Structural Formula Vector Image
Title: Hemicholinium
CAS Registry Number: 16478-59-4
CAS Name: 2,2¢-[1,1¢-Biphenyl]-4,4¢-diylbis[2-hydroxy-4,4-dimethylmorpholinium]
Additional Names: 2,2¢-(4,4¢-biphenylylene)bis[2-hydroxy-4,4-dimethylmorpholinium]
Molecular Formula: [C24H34N2O4]2+
Literature References: Specific, competitive inhibitor of the sodium-dependent high-affinity choline uptake system (HACU) localized on cholinergic presynaptic nerve terminals, resulting in the inhibition of acetylcholine synthesis. Prepn of seco tautomer: J. P. Long, F. W. Schueler, J. Am. Pharm. Assoc. 43, 79 (1954). In vitro pharmacology and revised hemiacetal structure: F. W. Schueler, J. Pharmacol. Exp. Ther. 115, 127 (1955). Structure-activity studies: R. P. DiAugustine, V. B. Haarstad, Biochem. Pharmacol. 19, 559 (1970); J. G. Cannon et al., Pharm. Res. 5, 359 (1988). Pharmacology: J. J. Freeman et al., J. Pharmacol. Exp. Ther. 210, 91 (1979); J. J. Hagan et al., Psychopharmacology 98, 347 (1989). Receptor binding studies in human brain: J. Pascual et al., J. Neurochem. 54, 792 (1990); in rat brain: eidem, Pharmacol. Res. 24, 345 (1991). Potential uses of tritium labeled compound: T. W. Vickroy et al. in Synth. Appl. Isotop. Labeled Compd. 1985, R. R. Muccino, Ed. (Elsevier, Amsterdam, 1986) pp 145-150; H. K. Happe, L. C. Murrin, J. Neurochem. 60, 1191 (1993).
Derivative Type: Dibromide
CAS Registry Number: 312-45-8
Additional Names: Hemicholinium-3; HC-3
Molecular Formula: C24H34Br2N2O4
Molecular Weight: 574.35
Percent Composition: C 50.19%, H 5.97%, Br 27.82%, N 4.88%, O 11.14%
Properties: mp 180°. Moderately soluble in water, soluble in ethanol. Occurs as the monohydrate, white solid from ethanol/ether, mp 226- 228° (dec). LD50 i.p. in female mice: 0.048-0.082 mg/kg (DiAugustine, Haarstad).
Melting point: mp 180°; mp 226- 228° (dec)
Toxicity data: LD50 i.p. in female mice: 0.048-0.082 mg/kg (DiAugustine, Haarstad)
Use: Research tool as cholinergic probe, to deplete acetylcholine stores.

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