Anatoxin-a - Knowledge (XXG)

860:, which has similar stereochemistry to anatoxin-a. Cocaine is first converted into the endo isomer of a cyclopropane, which is then photolytically cleaved to obtain an alpha, beta unsaturated ketone. Through the use of diethyl azodicarboxylate, the ketone is demethylated and anatoxin-a is formed. A similar, more recent synthesis pathway involves producing 2-tropinone from cocaine and treating the product with ethyl chloroformate producing a bicyclic ketone. This product is combined with trimethylsilyldiazylmethane, an organoaluminum Lewis acid and trimethylsinyl enol ether to produce tropinone. This method undergoes several more steps, producing useful intermediates as well as anatoxin-a as a final product. 42: 270: 175: 811: 864: 819:

of the United States in 2002 and 2006, in Scotland in 1992, in Ireland in 1997 and 2005, in Germany in 2017 and 2020. In each case, the dogs began showing muscle convulsions within minutes, and were dead within a matter of hours. Numerous cattle fatalities arising from the consumption of water contaminated with cyanobacteria that produce anatoxin-a have been reported in the United States, Canada, and Finland between 1980 and the present.

476:. 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 3494: 834:. The cyanotoxin, which was identified in the stomachs and fecal pellets of the birds, killed roughly 30,000 flamingos in the second half of 1999, and continues to cause mass fatalities annually, devastating the flamingo population. The toxin is introduced into the birds via water contaminated with cyanobacterial mat communities that arise from the hot springs in the lake bed. 33: 382: 742: 710:; it has a 100 fold lesser selectivity for these types of receptors than it has for nAchRs. Anatoxin-a also shows much less potency in the CNS than in neuromuscular junctions. In hippocampal and brain stem neurons, a 5 to 10 times greater concentration of anatoxin-a was necessary to activate nAchRs than what was required in the PNS. 1030:(CCL) which included anatoxin-a (among other cyanotoxins), indicating that anatoxin-a may be present in public water systems but is not regulated by the EPA. Anatoxin-a's presence on the CCL means that it may need to be regulated by the EPA in the future, pending further information on its health effects in humans. 975:, and various insect larvae. Problems with this methodology include an inability to determine whether it is anatoxin-a or another neurotoxin that causes the resulting deaths. Large amounts of sample material are also needed for such testing. In addition to the biological methods, scientists have used 903:

Enyne metathesis of anatoxin-a involves the use of a ring closing mechanism and is one of the more recent advances in anatoxin-a synthesis. In all methods involving this pathway, pyroglutamic acid is used as a starting material in conjunction with a Grubb's catalyst. Similar to iminium cyclization,

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Iminium ion cyclization utilizes several different pathways to create anatoxin-a, but each of these produces and progresses with a pyrrolidine iminium ion. The major differences in each pathway relate to the precursors used to produce the imium ion and the total yield of anatoxin-a at the end of the

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The first and most extensively explored approach used to synthesize anatoxin-a in vitro, cyclooctene cyclization involves 1,5-cyclooctadiene as its initial source. This starting substance is reacted to form methyl amine and combined with hypobromous acid to form anatoxin-a. Another method developed

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Many cases of wildlife and livestock deaths due to anatoxin-a have been reported since its discovery. Domestic dog deaths due to the cyanotoxin, as determined by analysis of stomach contents, have been observed at the lower North Island in New Zealand in 2005, in eastern France in 2003, in California

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Ingestion of drinking water or recreational water that is contaminated with anatoxin-a can pose fatal consequences since anatoxin-a was found to be quickly absorbed through the gastrointestinal tract in animal studies. Dozens of cases of animal deaths due to ingestion of anatoxin-a contaminated water

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Anatoxin-a is a neurotoxin produced by multiple genera of freshwater cyanobacteria that are found in water bodies globally. Some freshwater cyanobacteria are known to be salt tolerant and thus it is possible for anatoxin-a to be found in estuarine or other saline environments. Blooms of cyanobacteria

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There have been cases of non-lethal poisoning in humans who have ingested water from streams and lakes that contain various genera of cyanobacteria that are capable of producing anatoxin-a. The effects of non-lethal poisoning were primarily gastrointestinal: nausea, vomiting, diarrhea, and abdominal

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This method for anatoxin-a production was one of the first used that does not utilize a chimerically analogous starting substance for anatoxin formation. Instead, a racemic mixture of 3-tropinone is used with a chiral lithium amide base and additional ring expansion reactions in order to produce a

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Despite the relatively low frequency of anatoxin-a relative to other cyanotoxins, its high toxicity (the lethal dose is not known for humans, but is estimated to be less than 5 mg for an adult male) means that it is still considered a serious threat to terrestrial and aquatic organisms, most

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was capable of degrading anatoxin-a at a rate of 2–10 μg/ml per day. Later experiments done by Rapala and colleagues (1994) supported these results. They compared the effects of sterilized and non-sterilized sediments on anatoxin-a degradation over the course of 22 days, and found that after that

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Anatoxin-a producing cyanobacteria have also been found in soils and aquatic plants. Anatoxin-a sorbs well to negatively charged sites in clay-like, organic-rich soils and weakly to sandy soils. One study found both bound and free anatoxin-a in 38% of aquatic plants sampled across 12 Nebraskan

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As of now, there is no official guideline level for anatoxin-a, although scientists estimate that a level of 1 μg l would be sufficiently low. Likewise, there are no official guidelines regarding testing for anatoxin-a. Among methods of reducing the risk for cyanotoxins, including anatoxin-a,

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into the stomachs of two young male calves, and observed that muscular fasciculations and loss of coordination occurred in a matter of minutes, while death due to respiratory failure occurred anywhere between several minutes and a few hours. They also established that extensive periods of

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ketone intermediate. Addition of an organocuprate to the ketone produces an enol triflate derivative, which is then lysed hydrogenously and treated with a deprotecting agent in order to produce anatoxin-a. Similar strategies have also been developed and utilized by other laboratories.

943:, being converted to the less toxic products dihydroanatoxin-a and epoxyanatoxin-a. The photodegradation of anatoxin-a is dependent on pH and sunlight intensity but independent of oxygen, indicating that the degradation by light is not achieved through the process of photo-oxidation. 629:

from lakes or rivers have been recorded, and it is suspected to have also been the cause of death of one human. One study found that anatoxin-a is capable of binding to acetylcholine receptors and inducing toxic effects with concentrations in the nano-molar (nM) range if ingested.

1118:(BAC) has also been tested as a method of biodegradation, but it is inconclusive whether biodegradation occurred or if anatoxin-a was simply adsorbing the activated carbon. Others have called for additional studies to determine more about how to use activated carbon effectively. 572:βγδ nAChR. Anatoxin-a induced depolarizing neuromuscular blockade, contracture of the frog's rectus abdominis muscle, depolarization of the frog sartorius muscle, desensitization, and alteration of the action potential. Later, Thomas et al., (1993) through his work with chicken α 920:, as well as several other genera of cyanobacteria. Anatoxin-a and related chemical structures are produced using acetate and glutamate. Further enzymatic reduction of these precursors results in the formation of anatoxin-a. Homoanatoxin, a similar chemical, is produced by 1026:, but states are allowed to create their own standards for contaminants that are unregulated. Currently there are four states that have set drinking water advisory levels for anatoxin-a as seen in the table below. On October 8, 2009 the EPA published the third Drinking Water 2461:

Méjean A, Mann S, Maldiney T, Vassiliadis G, Lequin O, Ploux O (2009-05-13). "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".

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Anatoxin-a is a very powerful nicotinic acetylcholine receptor agonist and as such has been extensively studied for medicinal purposes. It is mainly used as a pharmacological probe in order to investigate diseases characterized by low acetylcholine levels, such as

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did not allow for detoxification to occur and natural neuromuscular functioning to resume. From these experiments, they calculated that the oral minimum lethal dose (MLD) (of the algae, not the anatoxin molecule), for calves is roughly 420 mg/kg body weight.

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scientists look favorably on biological treatment methods because they do not require complicated technology, are low maintenance, and have low running costs. Few biological treatment options have been tested for anatoxin-a specifically, although a species of

786:, which results in a lack of an oxygen supply to the brain, is the most evident and lethal effect of anatoxin-a. Injections of mice, rats, birds, dogs, and calves with lethal doses of anatoxin-a have demonstrated that death is preceded by a sequence of muscle 637:

Dermal exposure is the most likely form of contact with cyanotoxins in the environment. Recreational exposure to river, stream, and lake waters contaminated with algal blooms has been known to cause skin irritation and rashes. The first study that looked at

523:, known as cyanoHABs, increase the amount of cyanotoxins in the surrounding water, threatening the health of both aquatic and terrestrial organisms. Some species of cyanobacteria that produce anatoxin-a don't produce surface water blooms but instead form 924:

and utilizes the same precursor. However, homoanatoxin undergoes a methyl addition by S-adenosyl-L-methionine instead of an addition of electrons, resulting in a similar analogue. The biosynthetic gene cluster (BGC) for anatoxin-a was described from

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In the same year, Devlin and colleagues discovered the bicyclic secondary amine structure of anatoxin-a. They also performed experiments similar to those of Carmichael et al. on mice. They found that anatoxin-a kills mice 2–5 minutes after

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in the same laboratory uses aminoalcohol in conjunction with mercuric (II) acetate and sodium borohydride. The product of this reaction was transformed into an alpha, beta ketone and oxidized by ethyl azodicarboxylate to form anatoxin-a.

