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Cocculus solid

HCID 5458938
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Basic information

CAS
124-87-8
Standard SMILES
C=C(C)[C@H]1[C@@H]2OC(=O)[C@H]1[C@]1(O)C[C@H]3OC34C(=O)O[C@H]2[C@@]41C.CC(C)(O)[C@H]1[C@@H]2OC(=O)[C@H]1[C@]1(O)C[C@H]3OC34C(=O)O[C@H]2[C@@]41C
InChIKey
VJKUPQSHOVKBCO-RYVYVXLVSA-N
Molecular formula
C30H34O13
Average molar mass
602.6 g/mol
Monoisotopic mass
602.19994113

Names & identifiers

Preferred name
Cocculus solid
IUPAC
(1R,3R,8S,9S,12R,13R,14R)-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,3R,8S,9S,12R,13R,14S)-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
English name
PICROTOXIN
Molecular formula
C30H34O13
Molecular weight
602.58

Names & synonyms

Cocculus solidNSC403139Picrotoxin of fishberriesCocculininWLN: T D3556 J5 K 2AF N EOXVO MVO DH & TTTTJ A1 BQ KY1 & U1CHEMBL1993098Picrotoxin from Cocculus pendulusNSC106973NSC-106973NCI60_003792PICROTIN CMPD WITH PICROTOXININ (1:1)Cocculus
Show more names
Picrotoxin (Picrotoxinin + Picrotin)COCCULIN1:1)[qr]COCCULINEfishberryPICROTOXINindianberrypicrotoxinecocculin[qr]

Database identifiers

CAS
124-87-8
PubChem CID
5458938

Properties

Computed structural properties

Topological polar surface area
191 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
13
Rotatable bonds
2
Heavy atoms
43
Formal charge
0
Complexity
1,290

Physicochemical properties

Melting point
203 °C · 203 °C(lit.)
alpha
16 · D16 -29.3° (c = 4 in abs ethanol)
Boiling point
571.75 °C · 571.75°C (rough estimate)
Density
1 · 1,28 g/cm3
refractive index
1.6 · 1.6000 (estimate)
storage temp.
Store at RT
solubility
50 mg/mL, · ethanol: 50 mg/mL, clear to slightly hazy
form
powder
color
white to light yellow
Water Solubility
4.083 g/L · 4.083g/L(room temperature)
Merck
14 · 14,7415
BRN
3894406 · 3894406
InChIKey
VJKUPQSHOVKBCO-NGKRNLQBSA-N
FDA 21 CFR
310.545 · 310.545
EWG's Food Scores
1 · 1-3
FDA UNII
174 DL7U · ZLT174DL7U
EPA Substance Registry System

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

F
8-10
PPE
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
3
rtecs
TJ9100000
ridadr
UN 3462 6.1/PG 2
hs_code
29322985
Toxicity
LD50 i.p. in mice: 7.2 mg/kg (Setnikar)
risk_code
28-52/53
Signal word
Danger
Symbol(GHS)
GHS06,GHS09
hazard_code
T+,T,N
hazard_note
Very Toxic
safety_code
28-36/37/39-45-61
hazard_class
6.1(a)
Storage Class
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
packing_group
I
Hazard statements
H300-H411
Hazard Classifications
Acute Tox. 2 Oral
Precautionary statements
P501-P273-P270-P264-P391-P301+P310+P330-P405
Hazardous Substances Data
124-87-8(Hazardous Substances Data)

Chemistry & industry

Applications · 4 items

DescriptionPicrotoxin, also known as cocculin, appears as white to light beige crystalline material. It is isolated from Cocculus indicus (Fructus cocculi), fishberries, or Indian berries. Picrotoxin is a colourless, flexible, shining, prismatic crystals, or a micro-crystalline powder. It is odourless, has a very bitter taste, and is permanent in the air. Picrotoxin is soluble in hot water, readily soluble in strong ammonia water, and in aqueous solutions of sodium hydroxide, soluble in dilute acids, and alkalis as well as in glacial acetic acid, sparingly soluble in chloroform and very slightly soluble in cold water and alcohol. Picrotoxin is stable under normal temperatures and pressures and decompose when exposed to light. Picrotoxin is incompatible with strong oxidising agents, strong acids, strong bases, light.

HistoryThe seeds of Menispermaceae are traditionally used as fishing bait or pesticide, as well as pediculicide . Once it was used for brewing beer to impart a more intoxicating quality to beer in the nineteenth century . In 1812, cocculin was firstly isolated by Pierre Boullay and named picrotoxin, a combination of the Greek words “picros” and “toxicon.” Picrotoxin showed strong physiological action and was once extensively studied.The action mechanism of picrotoxin is a controversial issue. Newland etal. considered that picrotoxin enhanced the occurrence of a desensitized state or an allosterically blocked state of GABAA receptor , while Jong etal. showed that picrotoxinacts as a noncompetitive channel blocker for the GABAA receptor chloride channels, rather than a receptor antagonist .

UsesPicrotoxin has been used:as non-competitive antagonist for the γ-aminobutyric acid (GABAA) for studying synchronized burst (SB) dynamicsas a component of extracellular saline for blocking glutamate and acetylcholine receptors in neuronsas a component of artificial cerebrospinal fluid (ACSF) for voltage-clamp recordings studies in dissociated cortical neurons

General DescriptionA poisonous berry, the dried fruit of Anamirta PICROTOXIN L. Contains several substances including about one percent picrotoxin. Pure picrotoxin occurs as shiny leaflets with an intensely bitter taste or as a microcrystalline powder. Very poisonous!. Used in medicine as a central nervous system stimulant and antidote for barbiturate poisoning. Not currently regarded as a useful therapeutic agent.

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Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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ChEMBL
CHEMBL1993098
Picrotoxin (124-87-8)
UNSPSC Code
12352200 · 12352200
NACRES
77 · NA.77
Symbol(GHS)
6 · GHS06,GHS09
Signal word
Danger
Hazard statements
300 · H300-H411
Precautionary statements
501 · P501-P273-P270-P264-P391-P301+P310+P330-P405
PPE
3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes
T+,T,N
Risk Statements
28 · 28-52/53
Safety Statements
28 · 28-36/37/39-45-61
RIDADR
3462 · UN 3462 6.1/PG 2
WGK Germany
3 · 3
RTECS
9100000 · TJ9100000
F
8 · 8-10
Hazard Note
Very Toxic
HazardClass
6.1 · 6.1(a)
PackingGroup
I
HS Code
29322985 · 29322985
Storage Class
6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications
2 Oral · Acute Tox. 2 Oral
Hazardous Substances Data
124 · 124-87-8(Hazardous Substances Data)
Toxicity
50 i.p · LD50 i.p. in mice: 7.2 mg/kg (Setnikar)