Picrotoxinin (CAS 17617-45-7)
QUICK LINKS
Picrotoxinin, a compound belonging to the picrotoxane sesquiterpenoid family, possesses a unique molecular structure. It consists of a 3a,4,5,6,7,7a-hexahydro-1H-indene-3,7-dicarboxylic acid backbone, which undergoes specific substitutions at positions 3a, 6, and 7a by methyl, isopropenyl, and hydroxy groups, respectively. Additionally, the double bond at position 2-3 is epoxidized, while the carboxy groups at positions 3 and 7 undergo gamma-lactone formation, resulting in O-alkylation to positions 4 and 5. Picrotoxinin is a constituent of picrotoxin and exhibits various roles as a plant metabolite, GABA antagonist, and serotonergic antagonist. Its chemical nature encompasses multiple characteristics, including being an organic heteropentacyclic compound, an epoxide, a tertiary alcohol, a gamma-lactone, and a picrotoxane sesquiterpenoid.
Picrotoxinin (CAS 17617-45-7) References
- Reduced neuronal sensitivity to dieldrin and picrotoxinin in a cyclodiene-resistant strain of Drosophila melanogaster (Meigen). | Bloomquist, JR., et al. 1992. Arch Insect Biochem Physiol. 19: 17-25. PMID: 1311215
- Mechanisms for picrotoxinin and picrotin blocks of alpha2 homomeric glycine receptors. | Wang, DS., et al. 2007. J Biol Chem. 282: 16016-35. PMID: 17405877
- Binding sites for bilobalide, diltiazem, ginkgolide, and picrotoxinin at the 5-HT3 receptor. | Thompson, AJ., et al. 2011. Mol Pharmacol. 80: 183-90. PMID: 21505038
- Studies on the mechanism of action of picrotoxinin and other convulsants at the crustacean muscle GABA receptor. | Smart, TG. and Constanti, A. 1986. Proc R Soc Lond B Biol Sci. 227: 191-216. PMID: 26151987
- Neurite outgrowth enhancement by jiadifenolide: possible targets. | Shenvi, RA. 2016. Nat Prod Rep. 33: 535-9. PMID: 26891462
- The binding mode of picrotoxinin in GABAA-ρ receptors: Insight into the subunit's selectivity in the transmembrane domain. | Naffaa, MM. and Samad, A. 2016. Comput Biol Chem. 64: 202-209. PMID: 27423910
- Effects of bilobalide, ginkgolide B and picrotoxinin on GABAA receptor modulation by structurally diverse positive modulators. | Ng, CC., et al. 2017. Eur J Pharmacol. 806: 83-90. PMID: 28416372
- The picrotoxinin binding site and its relationship to the GABA receptor complex. | White, WF., et al. 1985. J Neurochem. 44: 812-7. PMID: 2983020
- Comparison of the toxicokinetics of the convulsants picrotoxinin and tetramethylenedisulfotetramine (TETS) in mice. | Pressly, B., et al. 2020. Arch Toxicol. 94: 1995-2007. PMID: 32239239
- Picrotoxinin and related substances. | Porter, LA. 1967. Chem Rev. 67: 441-64. PMID: 4859924
- Picrotoxinin and diazepam bind to two distinct proteins: further evidence that pentobarbital may act at the picrotoxinin site. | Davis, WC. and Ticku, MK. 1981. J Neurosci. 1: 1036-42. PMID: 6270285
- Multiple picrotoxinin effect on glycine channels in rat hippocampal neurons. | Yoon, KW., et al. 1998. Neuroscience. 87: 807-15. PMID: 9759968
- Dieldrin and picrotoxinin modulation of GABA(A) receptor single channels. | Ikeda, T., et al. 1998. Neuroreport. 9: 3189-95. PMID: 9831449
Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Picrotoxinin, 250 mg | sc-253277 | 250 mg | $210.00 |