U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H15NO
Molecular Weight 165.2322
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANATOXIN A

SMILES

CC(=O)C1=CCC[C@@H]2CC[C@H]1N2

InChI

InChIKey=SGNXVBOIDPPRJJ-PSASIEDQSA-N
InChI=1S/C10H15NO/c1-7(12)9-4-2-3-8-5-6-10(9)11-8/h4,8,10-11H,2-3,5-6H2,1H3/t8-,10-/m1/s1

HIDE SMILES / InChI

Molecular Formula C10H15NO
Molecular Weight 165.2322
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
48.0 nM [EC50]
110.0 nM [EC50]
1.1 nM [Ki]
PubMed

PubMed

TitleDatePubMed
Fine-scale spatial variability in anatoxin-a and homoanatoxin-a concentrations in benthic cyanobacterial mats: implication for monitoring and management.
2010-12
First report of anatoxin-a-producing cyanobacterium Aphanizomenon issatschenkoi in northeastern Germany.
2010-11
Neurotoxic cyanobacterial toxins.
2010-10
Vulnerability of Quebec drinking-water treatment plants to cyanotoxins in a climate change context.
2010-09
A review of cyanobacteria and cyanotoxins removal/inactivation in drinking water treatment.
2010-07
Development of a fast and selective method for the sensitive determination of anatoxin-a in lake waters using liquid chromatography-tandem mass spectrometry and phenylalanine-d5 as internal standard.
2010-07
Ligand-binding assays for cyanobacterial neurotoxins targeting cholinergic receptors.
2010-07
Detection of various freshwater cyanobacterial toxins using ultra-performance liquid chromatography tandem mass spectrometry.
2010-05
State of the art on cyanotoxins in water and their behaviour towards chlorine.
2010-04-01
Cylindrospermopsin: a decade of progress on bioaccumulation research.
2010-03-09
Toxicity of cyanobacterial bloom in the eutrophic dam reservoir (Southeast Poland).
2010-03
In vivo modulation of alpha7 nicotinic receptors on striatal glutamate release induced by anatoxin-A.
2010-02-22
The smallest known genomes of multicellular and toxic cyanobacteria: comparison, minimal gene sets for linked traits and the evolutionary implications.
2010-02-16
In vitro reconstitution of the first steps of anatoxin-a biosynthesis in Oscillatoria PCC 6506: from free L-proline to acyl carrier protein bound dehydroproline.
2010-01-12
Anatoxin-a degradation by Advanced Oxidation Processes: vacuum-UV at 172 nm, photolysis using medium pressure UV and UV/H(2)O(2).
2010-01
Occupational and environmental hazard assessments for the isolation, purification and toxicity testing of cyanobacterial toxins.
2009-11-19
Production of anatoxin-a by cyanobacterial strains isolated from Portuguese fresh water systems.
2009-11
First detection of anatoxin-a in human and animal dietary supplements containing cyanobacteria.
2009-09
Evidence that biosynthesis of the neurotoxic alkaloids anatoxin-a and homoanatoxin-a in the cyanobacterium Oscillatoria PCC 6506 occurs on a modular polyketide synthase initiated by L-proline.
2009-06-10
Hindcasting cyanobacterial communities in Lake Okaro with germination experiments and genetic analyses.
2009-02
Effects of cyanobacterial extracts containing anatoxin-a and of pure anatoxin-a on early developmental stages of carp.
2009-02
Evaluation of in vivo and in vitro recovery rate of anatoxin-a through the microdialysis probe.
2008-12-01
New measurements of cyanobacterial toxins in natural waters using high performance liquid chromatography coupled to tandem mass spectrometry.
2008-08-12
A two-directional approach to the anatoxin alkaloids: second synthesis of homoanatoxin and efficient synthesis of anatoxin-a.
2008-08-07
Toxic effects of anatoxin-a on testes and sperm counts of male mice.
2008-08
Uptake and depuration of anatoxin-a by the mussel Mytilus galloprovincialis (Lamarck, 1819) under laboratory conditions.
2008-07
MALDI-TOF-MS detection of the low molecular weight neurotoxins anatoxin-a and homoanatoxin-a on lyophilized and fresh filaments of axenic Oscillatoria strains.
2008-06-01
Mycosporine-like amino acids and marine toxins--the common and the different.
2008-05-22
Cyanobacterial toxins as allelochemicals with potential applications as algaecides, herbicides and insecticides.
2008-05-15
