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Huperzine A
Monograph Number: 4774Title:Huperzine ACASRegistry Number: 102518-79-6CASName: [5R-(5a,9b,11E)]-5-Amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocyclooctapyridin-2(1H)-oneAdditionalNames: selagine; HUPMolecularFormula: C15H18N2OMolecularWeight: 242.32. Percent Composition: C 74.35%, H 7.49%, N 11.56%,O 6.60%Literature References:Reversible alkaloid inhibitor of AChE which crosses the blood-brain barrier.Occurs as the (-)-form in the vegetative part of clubmosses; teas brewed fromthese mosses have traditionally been used in China to alleviate memoryproblems. Isolated as selagine from Lycopodium selago L., Lycopodiaceae:J. Muszynski, Quart. J. Pharm. Pharmacol. 21, 34 (1948); from Huperziaserrata as huperzine: Chin. Co-op Res. Group, J. Tradit. Chin. Med. 2,45 (1982). Original structure: Z. Valenta et al., Tetrahedron Letters1960, 26; revised structure as huperzine A: J.-S. Liu et al., Can.J. Chem. 64, 837 1986. Identity with selagine: W. A. Ayer et al.,ibid. 67, 1538 (1989). Synthesis of (?-form: A. P. Kozikowski etal., J. Org. Chem. 56, 4636 (1991); G. Campiani et al.,ibid. 58, 7660 (1993). NMR spectra: B. N. Zhou et al., Phytochemistry34, 1425 (1993). Anticholinesterase activity: Y.-E. Wang et al., ActaPharmacol. Sin. 7, 110 (1986); binding profile of enantiomers: M.McKinney et al., Eur. J. Pharmacol. 203, 303 (1991);binding specificity: Y. Ashani et al., Mol. Pharmacol. 45,555 (1994). Clinical evaluation in senile dementia: R.-W. Zhang et al., ActaPharmacol. Sin. 12, 259 (1991). Brief review of chemistry andclinical use: D. Bai, Pure Appl. Chem. 65, 1103-1112 (1993).Properties:Monoclinic crystals from acetone, mp 214-215? [a]D-147?(c = 0.36 in CH3OH) (Ayer). Also reported as mp 230? [a]24.5D -150.4?(c = 0.498 in MeOH) (Liu). uv max (EtOH): 231, 313 nm (loge 4.01,3.89).Melting point:mp 214-215? mp 230°OpticalRotation: [a]-147?(c = 0.36 in CHOH) (Ayer); [a]24.5D3D-150.4?(c = 0.498 in MeOH) (Liu)Absorptionmaximum: uv max (EtOH): 231, 313 nm (log e 4.01, 3.89)Therap-Cat:In treatment of memory disorders.
