From Wikipedia, the free encyclopedia
1-(4-Chlorophenyl)silatrane
Names
IUPAC name
1-(4-Chlorophenyl)-2,8,9-trioxa-5-aza-1-silabicyclo[3.3.3]undecane
Other names
RS-150 Caswell No. 213B 1-(p-Chlorophenyl)silatrane 5-(p-Chlorophenyl)silatrane 5-(4-Chlorophenyl)silatrane
Identifiers
ChemSpider
ECHA InfoCard
100.252.129
UNII
InChI=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
Key: IKFVTMCLFHXPQF-UHFFFAOYSA-N
c1cc(ccc1[Si]23OCCN(CCO2)CCO3)Cl
Properties
C 12 H 16 Cl N O 3 Si
Molar mass
285.8 g/mol
Appearance
odorless, white powder
[1]
Melting point
230-235 °C
[1]
<0.2 g/L
[1]
Solubility in Chloroform, Benzene
soluble
[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Extremely toxic
Lethal dose or concentration (LD, LC):
1-4 mg/kg (rats, oral)
[1] 3000 mg/kg (rats, dermal)
[1] 0.9-2.0 mg/kg (mice, oral)
[1]
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
1-(4-Chlorophenyl)silatrane is an extremely toxic
[2]
organosilicon compound which was developed by
M&T Chemicals as a single-dose
rodenticide .
[1] It was never registered as rodenticide,
[2] except for experimental use.
[1] 1-(4-Chlorophenyl)silatrane was one of the chemicals studied in the
Project Coast .
[3]
[4]
Toxicity
1-(4-Chlorophenyl)silatrane is a
GABA receptor antagonist
[5] and it destroys nervous functions in the central nervous system of vertebrates, primarily in the brain and possibly in the brain stem.
[6]
[7]
[8] It's a rapid acting
convulsant , causing convulsions within 1 minute in mice and rats. Death occurred within 5 minutes.
[9] It is therefore likely to induce
poison shyness .
[2] In field trials, it was less effective than
zinc phosphide against wild rats.
[10]
See also
References
^
a
b
c
d
e
f
g
h
i Crabtree, D. Glen; Beiter, Charles B.; Schwarcz, Morton (1970).
"5-p-Chlorophenyl silatrane, a new single-dose rodenticide" . Chemical Report by M&T Chemicals Inc .
^
a
b
c Lund, M. (1977). "New Rodenticides Against Anticoagulant-resistant Rats and Mice". EPPO Bulletin . 7 (2). Wiley: 503–508.
doi :
10.1111/j.1365-2338.1977.tb02750.x .
ISSN
0250-8052 .
^
"South Africa Chemical Chronology" (PDF) . NTI.org . Nuclear Threat Initiative. 2005-04-23. Retrieved 2020-07-31 .
^ Bale, Jeffrey M. (2006). "South Africa's Project Coast: "Death Squads," Covert State-Sponsored Poisonings, and the Dangers of CBW Proliferation". Democracy and Security . 2 (1). Informa UK Limited: 27–59.
doi :
10.1080/17419160600623434 .
ISSN
1741-9166 .
S2CID
143175071 .
^ Casida, JE; Lawrence, LJ (September 1985).
"Structure-activity correlations for interactions of bicyclophosphorus esters and some polychlorocycloalkane and pyrethroid insecticides with the brain-specific t-butylbicyclophosphorothionate receptor" . Environmental Health Perspectives . 61 : 123–32.
doi :
10.2307/3430066 .
JSTOR
3430066 .
PMC
1568750 .
PMID
2415350 .
^ Casida, John E.; Eto, Morifusa; Moscioni, A.David; Engel, Judith L.; Milbrath, Dean S.; Verkade, John G. (1976). "Structure-toxicity relationships of 2,6,7-trioxabicyclo[2.2.2]-octanes and related compounds". Toxicology and Applied Pharmacology . 36 (2). Elsevier BV: 261–279.
doi :
10.1016/0041-008x(76)90006-5 .
ISSN
0041-008X .
PMID
1084063 .
^ Mattson, H.; Brandt, K.; Heilbronn, E. (21–26 August 1977). Proceedings of the International Society of Neurochemistry . Sixth International Meeting of the International Society for Neurochemistry. Copenhagen, Denmark. p. 56.
^ Voronkov, Michail G. (1979). "Biological activity of silatranes". Topics in Current Chemistry . Vol. 84. Berlin/Heidelberg: Springer-Verlag. pp. 77–135.
doi :
10.1007/bfb0048523 .
ISBN
3-540-09347-8 .
PMID
388722 .
^ Greaves, JH; Redfern, R; Tinworth, H (August 1974).
