Anatoxin-as

Anatoxin-a(S)

Names
IUPAC name (5S)-5-[(Dimethylamino)methyl]-1-{[hydroxy(methoxy)phosphoryl]oxy}-4,5-dihydro-1H-imidazol-2-amine
Identifiers
CAS Number	103170-78-1
3D model (JSmol)	Interactive image
ChemSpider	102921
KEGG	C19998
PubChem CID	114989
UNII	4258P76E76
InChI InChI=1S/C7H17N4O4P/c1-10(2)5-6-4-9-7(8)11(6)15-16(12,13)14-3/h6H,4-5H2,1-3H3,(H2,8,9)(H,12,13)/t6-/m1/s1 Key: FYXHGVMFJYHPFX-ZCFIWIBFSA-N
SMILES CN(C)C[C@H]1CN=C(N1OP(=O)(O)OC)N
Properties
Chemical formula	C7H17N4O4P
Molar mass	252.21 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Anatoxin-a(S) "Salivary" is a naturally occurring cyanotoxin commonly isolated from cyanobacteria (specifically of the genus Anabaena) and causes excess salivation in mammals via inhibition of acetylcholinesterase. Anatoxin-a(S) is structurally a cyclic N-hydroxyguanine organophosphate with a phosphate ester moiety.

The main mechanism of action for anatoxin-a(S) is by irreversibly inhibiting the active site of acetylcholinesterase leading to excess acetylcholine in the parasympathetic and peripheral nervous systems; inducing poisoning via nicotinic and muscarinic cholinergic receptor stimulation. Treatment of afflicted case by atropine has attested to suppress the muscarinic mediated toxicity; which prevents the namesake salivation that similarly reacts to prevent the toxin's other poisoning symptoms which include lacrimation, urinary incontinence and defecation. Atropine will not, however, counter another mechanism of the compounds toxicity as it also mediates a nicotinic adverse toxicity affecting muscle tremors, fasciculation, convulsions and respiratory failure.