paxilline

{{distinguish|text=the protein Paxillin}}

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 464197482

| ImageFile=Paxilline.png

| ImageSize=200px

| PIN= (2R,4bS,6aS,12bS,12cR,14aS)-4b-Hydroxy-2-(2-hydroxypropan-2-yl)-12b,12c-dimethyl-5,6,6a,7,12,12b,12c,13,14,14a-decahydro-2H-[1]benzopyrano[5′,6′:6,7]indeno[1,2-b]indol-3(4bH)-one

| OtherNames=

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 94753

| 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

| InChIKey = ACNHBCIZLNNLRS-UBGQALKQBX

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = ACNHBCIZLNNLRS-UBGQALKQSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo=57186-25-1

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 3T9U9Z96L7

| ChEBI = 34907

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 410063

| PubChem=105008

| 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

| MeSHName=Paxilline

}}

|Section2={{Chembox Properties

| C=27 | H=33 | N=1 | O=4

| MolarMass=435.56 g/mol

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

}}

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

}}

Paxilline is a toxic, tremorgenic diterpene indole polycyclic alkaloid molecule produced by Penicillium paxilli which was first characterized in 1975.[http://www.fermentek.com/product/paxilline Paxilline] product page from Fermentek{{Cite journal|date=1975-01-01|title=The structure of paxilline, a tremorgenic metabolite of penicillium paxilli bainier|url=https://www.sciencedirect.com/science/article/abs/pii/S0040403900751707|journal=Tetrahedron Letters|language=en|volume=16|issue=30|pages=2531–2534|doi=10.1016/S0040-4039(00)75170-7|issn=0040-4039|url-access=subscription}} Paxilline is one of a class of tremorigenic mycotoxins, is a potassium channel blocker, and is potentially genotoxic.{{Cite journal|date=2018-01-01|title=Tremorgenic Mycotoxins|url=https://www.sciencedirect.com/science/article/pii/B978012811410000074X|journal=Veterinary Toxicology|language=en|pages=1033–1041|doi=10.1016/B978-0-12-811410-0.00074-X |last1=Evans |first1=Tim J. |last2=Gupta |first2=Ramesh C. |isbn=9780128114100 |url-access=subscription}}

Paxilline was found to significantly extend the lifespan, healthspan, and mobility of aged C. elegans worms, but had no such effect on young worms.{{Cite journal | doi=10.1126/sciadv.aau5041| title=Genetic and pharmacological interventions in the aging motor nervous system slow motor aging and extend life span in C. Elegans| journal=Science Advances| volume=5| pages=eaau5041| year=2019| last1=Li| first1=Guang| last2=Gong| first2=Jianke| last3=Liu| first3=Jie| last4=Liu| first4=Jinzhi| last5=Li| first5=Huahua| last6=Hsu| first6=Ao-Lin| last7=Liu| first7=Jianfeng| last8=Xu| first8=X.Z. Shawn| issue=1| pmid=30613772| pmc=6314820}} Paxilline was not found to induce seizures when injected intracerebroventricularly in mice{{cite journal |last1=Juhng |first1=KN |last2=Kokate |first2=TG |last3= Yamaguchi| first3=S|last4= Kim|first4=BY|last5=Rogowski | first5=RS|last6= Blaustein| first6=MP|last7= Rogawski| first7=MA|date=1999 |title= Induction of seizures by the potent K+ channel-blocking scorpion venom peptide toxins tityustoxin-K(alpha) and pandinustoxin-K(alpha)|journal=Epilepsy Res |volume=34 |issue= 2–3|pages=177–86|doi=10.1016/S0920-1211(98)00111-9 |pmid=10210033 |s2cid=140209807 }} but paradoxically had anticonvulsant activity against picrotoxin and pentylenetetrazol seizures in mice.{{cite journal |last1=Sheehan |first1=JJ |last2=Benedetti |first2=BL |last3=Barth |first3=AL |author-link3=Alison Barth |date=2009 |title=Anticonvulsant effects of the BK-channel antagonist paxilline |journal=Epilepsia |volume=50 |issue=4 |pages=711–20 |doi=10.1111/j.1528-1167.2008.01888.x |pmid=19054419 |s2cid=14129074 |doi-access=free}} It has also been used in mice to induce autism-like behaviors through inhibition of the BK channel.{{Cite journal|last1=Fyke|first1=William|last2=Alarcon|first2=Juan M.|last3=Velinov|first3=Milen|last4=Chadman|first4=Kathryn K.|date=2021|title=Pharmacological inhibition of BKCa channels induces a specific social deficit in adult C57BL6/J mice|url=https://doi.org/10.1037/bne0000459|journal=Behavioral Neuroscience|volume=135 |issue=4 |pages=462–468 |doi=10.1037/bne0000459 |pmid=33734729 |s2cid=232300623 |via=APA PsycArticles|url-access=subscription}}