A neurotoxin and Nav activator
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Brevetoxin B

Item No. 10011498

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-(((1S,3R,4aR,5aS,6aR,9aS,10aR,11aS,12aR,13R,14aS,15aR,16aS,20aR,21aS,22aR,23aS,25aR,26aS,27aR,28aS,29aR,30aS,Z)-1-hydroxy-9a,13,20,21a,25a,26a,30a-heptamethyl-18-oxo-2,3,4a,5,5a,6a,9,9a,10a,11,11a,12a,13,14,14a,15a,16,16a,18,20a,21a,22,22a,23a,24,25,25a,26a,27,27a,28a,29,29a,30a-tetratriacontahydro-1H-pyrano[2'''''',3'''''':5''''',6''''']pyrano[2''''',3''''':5'''',6'''']pyrano[2'''',3'''':6''',7''']oxepino[2''',3''':6'',7'']oxepino[2'',3'':5',6']pyrano[2',3':5,6]pyrano[3,2-b]pyrano[2'',3'':5',6']pyrano[2',3':5,6]pyrano[2,3-g]oxocin-3-yl)methyl)acrylaldehyde
CAS Number
79580-28-2
Synonyms
  • Brevetoxin PbTx 2
  • GB-2 Toxin
  • T-34 Toxin
  • Ptychodiscus brevis toxin 2
Molecular Formula
C50H70O14
Formula Weight
895.1
Purity
≥95%
Formulation (Request formulation change)
A film
Solubility(Learn about Variance in Solubility)
Ethyl Acetate: Soluble
SMILES
CC1=CC(OC2C1OC3(C)C(OC4C(OC5C(OC(CC(OC6(C)C(OC7C(OC(CC(OC(CC(C=O)=C)CC8O)C8(C)O9)C9C7)/C=C\C6)C%10)C%10(C)O%11)C%11(C)CC5)C(C)C4)C3)C2)=O
InChi Code
InChI=1S/C50H70O14/c1-25(24-51)14-28-17-37(52)50(8)41(54-28)19-33-34(61-50)18-32-29(55-33)10-9-12-46(4)42(58-32)23-49(7)40(62-46)21-39-47(5,64-49)13-11-30-44(60-39)26(2)15-31-36(56-30)22-48(6)38(57-31)20-35-45(63-48)27(3)16-43(53)59-35/h9-10,16,24,26
InChi Key
LYTCVQQGCSNFJU-KTKRTIGZSA-N
Origin
Plant/Karenia brevis
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    100 µg

    $699

    Add
    Cayman Chemical
    Visit Our Environmental Toxicology Resource Center

    Explore additional resources to study natural toxins, pollutants including PFAS and 6-PPD-Q, and their biological effects.

    ENVIRONMENTAL TOXICOLOGY TOOLS & SERVICES
    Product Description

    Brevetoxin B is a neurotoxin produced by the dinoflagellate K. brevis.1 It has been found in water samples collected during red tide blooms.2,3 Brevetoxin B is an activator of voltage-gated sodium channels (Nav) that binds to neurotoxin site 5 on the α subunit of the channel.3 Brevetoxins reduce the activation potential required to open the channel, increase the mean open time of the channel, and slow inactivation of the channel.4 It increases intracellular calcium levels in primary rat cerebellar granule cells (EC50 = 53.4 nM).3 Brevetoxin B induces the release of lactate dehydrogenase (LDH), L-glutamate, and L-aspartate from primary rat cerebellar granule neurons (EC50s = 37.7, 59.6, and 60.7 nM, respectively).5 It is lethal to fish (LC50 = 14.3 nM in G. affinis) and mice (LD50s = 0.2, 0.2, and 6.6 mg/kg, i.v., i.p., and p.o., respectively).6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Weniger, B., Italiano, L., Beck, J.-P., et al. Cytotoxic activity of amaryllidaceae alkaloids. Planta Med. 61(1), 77-79 (1995).

    2. Pierce, R.H., and Henry, M.S. Harmful algal toxins of the Florida red tide (Karenia brevis): Natural chemical stressors in South Florida coastal ecosystems. Ecotoxicology 17(7), 623-631 (2008).

    3. LePage, K.T., Baden, D.G., and Murray, T.F. Brevetoxin derivatives act as partial agonists at neurotoxin site 5 on the voltage-gated Na+ channel. Brain Res. 959(1), 120-127 (2003).

    4. Stevens, M., Peigneur, S., and Tytgat, J. Neurotoxins and their binding areas on voltage-gated sodium channels. Front. Pharmacol. 2, 71 (2011).

    5. Berman, F.W., and Murray, T.F. Brevetoxins cause acute excitotoxicity in primary cultures of rat cerebellar granule neurons. J. Pharmacol. Exp. Ther. 290(1), 439-444 (1999).

    6. Baden, B.G., and Mende, T.J. Toxicity of two toxins from the Florida red tide marine dinoflagellate, Ptychodiscus brevis. Toxicon. 20(2), 457-461 (1982).

    7. Rein, K.S., Lynn, B., Gawley, R.E., et al. Brevetoxin B: Chemical modifications, synaptosome binding, toxicity, and an unexpected conformational effect. The Journal of Organic Chemistry 59, 2107-2113 (1994).