4643. Hemicholinium

Nomenclature

CAS number: 16478-59-4
2,2′-[1,1′-Biphenyl]-4,4′-diylbis[2-hydroxy-4,4-dimethylmorpholinium]; 2,2′-(4,4′-biphenylylene)bis[2-hydroxy-4,4-dimethylmorpholinium].
[C24H34N2O4]2+.

Description and 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).

Chemical structure

Derivative

Dibromide.

Nomenclature

CAS number: 312-45-8
Hemicholinium-3; HC-3.
C24H34Br2N2O4; mol wt 574.35.
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).

Use

Research tool as cholinergic probe, to deplete acetylcholine stores.