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binds to nAchRs in the post-synaptic neuronal membrane, causing a conformational change in the extracellular domain of the receptor which in turn opens the channel pore. This allows Na and Ca ions to move into the neuron, causing cell

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Gugger M, Lenoir S, Berger C, Ledreux A, Druart JC, Humbert JF, et al. (June 2005). "First report in a river in France of the benthic cyanobacterium Phormidium favosum producing anatoxin-a associated with dog neurotoxicosis".

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significantly to livestock and to humans. Anatoxin-a is suspected to have been involved in the death of at least one person. The threat posed by anatoxin-a and other cyanotoxins is increasing as both fertilizer runoff, leading to

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Park HD, Watanabe MF, Harda K, Nagai H, Suzuki M, Watanabe M, et al. (1993). "Hepatotoxin (microcystin) and neurotoxin (anatoxin-a) contained in natural blooms and strains of cyanobacteria from Japanese freshwaters".

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in 2006 both came to the conclusion that there was not enough toxicity data for anatoxin-a to establish a formal tolerable daily intake (TDI) level, though some places have implemented levels of their own.

480:(formerly 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. 961:

There are two categories of anatoxin-a detection methods. Biological methods have involved administration of samples to mice and other organisms more commonly used in ecotoxicological testing, such as

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In 2008 the state of Washington implemented a recreational advisory level for anatoxin-a of 1 μg/L in order to better manage algal blooms in lakes and protect users from exposure to the blooms.

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proliferation and migration found that anatoxin-a exerted no effect at 0.1 μg/mL or 1 μg/mL, and a weak toxic effect at 10 μg/mL only after an extended period of contact (48 hours).

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and lyse, so physical treatment may not remove all of the anatoxin-a present. Additional research needs to be done to find more reliable and efficient methods of both detection and treatment.

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time vials with the sterilized sediments showed similar levels of anatoxin-a as at the commencement of the experiment, while vials with non-sterilized sediment showed a 25-48% decrease.

1152:) is another option because most of the anatoxin-a is contained within the cells when the bloom is growing. However, anatoxin-a is released from cyanobacteria into water when they 5188: 395: 4100: 2198:

Wood SA, Selwood AI, Rueckert A, Holland PT, Milne JR, Smith KF, et al. (August 2007). "First report of homoanatoxin-a and associated dog neurotoxicosis in New Zealand".

2363:"Mass Occurrence of Anatoxin-a- and Dihydroanatoxin-a-Producing Tychonema sp. In Mesotrophic Reservoir Mandichosee (River Lech, Germany) as a Cause of Neurotoxicosis in Dogs" 2037:

Adamski M, Zimolag E, Kaminski A, Drukała J, Bialczyk J (October 2020). "Effects of cylindrospermopsin, its decomposition products, and anatoxin-a on human keratinocytes".

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Chemical treatment methods are more common in drinking water treatment compared to biological treatment, and numerous processes have been suggested for anatoxin-a.

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Studies have shown that some microorganisms are capable of degrading anatoxin-a. A study done by Kiviranta and colleagues in 1991 showed that the bacterial genus

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Osswald J, Rellán S, Gago A, Vasconcelos V (November 2007). "Toxicology and detection methods of the alkaloid neurotoxin produced by cyanobacteria, anatoxin-a".

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Wood SA, Rasmussen JP, Holland PT, Campbell R, Crowe AL (2007). "First Report of the Cyanotoxin Anatoxin-A from Aphanizomenon issatschenkoi (cyanobacteria)".

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Christensen VG, Khan E (September 2020). "Freshwater neurotoxins and concerns for human, animal, and ecosystem health: A review of anatoxin-a and saxitoxin".

5249: 611:, tremors, staggering, gasping, respiratory paralysis, and death within minutes. Zebrafish exposed to anatoxin-a contaminated water had altered heart rates. 319: 1597: 2901:

Westrick JA, Szlag DC, Southwell BJ, Sinclair J (July 2010). "A review of cyanobacteria and cyanotoxins removal/inactivation in drinking water treatment".

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mats. Many cases of anatoxin-a related animal deaths have occurred due to ingestion of detached benthic cyanobacterial mats that have washed ashore.

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and has been reported in North America, South America, Central America, Europe, Africa, Asia, and Oceania. Symptoms of anatoxin-a toxicity include

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to detect anatoxin-a. This is complicated by the rapid degradation of the toxin and the lack of commercially available standards for anatoxin-a.

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Botana LM, James K, Crowley J, Duphard J, Lehane M, Furey A (March 2007). "Anatoxin-a and Analogues: Discovery, Distribution, and Toxicology.".

1924: 3530: 3330: 2545: 1821: 1394: 726:, which allows for muscle contraction. The acetylcholine neurotransmitter then dissociates from the nAchR, where it is rapidly cleaved into 488:

Anatoxin-a was first discovered by P.R. Gorham in the early 1960s, after several herds of cattle died as a result of drinking water from

1679:"Two laboratory case studies on the oral toxicity to calves of the freshwater cyanophyte (blue-green alga) Anabaena flos-aquae NRC-44-1" 764:, (+)-anatoxin-a, is 150 fold more potent than the synthetic negative enantiomer, (−)-anatoxin-a. This is because (+)-anatoxin-a, the s- 564:

Electrophysiological experiments done by Spivak et al. (1980) on frogs showed that anatoxin-a is a potent agonist of the muscle-type (α

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Kaminski A, Bober B, Chrapusta E, Bialczyk J (October 2014). "Phytoremediation of anatoxin-a by aquatic macrophyte Lemna trisulca L".

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preceded by twitching, muscle spasms, paralysis and respiratory arrest, hence the name Very Fast Death Factor. They determined the

2312:"Fatal Neurotoxicosis in Dogs Associated with Tychoplanktic, Anatoxin-a Producing Tychonema sp. in Mesotrophic Lake Tegel, Berlin" 757:. Thus, the nAchR is temporarily locked open, which leads to overstimulation due to the constant generation of action potentials. 4123: 687: 465: 2845:

Fawell JK, Mitchell RE, Hill RE, Everett DJ (March 1999). "The toxicity of cyanobacterial toxins in the mouse: II anatoxin-a".

1181:. Further research on anatoxin-a and other less potent analogues are being tested as possible replacements for acetylcholine. 992:

in lakes and rivers, and higher global temperatures contribute to a greater frequency and prevalence of cyanobacterial blooms.

440:. It was first discovered in the early 1960s in Canada, and was isolated in 1972. The toxin is produced by multiple genera of 5219: 4557: 4153: 3813: 615:

pain. A case of lethal poisoning was reported in Wisconsin after a teen jumped into a pond contaminated with cyanobacteria.

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Merel S, Clément M, Thomas O (April 2010). "State of the art on cyanotoxins in water and their behaviour towards chlorine".

1548:"Cyanobacterial Toxins of the Laurentian Great Lakes, Their Toxicological Effects, and Numerical Limits in Drinking Water" 1466: 3248:"The Chemistry and Pharmacology of Anatoxin-a and Related Homotropanes with respect to Nicotinic Acetylcholine Receptors" 1955:"The Chemistry and Pharmacology of Anatoxin-a and Related Homotropanes with respect to Nicotinic Acetylcholine Receptors" 895:

process. These separate pathways include production of alkyl iminium salts, acyl iminium salts and tosyl iminium salts.

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Ho L, Sawade E, Newcombe G (April 2012). "Biological treatment options for cyanobacteria metabolite removal--a review".

227: 5264: 4247: 248: 4571: 4297: 4167: 3679: 3370: 1134: 1027: 3523: 3323: 1001: 604: 554: 5157: 4757: 112: 2414:"Contribution of hot spring cyanobacteria to the mysterious deaths of Lesser Flamingos at Lake Bogoria, Kenya" 971: 904:

the first attempted synthesis of anatoxin-a using this pathway used a 2,5-cis-pyrrolidine as an intermediate.

1628:"Co-occurrence of the cyanotoxins BMAA, DABA and anatoxin-a in Nebraska reservoirs, fish, and aquatic plants" 1093:

The Canadian province of Québec has a drinking water Maximum Accepted Value for anatoxin-a of 3.7 μg/L.

4287: 2689:"Washington State Recreational Guidance for Microcystins (Provisional) and Anatoxin-a (Interim/Provisional)" 1023: 780:

group, which corresponds well to the 5.9 Å distance that separate the nitrogen and oxygen in acetylcholine.

