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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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Ling Yang et al.
Journal of Alzheimer's disease : JAD, 31(1), 131-142 (2012-04-26)
A number of recent discoveries indicate that huperzine A, an active herbal medicine employed for the treatment of Alzheimer's disease (AD) in China, can afford neuroprotection on in vitro and in vivo models related to mitochondrial dysfunction. However, it is
Marcus Trapp et al.
The journal of physical chemistry. B, 116(51), 14744-14753 (2012-11-29)
Enzymes are animated by a hierarchy of motions occurring on time scales that span more than 15 orders of magnitude from femtoseconds (10(-15) s) to several minutes. As a consequence, an enzyme is characterized by a large number of conformations
Liu, J.-S., et al.
Canadian Journal of Chemistry, 64, 837-837 (1986)
Paula Lunardi et al.
Life sciences, 92(12), 701-707 (2013-02-13)
The loss of cholinergic function in the central nervous system contributes significantly to the cognitive decline associated with advanced age and dementias. Huperzine A (HupA) is a selective inhibitor of acetylcholinesterase (AChE) and has been shown to significantly reduce cognitive
Hai-Yan Zhang
Acta pharmacologica Sinica, 33(9), 1170-1175 (2012-09-04)
Huperzine A, an active Lycopodium alkaloid extracted from traditional Chinese herb, is a potent, selective and reversible acetylcholinesterase (AChE) inhibitor and has been widely used in China for the treatment of Alzheimer's disease (AD). Accordingly, some new mechanisms of action
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