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H5777

Sigma-Aldrich

(±)-Huperzine A

synthetic, ≥98% (TLC)

Synonym(s):

(±)-Selagine

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About This Item

Empirical Formula (Hill Notation):
C15H18N2O
CAS Number:
120786-18-7
Molecular Weight:
242.32
MDL number:
MFCD00171439
UNSPSC Code:
12352200
PubChem Substance ID:
24895708
NACRES:
NA.77

biological source

synthetic

assay

≥98% (TLC)

form

powder

solubility

methanol: 10 mg/mL, clear, colorless

storage temp.

2-8°C

SMILES string

C\C=C1/C2CC3=C(C=CC(=O)N3)C1(N)CC(C)=C2

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+

InChI key

ZRJBHWIHUMBLCN-QDEBKDIKSA-N

Gene Information

human ... BCHE(590)
rat ... Ache(83817)

General description

Huperzine A is an alkaloid derived from Chinese club moss Huperzia serrata.

Application

(±)-Huperzine A has been used in anti-acetylcholinesterase bioautographic assay.

Biochem/physiol Actions

Huperzine A is an effective acetylcholinesterase inhibitor and can cross the blood-brain barrier. Huperzine A is known to prevent cognitive defects, glutamate-induced nerve cell death.It is recognized for its use in the treatment of Alzheimer′s disease and organophosphate poisoning.

Chem/Phys Resistance

Acetylcholinesterase inhibitor.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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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Coumarins from Peucedanum ostruthium. as Inhibitors of Acetylcholinesterase
Urbain A, et al.
Pharmaceutical biology, 43(8), 647-650 (2005)
Yun Zhou et al.
Planta medica, 75(6), 568-574 (2009-02-14)
Three new saponins, bacopasides IX-XI (1- 3), together with their known analogues bacopaside I (4), bacopaside II (5), bacopasaponsin C (6), and bacopasaponsin D (7), were isolated from the whole plant of Bacopa monniera. Compounds 3, 4, and 6 showed
Women's Health in Complementary and Integrative Medicine, 138-138 (2004)
X C Tang et al.
Journal of neuroscience research, 24(2), 276-285 (1989-10-01)
The present study represents the first comprehensive investigation of the effect of huperzine A (HUP-A), a new cholinesterase inhibitor (ChEI) isolated from a Lycopodium species, upon acetylcholinesterase (AChE) activity, acetylcholine (ACh) levels and release, and cholinergic receptors in rat brain

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