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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

Quality Level

100

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

Signal Word

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 Code

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

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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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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