A natural antagonist of GlyRs
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Picrotin

Item No. 21870

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1aR,2aR,3S,6R,6aS,8aS,8bR,9S)-hexahydro-2a-hydroxy-9-(1-hydroxy-1-methylethyl)-8b-methyl-3,6-methano-8H-1,5,7-trioxacyclopenta[ij]cycloprop[a]azulene-4,8(3H)-dione
CAS Number
21416-53-5
Molecular Formula
C15H18O7
Formula Weight
310.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2)(1:9): 0.1 mg/ml
SMILES
C[C@]([C@@](C1)([C@]2([H])[C@]([H])(C(C)(O)C)[C@@]3([H])OC2=O)O)([C@]3([H])OC4=O)[C@@]54[C@@H]1O5
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
InChi Key
RYEFFICCPKWYML-QCGISDTRSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

    $36

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    50 mg

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    100 mg

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    250 mg

    $186

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    Cayman Chemical
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    Product Description

    Picrotin is a natural picrotoxane that antagonizes glycine receptors (GlyRs; IC50s = 57 and 117 µM for α1 and α2 homodimeric GlyRs, respectively).1,2 It also inhibits α3 homodimeric GlyRs.3 Picrotin is inactive in inhibiting γ-aminobutyric acid (GABA) type A and type C receptors. Picrotin occurs in the natural plant-derived poison picrotoxin (Item No. 20771), equimolar with picrotoxinin.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lynch, J.W., Rajendra, S., Barry, P.H., et al. Mutations affecting the glycine receptor agonist transduction mechanism convert the competitive antagonist, picrotoxin, into an allosteric potentiator. The Journal of Biological Chemisty 270(23), 13799-13806 (1995).

    2. Wang, D.-S., Buckinx, R., Lecorronc, H., et al. Mechanisms for picrotoxinin and picrotin blocks of α2 homomeric glycine receptors. The Journal of Biological Chemisty 282(22), 16016-16035 (2007).

    3. Yang, Z., Cromer, B.A., Harvey, R.J., et al. A proposed structural basis for picrotoxinin and picrotin binding in the glycine receptor pore. J. Neurochem. 103(2), 580-589 (2007).