trademarks: Antepar (Glaxo Wellcome); Pinrou (Century); Piperverm (Wild); Piperazate (Leeming); Tasnon (tabl.) (Tropon)
Molecular Formula: C4H10N2.H3PO4
Molecular Weight: 184.13
Percent Composition: C 26.09%, H 7.12%, N 15.21%, P 16.82%, O 34.76%
Properties: Minute crystals. Very slightly sol in water. pH of saturated aq soln, 6.5.
 
Derivative Type: Tartrate
CAS Registry Number: 133-36-8
Trademarks: Noxiurotan; Piperate
Molecular Formula: C4H10N2.C4H6O6
Molecular Weight: 236.22
Percent Composition: C 40.68%, H 6.83%, N 11.86%, O 40.64%
Properties: Crystals, dec 258-263°. Soly in g/100 ml at 25°: water 26; alcohol 0.01; chloroform 0.01. pH of 1% soln: 4.8.
 
Derivative Type: N1,N4-Dibenzoylpiperazine
Molecular Formula: C18H18N2O2
Molecular Weight: 294.35
Percent Composition: C 73.45%, H 6.16%, N 9.52%, O 10.87%
Properties: Prepd from piperazine and benzoyl chloride in dil NaOH. Crystals from alc, mp 191°.
Melting point: mp 191°
 
Therap-Cat: Anthelmintic (Nematodes).
Therap-Cat-Vet: Anthelmintic (Nematodes).
Keywords: Anthelmintic (Nematodes).

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