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H5902

Sigma-Aldrich

(−)-Huperzine A

Synonym(s):

(−)-Selagine, Kimpukan A

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About This Item

Empirical Formula (Hill Notation):
C15H18N2O
CAS Number:
102518-79-6
Molecular Weight:
242.32
MDL number:
MFCD01714949
UNSPSC Code:
12352200
PubChem Substance ID:
24895719

storage temp.

−20°C

SMILES string

[H][C@@]12CC3=C(C=CC(=O)N3)[C@@](N)(CC(C)=C1)C2=CC

InChI

1S/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)/b11-3+/t10-,15+/m0/s1

InChI key

ZRJBHWIHUMBLCN-YQEJDHNASA-N

Gene Information

human ... ACHE(43) , BCHE(590)
rat ... Ache(83817)

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Biochem/physiol Actions

Acetylcholinesterase inhibitor; active enantiomer.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310 + H330

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Qinghai Shi et al.
Neurochemical research, 37(9), 2042-2052 (2012-06-20)
Acute exposure to high altitudes can cause neurological dysfunction due to decreased oxygen availability to the brain. In this study, the protective effects of Huperzine A on cognitive deficits along with oxidative and apoptotic damage, due to acute hypobaric hypoxia
E L Konrath et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 19(14), 1321-1324 (2012-10-02)
Huperzine A, a Lycopodium alkaloid produced by Chinese folk herb Huperzia serrata (Lycopodiaceae), has been shown to be a promising agent for the treatment of Alzheimer's disease due to its potent acetylcholinesterase (AChE) activity, as well its efficacy in the
Ramachandra S Naik et al.
Journal of applied toxicology : JAT, 33(4), 290-300 (2012-03-13)
Current methods for measuring acetylcholinesterase (AChE) activities in whole blood use butyrylcholinesterase (BChE)-selective inhibitors. However, the poor selectivity of these inhibitors results in the inhibition of AChE activity to some degree, leading to errors in reported values. The goal of
Ying Wang et al.
Chemico-biological interactions, 203(1), 120-124 (2012-11-06)
The neuropathologic mechanisms after exposure to lethal doses of nerve agent are complex and involve multiple biochemical pathways. Effective treatment requires drugs that can simultaneously protect by reversible binding to the acetylcholinesterase (AChE) and blocking cascades of seizure related brain
Dou Yu et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(8), E746-E755 (2013-02-07)
Diverse mechanisms including activation of NMDA receptors, microglial activation, reactive astrogliosis, loss of descending inhibition, and spasticity are responsible for ∼40% of cases of intractable neuropathic pain after spinal cord injury (SCI). Because conventional treatments blocking individual mechanisms elicit only
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