| Identification | Back Directory | [Name]
PICROTIN | [CAS]
21416-53-5 | [Synonyms]
PICROTIN
Picrotin CRS
(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
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,2aR,3S,6R,6aS,8aS,8bR,9S)-
(1aR,8aS,9S)-1aβ,2,2a,6,6aα,8b-Hexahydro-2aα-hydroxy-9-(1-hydroxy-1-methylethyl)-8bα-methyl-3α,6α-methano-8H-1,5,7-trioxacyclopenta[ij]cycloprop[a]azulene-4,8(3H)-dione | [Molecular Formula]
C15H18O7 | [MDL Number]
MFCD00868514 | [MOL File]
21416-53-5.mol | [Molecular Weight]
310.3 |
| Chemical Properties | Back Directory | [Melting point ]
256-258°C | [alpha ]
D -64.7° (c = 2.31 in abs alc) | [Boiling point ]
595.8±50.0 °C(Predicted) | [density ]
1.59 | [storage temp. ]
2-8°C | [solubility ]
DMF: 30 mg/ml; DMSO: 30 mg/ml; DMSO:PBS (pH 7.2)(1:9): 0.1 mg/ml | [form ]
neat | [pka]
13.28±0.60(Predicted) | [color ]
White to off-white | [EPA Substance Registry System]
Picrotin (21416-53-5) |
| Hazard Information | Back Directory | [Description]
Picrotin is a natural picrotoxane that antagonizes glycine receptors (GlyRs; IC50s = 57 and 117 μM for α1 and α2 homodimeric GlyRs, respectively). It also inhibits α3 homodimeric GlyRs. Picrotin is inactive in inhibiting γ-aminobutyric acid (GABA) type A and type C receptors. Picrotin occurs in the natural plant-derived poison picrotoxin , equimolar with picrotoxinin. | [Uses]
GABAa receptor antagonist | [Definition]
ChEBI: Picrotin is an organic heteropentacyclic compound that is picrotoxinin in which the olefinic double bond has undergone addition of water to give the corresponding tertiary alcohol. It is the less toxic component of picrotoxin, lacking GABA activity. It has a role as a plant metabolite. It is an organic heteropentacyclic compound, an epoxide, a tertiary alcohol, a gamma-lactone, a diol and a picrotoxane sesquiterpenoid. It is functionally related to a picrotoxinin. | [storage]
Store at -20°C | [References]
[1] J W LYNCH. Mutations affecting the glycine receptor agonist transduction mechanism convert the competitive antagonist, picrotoxin, into an allosteric potentiator.[J]. The Journal of Biological Chemistry, 1995, 270 23: 13799-13806. DOI: 10.1074/jbc.270.23.13799
[2] DIAN-SHI WANG. Mechanisms for picrotoxinin and picrotin blocks of alpha2 homomeric glycine receptors.[J]. The Journal of Biological Chemistry, 2007, 282 22: 16016-16035. DOI: 10.1074/jbc.m701502200
[3] ZHE YANG. A proposed structural basis for picrotoxinin and picrotin binding in the glycine receptor pore[J]. Journal of Neurochemistry, 2007, 103 2: 580-589. DOI: 10.1111/j.1471-4159.2007.04850.x |
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