(-)-Huperzine A

(-)-Huperzine A (CAS 102518-79-6)

(-)-Huperzine A | CAS 102518-79-6 is rated 5.0 out of 5 by 1.
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Synonym: (-)-Selagine
Application: An inhibitor of AChE and antagonist of NMDA receptors
CAS Number: 102518-79-6
Purity: ≥95%
Molecular Weight: 242.32
Molecular Formula: C15H18N2O
Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
* Refer to Certificate of Analysis for lot specific data (including water content).
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(-)-Huperzine A is a natural product that acts as an NMDA receptor antagonist and reversible inhibitor of AChE (acetylcholinesterase), the enzyme primarily responsible for degradation of the neurotransmitter acetylcholine and termination of the acetylcholine synaptic signal. (-)-Huperzine A is the more potent stereoisomer of racemic (±)-Huperzine A (sc-218582) preparations, an approximately 38-fold more potent inhibitor of AChE than (+)-Huperzine A. Both the (-) and (+) stereoisomers also demonstrate NMDA receptor antagonism with similar affinity. Pretreatment of cerebral neuronal cells with (-)-Huperzine A confers protection against glutamate-mediated Ca2+ influx and excitotoxicity, moderated by blockade of NMDA-associated ion channel activity. Disruption of spatial memory induced by scopolamine (sc-203259) and muscimol (sc-200460) was reversed by introduction of (-)-Huperzine A. Excitotoxicity resulting from organophosphorous nerve agent-induced accumulation of acetylcholine, also mediated through NMDA receptor stimulation, is diminished by exposure to the enantiomer (+)-Huperzine A and preparations of (±)-Huperzine A are suggested for use in nerve agent protection. (-)-Huperzine A is demonstrated to suppress cerebral hypoperfusion-related inflammation through its indirect effects upon the nicotinic acetylcholine receptor.


References

1. Tang, X.C., et al. 1986. Zhongguo Yao Li Xue Bao. 7: 507-511. PMID: 2955639
2. Xu, H. and Tang, X.C. 1987. Zhongguo Yao Li Xue Bao. 8: 18-22. PMID: 2955654
3. Ved, H.S., et al. 1997. Neuroreport. 8: 963-968. PMID: 9141073
4. Gao, Y., et al. 2000. Acta Pharmacol. Sin. 21: 1169-1173. PMID: 11603295
5. Coleman, B.R., et al. 2008. Chem. Biol. Interact. 175: 387-395. PMID: 18588864
6. Wang, J., et al. 2010. J. Neurosci. Res. 88: 807-815. PMID: 19795377
7. Luo, H., et al. 2010. Physiol Plant. 139: 1-12. PMID: 20059733

Physical State :
Solid
Derived From :
Lycopodium sp.
Solubility :
Soluble in methanol, and DMSO. Insoluble in water.
Storage :
Store at -20° C
Melting Point :
214-215° C
Boiling Point :
505.01° C at 760 mmHg
Density :
1.20 g/cm3
Refractive Index :
n20D 1.63
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
PB9185700
Transport :
UN 1544, Class 6.1, Packing group II
PubChem CID :
907504
Merck Index :
14: 4755
MDL Number :
MFCD01714949
SMILES :
C/C=C\1/[C@@H]2CC3=C([C@]1(CC(=C2)C)N)C=CC(=O)N3

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Certificate of Analysis

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Rated 5 out of 5 by from Wang Wang, J. et al. (PubMed 19795377) reported that (-)-Huperzine A improves chronic inflammation and cognitive decline in rats with cerebral hypoperfusion. -SCBT Publication Review
Date published: 2015-01-02
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