| Identification | Back Directory | [Name]
SECURININE | [CAS]
5610-40-2 | [Synonyms]
securinin
SECURININE
Securan one
(-)-securinin
SECURININE(RG)
SECURAN-11-ONE
Securinan-11-on
securinan-11-one
(2β,7S,9S)-Securinan-11-one
1,2,3,4,10,10a-Hexahydro-10-hydroxy-
(6S,11aR,11bS)-9,10,11,11a-Tetrahydro-8H-6,11b-Methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one | [EINECS(EC#)]
694-738-6 | [Molecular Formula]
C13H15NO2 | [MDL Number]
MFCD00867422 | [MOL File]
5610-40-2.mol | [Molecular Weight]
217.26 |
| Chemical Properties | Back Directory | [Appearance]
Yellow Solid | [Melting point ]
140-1420C | [alpha ]
D20 -1042° (c = 1 in alc) | [Boiling point ]
357.82°C (rough estimate) | [density ]
1.30±0.1 g/cm3 (20 ºC 760 Torr) | [refractive index ]
1.5300 (estimate) | [storage temp. ]
-20°C Freezer | [solubility ]
DMSO: ≥25mg/mL | [form ]
powder | [pka]
8.29±0.20(Predicted) | [color ]
yellow | [optical activity]
[α]/D -980 to -1015 (C=1, MeOH) |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow Solid | [Uses]
Extracted 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. | [Uses]
GABAA receptor blocker, CNS stimulant | [Description]
A 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. | [Definition]
ChEBI: Securinine is a member of indolizines. | [References]
Murav'eva, Ban'kovskii., Dokl. Akad. Nauk, SSSR, 110,998 (1956)
Saito et al., Chem. & Ind., 1652 (1962)
Satoda et al., Tetrahedron Lett., 1199 (1962)
Mukherjee et al., Naturwiss., 50, 155 (1963)
Nakano et aI., Chem. & Ind., 1763 (1963)
Horii et al., ibid, 664 (1964)
Bevan et aI., ibid, 838 (1964)
Absolute configuration:
Bevan et al., Chern. Ind., 838 (1964)
Imadoetal., ibid, 1691 (1964)
Synthesis:
Horii et al., Tetrahedron, 23, 2265 (1967) |
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