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that produce anatoxin-a among other cyanotoxins are increasing in frequency due to increasing temperatures,

4045: 4025: 1114:, capable of biodegrading anatoxin-a at a rate of 2–10 μg ml d, has been identified. Biological (granular) 170: 4576: 4317: 1126: 702:. (Anatoxin-a has an affinity for these muscle-type receptors that is about 20 times greater than that of 699: 545: 512: 41: 5239: 5142: 5091: 5052: 3848: 939:

Anatoxin-a is unstable in water and other natural conditions, and in the presence of UV light undergoes

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occurred in a water skier after they inhaled water spray containing a fellow cyanobacterial neurotoxin,

457: 132: 54: 2688: 810: 667:. It is possible that inhalation of water spray containing anatoxin-a could pose similar consequences. 539:

In 1977, Carmichael, Gorham, and Biggs experimented with anatoxin-a. They introduced toxic cultures of

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Toxic cyanobacteria in water: a guide to their public health consequences, monitoring, and management

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Directly removing the cyanobacteria in the water treatment process through physical treatment (e.g.,

754: 750: 735: 265: 4442: 2719:"Vulnerability of Quebec drinking-water treatment plants to cyanotoxins in a climate change context" 1495:

Paerl HW, Otten TG (May 2013). "Harmful cyanobacterial blooms: causes, consequences, and controls".

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Laboratory studies using mice showed that characteristic effects of acute anatoxin-a poisoning via

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at the School of Chemistry, Physics, and Environmental Studies, University of Sussex at Brighton

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Shams S, Capelli C, Cerasino L, Ballot A, Dietrich DR, Sivonen K, et al. (February 2015).

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Weirich CA, Miller TR (2014). "Freshwater harmful algal blooms: toxins and children's health".

798:. In mice, anatoxin-a also seriously impacted blood pressure and heart rate, and caused severe 5162: 4882: 4762: 4661: 4657: 4642: 4585: 4322: 4092: 3853: 3194: 3147: 3103: 3020: 2961: 2918: 2870: 2827: 2789: 2740: 2620: 2610: 2487: 2479: 2443: 2394: 2343: 2292: 2251: 2215: 2165: 2105: 2054: 2019: 1903: 1860: 1817: 1784: 1700: 1659: 1579: 1520: 1440: 1390: 1336: 1178: 1174: 1170: 489: 4599: 4542: 4507: 4482: 4387: 4212: 4207: 5229: 5032: 4842: 4737: 4624: 4609: 4172: 4148: 3946: 3941: 3936: 3931: 3926: 3921: 3916: 3613: 3269: 3259: 3226: 3186: 3139: 3095: 3010: 3000: 2953: 2910: 2862: 2819: 2779: 2730: 2518: 2471: 2433: 2384: 2374: 2333: 2323: 2310:

Fastner J, Beulker C, Geiser B, Hoffmann A, Kröger R, Teske K, et al. (February 2018).

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The effects of anatoxin-a on nicotinic acetylcholine receptors at the neuromuscular junction

723: 342: 152: 2981:"Widespread anatoxin-a detection in benthic cyanobacterial mats throughout a river network" 236: 88: 5254: 5244: 4687: 4076: 4066: 4061: 3843: 3646: 3638: 3479: 1319:

Aráoz R, Molgó J, Tandeau de Marsac N (October 2010). "Neurotoxic cyanobacterial toxins".

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Anatoxin-a binding to these nAchRs cause the same effects in neurons. However, anatoxin-a

4589: 4581: 1137:) have worked in lowering levels of anatoxin-a, but others, including photocatalysis, UV 269: 174: 3182: 3091: 2996: 2858: 2775: 2429: 2412:

Krienitz L, Ballot A, Kotut K, Wiegand C, Pütz S, Metcalf JS, et al. (March 2003).

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New Zealand has a drinking water Maximum Accepted Value for anatoxin-a of 6 μg/L.

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Bauer F, Fastner J, Bartha-Dima B, Breuer W, Falkenau A, Mayer C, et al. (2020).

2015: 5208: 5147: 4977: 4947: 4887: 4837: 4832: 4722: 4692: 4638: 4467: 4282: 4217: 3828: 3808: 3780: 3747: 3727: 3651: 3573: 3553: 3454: 3449: 3230: 3075: 2930: 2066: 1452: 1199: 714: 703: 608: 473: 449: 441: 437: 163: 19: 3238: 3040:"Notification of Recent Name Changes for Cyanobacteria Adopted and Reported by AWQC" 2882: 2530: 2050: 1980: 1436: 216: 5062: 4992: 4987: 4902: 4712: 4702: 4653: 4634: 4432: 4352: 4342: 3608: 3603: 3568: 3474: 3429: 3365: 3115: 1532: 1253: 1241: 962: 927: 827: 659:

No data on inhalation toxicity of anatoxin-a is currently available, though severe

648: 644: 524: 493: 2957: 2247: 2211: 1332: 3190: 3005: 2823: 2784: 2759: 2161: 2101: 2080:

Falconer IR (1996). "Potential impact on human health of toxic cyanobacteria 1".

1856: 1813: 5167: 5132: 5112: 5027: 5017: 4972: 4952: 4872: 4802: 4792: 4782: 4777: 4747: 4537: 4532: 4522: 4512: 4457: 4422: 4412: 4407: 4402: 4392: 4332: 4307: 4302: 4222: 3971: 3878: 3818: 3762: 3737: 3707: 3694: 3628: 3618: 3593: 3444: 3439: 3434: 3403: 3390: 1878:

Taylor JA (1995). "A review of: "Detection Methods for Cyanobacterial Toxins"".

1286: 1227: 948: 795: 3302: 2866: 2287: 2270: 863: 5127: 5107: 5067: 5042: 5007: 4997: 4942: 4932: 4927: 4917: 4892: 4857: 4812: 4807: 4787: 4772: 4732: 4697: 4629: 4614: 4604: 4357: 4347: 4292: 4252: 3976: 3886: 3833: 3722: 3717: 3712: 3674: 3661: 3588: 3583: 3539: 3375: 3360: 3347: 3339: 3099: 2914: 1899: 1718:

Devlin JP, Edwards OE, Gorham PR, Hunter NR, Pike RK, Stavric B (2011-02-04).

1516: 1386: 1281: 1153: 1138: 761: 477: 453: 433: 361: 143: 2758:

Merel S, Walker D, Chicana R, Snyder S, Baurès E, Thomas O (September 2013).

2483: 2109: 1931:(Report). U.S. Environmental Protection Agency. November 2006. Archived from 1907: 4967: 4962: 4937: 4912: 4907: 4877: 4827: 4817: 4797: 4667: 4452: 4447: 4437: 4262: 4242: 4232: 4227: 4182: 3823: 3800: 3785: 3772: 3757: 3742: 3702: 3684: 3598: 3578: 3459: 3413: 3380: 2624: 1802:

Schwimmer D, Schwimmer M (1964). "Algae and Medicine". In Jackson DF (ed.).

664: 3198: 3107: 3024: 2965: 2922: 2874: 2831: 2793: 2744: 2717:

Carrière A, Prévost M, Zamyadi A, Chevalier P, Barbeau B (September 2010).

2507:"Production and biodegradation of cyanobacterial toxins-a laboratory study" 2491: 2447: 2398: 2379: 2347: 2328: 2296: 2255: 2219: 2183:

Purves D, Augustine G, Fitzpatrick D, Hall W, Lamantia AS, White L (2012).

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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

3151: 3143: 2760:"State of knowledge and concerns on cyanobacterial blooms and cyanotoxins" 1644: 303:

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

5121: 5047: 4862: 4852: 4672: 4427: 4417: 4377: 4372: 4362: 4327: 4277: 4272: 4177: 3863: 3838: 3790: 3732: 3563: 3558: 1704: 1467:"Health Effects Support Document for the Cyanobacterial Toxin Anatoxin-A" 1191: 799: 791: 777: 773: 640: 429: 3167:"Anatoxin-a producing Tychonema (Cyanobacteria) in European waterbodies" 2735: 5117: 5097: 4677: 4648: 4502: 4497: 4492: 4487: 4477: 4381: 4267: 4202: 4197: 3981: 3956: 3951: 3891: 3868: 3858: 3752: 1564: 1220: 857: 853: 731: 727: 203: 32: 2475: 1769: 741: 531:

reservoirs, with much higher incidence of bound anatoxin-a than free.

4707: 4527: 4337: 3961: 3264: 2979:

Bouma-Gregson K, Kudela RM, Power ME (2018-05-18). Humbert JF (ed.).

2577:"2015 Drinking Water Health Advisories for Two Cyanobacterial Toxins" 1971: 1954: 1234: 590:, showed that anatoxin-a is also a potent agonist of neuronal nAChR. 469: 445: 123: 1736: 1719: 372:

Except where otherwise noted, data are given for materials in their

3076:"Harmful cyanobacterial blooms: causes, consequences, and controls" 2187:(5th ed.). Sunderland, Massachusetts: Sinauer Associates, Inc. 822:

A particularly interesting case of anatoxin-a poisoning is that of

191: 5077: 4009: 3906: 3901: 2505:

Kiviranta J, Sivonen K, Lahti K, Luukkainen R, Niemelä SI (1991).

1130: 862: 831: 809: 740: 426: 111: 101: 790:, decreased movement, collapse, exaggerated abdominal breathing, 4004: 3999: 558: 496:. It was isolated in 1972 by J.P. Devlin from the cyanobacteria 182: 4096: 3512: 3312: 1720:"Anatoxin-a, a toxic alkaloid from Anabaena flos-aquae NRC-44h" 1546:

Miller TR, Beversdorf LJ, Weirich CA, Bartlett SL (June 2017).

