Securinine
Basic information
- CAS
5610-40-2- Standard SMILES
O=C1C=C2C=C[C@@H]3C[C@@]2(O1)[C@H]1CCCCN31- InChIKey
SWZMSZQQJRKFBP-WZRBSPASSA-N- Molecular formula
- C13H15NO2
- Average molar mass
- 217.26 g/mol
- Monoisotopic mass
- 217.11027872
Overview
Securinine is a member of indolizines.
Names & identifiers
- Preferred name
- Securinine
- IUPAC
- (1S,2R,8S)-14-oxa-7-azatetracyclo[6.6.1.01,11.02,7]pentadeca-9,11-dien-13-one
- English name
- SECURININE
- Molecular formula
- C13H15NO2
- Molecular weight
- 217.26
Names & synonyms
Securinine5610-40-2(-)-SecurinineSecurininSecurinina(6S,11aR,11bS)-9,10,11,11a-Tetrahydro-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-oneSecurininuml-SecurinineSecurinan-11-oneDTXSID7045944G4VS580P5ENSC-107413
Show more names
Securan one(-)-securininSECURAN-11-ONESECURININE(RG)(–)-SecurinineSecurinan-11-on
DTXCID5025944(6S,11aR,11bS)-9,10,11,11a-Tetrahydro-8H-6,11b-methanofuro(2,3-c)pyrido(1,2-a)azepin-2(6H)-one(1S,2R,8S)-14-oxa-7-azatetracyclo[6.6.1.01,11.02,7]pentadeca-9,11-dien-13-one(1S,2R,8S)-14-oxa-7-azatetracyclo(6.6.1.01,11.02,7)pentadeca-9,11-dien-13-oneRefChem:491695588-52-3Securinine [INN]Securinine, (-)-
Database identifiers
- CAS
5610-40-2- PubChem CID
- 442872
- DTXSID
DTXSID7045944- ChEMBL
CHEMBL303062- ChEBI
CHEBI:9079- UNII
- G4VS580P5E
- EC Number
- 694-738-6
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 29.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 426
Experimental & physicochemical properties
Collision Cross Section
145.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
146.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 140 · 140-1420C
- alpha
- 20 · D20 -1042° (c = 1 in alc)
- Boiling point
- 357.82 °C · 357.82°C (rough estimate)
- Density
- 1.3 · 1.30±0.1 g/cm3 (20 ºC 760 Torr)
- refractive index
- 1.53 · 1.5300 (estimate)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- 25 mg/mL · DMSO: ≥25mg/mL
- form
- powder
- pka
- 8.29 · 8.29±0.20(Predicted)
- color
- yellow
- optical activity
- -980 to · [α]/D -980 to -1015 (C=1, MeOH)
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
Warning
H302 (97.4%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (97.4%)
Safety data
- wgk
- 3
- rtecs
- VS4115000
- risk_code
- 23/24/25-22
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T,Xn
- safety_code
- 36/37/39-45
- Hazard statements
- H301
- Precautionary statements
- P264-P270-P301+P310-P405-P501
Chemistry & industry
Applications
DescriptionA constituent of the leaves of Securinega suffructicosa Rehd., the base also occurs in Phyllanthus disco ides. It is obtained as yellow crystals and is strongly laevorotatory having [α]20D - 1106°(CHC13), [α]30D - 1106°(CHC13) and[α]20D - 1042° (c 1.0, EtOH). The alkaloid yields a crystalline methiodide, m.p. 235-6°C.
UsesGABAA receptor blocker, CNS stimulant
UsesExtracted from leaves and roots of Securinega suffruticosa Rehder. The most widely studied of these alkaloids, Securinine, is a specific GABA receptor antagonist and has been found to have significant in vivo CNS activity.
Additional notes
DefinitionChEBI: Securinine is a member of indolizines.
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