Title: Tacrine
CAS Registry Number: 321-64-2
CAS Name: 1,2,3,4-Tetrahydro-9-acridinamine
Additional Names: 9-amino-1,2,3,4-tetrahydroacridine; 5-amino-1,2,3,4-tetrahydroacridine; 1,2,3,4-tetrahydro-5-aminoacridine
Molecular Formula: C13H14N2
Molecular Weight: 198.26
Percent Composition: C 78.75%, H 7.12%, N 14.13%
Literature References: Centrally active anticholinesterase; cognition enhancer. Prepn: Braun et al., Ber. 64, 227 (1931); Albert, Gledhill, J. Soc. Chem. Ind. 64, 169T (1945); Petrow, J. Chem. Soc. 1947, 634; J. A. Moore, L. D. Kornreich, Tetrahedron Lett. 4, 1277 (1963). Pharmacology and toxicity: S. Gershon, F. H. Shaw, J. Pharm. Pharmacol. 10, 638 (1958). Enzyme inhibiting activity: P. N. Kaul, ibid. 14, 243 (1962). Neuropharmacology: B. Drukarch et al., Life Sci. 42, 1011 (1988). Spectrofluorimetric determn in serum: I. Aparico et al., Analyst 123, 1575 (1998). Clinical trial in severe Alzheimer's disease: W. K. Summers et al., N. Engl. J. Med. 315, 1241 (1986). See also: ibid. 316, 1603-1606. Clinical evaluation of reduced mortality in dementia: B. R. Ott, K. L. Lapane, J. Am. Geriatr. Soc. 50, 35 (2002). Review of pharmacology and clinical uses: W. K. Summers et al., Clin. Toxicol. 16, 269-281 (1980); of cholinesterase inhibition in Alzheimer's disease: N. Qizilbash et al., J. Am. Med. Assoc. 280, 1777-1782 (1998).
Properties: Octahedra from very dil alc, mp 183-184°.
Melting point: mp 183-184°
Derivative Type: Hydrochloride
CAS Registry Number: 1684-40-8
Trademarks: Cognex (Warner-Lambert); THA (Woods)
Molecular Formula: C13H14N2.HCl
Molecular Weight: 234.72
Percent Composition: C 66.52%, H 6.44%, N 11.93%, Cl 15.10%
Properties: Yellow needles from concd hydrochloric acid, mp 283-284°. Bitter taste. Sol in water. pH of 1.5% soln: 4.5-6. uv max (acetate buffer, pH 1-7): 242 nm. Emission max: 362 nm.
Melting point: mp 283-284°
Absorption maximum: uv max (acetate buffer, pH 1-7): 242 nm
Therap-Cat: Nootropic. Antidote to curare. Respiratory stimulant.
Keywords: Antidote (Curare); Cholinesterase Inhibitor; Nootropic; Respiratory Stimulant.

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