3508: 3308: 2271:"Diagnosis of anatoxin-a poisoning in dogs from North America" 1626:

Al-Sammak MA, Hoagland KD, Cassada D, Snow DD (January 2014).

468:(nAchR) where it mimics the binding of the receptor's natural 1753:"Cyanotoxins: bioaccumulation and effects on aquatic animals" 753:, and the anatoxin-a nAchR complex cannot be broken down by 3967:

Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)

253: 2639:"Rules and Regulations: Drinking Water HABs Response Plan" 1925:

Toxicological Reviews of Cyanobacterial Toxins: Anatoxin-A

580:

nAChR subunits expressed on mouse M 10 cells and chicken α

4135: 1845:

Current Problems in Pediatric and Adolescent Health Care

852:

The first biologically occurring initial substance for

519:

due to nutrient runoff. These expansive cyanobacterial

390: 4558: 4154: 1751:

Ferrão-Filho A, Kozlowsky-Suzuki B (December 2011).

5090: 4551: 4147: 4133: 4054: 4018: 3990: 3877: 3799: 3771: 3693: 3660: 3637: 3546: 3422: 3389: 3346: 2664:"Drinking Water Contaminant Candidate List 3-Final" 2470:(22). American Chemical Society (ACS): 7512–7513. 1919: 1917: 1677:Carmichael WW, Gorham PR, Biggs DF (March 1977). 2546:"Brief review of natural nonprotein neurotoxins" 706:.) However, the cyanotoxin has little effect on 215: 1185:Genera of cyanobacteria that produce anatoxin-a 698:βγδ muscle-type nAchRs that are present at the 266:DTXSID301338831 DTXSID50867064, DTXSID301338831 87: 5053:Trimetaphan camsilate (trimethaphan camsylate) 3038:Australian Water Quality Centre (2015-12-04). 2275:Journal of Veterinary Diagnostic Investigation 5194:Acetylcholine metabolism/transport modulators 4108: 3524: 3324: 3069: 3067: 3065: 3063: 3061: 3059: 2605:Chorus, Ingrid, Bartram, Jamie, eds. (1999). 2584:United States Environmental Protection Agency 1808:. Boston, MA: Springer US. pp. 368–412. 1474:United States Environmental Protection Agency 867:Cocaine, a precursor for anatoxin-a synthesis 8: 5189:Muscarinic acetylcholine receptor modulators 1929:National Center for Environmental Assessment 760:Two enantiomers of anatoxin-a, the positive 2896: 2894: 2892: 2269:Puschner B, Hoff B, Tor ER (January 2008). 675:Anatoxin-a is an agonist of both neuronal α 561:for mice to be 250 μg/kg body weight. 4144: 4115: 4101: 4093: 3531: 3517: 3509: 3331: 3317: 3309: 2135: 2133: 2131: 2129: 2127: 2125: 2123: 2121: 2119: 890:Intramolecular cyclization of iminium ions 492:in Ontario, Canada, which contained toxic 268: 173: 151: 24: 4140:Tooltip Nicotinic acetylcholine receptors 3273: 3263: 3014: 3004: 2783: 2734: 2437: 2388: 2378: 2337: 2327: 2286: 1970: 1778: 1768: 1735: 1694: 1653: 1643: 1573: 1563: 1381:. Blackwell Publishing. pp. 141–58. 1372: 1370: 768:enone conformation, has a distance a 6.0 235: 4683:Candocuronium iodide (chandonium iodide) 2643:Utah Department of Environmental Quality 2464:Journal of the American Chemical Society 1368: 1366: 1364: 1362: 1360: 1358: 1356: 1354: 1352: 1350: 1032: 58:1-(9-azabicyclonon-2-en-2-yl)ethan-1-one 3246:Wonnacott S, Gallagher T (April 2006). 1953:Wonnacott S, Gallagher T (2006-04-06). 1379:Phycotoxins: Chemistry and Biochemistry 1314: 1312: 1310: 1308: 1306: 1304: 1302: 1298: 969:), larvae of the freshwater crustacean 324: 289: 264: 4563:Tooltip negative allosteric modulators 4159:Tooltip positive allosteric modulators 2903:Analytical and Bioanalytical Chemistry 1022:Anatoxin-a is not regulated under the 164: 2805: 2803: 2696:Washington State Department of Health 2571: 2569: 2567: 2523:10.1127/archiv-hydrobiol/121/1991/281 881:Enantioselective enolization strategy 296:Key: SGNXVBOIDPPRJJ-UHFFFAOYSA-N 131: 7: 2039:The Science of the Total Environment 1417:The Science of the Total Environment 1410: 1408: 1406: 1133:, and advanced oxidation processes ( 690:present in the CNS as well as the (α 5250:Heterocyclic compounds with 2 rings 3291:Very Fast Death Factor (Anatoxin-a) 2847:Human & Experimental Toxicology 1598:"Cyanobacterial toxins: Anatoxin-a" 306:Key: SGNXVBOIDPPRJJ-UHFFFAOYAZ 206: 190: 2439:10.1111/j.1574-6941.2003.tb01053.x 1081:Recreational water advisory levels 708:muscarinic acetylcholine receptors 14: 4768:Dimethyltubocurarine (metocurine) 2016:10.1016/j.chemosphere.2014.04.064 1145:, have not shown great efficacy. 688:nicotinic acetylcholine receptors 4124:Nicotinic acetylcholine receptor 3493: 3492: 3231:10.1111/j.1529-8817.2007.00318.x 584:nAChR expressed in oocytes from 466:nicotinic acetylcholine receptor 380: 40: 31: 5148:Meclofenoxate (centrophenoxine) 4473:Suxethonium (succinyldicholine) 4468:Suxamethonium (succinylcholine) 3303:Molecule of the Month: Anatoxin 3074:Paerl HW, Otten TG (May 2013). 2051:10.1016/j.scitotenv.2020.142670 1683:The Canadian Veterinary Journal 1437:10.1016/j.scitotenv.2020.139515 1034:Drinking Water Advisory Levels 722:and inducing the generation of 647:effects of anatoxin-a on human 376:(at 25 °C , 100 kPa). 3814:Tetramethylenedisulfotetramine 2544:Patockaa J, Stredab L (2002). 1018:Drinking water advisory levels 856:expansion into anatoxin-a was 1: 5184:Receptor/signaling modulators 4838:Hexamethonium (benzohexonium) 2958:10.1016/j.toxicon.2009.10.028 2248:10.1016/j.toxicon.2005.02.031 2212:10.1016/j.toxicon.2007.03.025 1724:Canadian Journal of Chemistry 1333:10.1016/j.toxicon.2009.07.036 3296:The Periodic Table of Videos 3191:10.1016/j.watres.2014.11.006 3006:10.1371/journal.pone.0197669 2824:10.1016/j.watres.2011.11.018 2785:10.1016/j.envint.2013.06.013 2162:10.1016/j.envint.2007.06.003 2102:10.2216/i0031-8884-35-6S-6.1 1857:10.1016/j.cppeds.2013.10.007 1814:10.1007/978-1-4684-1719-7_17 848:Cyclic expansion of tropanes 425:), is a secondary, bicyclic 4918:Methorphan (racemethorphan) 4248:Bephenium hydroxynaphthoate 2723:Journal of Water and Health 2609:. London: E & FN Spon. 872:Cyclization of cyclooctenes 5281: 4298:Dimethylphenylpiperazinium 3299:(University of Nottingham) 2867:10.1177/096032719901800306 2556:(2): 16–24. Archived from 2288:10.1177/104063870802000119 1028:Contaminant Candidate List 912:Anatoxin-a is synthesized 17: 5176: 3488: 3100:10.1007/s00248-012-0159-y 2915:10.1007/s00216-010-3709-5 2764:Environment International 2418:FEMS