Saxitoxinol

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 461846

CAS#: 75420-34-7

Description: Saxitoxinol is an analog of saxitoxin, a known voltage-gated sodium channel blocker.


Chemical Structure

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Saxitoxinol
CAS# 75420-34-7

Theoretical Analysis

MedKoo Cat#: 461846
Name: Saxitoxinol
CAS#: 75420-34-7
Chemical Formula: C10H17N7O3
Exact Mass: 283.14
Molecular Weight: 283.290
Elemental Analysis: C, 42.40; H, 6.05; N, 34.61; O, 16.94

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

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

Appearance: Solid powder

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

More Info:

Biological target:
In vitro activity:
In vivo activity:

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.

Recalculate based on batch purity %
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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.