"Laboratory tests of 5-p-chlorophenyl silatrane as a rodenticide" . The Journal of Hygiene . 73 (1): 39–43.
doi :
10.1017/s0022172400023810 .
PMC
2130561 .
PMID
4529452 .
^ Rennison, B. D. (1974).
"Field trials of the rodenticide 5-p-chlorophenyl silatrane against wild rats (Rattus norvegicus Berk.)" . Journal of Hygiene . 73 (1). Cambridge University Press: 45–48.
doi :
10.1017/s0022172400023822 .
ISSN
0022-1724 .
PMC
2130558 .
PMID
4529041 .
Ionotropic
GABAA Tooltip γ-Aminobutyric acid A receptor
Positive modulators (abridged; see
here for a full list):
α-EMTBL
Alcohols (e.g.,
drinking alcohol ,
2M2B )
Anabolic steroids
Avermectins (e.g.,
ivermectin )
Barbiturates (e.g.,
phenobarbital )
Benzodiazepines (e.g.,
diazepam )
Bromide compounds (e.g.,
potassium bromide )
Carbamates (e.g.,
meprobamate )
Carbamazepine
Chloralose
Chlormezanone
Clomethiazole
Dihydroergolines (e.g.,
ergoloid (dihydroergotoxine) )
Etazepine
Etifoxine
Fenamates (e.g.,
mefenamic acid )
Flavonoids (e.g.,
apigenin ,
hispidulin )
Fluoxetine
Flupirtine
Imidazoles (e.g.,
etomidate )
Kava constituents (e.g.,
kavain )
Lanthanum
Loreclezole
Monastrol
Neuroactive steroids (e.g.,
allopregnanolone ,
cholesterol ,
THDOC )
Niacin
Niacinamide
Nonbenzodiazepines (e.g.,
β-carbolines (e.g.,
abecarnil ),
cyclopyrrolones (e.g.,
zopiclone ),
imidazopyridines (e.g.,
zolpidem ),
pyrazolopyrimidines (e.g.,
zaleplon ))
Norfluoxetine
Petrichloral
Phenols (e.g.,
propofol )
Phenytoin
Piperidinediones (e.g.,
glutethimide )
Propanidid
Pyrazolopyridines (e.g.,
etazolate )
Quinazolinones (e.g.,
methaqualone )
Retigabine (ezogabine)
ROD-188
Skullcap constituents (e.g.,
baicalin )
Stiripentol
Sulfonylalkanes (e.g.,
sulfonmethane (sulfonal) )
Topiramate
Valerian constituents (e.g.,
valerenic acid )
Volatiles /
gases (e.g.,
chloral hydrate ,
chloroform ,
diethyl ether ,
paraldehyde ,
sevoflurane )
Negative modulators:
1,3M1B
3M2B
11-Ketoprogesterone
17-Phenylandrostenol
α3IA
α5IA (LS-193,268)
β-CCB
β-CCE
β-CCM
β-CCP
β-EMGBL
Anabolic steroids
Amiloride
Anisatin
β-Lactams (e.g.,
penicillins ,
cephalosporins ,
carbapenems )
Basmisanil
Bemegride
Bicyclic phosphates (
TBPS ,
TBPO ,
IPTBO )
BIDN
Bilobalide
Bupropion
CHEB
Chlorophenylsilatrane
Cicutoxin
Cloflubicyne
Cyclothiazide
DHEA
DHEA-S
Dieldrin
(+)-DMBB
DMCM
DMPC
EBOB
Etbicyphat
FG-7142 (ZK-31906)
Fiproles (e.g.,
fipronil )
Flavonoids (e.g.,
amentoflavone ,
oroxylin A )
Flumazenil
Fluoroquinolones (e.g.,
ciprofloxacin )
Flurothyl
Furosemide
Golexanolone
Iomazenil (123 I)
IPTBO
Isopregnanolone (sepranolone)
L-655,708
Laudanosine
Lindane
MaxiPost
Morphine
Morphine-3-glucuronide
MRK-016
Naloxone
Naltrexone
Nicardipine
Nonsteroidal antiandrogens (e.g.,
apalutamide ,
bicalutamide ,
enzalutamide ,
flutamide ,
nilutamide )
Oenanthotoxin
Pentylenetetrazol (pentetrazol)
Phenylsilatrane
Picrotoxin (i.e.,
picrotin ,
picrotoxinin and
dihydropicrotoxinin )
Pregnenolone sulfate
Propybicyphat
PWZ-029
Radequinil
Ro 15-4513
Ro 19-4603
RO4882224
RO4938581
Sarmazenil
SCS
Suritozole
TB-21007
TBOB
TBPS
TCS-1105
Terbequinil
TETS
Thujone
U-93631
Zinc
ZK-93426
GABAA -ρ Tooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABAB Tooltip γ-Aminobutyric acid B receptor