Paxilline

Paxilline is a potassium channel blocker. Paxilline is a toxic, tremorgenic indole alkaloid produced by Penicillium paxilli .[1] Paxilline was found to significantly extend the lifespan healthspan and mobility of C. elegans aged worms, but had no such effect on young worms. [2]

Paxilline

Names
IUPAC name (2R,4bS,6aS,12bS,12cR,14aS)-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-5,6,6a,7,12,12b,12c,13,14,14a-decahydro-2H-chromeno[5',6':6,7]indeno[1,2-b]indol-3(4bH)-one
Identifiers
CAS Number	57186-25-1
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL410063
ChemSpider	94753
ECHA InfoCard	100.164.932
MeSH	Paxilline
PubChem CID	105008
UNII	3T9U9Z96L7
CompTox Dashboard (EPA)	DTXSID10972643
InChI InChI=1S/C27H33NO4/c1-24(2,30)23-20(29)14-18-21(32-23)10-11-25(3)26(4)15(9-12-27(18,25)31)13-17-16-7-5-6-8-19(16)28-22(17)26/h5-8,14-15,21,23,28,30-31H,9-13H2,1-4H3/t15-,21-,23-,25+,26+,27+/m0/s1 Key: ACNHBCIZLNNLRS-UBGQALKQSA-N InChI=1/C27H33NO4/c1-24(2,30)23-20(29)14-18-21(32-23)10-11-25(3)26(4)15(9-12-27(18,25)31)13-17-16-7-5-6-8-19(16)28-22(17)26/h5-8,14-15,21,23,28,30-31H,9-13H2,1-4H3/t15-,21-,23-,25+,26+,27+/m0/s1 Key: ACNHBCIZLNNLRS-UBGQALKQBX
SMILES O=C5/C=C6/[C@]4(O)CC[C@H]3Cc2c1ccccc1[nH]c2[C@@]3([C@]4(CC[C@@H]6O[C@@H]5C(O)(C)C)C)C
Properties
Chemical formula	C27H33NO4
Molar mass	435.56 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Paxilline was not found to induce seizures when injected intracerebroventricularly in mice[3] but paradoxically had anticonvulsant activity against picrotoxin and pentylenetetrazol seizures in mice.[4]

Sources and references

1. Paxilline product page from Fermentek
2. Li, Guang; Gong, Jianke; Liu, Jie; Liu, Jinzhi; Li, Huahua; Hsu, Ao-Lin; Liu, Jianfeng; Xu, X.Z. Shawn (2019). "Genetic and pharmacological interventions in the aging motor nervous system slow motor aging and extend life span in C. Elegans". Science Advances. 5: eaau5041. doi:10.1126/sciadv.aau5041. PMC 6314820.
3. Juhng, KN; Kokate, TG; Yamaguchi, S; Kim, BY; Rogowski, RS; Blaustein, MP; Rogawski, MA (1999). "Induction of seizures by the potent K+ channel-blocking scorpion venom peptide toxins tityustoxin-K(alpha) and pandinustoxin-K(alpha)". Epilepsy Res. 34 (2–3): 177–86.
4. Sheehan, JJ; Benedetti, BL; Barth, AL (2009). "Anticonvulsant effects of the BK-channel antagonist paxilline". Epilepsia. 50: 711–20.