Cloflubicyne

Cloflubicyne
Names
	IUPAC name 5,6-dichloro-3,3-bis(trifluoromethyl)bicyclo[2.2.1]heptane-2,2-dicarbonitrile
Identifiers
CAS Number	224790-70-9;
3D model (JSmol)	Interactive image;
ChemSpider	2328106;
PubChem CID	5067794;
CompTox Dashboard (EPA)	DTXSID80274166 ;
	InChI InChI=1S/C11H6Cl2F6N2/c12-6-4-1-5(7(6)13)9(10(14,15)16,11(17,18)19)8(4,2-20)3-21/h4-7H,1H2 Key: NTESZNJQNKSALM-UHFFFAOYSA-N;
	SMILES C1C2C(C(C1C(C2(C#N)C#N)(C(F)(F)F)C(F)(F)F)Cl)Cl;
Properties
Chemical formula	C11H6Cl2F6N2
Molar mass	351.07 g·mol−1
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Extremely toxic
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	0.1 mg/kg (intraperitoneal, mice)
LDLo (lowest published)	0.2 mg/kg (oral, rats)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Cloflubicyne is a chemical compound which is a chlorinated derivative of BIDN. It is an irreversible GABA receptor antagonist with powerful convulsant effects.^[3]^[4]^[5]^[6]

References

^ Fetisov, V.I.; Maslov, A.A.; Panarin, V.A.; Trefilov, N.V. (August 1992). "Fluoro-containing 'cage' convulsants: inhibition of gamma-aminobutyric acid induced Cl−currents". Journal of Fluorine Chemistry. 58 (2–3): 368. doi:10.1016/S0022-1139(00)80833-7.
^ Middleton, W.J; Bingham, E.M (May 1982). "Fluorine-containing 1,1-dicyanoethylenes: their preparation, diels-alder reactions, and derived norbornenes and norbornanes". Journal of Fluorine Chemistry. 20 (3): 397–418. Bibcode:1982JFluC..20..397M. doi:10.1016/S0022-1139(00)82232-0.
^ Golovko, A. I.; Sofronov, G. A.; Klyuntina, T. V. (April 1996). "Norbornan, a new irreversible ligand of the GABAA-receptor chloride channels". Bulletin of Experimental Biology and Medicine. 121 (4): 404–406. doi:10.1007/BF02446741. S2CID 35092380.
^ Golovko, A. I.; Sofronov, G. A.; Klyuntina, T. V.; Suftin, S. G.; Garbuz, L. A. (July 1996). "Norbornane-induced changes in the density of chloride-ion channels in the brain of rodents". Bulletin of Experimental Biology and Medicine. 122 (1): 660–662. doi:10.1007/BF02446014. S2CID 46036353.
^ Golovko, A. I.; Ivanov, M. B.; Klyuntina, T. V.; Sofronov, G. A.; Sviderskii, O. A.; Shilov, V. V. (January 1997). "Development of increased convulsibility in mice after a single norbornan injection". Bulletin of Experimental Biology and Medicine. 123 (1): 52–54. doi:10.1007/BF02764378. S2CID 27826524.
^ Golovko, A. I.; Ivanov, M. B.; Sviderskii, O. A.; Sofronov, G. A.; Shilov, V. V. (June 1998). "Mechanisms of kindling induced by norbornan intoxication". Bulletin of Experimental Biology and Medicine. 125 (6): 579–581. doi:10.1007/BF02445245. S2CID 26207399.

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[1] Fetisov, V.I.; Maslov, A.A.; Panarin, V.A.; Trefilov, N.V. (August 1992). "Fluoro-containing 'cage' convulsants: inhibition of gamma-aminobutyric acid induced Cl−currents". Journal of Fluorine Chemistry. 58 (2–3): 368. doi:10.1016/S0022-1139(00)80833-7.

[2] Middleton, W.J; Bingham, E.M (May 1982). "Fluorine-containing 1,1-dicyanoethylenes: their preparation, diels-alder reactions, and derived norbornenes and norbornanes". Journal of Fluorine Chemistry. 20 (3): 397–418. Bibcode:1982JFluC..20..397M. doi:10.1016/S0022-1139(00)82232-0.

