64285-06-9 Usage
Description
(+/-)-2-ACETYL-9-AZA BICYCLO[4.2.1]NON-2-ENE FUMARATE is a bicyclic amine alkaloid and a cyanotoxin with acute neurotoxicity. It is a secondary metabolite produced by certain cyanobacteria genera and has been reported in various regions across the globe, including North America, Europe, Africa, Asia, and New Zealand. (+/-)-2-ACETYL-9-AZA BICYCLO[4.2.1]NON-2-ENE FUMARATE exhibits potent neurotoxic effects, posing a significant threat to both human and animal health.
Uses
Used in Neurotoxin Research:
(+/-)-2-ACETYL-9-AZA BICYCLO[4.2.1]NON-2-ENE FUMARATE is used as a research tool in the field of neurotoxin studies. Its acute neurotoxic properties make it valuable for understanding the mechanisms of neurotoxicity and developing potential countermeasures or treatments for exposure.
Used in Environmental Monitoring and Water Quality Assessment:
Due to its presence in certain cyanobacterial blooms, (+/-)-2-ACETYL-9-AZA BICYCLO[4.2.1]NON-2-ENE FUMARATE can be used as a bioindicator for assessing water quality and monitoring the presence of harmful cyanobacterial species in aquatic ecosystems.
Used in Pharmaceutical Development:
Although (+/-)-2-ACETYL-9-AZA BICYCLO[4.2.1]NON-2-ENE FUMARATE is a toxic compound, its unique structure and biological activity may provide insights for the development of new pharmaceutical agents with targeted neurotoxic effects for specific therapeutic applications.
Used in Public Health and Safety Education:
Awareness and education about the dangers of (+/-)-2-ACETYL-9-AZA BICYCLO[4.2.1]NON-2-ENE FUMARATE and other cyanotoxins are crucial for public health and safety. (+/-)-2-ACETYL-9-AZA BICYCLO[4.2.1]NON-2-ENE FUMARATE can be used as a case study in educational programs to inform the public about the risks associated with cyanobacterial blooms and the importance of proper water treatment and management practices.
Acute toxicity
Intraperitoneal-mouse LDL0: 0.25 mg/kg
Synthesis Reference(s)
Journal of the American Chemical Society, 106, p. 4539, 1984 DOI: 10.1021/ja00328a040
Biological Activity
A potent nicotinic agonist (K i values are 1.25 and 1840 nM for α 4 β 2 and α 7 nicotinic receptors respectively). Stimulates [ 3 H]-dopamine release from rat striatal synaptosomes (EC 50 = 136 nM).
Safety Profile
Poison by intraperitoneal route.An experimental teratogen. When heated todecomposition it emits toxic fumes of NOx.
Check Digit Verification of cas no
The CAS Registry Mumber 64285-06-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,4,2,8 and 5 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 64285-06:
(7*6)+(6*4)+(5*2)+(4*8)+(3*5)+(2*0)+(1*6)=129
129 % 10 = 9
So 64285-06-9 is a valid CAS Registry Number.
InChI:InChI=1/C10H15NO/c1-7(12)9-4-2-3-8-5-6-10(9)11-8/h4,8,10-11H,2-3,5-6H2,1H3
64285-06-9Relevant articles and documents
Efficient new syntheses of (+)and (-)-anatoxin-a. Revised configuration of resolved 9-methyl-9-azabicyclo[4.2.1]nonan-2-one
Ferguson, John R.,Lumbard, Keith W.,Scheinmann, Feodor,Stachulski, Andrew V.,Stjernloef, Peter,Sundell, Staffan
, p. 8867 - 8870 (1995)
The bicyclic ketone 2, as either enantiomer, was converted in high yield to the glycidonitrile 4 by successive base-catalysed condensation with 2-chloropropionitrile and N-dealkylation. Opening of the epoxide followed by elimination of HCl from the resulting α-chloroketone gave the enone 7 which was converted to anatoxin-a 1 by mild acidolysis. Maintenance of chiral homogeneity from both (+)- and (-)2 was demonstrated by diastereomeric amide formation from (+)- and (-)-1. However, the prior correlation of (+)- 2 with (+)- 1 was found to be incorrect; in fact (-)- 2 gives (+)- 1.
Investigation of a unified strategy for the synthesis of anatoxin analogues: Scope and limitations
Roe, Stephen J.,Hughes, David L.,Aggarwal, Pooja,Stockman, Robert A.
experimental part, p. 3775 - 3784 (2010/03/30)
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
Enantioselective synthesis of (+)-anatoxin-a via enyne metathesis
Brenneman, Jehrod B.,Machauer, Rainer,Martin, Stephen F.
, p. 7301 - 7314 (2007/10/03)
A concise synthesis of the potent nAChR agonist (+)-anatoxin-a (1) has been completed by a series of nine chemical operations and in 27% overall yield from commercially available D-methyl pyroglutamate (12). The strategy featured the application of a new protocol for the diastereoselective synthesis of cis-2,5-disubstituted pyrrolidines bearing unsaturated side chains and an intramolecular enyne metathesis to provide the bridged bicyclic framework of 1. Thus, D-methyl pyroglutamate (12) was converted in five steps to 32, which underwent facile enyne metathesis to deliver the bicyclic diene 33. Selective oxidative cleavage of the less substituted carbon-carbon double bond in 33 followed by deprotection furnished (+)-anatoxin-a (1).
Tandem reactions of anions: A short and efficient route to ±anatoxin-a
Parsons, Philip J.,Camp, Nicholas P.,Underwood, J. Mark,Harvey, Darren M.
, p. 11637 - 11642 (2007/10/03)
A new route to anatoxin-a (1) is reported which involves an anionically induced small ring opening/ring closure/ring opening cascade. The azabicyclo [4.2.1]nonane ring system of anatoxin-α is hence formed in one synthetic operation.