Basic information
- CAS
17617-45-7- Standard SMILES
C=C(C)[C@@H]1[C@H]2OC(=O)[C@@H]1[C@]1(O)C[C@H]3O[C@]34C(=O)O[C@H]2[C@]14C- InChIKey
PIMZUZSSNYHVCU-YKWPQBAZSA-N- Molecular formula
- C15H16O6
- Average molar mass
- 292.28 g/mol
- Monoisotopic mass
- 292.09468823
Overview
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 serotonergic antagonist, a GABA antagonist and a plant metabolite. It is a picrotoxane sesquiterpenoid, a tertiary alcohol, an epoxide, a gamma-lactone and an organic heteropentacyclic compound.
Names & identifiers
- Preferred name
- Picrotoxinin
- IUPAC
- (1R,3R,5S,8S,9R,12S,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
- English name
- PICROTOXININ
- Molecular formula
- C15H16O6
- Molecular weight
- 292.28
Names & synonyms
picrotoxinin17617-45-7(-)-PicrotoxininPicrotoxinine9K011NUF0RDTXSID3074311CHEBI:8206NSC-129537(1R,3R,5S,8S,9R,12S,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(1R,3R,5S,8S,9R,12S,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-dioneRefChem:174202DTXCID6035603
Show more names
Picrotoxinin-RMPicrotoxinin CRSPICROTOXININ USP/EP/BPPicrotoxinin (Standard)Yellowmouth Dutchmanspipe Root6a-beta,8as*,8b-beta,9r*))-6-betaahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)-,(1ar-(1a-alpha,2a-beta,3-bet
(1aR-(1a alpha,2a beta,3 beta,6 beta,6a beta,8aS*,8b beta,9R*))-hexahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)-3,6-methano-8H-1,5,7-trioxa cyclopenta(ij)cycloprop(a)azulene-4,8(3H)-dione(1S,3S,5R,9S,12R,13S,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-dione634-009-1CHEMBL47244(1aR-(1aalpha,2abeta,3beta,6beta,6abeta,8aS*,8bbeta,9R*))-Hexahydro-2a-hydroxy-8b-methyl-9-(1-methylethenyl)-3,6-methano-8H-1,5,7-trioxa cyclopenta(ij)cycloprop(a)azulene-4,8(3H)-dione(5S,8S,12S,1R,3R,9R,13R,14R)-1-hydroxy-13-methyl-14-(1-methylvinyl)-4,7,10-tri oxapentacyclo[6.4.1.1<9,12>.0<3,5>.0<5,13>]tetradecane-6,11-dione3,6-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)-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)-
Properties
Computed structural properties
- XLogP
- 0.5
- Topological polar surface area
- 85.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 1
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 642
Experimental & physicochemical properties
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C15 isoprenoids (sesquiterpenes) [PR0103]
Human DrugsPharmaceuticals
Collision Cross Section
157.29 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
168.7 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 203 · 203-205°C
- alpha
- 17 · D17 +4.4° (c = 4.28 in abs alc), +3.49° (c = 7.57 in acetone)
- Boiling point
- 354.22 °C · 354.22°C (rough estimate)
- Density
- 1.2207 · 1.2207 (rough estimate)
- refractive index
- 1.4359 · 1.4359 (estimate)
- storage temp.
- 2 · 2-8°C
- pka
- 13.18 · 13.18±0.60(Predicted)
- form
- Solid
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 2 (100%)
Safety data
- wgk
- 3
- rtecs
- PC5150000
- ridadr
- 3172
- Toxicity
- LD50 i.p. in mice: 3 mg/kg (Jarboe)
- risk_code
- 25-28
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T+
- safety_code
- 13-20-45-36/37-28
- 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
- Hazard Classifications
- Acute Tox. 2 Oral
- Precautionary statements
- P301+P310+P330
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationDrugs that bind to but do not activate GABA-A RECEPTORS thereby blocking the actions of endogenous or exogenous GABA-A RECEPTOR AGONISTS.
Uses & manufacturing
Use ClassificationPharmaceuticals
Applications
UsesPicrotoxinin is a L-glutamate and channel blockers.
Suppliers32 total
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
武汉众志诚生物技术有限公司13628624121 13628604890 · [email protected]
United Life Science020-82099279 18988968278 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
佛山宝诺生物科技有限公司0757-85921206 18520245316 · [email protected]
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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