[3] Golovko, A. I.; Sofronov, G. A.; Klyuntina, T. V. (April 1996). "Norbornan, a new irreversible ligand of the GABAA-receptor chloride channels". Bulletin of Experimental Biology and Medicine. 121 (4): 404–406. doi:10.1007/BF02446741. S2CID 35092380.

[4] Golovko, A. I.; Sofronov, G. A.; Klyuntina, T. V.; Suftin, S. G.; Garbuz, L. A. (July 1996). "Norbornane-induced changes in the density of chloride-ion channels in the brain of rodents". Bulletin of Experimental Biology and Medicine. 122 (1): 660–662. doi:10.1007/BF02446014. S2CID 46036353.

[5] Golovko, A. I.; Ivanov, M. B.; Klyuntina, T. V.; Sofronov, G. A.; Sviderskii, O. A.; Shilov, V. V. (January 1997). "Development of increased convulsibility in mice after a single norbornan injection". Bulletin of Experimental Biology and Medicine. 123 (1): 52–54. doi:10.1007/BF02764378. S2CID 27826524.

[6] Golovko, A. I.; Ivanov, M. B.; Sviderskii, O. A.; Sofronov, G. A.; Shilov, V. V. (June 1998). "Mechanisms of kindling induced by norbornan intoxication". Bulletin of Experimental Biology and Medicine. 125 (6): 579–581. doi:10.1007/BF02445245. S2CID 26207399.

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v t e Convulsants
GABA receptor antagonists	Bicuculline Bicyclic phosphates (TBPS, TBPO, IPTBO) BIDN Chlorophenylsilatrane Cicutoxin Cloflubicyne Coriamyrtin Dihydropicrotoxinin DMCM EBOB Endosulfan FG-7142 Fipronil Flurothyl Gabazine Oenanthotoxin Pentylenetetrazol Phenylsilatrane Picrotoxin p-CN-TBOB p-NCS-TBOB RDX TBOB Tetramethylenedisulfotetramine Thujone Trimethylolpropane phosphite Tutin
GABA synthesis inhibitors	3-Mercaptopropionic acid 4-Deoxypyridoxine Allylglycine Crimidine Decaborane Ginkgotoxin Isoniazid Pentaborane Thiocarbohydrazide Toxopyrimidine
Glycine receptor antagonists	Coriamyrtin Dendrobine Picrotoxin Strychnine Tutin
Glutamate receptor agonists	AMPA Domoic acid Kainic acid NMDA Quisqualic acid Tetrazolylglycine
Convulsant barbiturates	CHEB Diberal (DMBB) McN-481
Other	2,2,3,3-Tetrafluoropropyl trifluoromethyl ether Bromocamphor Camphor FAZ-4 Fluoroethyl fluoroacetate MC-2973 Methionine sulfoximine Methyl fluoroacetate Nitrocyclohexane Thebaine

Names

IUPAC name 5,6-dichloro-3,3-bis(trifluoromethyl)bicyclo[2.2.1]heptane-2,2-dicarbonitrile
Identifiers
CAS Number	224790-70-9
3D model (JSmol)	Interactive image
ChemSpider	2328106
PubChem CID	5067794
CompTox Dashboard (EPA)	DTXSID80274166
InChI InChI=1S/C11H6Cl2F6N2/c12-6-4-1-5(7(6)13)9(10(14,15)16,11(17,18)19)8(4,2-20)3-21/h4-7H,1H2 Key: NTESZNJQNKSALM-UHFFFAOYSA-N
SMILES C1C2C(C(C1C(C2(C#N)C#N)(C(F)(F)F)C(F)(F)F)Cl)Cl
Properties
Chemical formula	C₁₁H₆Cl₂F₆N₂
Molar mass	351.07 g·mol⁻¹
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Extremely toxic
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	0.1 mg/kg (intraperitoneal, mice)^[1]
LD_Lo (lowest published)	0.2 mg/kg (oral, rats)^[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Cloflubicyne

See also

References