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(-)-Picrotoxinin

(-)-Picrotoxinin structure

CAS No:
17617-45-7
Formula:
C15H16O6
Chemical Name:
(-)-Picrotoxinin
Synonyms:
3,6-Methano-8H-1,5,7-trioxacyclopenta[ij]cycloprop[a]azulene-4,8(3H)-dione,hexahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)-,(1aR,2aR,3S,6R,6aS,8aS,8bR,9R)-;Picrotoxinin;3,6-Methano-8H-1,5,7-trioxacyclopenta[ij]cycloprop[a]azulene-4,8(3H)-dione,hexahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)-,[1aR-(1aα,2aβ,3β,6β,6aβ,8aS*,8bβ,9R*)]-;(1aR,2aR,3S,6R,6aS,8aS,8bR,9R)-Hexahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)-3,6-methano-8H-1,5,7-trioxacyclopenta[ij]cycloprop[a]azulene-4,8(3H)-dione;(-)-Picrotoxinin;NSC 129537
Categories:
Biochemical Engineering > Chinese Herbs

Description

Picrotoxinin, a potent convulsant, is a chloride channel blocker. Picrotoxinin is a noncompetitive GABAA receptor antagonist, which negatively modulates the action of GABA on GABAA receptors[1].

(-)-Picrotoxinin Basic Attributes

Molecular Weight：

292.28

Exact Mass：

292.28

NSC Number：

129537

DSSTox ID：

DTXSID3074311

Characteristics

PSA：

85.36000

Density：

1.2207 (rough estimate)

Melting Point：

209.5 °C

Boiling Point：

354.22°C (rough estimate)

Flash Point：

214ºC

Refractive Index：

1.4359 (estimate)

Toxicity：

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

Specific rotation：

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

Safety Information

Packing level：

Hazard category：

6.1(a)

Transport codes：

3172

wgk germany：

hazard class code：

25-28

safety instructions：

13-20-45-36/37-28

RTECS Number：

PC5150000

Marks：

T+

Precautionary statement(s)：

Missing Phrase - N15.00950417

Hazard Statements：

H300

GHS Classification：

|Danger|H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]|P264, P270, P301+P310, P321, P330, P405, and P501|Aggregated GHS information provided by 40 companies from 2 notifications to the ECHA C&L Inventory.

Drug Information

MeSH：

Drugs that bind to but do not activate GABA-A RECEPTORS thereby blocking the actions of endogenous or exogenous GABA-A RECEPTOR AGONISTS. (See all compounds classified as GABA-A Receptor Antagonists.)

MeSH Entry Terms：

picrotoxinin

(-)-Picrotoxinin Use and Manufacturing

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,

Computed Properties

Molecular Weight:292.28
XLogP3:0.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:1
Exact Mass:292.09468823
Monoisotopic Mass:292.09468823
Topological Polar Surface Area:85.4
Heavy Atom Count:21
Complexity:642
Undefined Atom Stereocenter Count:8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Guide of (-)-Picrotoxinin

Description
Basic Attributes
Characteristics
Safety Information
Drug Information
Use and Manufacturing
Computed Properties
Learn More Other Chemicals

(-)-Picrotoxinin

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