Microbiology Ecology 2142:Environment International 1900:10.1080/02757549508039077 1605:World Health Organization 1517:10.1007/s00248-012-0159-y 1387:10.1002/9780470277874.ch8 1002:World Health Organization 935:Stability and degradation 814:Flamingos at Lake Bogoria 713:In normal circumstances, 605:intraperitoneal injection 555:intraperitoneal injection 370: 335: 315: 280: 71: 63: 53: 48: 39: 30: 5158:Phosphatidylethanolamine 2511:Archiv für Hydrobiologie 1248:Microcoleus (Phormidium) 972:Thamnocephalus platyurus 18:Not to be confused with 4938:Morphanol (racemorphan) 4878:Laudexium (laudolissin) 4288:Desformylflustrabromine 4019:Cholinergic neurotoxins 1024:Safe Drinking Water Act 751:binding is irreversible 450:muscular fasciculations 2380:10.3390/toxins12110726 2329:10.3390/toxins10020060 1127:potassium permanganate 868: 815: 746: 700:neuromuscular junction 546:artificial respiration 419:Very Fast Death Factor 5220:Nitrogen heterocycles 5143:Glycerophosphocholine 4046:Hemicholinium mustard 4026:Acetylcholine mustard 3849:Chlorophenylsilatrane 3144:10.1002/nt.2620010606 1880:Chemistry and Ecology 1645:10.3390/toxins6020488 1042:Concentration (μg/L) 866: 813: 744: 671:Mechanism of toxicity 609:muscle fasciculations 458:respiratory paralysis 366:165.232 5138:Dimethylethanolamine 5003:Rapacuronium bromide 4983:Pipecuronium bromide 4823:Gantacurium chloride 4783:Dizocilpine (MK-801) 4368:MEM-63,908 (RG-3487) 4318:Ethoxysebacylcholine 4041:Ethylcholine mustard 3219:Journal of Phycology 922:Oscillatoria formosa 843:Laboratory synthesis 755:acetylcholinesterase 736:acetylcholinesterase 661:respiratory distress 535:Experimental studies 521:harmful algal blooms 446:loss of coordination 327:CC(=O)C1=CCCC2CCC1N2 5260:Bacterial alkaloids 5153:Phosphatidylcholine 5038:Threohydrobupropion 5023:Stercuronium iodide 4958:Pancuronium bromide 3992:Bicyclic phosphates 3614:Spooky toxin (SsTx) 3465:Debromoaplysiatoxin 3183:2015WatRe..69...68S 3092:2013MicEc..65..995P 2997:2018PLoSO..1397669B 2859:1999HETox..18..168F 2776:2013EnInt..59..303M 2736:10.2166/wh.2009.207 2430:2003FEMME..43..141K 2154:2007EnInt..33.1070O 2094:1996Phyco..35S...6F 2008:2014Chmsp.112..305K 1892:1995ChEco..11..275T 1509:2013MicEc..65..995P 1429:2020ScTEn.736m9515C 1150:membrane filtration 1035: 918:Anabaena flos-aquae 499:Anabaena flos-aquae 27: 5265:Nicotinic agonists 5073:Vecuronium bromide 5013:Rocuronium bromide 4923:Methyllycaconitine 4848:Hydroxynorketamine 4743:Dextropropoxyphene 4728:Dehydronorketamine 4718:Dacuronium bromide 3399:Cylindrospermopsin 1565:10.3390/md15060160 1207:Cylindrospermopsis 1167:muscular dystrophy 1033: 931:PCC 6506 in 2009. 869: 816: 784:Respiratory arrest 747: 403:Infobox references 25: 5202: 5201: 5163:Phosphorylcholine 5101: 5086: 5085: 4883:Levacetylmethadol 4763:Dihydrochandonium 4643:sodium thiopental 4313:Ethanol (alcohol) 4090: 4089: 3854:Sulfuryl fluoride 3506: 3505: 3080:Microbial Ecology 2476:10.1021/ja9024353 1823:978-1-4684-1721-0 1770:10.3390/md9122729 1497:Microbial Ecology 1396:978-0-470-27787-4 1179:Parkinson disease 1175:Alzheimer disease 1171:myasthenia gravis 1078: 1077: 996:Water regulations 806:Cases of toxicity 724:action potentials 490:Saskatchewan Lake 411:Chemical compound 409: 408: 249:CompTox Dashboard 113:Interactive image 5272: 5095: 5033:Thiocolchicoside 4843:Hydroxybupropion 4738:Dextromethorphan 4610:Allopregnanolone 4564: 4560: 4463:Suberyldicholine 4173:6-Chloronicotine 4160: 4156: 4145: 4141: 4137: 4117: 4110: 4103: 4094: 3533: 3526: 3519: 3510: 3496: 3495: 3333: 3326: 3319: 3310: 3279: 3277: 3267: 3265:10.3390/md403228 3242: 3203: 3202: 3162: 3156: 3155: 3126: 3120: 3119: 3071: 3054: 3053: 3051: 3050: 3035: 3029: 3028: 3018: 3008: 2976: 2970: 2969: 2941: 2935: 2934: 2898: 2887: 2886: 2842: 2836: 2835: 2807: 2798: 2797: 2787: 2755: 2749: 2748: 2738: 2714: 2708: 2707: 2705: 2703: 2693: 2685: 2679: 2678: 2676: 2675: 2668:Federal Register 2660: 2654: 2653: 2651: 2650: 2635: 2629: 2628: 2602: 2596: 2595: 2593: 2591: 2581: 2573: 2562: 2561: 2541: 2535: 2534: 2502: 2496: 2495: 2458: 2452: 2451: 2441: 2409: 2403: 2402: 2392: 2382: 2358: 2352: 2351: 2341: 2331: 2307: 2301: 2300: 2290: 2266: 2260: 2259: 2230: 2224: 2223: 2195: 2189: 2188: 2180: 2174: 2173: 2137: 2114: 2113: 2077: 2071: 2070: 2034: 2028: 2027: 1991: 1985: 1984: 1974: 1972:10.3390/md403228 1950: 1944: 1943: 1941: 1940: 1921: 1912: 1911: 1875: 1869: 1868: 1840: 1834: 1833: 1831: 1830: 1799: 1793: 1792: 1782: 1772: 1748: 1742: 1741: 1739: 1730:(8): 1367–1371. 1715: 1709: 1708: 1698: 1674: 1668: 1667: 1657: 1647: 1623: 1617: 1616: 1614: 1612: 1602: 1594: 1588: 1587: 1577: 1567: 1543: 1537: 1536: 1492: 1486: 1485: 1483: 1481: 1471: 1463: 1457: 1456: 1412: 1401: 1400: 1374: 1345: 1344: 1316: 1194:(Dolichospermum) 1116:activated carbon 1036: 941:photodegradation 899:Enyne metathesis 824:lesser flamingos 417:, also known as 393: 387: 384: 383: 343:Chemical formula 273: 272: 257: 255: 239: 219: 208: 194: 177: 166: 155: 135: 115: 91: 44: 35: 28: 5280: 5279: 5275: 5274: 5273: 5271: 5270: 5269: 5205: 5204: 5203: 5198: 5172: 5094: 5082: 4688:Chlorisondamine 4562: 4555: 4547: 4158: 4151: 4139: 4129: 4121: 4091: 4086: 4067:Dimethylmercury 4062:Dimethylcadmium 4050: 4036:Choline mustard 4014: 3986: 3873: 3844:Phenylsilatrane 3795: 3767: 3689: 3656: 3647:Botulinum toxin 3633: 3542: 3537: 3507: 3502: 3484: 3480:Aetokthonotoxin 3418: 3385: 3342: 3337: 3287: 3282: 3245: 3216: 3212: 3210:Further reading 3207: 3206: 3164: 3163: 3159: 3128: 3127: 3123: 3086:(4): 995–1010. 3073: 3072: 3057: 3048: 3046: 3044:www.awqc.com.au 3037: 3036: 3032: 2991:(5): e0197669. 2978: 2977: 2973: 2943: 2942: 2938: 2900: 2899: 2890: 2844: 2843: 2839: 2809: 2808: 2801: 2757: 2756: 2752: 2716: 2715: 2711: 2701: 2699: 2691: 2687: 2686: 2682: 2673: 2671: 2662: 2661: 2657: 2648: 2646: 2637: 2636: 2632: 2617: 2604: 2603: 2599: 2589: 2587: 2579: 2575: 2574: 2565: 2543: 2542: 2538: 2504: 2503: 2499: 2460: 2459: 2455: 2411: 2410: 2406: 2360: 2359: 2355: 2309: 2308: 2304: 2268: 2267: 2263: 2232: 2231: 2227: 2197: 2196: 2192: 2182: 2181: 2177: 2139: 2138: 2117: 2079: 2078: 2074: 2036: 2035: 2031: 1993: 1992: 1988: 1952: 1951: 1947: 1938: 1936: 1923: 1922: 1915: 1877: 1876: 1872: 1842: 1841: 1837: 1828: 1826: 1824: 1801: 1800: 1796: 1763:(12): 2729–72. 