Co-occurrence of beta-N-methylamino-L-alanine, a neurotoxic amino acid with other cyanobacterial toxins in British waterbodies, 1990-2004.
2008-03
Diagnosis of anatoxin-a poisoning in dogs from North America.
2008-01
Effective doses, guidelines & regulations.
2008
Conventional laboratory methods for cyanotoxins.
2008
Cyanobacterial toxin removal in drinking water treatment processes and recreational waters.
2008
Production of the neurotoxin BMAA by a marine cyanobacterium.
2007-12-06
Toxicology and detection methods of the alkaloid neurotoxin produced by cyanobacteria, anatoxin-a.
2007-11
Improved conditions for the application of solid phase microextraction prior to HPLC-FLD analysis of anatoxin-a.
2007-10
Effects of weekly exposure to anatoxin-a and nicotine on operant performance of rats.
2007-09-11
Oxidative elimination of cyanotoxins: comparison of ozone, chlorine, chlorine dioxide and permanganate.
2007-08
First report of homoanatoxin-a and associated dog neurotoxicosis in New Zealand.
2007-08
Analysis of anatoxin-a in biological samples using liquid chromatography with fluorescence detection after solid phase extraction and solid phase microextraction.
2007-07-13
Selective oxidation of key functional groups in cyanotoxins during drinking water ozonation.
2007-06-15
Effects of acute and weekly episodic exposures to anatoxin-a on the motor activity of rats: comparison with nicotine.
2007-05-05
Kinetics of the oxidation of cylindrospermopsin and anatoxin-a with chlorine, monochloramine and permanganate.
2007-05
Acute effects of an anatoxin-a producing cyanobacterium on juvenile fish-Cyprinus carpio L.
2007-04
Anatoxin-a and its metabolites in blue-green algae food supplements from Canada and Portugal.
2007-03
Production of anatoxin-a and a novel biosynthetic precursor by the cyanobacterium Aphanizomenon issatschenkoi.
2007-01-15
[Effect of anatoxin-A on calcium-mediate signal system of brain tissue in mice].
2007-01
Toxins of cyanobacteria.
2007-01
Contribution of hot spring cyanobacteria to the mysterious deaths of Lesser Flamingos at Lake Bogoria, Kenya.
2003-03-01
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:05:24 GMT 2025
Edited
by admin
on Mon Mar 31 19:05:24 GMT 2025
Record UNII
80023A73NK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANATOXIN A
HSDB   MI  
Common Name English
C10841
Preferred Name English
ANATOXIN A [MI]
Common Name English
ETHANONE, 1-(9-AZABICYCLO(4.2.1)NON-2-EN-2-YL)-, (1R)-
Common Name English
ETHANONE, 1-(1R,6R)-9-AZABICYCLO(4.2.1)NON-2-EN-2-YL-
Systematic Name English
(+)-ANATOXIN A
Common Name English
1-((1R,6R)-9-AZABICYCLO(4.2.1)NON-4-EN-5-YL)ETHANONE
Systematic Name English
1-(9-AZABICYCLO(4.2.1)NON-4-EN-5-YL)ETHANONE
Systematic Name English
ANATOXIN I
Common Name English
(+)-ANATOXIN-A
Common Name English
ANATOXIN A [HSDB]
Common Name English
1-(9-AZABICYCLO(4.2.1)NON-2-EN-2-YL)ETHAN-1-ONE
Systematic Name English
(+)-ANATOXIN .ALPHA.
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID50867064
Created by admin on Mon Mar 31 19:05:24 GMT 2025 , Edited by admin on Mon Mar 31 19:05:24 GMT 2025
PRIMARY
FDA UNII
80023A73NK
Created by admin on Mon Mar 31 19:05:24 GMT 2025 , Edited by admin on Mon Mar 31 19:05:24 GMT 2025
PRIMARY
WIKIPEDIA
Anatoxin A
Created by admin on Mon Mar 31 19:05:24 GMT 2025 , Edited by admin on Mon Mar 31 19:05:24 GMT 2025
PRIMARY
MESH
C509783
Created by admin on Mon Mar 31 19:05:24 GMT 2025 , Edited by admin on Mon Mar 31 19:05:24 GMT 2025
PRIMARY
CAS
64285-06-9
Created by admin on Mon Mar 31 19:05:24 GMT 2025 , Edited by admin on Mon Mar 31 19:05:24 GMT 2025
PRIMARY
HSDB
7750
Created by admin on Mon Mar 31 19:05:24 GMT 2025 , Edited by admin on Mon Mar 31 19:05:24 GMT 2025
PRIMARY
PUBCHEM
3034748
Created by admin on Mon Mar 31 19:05:24 GMT 2025 , Edited by admin on Mon Mar 31 19:05:24 GMT 2025
PRIMARY
MERCK INDEX
m1891
Created by admin on Mon Mar 31 19:05:24 GMT 2025 , Edited by admin on Mon Mar 31 19:05:24 GMT 2025
PRIMARY Merck Index
Related Record Type Details
DEGRADENT -> PARENT
Scientific Literature
Related Record Type Details
PARENT -> IMPURITY
Unit: mcg/g; Anatoxin-a concentration in Spirulina supplements.
ASSAY (HPLC)
Batch Data