picrotoxin

Also known as cocculin

Picrotoxin, also known as cocculin, is a poisonous crystalline plant compound. It was first isolated by the French pharmacist and chemist Pierre François Guillaume Boullay (1777–1869) in 1812. The name "picrotoxin" is a combination of the Greek words "picros" (bitter) and "toxicon" (poison). A mixture of two different compounds, picrotoxin occurs naturally in the fruit of the Anamirta cocculus plant, although it can also be synthesized chemically.

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 464206410
Drug.imageL: Picrotoxinin.svg
Drug.image_classL: skin-invert-image
Drug.imageR: Picrotin.svg
Drug.image_classR: skin-invert-image
Drug.captionLR: Picrotoxinin (left) and picrotin (right)
Drug.smiles: CC(=C)[C@H]1[C@@H]2C(=O)O[C@H]1[C@H]3OC(=O)[C@@]54O[C@@H]5C[C@]2(O)[C@@]34C.CC(C)(O)[C@H]5[C@@H]1C(=O)O[C@H]5[C@H]2OC(=O)[C@@]43O[C@@H]4C[C@]1(O)[C@@]23C
Drug.StdInChI: 1S/C15H18O7.C15H16O6/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;1-5(2)7-8-11(16)19-9(7)10-13(3)14(8,18)4-6-15(13,21-6)12(17)20-10/h5-9,18-19H,4H2,1-3H3;6-10,18H,1,4H2,2-3H3/t5-,6+,7-,8-,9-,13-,14-,15+;6-,7+,8-,9-,10-,13-,14-,15+/m11/s1
Drug.StdInChIKey: VJKUPQSHOVKBCO-AHMKVGDJSA-N
Drug.CAS_number: 124-87-8
Drug.ATC_prefix: none
Drug.PubChem: 5360688
Drug.IUPHAR_ligand: 4051
Drug.DrugBank: DB00466
Drug.ChemSpiderID: 16736444
Drug.UNII: ZLT174DL7U

via Wikipedia infobox

Chemical data

Formula: C30H34O13
Molecular weight: 602.6 g/mol
IUPAC name: (1R,3R,5S,8S,13R,14S)-1-hydroxy-14-(2-hydroxypropan-2-yl)-13-methyl-4,7,10-trioxapentacyclo[6.4.1.19,12.03,5.05,13]tetradecane-6,11-dione;(1R,5S,8S,13R,14R)-1-hydroxy-13-methyl-14-prop-1-en-2-yl-4,7,10-trioxapentacyclo[6.4.1.19,12.03,5.05,13]tetradecane-6,11-dione
SMILES: CC(=C)[C@@H]1C2[C@@H]3[C@@]4([C@](C1C(=O)O2)(CC5[C@]4(O5)C(=O)O3)O)C.C[C@@]12[C@H]3C4[C@H](C([C@@]1(C[C@@H]5[C@]2(O5)C(=O)O3)O)C(=O)O4)C(C)(C)O
InChIKey: VJKUPQSHOVKBCO-ZTYBEOBUSA-N
Polar surface area: 191 Å²
H-bond donors: 3
H-bond acceptors: 13
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Research

6,339 papers

[Picrotoxin].Journal de pharmacie de Belgique · 1963
Picrotoxin-like lactones.Journal of pharmaceutical sciences · 1983
[Picrotoxin-barbituric chemical-pharmacological antagonism].Revista. Universidad Nacional Mayor de San Marcos. Facultad de Farmacia y Bioquimica · 1948
Intracellular picrotoxin blocks pentobarbital-gated Cl- conductance.Neuroscience research · 1988
[Picrotoxin in the treatment of Menière's disease].Laryngo- rhino- otologie · 2008

via PubMed

Wikidata facts

Mass: 602.199941

Show 7 more facts

chemical formula: C₃₀H₃₄O₁₃
Commons category: Picrotoxin
described by source: Encyclopædia Britannica 11th edition
isomeric SMILES: CC(=C)[C@@H]1C2[C@@H]3[C@@]4([C@](C1C(=O)O2)(CC5[C@]4(O5)C(=O)O3)O)C.C[C@@]12[C@H]3C4[C@H](C([C@@]1(C[C@@H]5[C@]2(O5)C(=O)O3)O)C(=O)O4)C(C)(C)O
canonical SMILES: CC(=C)C1C2C3C4(C(C1C(=O)O2)(CC5C4(O5)C(=O)O3)O)C.CC12C3C4C(C(C1(CC5C2(O5)C(=O)O3)O)C(=O)O4)C(C)(C)O
found in taxon: Anamirta cocculus
has characteristic: bitterness

Sources (2)

via Wikidata · CC0

~7 min read

Encyclopedic overview

7 sections

Contents

Chemical structure and synthesis
Mechanism of action
Toxicity
Clinical applications and other uses
See also
References
Further reading

Due to its interactions with the inhibitory neurotransmitter GABA, picrotoxin acts as a stimulant and convulsant. It mainly impacts the central nervous system, causing seizures and respiratory paralysis in high enough doses.

Excerpted from Wikipedia’s “picrotoxin” article, available under the CC BY-SA 4.0 licence.

Gallery (5)

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