1750: 1749: 1745: 1737:10.1139/v77-189 1717: 1716: 1712: 1676: 1675: 1671: 1625: 1624: 1620: 1610: 1608: 1607:. November 2019 1600: 1596: 1595: 1591: 1545: 1544: 1540: 1503:(4): 995–1010. 1494: 1493: 1489: 1479: 1477: 1469: 1465: 1464: 1460: 1414: 1413: 1404: 1397: 1376: 1375: 1348: 1318: 1317: 1300: 1295: 1278: 1214:Cylindrospermum 1187: 1162: 1160:Laboratory uses 1107: 1105:Water treatment 1099: 1091: 1083: 1020: 1015: 998: 985: 959: 937: 916:in the species 910: 901: 892: 883: 874: 850: 845: 840: 808: 697: 693: 686: 682: 678: 673: 657: 635: 626: 621: 619:Exposure routes 601: 596: 583: 579: 575: 571: 567: 537: 508: 486: 464:is through the 412: 405: 400: 399: 398: ?) 389: 385: 381: 377: 355: 351: 345: 331: 328: 323: 322: 311: 308: 307: 304: 298: 297: 294: 288: 287: 276: 258: 251: 242: 222: 209: 197: 158: 138: 118: 105: 94: 81: 67: 59: 23: 12: 11: 5: 5278: 5276: 5268: 5267: 5262: 5257: 5252: 5247: 5242: 5237: 5232: 5227: 5222: 5217: 5207: 5206: 5200: 5199: 5197: 5196: 5191: 5186: 5181: 5177: 5174: 5173: 5171: 5170: 5165: 5160: 5155: 5150: 5145: 5140: 5135: 5130: 5125: 5115: 5110: 5104: 5102: 5088: 5087: 5084: 5083: 5081: 5080: 5075: 5070: 5065: 5060: 5055: 5050: 5045: 5040: 5035: 5030: 5025: 5020: 5015: 5010: 5005: 5000: 4995: 4990: 4985: 4980: 4975: 4970: 4965: 4960: 4955: 4950: 4945: 4940: 4935: 4930: 4925: 4920: 4915: 4910: 4905: 4900: 4895: 4890: 4885: 4880: 4875: 4870: 4868:Kynurenic acid 4865: 4860: 4855: 4850: 4845: 4840: 4835: 4830: 4825: 4820: 4815: 4810: 4805: 4800: 4795: 4790: 4785: 4780: 4775: 4770: 4765: 4760: 4755: 4750: 4745: 4740: 4735: 4730: 4725: 4720: 4715: 4710: 4705: 4700: 4695: 4690: 4685: 4680: 4675: 4670: 4665: 4662:κ-bungarotoxin 4658:α-bungarotoxin 4651: 4646: 4632: 4627: 4622: 4617: 4612: 4607: 4602: 4597: 4596:, many others) 4586:α-bungarotoxin 4579: 4574: 4568: 4566: 4549: 4548: 4546: 4545: 4540: 4535: 4530: 4525: 4520: 4518:Tribendimidine 4515: 4510: 4505: 4500: 4495: 4490: 4485: 4480: 4475: 4470: 4465: 4460: 4455: 4450: 4445: 4443:Sebacylcholine 4440: 4435: 4430: 4425: 4420: 4415: 4410: 4405: 4400: 4395: 4390: 4385: 4375: 4370: 4365: 4360: 4355: 4350: 4345: 4340: 4335: 4330: 4325: 4320: 4315: 4310: 4305: 4300: 4295: 4290: 4285: 4280: 4275: 4270: 4265: 4260: 4258:Butyrylcholine 4255: 4250: 4245: 4240: 4235: 4230: 4225: 4220: 4215: 4210: 4205: 4200: 4195: 4190: 4185: 4180: 4175: 4170: 4164: 4162: 4142: 4131: 4130: 4122: 4120: 4119: 4112: 4105: 4097: 4088: 4087: 4085: 4084: 4082:Tetraethyllead 4079: 4074: 4072:Toxopyrimidine 4069: 4064: 4058: 4056: 4052: 4051: 4049: 4048: 4043: 4038: 4033: 4028: 4022: 4020: 4016: 4015: 4013: 4012: 4007: 4002: 3996: 3994: 3988: 3987: 3985: 3984: 3979: 3974: 3969: 3964: 3959: 3954: 3949: 3944: 3939: 3934: 3929: 3924: 3919: 3914: 3909: 3904: 3899: 3897:Novichok agent 3894: 3889: 3883: 3881: 3875: 3874: 3872: 3871: 3866: 3861: 3856: 3851: 3846: 3841: 3836: 3831: 3826: 3821: 3816: 3811: 3805: 3803: 3797: 3796: 3794: 3793: 3788: 3783: 3777: 3775: 3769: 3768: 3766: 3765: 3760: 3755: 3750: 3745: 3740: 3735: 3730: 3725: 3720: 3715: 3710: 3705: 3699: 3697: 3691: 3690: 3688: 3687: 3682: 3677: 3672: 3666: 3664: 3658: 3657: 3655: 3654: 3649: 3643: 3641: 3635: 3634: 3632: 3631: 3626: 3624:Zetekitoxin AB 3621: 3616: 3611: 3606: 3601: 3596: 3591: 3586: 3581: 3576: 3571: 3566: 3561: 3556: 3550: 3548: 3544: 3543: 3538: 3536: 3535: 3528: 3521: 3513: 3504: 3503: 3501: 3500: 3489: 3486: 3485: 3483: 3482: 3477: 3472: 3470:Lyngbyatoxin-a 3467: 3462: 3457: 3452: 3447: 3442: 3437: 3432: 3426: 3424: 3420: 3419: 3417: 3416: 3411: 3408:Microcystin-LR 3401: 3395: 3393: 3387: 3386: 3384: 3383: 3378: 3373: 3368: 3363: 3358: 3352: 3350: 3344: 3343: 3338: 3336: 3335: 3328: 3321: 3313: 3307: 3306: 3300: 3286: 3285:External links 3283: 3281: 3280: 3258:(3): 228–254. 3243: 3225:(2): 356–365. 3213: 3211: 3208: 3205: 3204: 3171:Water Research 3157: 3132:Natural Toxins 3121: 3055: 3030: 2971: 2936: 2909:(5): 1705–14. 2888: 2837: 2818:(5): 1536–48. 2812:Water Research 2799: 2750: 2709: 2680: 2655: 2630: 2615: 2597: 2563: 2560:on 2013-01-04. 2550:ASA Newsletter 2536: 2497: 2453: 2404: 2353: 2302: 2261: 2225: 2206:(2): 292–301. 2190: 2175: 2148:(8): 1070–89. 2115: 2088:(sup6): 6–11. 2072: 2029: 1986: 1965:(3): 228–254. 1945: 1913: 1886:(4): 275–276. 1870: 1835: 1822: 1794: 1743: 1710: 1669: 1638:(2): 488–508. 1618: 1589: 1538: 1487: 1458: 1402: 1395: 1346: 1297: 1296: 1294: 1291: 1290: 1289: 1284: 1277: 1274: 1273: 1272: 1267: 1262: 1257: 1250: 1245: 1238: 1231: 1224: 1217: 1210: 1203: 1196: 1186: 1183: 1161: 1158: 1106: 1103: 1098: 1095: 1090: 1087: 1082: 1079: 1076: 1075: 1072: 1068: 1067: 1064: 1060: 1059: 1056: 1052: 1051: 1048: 1044: 1043: 1040: 1019: 1016: 1014: 1011: 997: 994: 990:eutrophication 984: 981: 977:chromatography 967:Artemia salina 958: 955: 936: 933: 909: 906: 900: 897: 891: 888: 882: 879: 873: 870: 849: 846: 844: 841: 839: 836: 807: 804: 788:fasciculations 720:depolarization 695: 691: 684: 680: 676: 672: 669: 656: 653: 634: 631: 625: 622: 620: 617: 600: 597: 595: 592: 587:Xenopus laevis 581: 577: 573: 569: 565: 536: 533: 517:eutrophication 513:stratification 507: 504: 485: 482: 462:mode of action 410: 407: 406: 401: 379: 378: 374:standard state 371: 368: 367: 364: 358: 357: 353: 349: 346: 341: 338: 337: 333: 332: 330: 329: 326: 318: 317: 316: 313: 312: 310: 309: 305: 302: 301: 299: 295: 292: 291: 283: 282: 281: 278: 277: 275: 274: 261: 259: 247: 244: 243: 241: 240: 232: 230: 224: 223: 221: 220: 212: 210: 202: 199: 198: 196: 195: 187: 185: 179: 178: 168: 160: 159: 157: 156: 148: 146: 140: 139: 137: 136: 128: 126: 120: 119: 117: 116: 108: 106: 99: 96: 95: 93: 92: 84: 82: 77: 74: 73: 69: 68: 65: 61: 60: 57: 51: 50: 46: 45: 37: 36: 13: 10: 9: 6: 4: 3: 2: 5277: 5266: 5263: 5261: 5258: 5256: 5253: 5251: 5248: 5246: 5243: 5241: 5238: 5236: 5233: 5231: 5228: 5226: 5223: 5221: 5218: 5216: 5213: 5212: 5210: 5195: 5192: 5190: 5187: 5185: 5182: 5179: 5178: 5175: 5169: 5166: 5164: 5161: 5159: 5156: 5154: 5151: 5149: 5146: 5144: 5141: 5139: 5136: 5134: 5131: 5129: 5126: 5123: 5119: 5116: 