Huperzine A

Structural formula
General
Surname	Huperzine A
other names	9-Amino-13-ethylidene-11-methyl-4-aza-tricyclo [7.3.1.0 3,8 ] trideca-3 (8), 6,11-trien-5-one ( IUPAC ); HupA; Huperaine A.; Selagine;
Molecular formula	C 15 H 18 N 2 O
External identifiers / databases
ECHA InfoCard	100.132.430
PubChem	854026
DrugBank	DB04864
Wikidata	Q425198
Drug information
Drug class	Antidementia drugs
Mechanism of action	reversible acetylcholinesterase - inhibitory
properties
Molar mass	242.32 g · mol -1
Physical state	firmly
Melting point	230 ° C
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 300-310-315-319-330-335
	P: 260-264-280-284-302 + 350-305 + 351 + 338
Toxicological data	1.8 mg kg −1 ( LD 50 , mouse , ip , (-) - HupA) ; 2.5 mg kg −1 ( LD 50 , rat , iv , (-) - HupA) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Huperzine A is a strong acetylcholinesterase inhibiting agent . It belongs to the Lycopodium alkaloids . It is being tested as an experimental drug for the therapy of Alzheimer's disease .

Occurrence

Fir club moss ( Huperzia selago )

Huperzine A is a natural substance that occurs in the bear moss family ( Huperzia selago , Huperzia serrata ).

Pharmacological properties

Mechanism of action (pharmacodynamics)

Huperzine A reversibly inhibits acetylcholinesterase , which means that a certain acetylcholine level can be maintained. This slows down the degeneration process of nerve cells. It also protects the nerve cell from free radicals.

toxicology

Huperzine A is a powerful active ingredient that has a therapeutic effect in the microgram range (300–500 µg) and is relatively well tolerated. Otherwise, larger amounts of huperzine A are very toxic, both when inhaled and swallowed, as well as when in contact with the skin.

literature

G. Yang, Y. Wang, J. Tian, JP Liu: Huperzine A for Alzheimer's disease: a systematic review and meta-analysis of randomized clinical trials. In: PloS one. Volume 8, number 9, 2013, p. E74916, doi : 10.1371 / journal.pone.0074916 , PMID 24086396 , PMC 3781107 (free full text) (review).
QP Yang, et al .: Determination of huperzine A in formulated products by reversed-phase-liquid chromatography using diode array and electrospray ionization mass spectrometric detection . In: Phytomedicine , Vol. 10 (2003), pp. 200-206, PMID 12725577
Xu-Chang He, et al .: Studies on analogues of huperzine A for treatment of senile dementia. VI. Asymmetric total synthesis of 14-nor-huperzine A and its inhibitory activity of acetylcholinesterase . In: Acta Pharmaceutica Sinica , Vol. 38 (2003), No. 5, pp. 346-349, PMID 12958837 .

Individual evidence

↑ ^a ^b Entry on Huperzin A. In: Römpp Online . Georg Thieme Verlag, accessed on June 7, 2014.
↑ ^a ^b data sheet (-) - Huperzine A at Sigma-Aldrich , accessed on April 4, 2011 ( PDF ).
↑ ^a ^b ACToR (Aggregated Computational Toxicology Resource) Chemical Summary: huperzine A (102518-79-6) ( Memento from April 30, 2013 in the Internet Archive )
^ ^A ^b X. F. Yan, WH Lu, WJ Lou, XC Tang: [Effects of huperzine A and B on skeletal muscle and the electroencephalogram]. In: Zhongguo yao li xue bao = Acta Pharmacologica Sinica . Volume 8, Number 2, March 1987, pp. 117-123, PMID 2958995 .
↑ Wang BS, Wang H, Wei ZH, Song YY, Zhang L, Chen HZ: Efficacy and safety of natural acetylcholinesterase inhibitor huperzine A in the treatment of Alzheimer's disease: an updated meta-analysis . In: Journal of Neural Transmission . 116, No. 4, 2009, pp. 457-65. doi : 10.1007 / s00702-009-0189-x . PMID 19221692 .

[Römpp-1] Entry on Huperzin A. In: Römpp Online . Georg Thieme Verlag, accessed on June 7, 2014.

[Sigma-2] ta sheet (-) - Huperzine A at Sigma-Aldrich , accessed on April 4, 2011 ( PDF ).

[actor-3] ACToR (Aggregated Computational Toxicology Resource) Chemical Summary: huperzine A (102518-79-6) ( Memento from April 30, 2013 in the Internet Archive )

[PMID2958995-4] A ^b X. F. Yan, WH Lu, WJ Lou, XC Tang: [Effects of huperzine A and B on skeletal muscle and the electroencephalogram]. In: Zhongguo yao li xue bao = Acta Pharmacologica Sinica . Volume 8, Number 2, March 1987, pp. 117-123, PMID 2958995 .

[5] Wang BS, Wang H, Wei ZH, Song YY, Zhang L, Chen HZ: Efficacy and safety of natural acetylcholinesterase inhibitor huperzine A in the treatment of Alzheimer's disease: an updated meta-analysis . In: Journal of Neural Transmission . 116, No. 4, 2009, pp. 457-65. doi : 10.1007 / s00702-009-0189-x . PMID 19221692 .