Chlorophenylsilatrane
{{Chembox
| Name = 1-(4-Chlorophenyl)silatrane
| ImageFile = Chlorophenylsilatrane dativebond.svg
| ImageSize = 100px
| IUPACName = 1-(4-Chlorophenyl)-2,8,9-trioxa-5-aza-1-silabicyclo[3.3.3]undecane
| OtherNames = RS-150
Caswell No. 213B
1-(p-Chlorophenyl)silatrane
5-(p-Chlorophenyl)silatrane
5-(4-Chlorophenyl)silatrane
| SystematicName =
| Section1 = {{Chembox Identifiers
| SMILES = c1cc(ccc1[Si]23OCCN(CCO2)CCO3)Cl
| ChemSpiderID = 90808
| PubChem = 100508
| CASNo = 29025-67-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 92E5GUJ2UJ
| StdInChI=1S/C12H16ClNO3Si/c13-11-1-3-12(4-2-11)18-15-8-5-14(6-9-16-18)7-10-17-18/h1-4H,5-10H2
| StdInChIKey = IKFVTMCLFHXPQF-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C=12|H=16|Cl=1|N=1|O=3|Si=1
| MolarMass = 285.8 g/mol
| Appearance = odorless, white powder
| Solvent = Chloroform, Benzene
}}
| Section3 = {{Chembox Hazards
| MainHazards = Extremely toxic
| LD50 = 1-4 mg/kg (rats, oral)
3000 mg/kg (rats, dermal)
0.9-2.0 mg/kg (mice, oral)
}}
| Section4 =
| Section5 =
| Section6 =
}}
1-(4-Chlorophenyl)silatrane is an extremely toxic{{cite journal | last=Lund | first=M. | title=New Rodenticides Against Anticoagulant-resistant Rats and Mice | journal=EPPO Bulletin | publisher=Wiley | volume=7 | issue=2 | year=1977 | issn=0250-8052 | doi=10.1111/j.1365-2338.1977.tb02750.x | pages=503–508}} organosilicon compound which was developed by M&T Chemicals as a single-dose rodenticide.{{cite journal | last1=Crabtree | first1=D. Glen | last2=Beiter | first2=Charles B. | last3=Schwarcz | first3=Morton | title=5-p-Chlorophenyl silatrane, a new single-dose rodenticide | journal=Chemical Report by M&T Chemicals Inc. | year=1970 | url=https://nwrc.contentdm.oclc.org/digital/collection/NWRCPubs1/id/4582}} It was never registered as rodenticide, except for experimental use. 1-(4-Chlorophenyl)silatrane was one of the chemicals studied in the Project Coast.{{cite web |url=https://media.nti.org/pdfs/south_africa_chemical.pdf |title=South Africa Chemical Chronology |author= |date=2005-04-23 |website=NTI.org |publisher=Nuclear Threat Initiative |access-date=2020-07-31}}{{cite journal | last=Bale | first=Jeffrey M. | title=South Africa's Project Coast: "Death Squads," Covert State-Sponsored Poisonings, and the Dangers of CBW Proliferation | journal=Democracy and Security | publisher=Informa UK Limited | volume=2 | issue=1 | year=2006 | issn=1741-9166 | doi=10.1080/17419160600623434 | pages=27–59| s2cid=143175071 }}
Toxicity
1-(4-Chlorophenyl)silatrane is a GABA receptor antagonist{{cite journal |last1=Casida |first1=JE |last2=Lawrence |first2=LJ |title=Structure-activity correlations for interactions of bicyclophosphorus esters and some polychlorocycloalkane and pyrethroid insecticides with the brain-specific t-butylbicyclophosphorothionate receptor |journal=Environmental Health Perspectives |date=September 1985 |volume=61 |pages=123–32 |pmid=2415350 |pmc=1568750 |doi=10.2307/3430066|jstor=3430066 }} and it destroys nervous functions in the central nervous system of vertebrates, primarily in the brain and possibly in the brain stem.{{cite journal | last1=Casida | first1=John E. | last2=Eto | first2=Morifusa | last3=Moscioni | first3=A.David | last4=Engel | first4=Judith L. | last5=Milbrath | first5=Dean S. | last6=Verkade | first6=John G. | title=Structure-toxicity relationships of 2,6,7-trioxabicyclo[2.2.2]-octanes and related compounds | journal=Toxicology and Applied Pharmacology | publisher=Elsevier BV | volume=36 | issue=2 | year=1976 | issn=0041-008X | doi=10.1016/0041-008x(76)90006-5 | pages=261–279| pmid=1084063 | bibcode=1976ToxAP..36..261C }}{{cite conference |title=Proceedings of the International Society of Neurochemistry |last1=Mattson |first1=H. |last2=Brandt |first2=K. |last3=Heilbronn |first3=E. |date=21–26 August 1977 |pages=56 |location=Copenhagen, Denmark |conference=Sixth International Meeting of the International Society for Neurochemistry }}{{cite book | last=Voronkov | first=Michail G. | title=Topics in Current Chemistry | chapter=Biological activity of silatranes | year=1979 | volume=84 | publisher=Springer-Verlag | location=Berlin/Heidelberg | isbn=3-540-09347-8 | doi=10.1007/bfb0048523 | pages=77–135| pmid=388722 }} It's a rapid acting convulsant, causing convulsions within 1 minute in mice and rats. Death occurred within 5 minutes.{{cite journal |last1=Greaves |first1=JH |last2=Redfern |first2=R |last3=Tinworth |first3=H |title=Laboratory tests of 5-p-chlorophenyl silatrane as a rodenticide |journal=The Journal of Hygiene |date=August 1974 |volume=73 |issue=1 |pages=39–43 |pmid=4529452 |pmc=2130561 |doi=10.1017/s0022172400023810}} It is therefore likely to induce poison shyness. In field trials, it was less effective than zinc phosphide against wild rats.{{cite journal | last=Rennison | first=B. D. | title=Field trials of the rodenticide 5-p-chlorophenyl silatrane against wild rats (Rattus norvegicus Berk.) | journal=Journal of Hygiene | publisher=Cambridge University Press | volume=73 | issue=1 | year=1974 | issn=0022-1724 | doi=10.1017/s0022172400023822 | pages=45–48 | pmid=4529041 | pmc=2130558 }}
See also
References
{{reflist}}
{{Convulsants}}
{{Chemical agents}}
{{Neurotoxins}}
{{Rodenticides}}
{{GABA receptor modulators}}
Category:Organosilicon compounds
Category:Nitrogen heterocycles
Category:GABAA receptor negative allosteric modulators