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MedKoo Cat#: 592179 | Name: Picrotin
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Description:

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

Picrotin is the less toxic component of picrotoxin lacking GABA activity. Picrotin is a potential biomarker of Schistosoma mekongi.

Chemical Structure

Picrotin
Picrotin
CAS#21416-53-5

Theoretical Analysis

MedKoo Cat#: 592179

Name: Picrotin

CAS#: 21416-53-5

Chemical Formula: C15H18O7

Exact Mass: 310.1053

Molecular Weight: 310.30

Elemental Analysis: C, 58.06; H, 5.85; O, 36.09

Price and Availability

Size Price Availability Quantity
100mg USD 280.00
250mg USD 440.00
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Related CAS #
No Data
Synonym
Picrotin; NSC 129536; NSC-129536; NSC129536
IUPAC/Chemical Name
3,6-Methano-8H-1,5,7-trioxacyclopenta(ij)cycloprop(a)azulene-4,8(3H)-dione, hexahydro-2a-hydroxy-9-(1-hydroxy-1-methylethyl)-8b-methyl-, (1aR-(1a alpha,2a beta,3beta,6beta,6a beta,8aS*,8b beta,9S*))-
InChi Key
RYEFFICCPKWYML-QCGISDTRSA-N
InChi Code
InChI=1S/C15H18O7/c1-12(2,18)6-7-10(16)20-8(6)9-13(3)14(7,19)4-5-15(13,22-5)11(17)21-9/h5-9,18-19H,4H2,1-3H3/t5-,6+,7-,8-,9-,13-,14-,15+/m1/s1
SMILES Code
O=C1[C@]([C@@H]2C(C)(O)C)([H])[C@]3(O)C[C@]4([H])[C@](O4)(C(O5)=O)[C@]3(C)[C@@]5([H])[C@]2([H])O1
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Picrotin is an active compound, also is one of the composition of picrotoxin (an antagonist of GABAA receptors (GABAARs) and glycine receptors (GlyRs)).
In vitro activity:
Picrotoxin antagonism of the embryonic alpha2 homomeric GlyR is known to be use-dependent and reflects a channel-blocking mechanism, but the selectivity of picrotoxin antagonism of the embryonic alpha2 homomeric GlyRs between picrotoxinin and picrotin is unknown. Hence, this study used the patch clamp recording technique in the outside-out configuration to investigate, at the single channel level, the mechanism of picrotin- and picrotoxinin-induced inhibition of currents, which were evoked by the activation of alpha2 homomeric GlyRs stably transfected into Chinese hamster ovary cells. Although both picrotoxinin and picrotin inhibited glycine-evoked outside-out currents, picrotin had a 30 times higher IC50 than picrotoxinin. Picrotin-evoked inhibition displayed voltage dependence, whereas picrotoxinin did not. Reference: J Biol Chem. 2007 Jun 1;282(22):16016-35. https://pubmed.ncbi.nlm.nih.gov/17405877/
In vivo activity:
TBD
Solvent mg/mL mM
Solubility
DMF 30.0 96.68
DMSO 65.0 209.47
DMSO:PBS (pH 7.2) (1:9) 0.1 0.32
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 310.30 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:
1. Wang DS, Buckinx R, Lecorronc H, Mangin JM, Rigo JM, Legendre P. Mechanisms for picrotoxinin and picrotin blocks of alpha2 homomeric glycine receptors. J Biol Chem. 2007 Jun 1;282(22):16016-35. doi: 10.1074/jbc.M701502200. Epub 2007 Apr 3. PMID: 17405877. 2. Steinbach JH, Bracamontes J, Yu L, Zhang P, Covey DF. Subunit-specific action of an anticonvulsant thiobutyrolactone on recombinant glycine receptors involves a residue in the M2 membrane-spanning region. Mol Pharmacol. 2000 Jul;58(1):11-7. doi: 10.1124/mol.58.1.11. PMID: 10860922.
In vitro protocol:
1. Wang DS, Buckinx R, Lecorronc H, Mangin JM, Rigo JM, Legendre P. Mechanisms for picrotoxinin and picrotin blocks of alpha2 homomeric glycine receptors. J Biol Chem. 2007 Jun 1;282(22):16016-35. doi: 10.1074/jbc.M701502200. Epub 2007 Apr 3. PMID: 17405877. 2. Steinbach JH, Bracamontes J, Yu L, Zhang P, Covey DF. Subunit-specific action of an anticonvulsant thiobutyrolactone on recombinant glycine receptors involves a residue in the M2 membrane-spanning region. Mol Pharmacol. 2000 Jul;58(1):11-7. doi: 10.1124/mol.58.1.11. PMID: 10860922.
In vivo protocol:
TBD
