Picrotoxin

Picrotoxin: picrotoxinin (left) and picrotin (right)

Picrotoxin

Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	124-87-8 Y
ATC code	None
PubChem	CID 5360688
IUPHAR ligand	4051
DrugBank	DB00466
ChemSpider	16736444 Y
UNII	ZLT174DL7U Y
KEGG	C09529 N
ChEMBL	CHEMBL506977 Y
Chemical data
Formula	C30H34O13
Mol. mass	602.583 g/mol
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
InChI InChI=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 Y Key:VJKUPQSHOVKBCO-AHMKVGDJSA-N Y
N (what is this?)  (verify)

Picrotoxin, also known as cocculin, is a poisonous crystalline plant compound, first isolated by Pierre Boullay in 1812. The name "picrotoxin" is a combination of the Greek words "picros" (bitter) and "toxicon" (poison).

Found primarily in the fruit of the climbing plant Anamirta cocculus, it has a strong physiological action. It acts as a noncompetitive antagonist for the GABA_A receptor chloride channels. It is therefore a channel blocker rather than a receptor antagonist. As GABA itself is an inhibitory neurotransmitter, infusion of picrotoxin has stimulant and convulsant effects. As such, picrotoxin can be used to counter barbiturate poisoning, that can occur during general anesthesia or during a large intake outside of the hospital.

Chemical structure

Picrotoxin (C₃₀H₃₄O₁₃) is an equimolar mixture of two compounds, picrotoxinin (C₁₅H₁₆O₆) and picrotin (C₁₅H₁₈O₇).

Other uses

Picrotoxin is classified as an illegal performance-enhancing "Class 1 substance" by the American Quarterhorse Association. The recommended penalty for a first offense is a one-year suspension and a $10,000 fine.

External links

• Ehrenberger, K.; Benkoe, E.; Felix, D. (1982). "Suppressive Action of Picrotoxin, a GABA Antagonist, on Labyrinthine Spontaneous Nystagmus and Vertigo in Man". Acta Oto-Laryngologica 93 (3–4): 269–273. doi:10.3109/00016488209130882. PMID 7064710. 
• Dupont, L.; Dideberg, O.; Lamotte-Brasseur, J.; Angenot, L. (1976). "Structure cristalline et moléculaire de la picrotoxine, C₁₅H₁₆O₆·C₁₅H₁₈O₇". Acta Crystallographica B (in French) 32 (11): 2987–2993. doi:10.1107/S0567740876009424. 
• Siegel G. J.; Agranoff, B. W.; Albers, R. W. et al., ed. (1999). "GABA Receptor Physiology and Pharmacology". Basic Neurochemistry: Molecular, Cellular and Medical Aspects (6th ed.). Philadelphia, PA, USA: Lippincott-Raven.