(-)-Huperzine A (CAS: 102518-79-6)

Chemical Information

• IUPAC Name: (1R,9R,13E)-1-Amino-13-ethylidene-11-methyl-7,11-diazatetracyclo[7.4.1.0^2,7.0^10,12]trideca-2(7),3,5-trien-8-one

• Synonyms: Huperzine A, Selagine

• Molecular Formula: C15H18N2O

• Molecular Weight: 242.32 g/mol

Structure and Properties

• Chemical Structure: Huperzine A is an alkaloid derived from the plant Huperzia serrata. It features a complex tetracyclic structure with a unique arrangement of nitrogen and oxygen atoms.

• Appearance: Typically a white to off-white crystalline powder.

• Solubility: Soluble in organic solvents such as ethanol and methanol; slightly soluble in water.

Biological Significance

• Mechanism of Action: Huperzine A is a potent inhibitor of acetylcholinesterase (AChE), the enzyme that breaks down the neurotransmitter acetylcholine. By inhibiting AChE, huperzine A increases the levels of acetylcholine in the brain, which is beneficial for cognitive functions.

• Therapeutic Uses:

• Cognitive Enhancer: Used for its potential to improve memory and cognitive function, particularly in conditions like Alzheimer's disease and other forms of dementia.

• Neuroprotective Effects: May offer protective benefits against neurodegenerative diseases due to its antioxidant properties and ability to protect neurons from glutamate-induced toxicity.

Applications and Uses

• Medical and Dietary Supplement:

• Available as an over-the-counter dietary supplement aimed at enhancing memory and cognitive functions.

• Investigated in clinical trials for the treatment of Alzheimer's disease and other cognitive disorders.

• Research: Extensively studied for its pharmacological effects on the nervous system and its potential therapeutic applications.

Safety and Handling

• Dosage and Administration: Common dosages in supplements range from 50 to 200 micrograms per day. It is important to follow dosage recommendations to avoid potential side effects.

• Side Effects: Generally well-tolerated, but possible side effects include nausea, diarrhea, vomiting, sweating, blurred vision, and cramping.

• Precautions: Should be used with caution in individuals with cardiovascular diseases or those taking medications that affect heart rate and rhythm.

References and Resources

Huperzine A is significant in both clinical and research contexts due to its potential cognitive-enhancing and neuroprotective properties. For precise safety guidelines and detailed information, always refer to the specific Material Safety Data Sheet (MSDS) provided by the manufacturer or supplier.