5114: 5111: 5109: 5106: 5105: 5103: 5099: 5093: 5089: 5079: 5076: 5074: 5071: 5069: 5066: 5064: 5061: 5059: 5056: 5054: 5051: 5049: 5046: 5044: 5041: 5039: 5036: 5034: 5031: 5029: 5026: 5024: 5021: 5019: 5016: 5014: 5011: 5009: 5006: 5004: 5001: 4999: 4996: 4994: 4991: 4989: 4986: 4984: 4981: 4979: 4978:Phencyclidine 4976: 4974: 4971: 4969: 4966: 4964: 4961: 4959: 4956: 4954: 4951: 4949: 4948:Nitrous oxide 4946: 4944: 4941: 4939: 4936: 4934: 4931: 4929: 4926: 4924: 4921: 4919: 4916: 4914: 4911: 4909: 4906: 4904: 4901: 4899: 4896: 4894: 4891: 4889: 4888:Levomethadone 4886: 4884: 4881: 4879: 4876: 4874: 4871: 4869: 4866: 4864: 4861: 4859: 4856: 4854: 4851: 4849: 4846: 4844: 4841: 4839: 4836: 4834: 4833:Hexafluronium 4831: 4829: 4826: 4824: 4821: 4819: 4816: 4814: 4811: 4809: 4806: 4804: 4801: 4799: 4796: 4794: 4791: 4789: 4786: 4784: 4781: 4779: 4776: 4774: 4771: 4769: 4766: 4764: 4761: 4759: 4756: 4754: 4751: 4749: 4746: 4744: 4741: 4739: 4736: 4734: 4731: 4729: 4726: 4724: 4723:Decamethonium 4721: 4719: 4716: 4714: 4711: 4709: 4706: 4704: 4701: 4699: 4696: 4694: 4693:Cisatracurium 4691: 4689: 4686: 4684: 4681: 4679: 4676: 4674: 4671: 4669: 4666: 4663: 4659: 4655: 4654:Bungarotoxins 4652: 4650: 4647: 4644: 4640: 4639:pentobarbital 4636: 4633: 4631: 4628: 4626: 4623: 4621: 4618: 4616: 4613: 4611: 4608: 4606: 4603: 4601: 4598: 4595: 4591: 4587: 4583: 4582:α-Neurotoxins 4580: 4578: 4575: 4573: 4570: 4569: 4567: 4561: 4554: 4550: 4544: 4541: 4539: 4536: 4534: 4531: 4529: 4526: 4524: 4521: 4519: 4516: 4514: 4511: 4509: 4506: 4504: 4501: 4499: 4496: 4494: 4491: 4489: 4486: 4484: 4481: 4479: 4476: 4474: 4471: 4469: 4466: 4464: 4461: 4459: 4456: 4454: 4451: 4449: 4446: 4444: 4441: 4439: 4436: 4434: 4431: 4429: 4426: 4424: 4421: 4419: 4416: 4414: 4411: 4409: 4406: 4404: 4401: 4399: 4396: 4394: 4391: 4389: 4386: 4383: 4379: 4376: 4374: 4371: 4369: 4366: 4364: 4361: 4359: 4356: 4354: 4351: 4349: 4346: 4344: 4341: 4339: 4336: 4334: 4331: 4329: 4326: 4324: 4321: 4319: 4316: 4314: 4311: 4309: 4306: 4304: 4301: 4299: 4296: 4294: 4291: 4289: 4286: 4284: 4283:Decamethonium 4281: 4279: 4276: 4274: 4271: 4269: 4266: 4264: 4261: 4259: 4256: 4254: 4251: 4249: 4246: 4244: 4241: 4239: 4236: 4234: 4231: 4229: 4226: 4224: 4221: 4219: 4218:Acetylcholine 4216: 4214: 4211: 4209: 4206: 4204: 4201: 4199: 4196: 4194: 4191: 4189: 4186: 4184: 4181: 4179: 4176: 4174: 4171: 4169: 4166: 4165: 4163: 4157: 4150: 4146: 4143: 4138: 4132: 4128: 4125: 4118: 4113: 4111: 4106: 4104: 4099: 4098: 4095: 4083: 4080: 4078: 4075: 4073: 4070: 4068: 4065: 4063: 4060: 4059: 4057: 4053: 4047: 4044: 4042: 4039: 4037: 4034: 4032: 4029: 4027: 4024: 4023: 4021: 4017: 4011: 4008: 4006: 4003: 4001: 3998: 3997: 3995: 3993: 3989: 3983: 3980: 3978: 3975: 3973: 3970: 3968: 3965: 3963: 3960: 3958: 3955: 3953: 3950: 3948: 3945: 3943: 3940: 3938: 3935: 3933: 3930: 3928: 3925: 3923: 3920: 3918: 3915: 3913: 3910: 3908: 3905: 3903: 3900: 3898: 3895: 3893: 3890: 3888: 3885: 3884: 3882: 3880: 3876: 3870: 3867: 3865: 3862: 3860: 3857: 3855: 3852: 3850: 3847: 3845: 3842: 3840: 3837: 3835: 3832: 3830: 3829:Methamidophos 3827: 3825: 3822: 3820: 3817: 3815: 3812: 3810: 3809:Fenpropathrin 3807: 3806: 3804: 3802: 3798: 3792: 3789: 3787: 3784: 3782: 3781:Ibotenic acid 3779: 3778: 3776: 3774: 3770: 3764: 3761: 3759: 3756: 3754: 3751: 3749: 3748:Oenanthotoxin 3746: 3744: 3741: 3739: 3736: 3734: 3731: 3729: 3726: 3724: 3721: 3719: 3716: 3714: 3711: 3709: 3706: 3704: 3701: 3700: 3698: 3696: 3692: 3686: 3683: 3681: 3678: 3676: 3673: 3671: 3668: 3667: 3665: 3663: 3659: 3653: 3652:Tetanospasmin 3650: 3648: 3645: 3644: 3642: 3640: 3636: 3630: 3627: 3625: 3622: 3620: 3617: 3615: 3612: 3610: 3607: 3605: 3602: 3600: 3597: 3595: 3592: 3590: 3587: 3585: 3582: 3580: 3577: 3575: 3574:Charybdotoxin 3572: 3570: 3567: 3565: 3562: 3560: 3557: 3555: 3554:Batrachotoxin 3552: 3551: 3549: 3547:Animal toxins 3545: 3541: 3534: 3529: 3527: 3522: 3520: 3515: 3514: 3511: 3499: 3491: 3490: 3487: 3481: 3478: 3476: 3473: 3471: 3468: 3466: 3463: 3461: 3458: 3456: 3455:Cyanopeptolin 3453: 3451: 3450:Cyanobacterin 3448: 3446: 3443: 3441: 3438: 3436: 3433: 3431: 3428: 3427: 3425: 3421: 3415: 3412: 3409: 3405: 3402: 3400: 3397: 3396: 3394: 3392: 3388: 3382: 3379: 3377: 3374: 3372: 3369: 3367: 3364: 3362: 3359: 3357: 3354: 3353: 3351: 3349: 3345: 3341: 3334: 3329: 3327: 3322: 3320: 3315: 3314: 3311: 3304: 3301: 3298: 3297: 3292: 3289: 3288: 3284: 3276: 3271: 3266: 3261: 3257: 3253: 3249: 3244: 3240: 3236: 3232: 3228: 3224: 3220: 3215: 3214: 3209: 3200: 3196: 3192: 3188: 3184: 3180: 3176: 3172: 3168: 3161: 3158: 3153: 3149: 3145: 3141: 3138:(6): 353–60. 3137: 3133: 3125: 3122: 3117: 3113: 3109: 3105: 3101: 3097: 3093: 3089: 3085: 3081: 3077: 3070: 3068: 3066: 3064: 3062: 3060: 3056: 3045: 3041: 3034: 3031: 3026: 3022: 3017: 3012: 3007: 3002: 2998: 2994: 2990: 2986: 2982: 2975: 2972: 2967: 2963: 2959: 2955: 2952:(4): 677–91. 2951: 2947: 2940: 2937: 2932: 2928: 2924: 2920: 2916: 2912: 2908: 2904: 2897: 2895: 2893: 2889: 2884: 2880: 2876: 2872: 2868: 2864: 2860: 2856: 2853:(3): 168–73. 2852: 2848: 2841: 2838: 2833: 2829: 2825: 2821: 2817: 2813: 2806: 2804: 2800: 2795: 2791: 2786: 2781: 2777: 2773: 2769: 2765: 2761: 2754: 2751: 2746: 2742: 2737: 2732: 2729:(3): 455–65. 2728: 2724: 2720: 2713: 2710: 2697: 2690: 2684: 2681: 2669: 2665: 2659: 2656: 2644: 2640: 2634: 2631: 2626: 2622: 2618: 2616:0-419-23930-8 2612: 2608: 2601: 2598: 2585: 2578: 2572: 2570: 2568: 2564: 2559: 2555: 2551: 2547: 2540: 2537: 2532: 2528: 2524: 2520: 2517:(3): 281–94. 2516: 2512: 2508: 2501: 2498: 2493: 2489: 2485: 2481: 2477: 2473: 2469: 2465: 2457: 2454: 2449: 2445: 2440: 2435: 2431: 2427: 2423: 2419: 2415: 2408: 2405: 2400: 2396: 2391: 2386: 2381: 2376: 2372: 2368: 2364: 2357: 2354: 2349: 2345: 2340: 2335: 2330: 2325: 2321: 2317: 2313: 2306: 2303: 2298: 2294: 2289: 2284: 2280: 2276: 2272: 2265: 2262: 2257: 2253: 2249: 2245: 2242:(7): 919–28. 