Decarbamoylsaxitoxin

Decarbamoylsaxitoxin

Structure of dcSTX
Ball and stick model of dcSTX Space filling molecule of dcSTX
Names
IUPAC name (3aS,4R,10aS)-2,6-diamino-4-(hydroxymethyl)-3a,4,8,9-tetrahydro-3H-pyrrolo[1,2-c]purine-10,10-diol
Identifiers
CAS Number	58911-04-9 Y
3D model (JSmol)	Interactive image
ChemSpider	19975972
KEGG	C20021
PubChem CID	24941628
UNII	EC89AU638S Y
CompTox Dashboard (EPA)	DTXSID70207660
InChI InChI=1S/C9H16N6O3/c10-6-13-5-4(3-16)12-7(11)15-2-1-8(17,18)9(5,15)14-6/h4-5,16-18H,1-3H2,(H2,11,12)(H3,10,13,14)/t4-,5-,9-/m0/s1 Key: VRRIYZJUSNMZMP-PJPYAQQDSA-N
SMILES NC1=N[C@H]2[C@H](CO)N=C(N)N3CCC(O)(O)[C@]23N1
Properties
Chemical formula	C9H16N6O3
Molar mass	256.26 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Decarbamoylsaxitoxin, abbreviated as dcSTX, is a neurotoxin which is naturally produced in dinoflagellate. DcSTX is one of the many analogues of saxitoxin (STX).

Saxitoxin is a tricyclic alkaloid compound, which has multiple structural related neurotoxins. One of those related neurotoxins is neosaxitoxin (NSTX) in which the nitrogen at position 2 is not bound to a hydrogen, but to a hydroxyl group. Another toxic analogue of saxitoxin is gonyautoxin (GTX). The difference between GTX and STX is that on the carbon at position 11, a hydrogensulfate is bound.

Between dcSTX, NSTX and GTX, dcSTX is the one which varies most from saxitoxin. In dcSTX there is a double bond between carbons 2 and 3, while there is a single bond in STX. This also results in that the double-bonded N to carbon number 3 in STX, is a single bound NH₂ in dcSTX. Another difference between decarbamoylsaxitoxin and saxitoxin is that the amino-carbonyl-oxy-methyl group at position 1 in STX, is only a CH₂OH group in dcSTX.

Even though there are slight differences between all saxitoxin-related compounds, all those saxitoxins are neurotoxins which affect the sodium channels. When in contact with one of the saxitoxins it can cause a severe illness, which is known as paralytic shellfish poisoning (PSP).