PICROTOXININ Chemical Properties

Melting point:

203-205°C

alpha 

D17 +4.4° (c = 4.28 in abs alc), +3.49° (c = 7.57 in acetone)

Boiling point:

354.22°C (rough estimate)

Density 

1.2207 (rough estimate)

refractive index 

1.4359 (estimate)

storage temp. 

2-8°C

pka

13.18±0.60(Predicted)

form 

Solid

color 

White to off-white

LogP

-0.130 (est)

EPA Substance Registry System

Picrotoxinin (17617-45-7)

Safety Information

Hazard Codes 

T+

Risk Statements 

25-28

Safety Statements 

13-20-45-36/37-28

RIDADR 

3172

WGK Germany 

3

RTECS 

PC5150000

HazardClass 

6.1(a)

PackingGroup 

I

Toxicity

LD50 i.p. in mice: 3 mg/kg (Jarboe)

PICROTOXININ Usage And Synthesis

Uses

Picrotoxinin is a L-glutamate and channel blockers.

Definition

ChEBI: Picrotoxinin is a picrotoxane sesquiterpenoid that is 3a,4,5,6,7,7a-hexahydro-1H-indene-3,7-dicarboxylic acid which is substituted at positions 3a, 6, and 7a by methyl, isopropenyl, and hydroxy groups, respectively; in which the double bond at position 2-3 has been epoxidised; and in which the carboxy groups at positions 3 and 7 have undergone gamma-lactone formation by O-alkylation to positions 4 and 5, respectively. A component of picrotoxin. It has a role as a plant metabolite, a GABA antagonist and a serotonergic antagonist. It is an organic heteropentacyclic compound, an epoxide, a tertiary alcohol, a gamma-lactone and a picrotoxane sesquiterpenoid.

Biochem/physiol Actions

GABAA receptor antagonist; binds to the GABA receptor-linked Cl? channel.

Enzyme inhibitor

These neurotoxic GABAA receptor antagonists, consisting of a nearly 1:1 mixture of picrotoxinin, (FW = 292.29 g/mol; CAS 17617-45-7) and picrotin (FW = 310.30 g/mol; CAS 124-87-8), is a bitter-tasting (hence the Greek prefix picros) principle, also known as cocculin, from fishberry seeds (Anamirta cocculus) and the Philippine bayating (Tinomiscium philippinense). Picrotoxin binds to the chloride channel of the receptor without displacing g-aminobutyric acid. Picrotoxin is highly toxic, exerting both stimulant and convulsant effects, and care must be exercised when handling this agent.

PICROTOXININ(17617-45-7)Related Product Information

• Dihydromyrcenol
• METHYL TUBERATE
• 2-(2-ISOBUTOXYETHOXY)ETHANOL
• BUTYL L-LACTATE
• 1,2-EPOXY-7-OCTENE
• Molecular complex (1:1) of picrotin and picrotoxinin,picrotoxinin,compd.withpicrotin(1:1
• PICROTOXININ
• Isopentyl isobutyrate
• ISOBUTYL LACTATE
• 4-METHOXYCYCLOHEXANECARBOXYLIC ACID
• (S)-5-Hydroxymethyldihydrofuran-2-one
• Undecenoic acid
• 1,3-CYCLOPENTANEDIOL
• (+)-3-METHYLHEXANEDIOIC ACID
• DIHYDRO-4,4-DIMETHYL-2(3H)-FURANONE
• Ethyl 2-hydroxyisobutyrate
• ETHYL 1-HYDROXYCYCLOPENTANE-CARBOXYLATE
• (R)-2-HYDROXY-4-METHYLPENTANOIC ACID