Home > Carbonyl Compounds> (±)-Anatoxin A fumarate,(±)-2-Acetyl-9-azabicyclo[4.2.1]non-2-enefumarate

(±)-Anatoxin A fumarate,(±)-2-Acetyl-9-azabicyclo[4.2.1]non-2-enefumarate

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Origin: China

Cas No: 64285-06-9

Specification: 99%min

Min order Quantity: 1 /kg

Supply Ability: 80 mt/month

Lead time: 7 days for OEM, 3 days for ready goods

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CAS No.: 64285-06-9 Formula: C10H15NO Molecular Weight: 165.23200

Description

Anatoxin-a, also known as Very Fast Death Factor (VFDF), is a secondary, bicyclic amine alkaloid and cyanotoxin with acute neurotoxicity. It was first discovered in the early 1960s in Canada, and was isolated in 1972. The toxin is produced by seven different genera of cyanobacteria and has been reported in North America, Europe, Africa, Asia, and New Zealand. Symptoms of anatoxin exposure include loss of coordination, muscular fasciculations, convulsions and death by respiratory paralysis. Its mode of action is through the nicotinic acetylcholine receptor (nAchR) where it acts as an agonist of acetylcholine. As such, anatoxin-a has been used for medicinal purposes to investigate diseases characterized by low acetylcholine levels. Due to its high toxicity and potential presence in drinking water, anatoxin-a poses a threat to animals, including humans. While methods for detection and water treatment exist, scientists have called for more research to improve reliability and efficacy. Anatoxin-a is not to be confused with anatoxin-a(S), another potent cyanotoxin that has a similar mechanism of action to that of anatoxin-a and is produced by many of the same cyanobacteria genera, but is structurally unrelated.

Basic Info

Chemical Name	(±)-Anatoxin A fumarate,(±)-2-Acetyl-9-azabicyclo[4.2.1]non-2-enefumarate
Synonyms	Anatoxin 1; anatoxini; Antx-a;
CAS No.	64285-06-9
Molecular Formula	C10H15NO
Molecular Weight	165.23200
PSA	29.10000
LogP	1.74500

Properties

Appearance & Physical State	Lyophilized Solid
Density	1.037 g/cm3
Boiling Point	291ºC at 760 mmHg
Flash Point	124.7ºC
Refractive Index	1.503
Storage Condition	Desiccate at +4ºC

Safety Info

HS Code	2933990090

Synthesis Route

(1R)-2-acetyl-9-(benzyloxycarbonyl)-9-azabicyclo[4.2.1]-2-nonene→(±)-Anatoxin A fumarate,(±)-2-Acetyl-9-azabicyclo[4.2.1]non-2-enefumarate
(-)-N-tosylanatoxin-a→(±)-Anatoxin A fumarate,(±)-2-Acetyl-9-azabicyclo[4.2.1]non-2-enefumarate
(-)-(5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-tosylpyrrolidin-2-one→(±)-Anatoxin A fumarate,(±)-2-Acetyl-9-azabicyclo[4.2.1]non-2-enefumarate

Precursor

(-)-(5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-tosylpyrrolidin-2-one
(2R,5R)-2-(but-3-en-1-yl)-5-methoxy-1-tosylpyrrolidine
(1R)-2-acetyl-9-(benzyloxycarbonyl)-9-azabicyclo[4.2.1]-2-nonene
((2S,5R)-5-methoxy-1-tosylpyrrolidin-2-yl)methanol

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