Synonym
Saxitoxinol; Dihydrosaxitoxin; STXOL;
IUPAC/Chemical Name
((3aS,4R,10R)-2,6-diamino-10-hydroxy-3a,4,9,10-tetrahydro-1H,8H-pyrrolo[1,2-c]purin-4-yl)methyl carbamate
InChi Key
NILHUXIFTLLDPJ-TXDDJGQJSA-N
InChi Code
InChI=1S/C10H17N7O3/c11-7-15-6-4(3-20-9(13)19)14-8(12)17-2-1-5(18)10(6,17)16-7/h4-6,18H,1-3H2,(H2,12,14)(H2,13,19)(H3,11,15,16)/t4-,5+,6-,10?/m0/s1
SMILES Code
NC(OC[C@@H]1N=C(N2CC[C@H](C23NC(N)=N[C@@H]13)O)N)=O
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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
283.29
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: Kao CY, Kao PN, James-Kracke MR, Koehn FE, Wichmann CF, Schnoes HK. Actions of epimers of 12-(OH)-reduced saxitoxin and of 11-(OSO3)-saxitoxin on squid axon. Toxicon. 1985;23(4):647-55. PubMed PMID: 2414863.
2: Pearson AD, Williams RM. Synthetic studies towards Zetekitoxin AB: preparation of 4,5-epi-11-hydroxy-saxitoxinol. Tetrahedron. 2014 Oct 28;70(43):7942-7949. PubMed PMID: 25313264; PubMed Central PMCID: PMC4192658.
3: Ueno S, Nakazaki A, Nishikawa T. A Synthetic Strategy for Saxitoxin Skeleton by a Cascade Bromocyclization: Total Synthesis of (+)-Decarbamoyl-α-saxitoxinol. Org Lett. 2016 Dec 16;18(24):6368-6371. Epub 2016 Dec 5. PubMed PMID: 27978691.
4: Naseem SM. Toxicokinetics of [3H]saxitoxinol in peripheral and central nervous system of rats. Toxicol Appl Pharmacol. 1996 Nov;141(1):49-58. PubMed PMID: 8917675.
5: Sawayama Y, Nishikawa T. A synthetic route to the saxitoxin skeleton: synthesis of decarbamoyl α-saxitoxinol, an analogue of saxitoxin produced by the cyanobacterium Lyngbya wollei. Angew Chem Int Ed Engl. 2011 Jul 25;50(31):7176-8. doi: 10.1002/anie.201102494. Epub 2011 Jun 17. PubMed PMID: 21688378.
6: Hines HB, Naseem SM, Wannemacher RW Jr. [3H]-saxitoxinol metabolism and elimination in the rat. Toxicon. 1993 Jul;31(7):905-8. PubMed PMID: 8212035.
7: Naseem SM, Creasia DA. Comparative binding and toxicity of saxitoxin and saxitoxinol in mice and in cultured cells. Biochem Mol Biol Int. 1997 Feb;41(2):377-88. PubMed PMID: 9063578.
8: Akimoto T, Masuda A, Yotsu-Yamashita M, Hirokawa T, Nagasawa K. Synthesis of saxitoxin derivatives bearing guanidine and urea groups at C13 and evaluation of their inhibitory activity on voltage-gated sodium channels. Org Biomol Chem. 2013 Oct 14;11(38):6642-9. doi: 10.1039/c3ob41398e. Epub 2013 Aug 30. PubMed PMID: 23989458.
9: Stafford RG, Hines HB. Urinary elimination of saxitoxin after intravenous injection. Toxicon. 1995 Nov;33(11):1501-10. PubMed PMID: 8744989.