2241: 2237: 2229: 2226: 2221: 2217: 2213: 2209: 2205: 2201: 2194: 2191: 2186: 2179: 2176: 2171: 2167: 2163: 2159: 2155: 2151: 2147: 2143: 2136: 2134: 2132: 2130: 2128: 2126: 2124: 2122: 2120: 2116: 2111: 2107: 2103: 2099: 2095: 2091: 2087: 2083: 2076: 2073: 2068: 2064: 2060: 2056: 2052: 2048: 2044: 2040: 2033: 2030: 2025: 2021: 2017: 2013: 2009: 2005: 2001: 1997: 1990: 1987: 1982: 1978: 1973: 1968: 1964: 1960: 1956: 1949: 1946: 1935:on 2018-09-23 1934: 1930: 1926: 1920: 1918: 1914: 1909: 1905: 1901: 1897: 1893: 1889: 1885: 1881: 1874: 1871: 1866: 1862: 1858: 1854: 1850: 1846: 1839: 1836: 1825: 1819: 1815: 1811: 1807: 1806: 1805:Algae and Man 1798: 1795: 1790: 1786: 1781: 1776: 1771: 1766: 1762: 1758: 1754: 1747: 1744: 1738: 1733: 1729: 1725: 1721: 1714: 1711: 1706: 1702: 1697: 1692: 1688: 1684: 1680: 1673: 1670: 1665: 1661: 1656: 1651: 1646: 1641: 1637: 1633: 1629: 1622: 1619: 1606: 1599: 1593: 1590: 1585: 1581: 1576: 1571: 1566: 1561: 1557: 1553: 1549: 1542: 1539: 1534: 1530: 1526: 1522: 1518: 1514: 1510: 1506: 1502: 1498: 1491: 1488: 1475: 1468: 1462: 1459: 1454: 1450: 1446: 1442: 1438: 1434: 1430: 1426: 1422: 1418: 1411: 1409: 1407: 1403: 1398: 1392: 1388: 1384: 1380: 1373: 1371: 1369: 1367: 1365: 1363: 1361: 1359: 1357: 1355: 1353: 1351: 1347: 1342: 1338: 1334: 1330: 1327:(5): 813–28. 1326: 1322: 1315: 1313: 1311: 1309: 1307: 1305: 1303: 1299: 1292: 1288: 1285: 1283: 1280: 1279: 1275: 1271: 1268: 1266: 1263: 1261: 1258: 1256: 1255: 1251: 1249: 1246: 1244: 1243: 1239: 1237: 1236: 1232: 1230: 1229: 1225: 1223: 1222: 1218: 1216: 1215: 1211: 1209: 1208: 1204: 1202: 1201: 1200:Aphanizomenon 1197: 1195: 1193: 1189: 1188: 1184: 1182: 1180: 1176: 1172: 1168: 1159: 1157: 1155: 1151: 1146: 1144: 1140: 1136: 1132: 1128: 1124: 1119: 1117: 1113: 1104: 1102: 1096: 1094: 1088: 1086: 1080: 1073: 1070: 1069: 1065: 1062: 1061: 1057: 1054: 1053: 1049: 1046: 1045: 1041: 1038: 1037: 1031: 1029: 1025: 1017: 1013:United States 1012: 1010: 1007: 1003: 995: 993: 991: 983:Public health 982: 980: 978: 974: 973: 968: 964: 956: 954: 951: 950: 944: 942: 934: 932: 930: 929: 923: 919: 915: 907: 905: 898: 896: 889: 887: 880: 878: 871: 865: 861: 859: 855: 847: 842: 837: 835: 833: 829: 825: 820: 812: 805: 803: 801: 797: 793: 789: 785: 781: 779: 775: 771: 767: 763: 758: 756: 752: 743: 739: 737: 733: 729: 725: 721: 716: 715:acetylcholine 711: 709: 705: 704:acetylcholine 701: 689: 670: 668: 666: 662: 654: 652: 650: 646: 643: 642: 632: 630: 623: 618: 616: 612: 610: 606: 598: 593: 591: 589: 588: 562: 560: 556: 550: 547: 542: 541:A. flos-aquae 534: 532: 528: 526: 522: 518: 514: 505: 503: 501: 500: 495: 491: 483: 481: 479: 475: 474:acetylcholine 471: 467: 463: 459: 456:and death by 455: 451: 447: 443: 442:cyanobacteria 439: 438:neurotoxicity 435: 431: 428: 424: 420: 416: 404: 397: 392: 375: 369: 365: 363: 360: 359: 347: 344: 340: 339: 334: 325: 321: 314: 300: 290: 286: 279: 271: 267: 263: 262: 260: 250: 246: 245: 238: 234: 233: 231: 229: 226: 225: 218: 214: 213: 211: 205: 201: 200: 193: 189: 188: 186: 184: 181: 180: 176: 172: 169: 167: 165:ECHA InfoCard 162: 161: 154: 150: 149: 147: 145: 142: 141: 134: 130: 129: 127: 125: 122: 121: 114: 110: 109: 107: 103: 98: 97: 90: 86: 85: 83: 80: 76: 75: 70: 62: 56: 52: 47: 43: 38: 34: 29: 21: 20:Anatoxin-a(S) 16: 5240:Cycloalkenes 5063:Tubocurarine 4993:Promegestone 4988:Progesterone 4903:Mecamylamine 4713:Cyclopropane 4703:Coronaridine 4635:Barbiturates 4620:Anatruxonium 4590:α-cobratoxin 4433:Sazetidine A 4353:JNJ-39393406 4343:Ispronicline 4237: 3879:Nerve agents 3695:Plant toxins 3669: 3609:Vanillotoxin 3604:Tetrodotoxin 3569:Bungarotoxin 3475:Microviridin 3430:Aplysiatoxin 3404:Microcystins 3391:Hepatotoxins 3366:Antillatoxin 3355: 3294: 3255: 3252:Marine Drugs 3251: 3222: 3218: 3174: 3170: 3160: 3135: 3131: 3124: 3083: 3079: 3047:. Retrieved 3043: 3033: 2988: 2984: 2974: 2949: 2945: 2939: 2906: 2902: 2850: 2846: 2840: 2815: 2811: 2767: 2763: 2753: 2726: 2722: 2712: 2700:. Retrieved 2695: 2683: 2672:. Retrieved 2670:. 2009-10-08 2667: 2658: 2647:. Retrieved 2645:. 2018-02-12 2642: 2633: 2606: 2600: 2588:. Retrieved 2583: 2558:the original 2553: 2549: 2539: 2514: 2510: 2500: 2467: 2463: 2456: 2424:(2): 141–8. 2421: 2417: 2407: 2370: 2366: 2356: 2319: 2315: 2305: 2281:(1): 89–92. 2278: 2274: 2264: 2239: 2235: 2228: 2203: 2199: 2193: 2185:Neuroscience 2184: 2178: 2145: 2141: 2085: 2081: 2075: 2042: 2038: 2032: 1999: 1995: 1989: 1962: 1959:Marine Drugs 1958: 1948: 1937:. Retrieved 1933:the original 1928: 1883: 1879: 1873: 1848: 1844: 1838: 1827:. Retrieved 1804: 1797: 1760: 1757:Marine Drugs 1756: 1746: 1727: 1723: 1713: 1686: 1682: 1672: 1635: 1631: 1621: 1609:. Retrieved 1604: 1592: 1555: 1552:Marine Drugs 1551: 1541: 1500: 1496: 1490: 1478:. Retrieved 1473: 1461: 1420: 1416: 1378: 1324: 1320: 1270:Woronichinia 1269: 1264: 1260:Raphidiopsis 1259: 1254:Planktothrix 1252: 1247: 1242:Oscillatoria 1240: 1233: 1226: 1219: 1212: 1205: 1198: 1190: 1163: 1147: 1143:chlorination 1120: 1111: 1108: 1100: 1092: 1084: 1021: 1004:in 1999 and 999: 986: 970: 966: 963:brine shrimp 960: 947: 945: 938: 928:Oscillatoria 926: 921: 917: 913: 911: 908:Biosynthesis 902: 893: 884: 875: 851: 828:Lake Bogoria 821: 817: 782: 772:between its 765: 759: 748: 712: 674: 658: 639: 636: 627: 613: 602: 585: 563: 551: 540: 538: 529: 509: 497: 494:algal blooms 487: 422: 418: 414: 413: 72:Identifiers 64:Other names 15: 5235:Cyanotoxins 5215:Neurotoxins 5168:Pirisudanol 5133:Cyprodenate 5113:Adafenoxate 5028:Surugatoxin 5018:Sevoflurane 4973:Pentolinium 4953:Norketamine 4873:Laudanosine 4803:Erythravine 4793:Encenicline 4778:Dipyrandium 4748:Dextrorphan 4594:α-conotoxin 4553:Antagonists 4538:WAY-317,538 4533:Varenicline 4523:Tropisetron 4513:Tebanicline 4458:SSR-180,711 4423:Rivanicline 4413:Pozanicline 4408:PNU-282,987 4403:PNU-120,596 4398:PHA-709,829 4393:PHA-543,613 4333:Galantamine 4308:Epiboxidine 4303:Epibatidine 4223:Altinicline 4031:Catecholine 3972:Fluorotabun 3819:Bromethalin 3763:Veratridine 3738:Ginkgotoxin 3708:Bicuculline 3662:Cyanotoxins 3629:Dendrotoxin 3619:Epibatidine 3594:Poneratoxin 3540:Neurotoxins 3445:Coibamide A 3440:Caldoramide 3435:Apratoxin A 3348:Neurotoxins 3340:Cyanotoxins 2702:October 25, 2698:. July 2008 2590:October 25, 2586:. June 2015 2373:(11): 726. 1996:Chemosphere 1851:(1): 2–24. 1689:(3): 71–5. 1611:October 25, 1480:October 25, 1476:. 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