Decarbamoylsaxitoxin

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

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
3D model (JSmol)
ChemSpider
KEGG
UNII
  • 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
  • NC1=N[C@H]2[C@H](CO)N=C(N)N3CCC(O)(O)[C@]23N1
Properties
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

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).

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