485-49-4 Usage
Description
(+)-Bicuculline, also known as Bicuculline, is a convulsant alkaloid that is naturally occurring in the d-form. It was originally isolated from the plant Dicentra cucullaria. (+)-Bicuculline is a pale yellow solid and is known for its GABA antagonist activity.
Uses
Used in Pharmaceutical Industry:
(+)-Bicuculline is used as a GABAA receptor antagonist for its ability to block the GABA receptors in the central nervous system. This property makes it a valuable tool in the study and treatment of various neurological disorders and conditions related to the GABAergic system.
Used in Research Applications:
(+)-Bicuculline is used as a GABAa antagonist in research settings to investigate the role of GABA receptors in the brain and their involvement in different physiological processes. This helps researchers understand the underlying mechanisms of various neurological conditions and develop potential therapeutic strategies.
Used in Natural Products:
(+)-Bicuculline, being an alkaloid naturally occurring in the d-form, is also used in the study of natural products and their potential applications in medicine. Its GABA antagonist activity provides insights into the interactions between natural compounds and neurotransmitter systems in the body.
Biological Activity
Classical GABA A antagonist.
Biochem/physiol Actions
(+)-Bicuculline acts as a competitive inhibitor of GABA liganding binding to the receptor.
Safety Profile
A poison by intraperitoneal route.When heated to decomposition it emits toxic vapors ofNOx.
Purification Methods
It crystallises from CHCl3/MeOH as plates. The crystals melt at 177o, then solidify and re-melt at 193-195o [Manske Canad J Research 21B 13 1943]. It is soluble in CHCl3, *C6H6, EtOAc but sparingly soluble in EtOH, MeOH and Et2O. [Stereochem: Blaha et al. Collect Czech Chem Commun 29 2328 1964, Snatzke et al. Tetrahedron 25 5059 1969, Pharmcol: Curtis et al. Nature 266 1222 1970, Beilstein 27 III/IV 1900].
Check Digit Verification of cas no
The CAS Registry Mumber 485-49-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,8 and 5 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 485-49:
(5*4)+(4*8)+(3*5)+(2*4)+(1*9)=84
84 % 10 = 4
So 485-49-4 is a valid CAS Registry Number.
InChI:InChI=1/C20H17NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)17(21)18-11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18H,4-5,8-9H2,1H3/p+1/t17-,18+/m0/s1
485-49-4Relevant articles and documents
Synthesis, anti-GABA activity and preferred conformation of bicuculline and norbicuculline enantiomers
Kardos,Blandl,Luyen,Doernyei,Gacs-Baitz,Simonyi,Cash,Blasko,Szantay
, p. 761 - 765 (1996)
Synthesis of erythro-(±)-[1SR,9RS]-norbicuculline and threo-(±)-[1SR,9SR]-noradlumidine from piperonal was performed using Bischler-Napieralski cyclization as a key step. Resolution gave rise to (+)-[1S,9R]-norbicuculline ([1S,9R] norBIC) and (-)-[1R,9S]-norbicuculline ([1R,9S] norBIC) in >99.5% enantiomeric purity. Bicuculline enantiomers were readily obtained by methylation of the latter products. [1S,9R]BIC was about 70 times more potent than [1R,9S]BIC as an inhibitor of GABA(A) receptor binding and was about 100 and 900 times more potent than [1S,9R] norBIC at pH 7.1 and 5.0 respectively. Similarly, [1S,9R] norBIC was much less potent than [1S,9R]BIC as an inhibitor of GABA-specific 36Cl- ion flux. The observed increase of about two orders of magnitude in the in vitro biological activity caused by N2-CH3 substitution in [1S,9R] norBIC was attributed to different conformations for erythro- and nor-erythro-bicucullines indicated by 1H nuclear Overhauser enhancements of [1S,9R]BIC and [1S,9R] norBIC.
Alkaloids of Corydalis incisa Pers. V. The structures of corydalispirone and corydalisol
Nonaka,Nishioka
, p. 294 - 298 (2007/10/04)
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