(+/-)-Huperzine A

Base Information

• Chemical Name: (+/-)-Huperzine A
• CAS No.: 120786-18-7
• Molecular Formula: C15H18N2O
• Molecular Weight: 242.321
• European Community (EC) Number: 600-320-6,634-239-2
• DSSTox Substance ID: DTXSID801115670
• Wikipedia: Huperzine_A
• NCI Thesaurus Code: C97271
• Metabolomics Workbench ID: 133445
• ChEMBL ID: CHEMBL394259
• Mol file: 120786-18-7.mol

Synonyms:huperzine A;huperzine A, (5alpha,9beta,11Z)-(-)-isomer;fordine

Chemical Property of (+/-)-Huperzine A

Chemical Property:

• Appearance/Colour: Brown to White Powder
• Refractive Index: 1.626
• Boiling Point: 505 °C at 760 mmHg
• PKA: 12.25±0.60(Predicted)
• Flash Point: 259.2 °C
• PSA: 58.88000
• Density: 1.2 g/cm³
• LogP: 2.69780
• Storage Temp.: 2-8°C
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 242.141913202
• Heavy Atom Count: 18
• Complexity: 551

Purity/Quality:

99.89% ^*data from raw suppliers

(+/-)-HuperzineA ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25-36/37/38
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC=C1C2CC3=C(C1(CC(=C2)C)N)C=CC(=O)N3
• Isomeric SMILES: C/C=C/1\C2CC3=C(C1(CC(=C2)C)N)C=CC(=O)N3
• Recent ClinicalTrials: A Study of Huperzine A Injection in Reducing Postoperative Delirium in Elderly Patients Undergoing Non-cardiac Surgery
• Description: Huperzine A is an alkaloid extract derived from the Chinese club moss Huperzia serrata. It is an acetylcholinesterase inhibitor. This means it helps promote higher levels of acetylcholine in the brain. Higher levels of acetylcholine support ones ability to perform cognitive tasks such as learning new things, memorizing information, and focusing at the task at hand. Huperzine A is considered to be a nootropic supplement because it supports cognitive function. It is considered a focus and memory nootropic similar to alpha gpc, bacopa, phosphatidylcholine, cdp choline, sulbutiamine, and uridine. It is also considered a brain booster as it is used for brain health and support.Huperzine A for many years has been widely used in traditional Chinese medicine to enhance memory and to treat fever and inflammation. In the United States it is commercially available as a food supplement, but has not been approved by the FDA as a treatment for AD or other cognition disorders.
• Uses: Huperzine A is used for dementia in Alzheimer’s disease and for muscle weakness in myasthenia gravis. (+/-)-Huperzine A is an NMDA antagonist.

Technology Process of (+/-)-Huperzine A

There total 77 articles about (+/-)-Huperzine A which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

methyl ((5S,E)-11-ethylidene-2-methoxy-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-5-yl)carbamate (185741-46-2) → natural Huperzine A (92138-20-0,102518-79-6,103735-86-0,120786-18-7,130791-77-4,132435-40-6,116-28-9)

Guidance literature:

methyl ((5S,E)-11-ethylidene-2-methoxy-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-5-yl)carbamate; With trimethylsilyl iodide; In chloroform; for 6h; Reflux; Inert atmosphere;

With methanol; In chloroform; for 3h; Reflux; Inert atmosphere;

DOI:10.1021/ol9022408

Reference yield: 74.0%

(-)-huperzine A 2,3-dibenzoyl-D-tartaric acid salt → natural Huperzine A (92138-20-0,102518-79-6,103735-86-0,120786-18-7,130791-77-4,132435-40-6,116-28-9)

Guidance literature:

With sodium hydroxide; In water; for 1h; pH=9 - 9.3;

Reference yield: 60.0%

C16H16N2O2 → natural Huperzine A (92138-20-0,102518-79-6,103735-86-0,120786-18-7,130791-77-4,132435-40-6,116-28-9)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 80 ℃; for 36h;

upstream raw materials:

(E)-(+/-)-(11-ethylidene-9,10-dihydro-2-methoxy-7-methyl-5,9-methanocyclooctapyridin-5(6H)-yl)carbamic acid methyl ester

[13-Eth-(E)-ylidene-5-methoxy-11-methylene-6-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-trien-1-yl]-carbamic acid methyl ester

(E)-11-ethylidene-5,6,9,10-tetrahydro-5-(methoxycarbonylamino)-7-methyl-5,9-methano-1H-cycloocta[b]pyridin-2-one

13-Eth-(E)-ylidene-5-methoxy-11-methylene-6-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene-1-carboxylic acid

Downstream raw materials:

(5R,9R,11E)-5-(3-phenylprop-2-en-1-ylideneamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one

C₂₄H₂₆N₂O₃

C₂₄H₂₆N₂O₃

(5R,9R,11E)-5-(4-methoxyphenylmethylidenylamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one

Refernces

• 1、 -. "METHODS OF RESOLVING RACEMIC MIXTURE TO OBTAIN (-)-HUPERZINE A". Page/Page column 10. . Retrieved 2016/04/26.
• 2、 White, James D.,Li, Yang,Kim, Jungchul,Terinek, Miroslav. "Cyclobutane Synthesis and Fragmentation. A Cascade Route to the Lycopodium Alkaloid (-)-Huperzine A". . p. 11806 - 11817. Retrieved 2015/12/11.