Synonym
Decarbamoylneosaxitoxin; 1-Hydroxydecarbamoylsaxitoxin; DECARBOMOYLNEOSAXITOXIN
IUPAC/Chemical Name
1H,10H-Pyrrolo(1,2-c)purine-10,10-diol, 2-amino-3a,4,5,6,8,9-hexahydro-5-hydroxy-4-(hydroxymethyl)-6-imino-, (3aS,4R,10aS)-
InChi Key
KUMXVBFFVVLQFX-PJPYAQQDSA-N
InChi Code
InChI=1S/C9H16N6O4/c10-6-12-5-4(3-16)15(19)7(11)14-2-1-8(17,18)9(5,14)13-6/h4-5,11,16-19H,1-3H2,(H3,10,12,13)/t4-,5-,9-/m0/s1
SMILES Code
OC1(O)CCN2[C@@]31NC(N)=N[C@@]3([H])[C@H](CO)N(O)C2=N
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
272.26
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Gao C, Lin S, Chen M, Hong J, Liu C. Prevalence of phycotoxin contamination in shellfish from the Northern Bering Sea and the Chukchi Sea. Toxicon. 2019 Sep;167:76-81. doi: 10.1016/j.toxicon.2019.06.001. Epub 2019 Jun 4. PubMed PMID: 31170406.
2: Yilmaz M, Foss AJ, Selwood AI, Özen M, Boundy M. Paralytic shellfish toxin producing Aphanizomenon gracile strains isolated from Lake Iznik, Turkey. Toxicon. 2018 Jun 15;148:132-142. doi: 10.1016/j.toxicon.2018.04.028. Epub 2018 Apr 27. PubMed PMID: 29705145.
3: Peake RW, Zhang VY, Azcue N, Hartigan CE, Shkreta A, Prabhakara J, Berde CB, Kellogg MD. Measurement of neosaxitoxin in human plasma using liquid-chromatography tandem mass spectrometry: Proof of concept for a pharmacokinetic application. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Nov 15;1036-1037:42-49. doi: 10.1016/j.jchromb.2016.09.043. Epub 2016 Oct 1. PubMed PMID: 27710889.
4: Turner AD, McNabb PS, Harwood DT, Selwood AI, Boundy MJ. Single-Laboratory Validation of a Multitoxin Ultra-Performance LC-Hydrophilic Interaction LC-MS/MS Method for Quantitation of Paralytic Shellfish Toxins in Bivalve Shellfish. J AOAC Int. 2015 May-Jun;98(3):609-21. doi: 10.5740/jaoacint.14-275. Epub 2015 May 28. PubMed PMID: 26024657.
5: Perez S, Vale C, Botana AM, Alonso E, Vieytes MR, Botana LM. Determination of toxicity equivalent factors for paralytic shellfish toxins by electrophysiological measurements in cultured neurons. Chem Res Toxicol. 2011 Jul 18;24(7):1153-7. doi: 10.1021/tx200173d. Epub 2011 Jun 8. PubMed PMID: 21619049.
6: Iwamoto O, Nagasawa K. Total synthesis of (+)-decarbamoylsaxitoxin and (+)-gonyautoxin 3. Org Lett. 2010 May 7;12(9):2150-3. doi: 10.1021/ol1006696. PubMed PMID: 20355743.
7: Vale C, Alfonso A, Vieytes MR, Romarís XM, Arévalo F, Botana AM, Botana LM. In vitro and in vivo evaluation of paralytic shellfish poisoning toxin potency and the influence of the pH of extraction. Anal Chem. 2008 Mar 1;80(5):1770-6. doi: 10.1021/ac7022266. Epub 2008 Jan 31. PubMed PMID: 18232710.
8: Yang L, Kao CY, Oshima Y. Actions of decarbamoyloxysaxitoxin and decarbamoylneosaxitoxin on the frog skeletal muscle fiber. Toxicon. 1992 May-Jun;30(5-6):645-52. PubMed PMID: 1325688.
