64314-16-5

Basic information

• Product Name: (+)-ANATOXIN A HYDROCHLORIDE
• Synonyms: (1r)-1-(9-azabicyclo(4.2.1)non-2-en-2-yl)ethanonehydrochloride;1-(9-azabicyclo(4.2.1)non-2-en-2-yl)-,hydrochloride,(1r)-ethanon;(+)-ANATOXIN A HYDROCHLORIDE;2-ACETYL-9-AZABICYCLO[4.2.1]NON-2-ENE HYDROCHLORIDE;Ethanone, 1-(1R,6R)-9-azabicyclo4.2.1non-2-en-2-yl-, hydrochloride;Ethanone, 1-(9-azabicyclo(4.2.1)non-2-en-2-yl)-, hydrochloride, (1R)-
• CAS NO: 64314-16-5
• Molecular Formula: C10H16ClNO
• Molecular Weight: 201.69
• Mol File: 64314-16-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 291°C at 760 mmHg
• Flash Point: 124.7°C
• Appearance: /
• Vapor Pressure: 0.002mmHg at 25°C
• CAS DataBase Reference: (+)-ANATOXIN A HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-ANATOXIN A HYDROCHLORIDE(64314-16-5)
• EPA Substance Registry System: (+)-ANATOXIN A HYDROCHLORIDE(64314-16-5)

Safety Data

• RIDADR: 3172
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 64314-16-5(Hazardous Substances Data)

Usage

General Description

(+)-Anatoxin A hydrochloride is a toxic secondary metabolite produced by certain species of cyanobacteria, also known as blue-green algae. It is a potent neurotoxin that acts as an agonist for nicotinic acetylcholine receptors, causing overstimulation and eventual paralysis of the muscles. Exposure to this chemical can lead to symptoms such as weakness, respiratory failure, and death in severe cases. (+)-Anatoxin A hydrochloride has been identified as a potential threat to water sources and has prompted research into methods for monitoring and removing cyanobacterial toxins from drinking water.

InChI:InChI=1/C10H15NO.ClH/c1-7(12)9-4-2-3-8-5-6-10(9)11-8;/h4,8,10-11H,2-3,5-6H2,1H3;1H/t8?,10-;/m0./s1

Upstream product

• 133038-46-7 ethyl 2-(methoxycarbonylamino)hepta-5,6-dienoate 
• 112009-90-2 ethyl 2-benzylideneaminohepta-5,6-dienoate 
• 353461-15-1 tert-butyl (1R,6R)-2-oxo-9-azabicyclo[4.2.1]nonane-9-carboxylate 
• 19740-90-0 (Z)-9-oxabicyclo[6.1.0]non-4-ene 
• 90741-53-0 (1R)-2-acetyl-9-(1-tert-butoxycarbonyl)-9-azobicyclo<4.2.1>-2-nonene 
• 895138-28-0 (1R,2R,6R)-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonan-2-ol 
• 895138-29-1 (1R,6R)-9-[(R)-1-phenylethyl]-9-azabicyclo[4.2.1]nonan-2-one 
• 143264-77-1 (-)-N-tosylanatoxin-a 
• 143264-76-0 (E)-6-[(2R,5R)-5-Methoxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-hex-3-en-2-one 

Relevant articles and documents

Concise Synthesis of (+)-[13C4]-Anatoxin-a by Dynamic Kinetic Resolution of a Cyclic Iminium Ion

An asymmetric total synthesis of [13C4]-anatoxin-a ([13C4]-1) has been developed from commercially available ethyl [13C4]-acetoacetate ([13C4]-15). The unique requirements associated with isotope incorporation inspired a new, robust, and highly scalable route, providing access to 0.110 g of this internal standard for use in the detection and precise quantification of anatoxin-a in freshwater. A highlight of the synthesis is a method that leverages a cyclic iminium ion racemization to achieve dynamic kinetic resolution in an enantioselective Morita–Baylis–Hillman (MBH) cyclization.

Investigation of a unified strategy for the synthesis of anatoxin analogues: Scope and limitations

Syntheses of the potent neurotoxins and biochemical probes anatoxin-a and homoanatoxin and several analogues by a combined two-directional synthesis-tandem reaction strategy are presented. Key steps include an oxidative desymmetrisation and a tandem Micha

Synthetic and Stereochemical Studies Directed Towards Anatoxin-a

The synthesis and stereocontrolled Ag1-catalysed cyclisation of a series of allenic amino esters 8a-e is described.For compounds 8a-d the cis-2,5-disubstituted pyrrolidine 9 is formed exclusively but the primary amine 8e undergoes cyclisation n