1: Yang M, Chen LJ, Zhang Y, Chen YG. Two new picrotoxane-type sesquiterpenoid lactones from Dendrobium williamsonii. J Asian Nat Prod Res. 2017 Oct 25:1-5. doi: 10.1080/10286020.2017.1394294. [Epub ahead of print] PubMed PMID: 29069925. 2: Ng CC, Duke RK, Hinton T, Johnston GA. GABAA receptor cysteinyl mutants and the ginkgo terpenoid lactones bilobalide and ginkgolides. Eur J Pharmacol. 2016 Apr 15;777:136-46. doi: 10.1016/j.ejphar.2016.03.007. Epub 2016 Mar 4. PubMed PMID: 26953225. 3: Rawat JM, Rawat B, Mehrotra S. Plant regeneration, genetic fidelity, and active ingredient content of encapsulated hairy roots of Picrorhiza kurrooa Royle ex Benth. Biotechnol Lett. 2013 Jun;35(6):961-8. doi: 10.1007/s10529-013-1152-3. Epub 2013 Feb 10. PubMed PMID: 23397268. 4: Li P, Slaughter MM. Gating effects on picrotin block of glycine receptors. Neuroreport. 2012 Dec 5;23(17):1017-20. doi: 10.1097/WNR.0b013e32835a8629. PubMed PMID: 23079787. 5: Thompson AJ, Jarvis GE, Duke RK, Johnston GA, Lummis SC. Ginkgolide B and bilobalide block the pore of the 5-HT₃receptor at a location that overlaps the picrotoxin binding site. Neuropharmacology. 2011 Feb-Mar;60(2-3):488-95. doi: 10.1016/j.neuropharm.2010.11.003. Epub 2010 Nov 5. PubMed PMID: 21059362; PubMed Central PMCID: PMC3070799. 6: Jablonski JE, Jackson LS. Stability of picrotoxin during yogurt manufacture and storage. J Food Sci. 2008 Oct;73(8):T121-8. doi: 10.1111/j.1750-3841.2008.00911.x. PubMed PMID: 19019133. 7: Yang Z, Cromer BA, Harvey RJ, Parker MW, Lynch JW. A proposed structural basis for picrotoxinin and picrotin binding in the glycine receptor pore. J Neurochem. 2007 Oct;103(2):580-9. Epub 2007 Aug 20. PubMed PMID: 17714449. 8: Li P, Slaughter M. Glycine receptor subunit composition alters the action of GABA antagonists. Vis Neurosci. 2007 Jul-Aug;24(4):513-21. Epub 2007 Jul 23. PubMed PMID: 17659095. 9: Wang DS, Buckinx R, Lecorronc H, Mangin JM, Rigo JM, Legendre P. Mechanisms for picrotoxinin and picrotin blocks of alpha2 homomeric glycine receptors. J Biol Chem. 2007 Jun 1;282(22):16016-35. Epub 2007 Apr 3. PubMed PMID: 17405877. 10: Thio LL, Shanmugam A, Isenberg K, Yamada K. Benzodiazepines block alpha2-containing inhibitory glycine receptors in embryonic mouse hippocampal neurons. J Neurophysiol. 2003 Jul;90(1):89-99. Epub 2003 Mar 26. PubMed PMID: 12660352. 11: Perry NB, Aiyaz M, Kerr DS, Lake RJ, Leach MT. NOESY on neurotoxins: NMR and conformational assignments of picrotoxins. Phytochem Anal. 2001 Jan-Feb;12(1):69-72. PubMed PMID: 11704965. 12: Steinbach JH, Bracamontes J, Yu L, Zhang P, Covey DF. Subunit-specific action of an anticonvulsant thiobutyrolactone on recombinant glycine receptors involves a residue in the M2 membrane-spanning region. Mol Pharmacol. 2000 Jul;58(1):11-7. PubMed PMID: 10860922. 13: Zhorov BS, Bregestovski PD. Chloride channels of glycine and GABA receptors with blockers: Monte Carlo minimization and structure-activity relationships. Biophys J. 2000 Apr;78(4):1786-803. PubMed PMID: 10733960; PubMed Central PMCID: PMC1300774. 14: Handford CA, Lynch JW, Baker E, Webb GC, Ford JH, Sutherland GR, Schofield PR. The human glycine receptor beta subunit: primary structure, functional characterisation and chromosomal localisation of the human and murine genes. Brain Res Mol Brain Res. 1996 Jan;35(1-2):211-9. PubMed PMID: 8717357. 15: Lynch JW, Rajendra S, Barry PH, Schofield PR. Mutations affecting the glycine receptor agonist transduction mechanism convert the competitive antagonist, picrotoxin, into an allosteric potentiator. J Biol Chem. 1995 Jun 9;270(23):13799-806. PubMed PMID: 7775436. 16: Shirai Y, Hosie AM, Buckingham SD, Holyoke CW Jr, Baylis HA, Sattelle DB. Actions of picrotoxinin analogues on an expressed, homo-oligomeric GABA receptor of Drosophila melanogaster. Neurosci Lett. 1995 Apr 7;189(1):1-4. PubMed PMID: 7603613. 17: Anthony NM, Holyoke CW Jr, Sattelle DB. Blocking actions of picrotoxinin analogues on insect (Periplaneta americana) GABA receptors. Neurosci Lett. 1994 Apr 25;171(1-2):67-9. PubMed PMID: 7916140. 18: Yamada H, Fujisaki H, Kaneko H, Ishii Y, Hamaguchi T, Oguri K. Picrotoxin as a potent inducer of rat hepatic cytochrome P450, CYP2B1 and CYP2B2. Biochem Pharmacol. 1993 May 5;45(9):1783-9. PubMed PMID: 8494537. 19: Soto-Otero R, Mendez-Alvarez E, Sierra-Paredes G, Galan-Valiente J, Aguilar-Veiga E, Sierra-Marcuño G. Simultaneous determination of the two components of picrotoxin in serum by reversed-phase high-performance liquid chromatography with application to a pharmacokinetic study in rats. J Pharm Biomed Anal. 1989;7(3):369-75. PubMed PMID: 2488637. 20: Sattelle DB, Pinnock RD, Wafford KA, David JA. GABA receptors on the cell-body membrane of an identified insect motor neuron. Proc R Soc Lond B Biol Sci. 1988 Jan 22;232(1269):443-56. PubMed PMID: 2451252.

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