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Phenylsilatrane
Names
Preferred IUPAC name
(TBPY -5-23)-8-Phenyltetrahydro-4H -4λ5 -8,4-(epoxyethano)[1,3,2]oxazasilolo[3,2-b ][1,3,2]oxazasilol-4-ylium-8-uide
Identifiers
2097-19-0 Y
3D model (JSmol )
ChemSpider
ECHA InfoCard
100.016.603
UNII
InChI=1S/C12H17NO3Si/c1-2-4-12(5-3-1)17-13(6-9-14-17,7-10-15-17)8-11-16-17/h1-5H,6-11H2
Key: LDOWJVBCZRHOKX-UHFFFAOYSA-N
C1C[N+]23CCO[Si-]2(O1)(OCC3)C1=CC=CC=C1
Properties
Chemical formula
C 12 H 17 N O 3 Si
Molar mass
251.357 g·mol−1
Hazards
Main hazards
Toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
Phenylsilatrane is a convulsant chemical which has been used as a rodenticide .[1] [2] Phenylsilatrane and some of its analogs with 4-substituents of H, CH3 , Cl, Br, and CSi(CH3 )3 are highly toxic to mice. They have been observed in the laboratory to inhibit the 35 S-tert -butylbicyclophosphorothionate (TBPS ) binding site (GABA -gated chloride channel ) of mouse brain membranes.[3]
See also [ ]
References [ ]
^ Voronkov MG (1966). "Silatranes: Intra-Complex Heterocyclic Compounds of Pentacoordinated Silicon" (pdf) . Pure and Applied Chemistry . 13 (1–2): 35–60. doi :10.1351/pac196613010035 .
^ Lukevics E, Ignatovich L, Khokhlova L, Belyakov S (1997). "Synthesis, Structure, and Toxicity of Arylgermatranes". Chemistry of Heterocyclic Compounds . 33 (2): 239–241. doi :10.1007/BF02256767 .
^ Horsham MA, Palmer CJ, Cole LM, Casida JE (1990). "4-Alkynylphenylsilatranes: Insecticidal Activity, Mammalian Toxicity, and Mode of Action". Journal of Agricultural and Food Chemistry . 38 (8): 1734–1738. doi :10.1021/jf00098a023 .
Ionotropic
GABAA
Positive modulators (abridged; see here for a full list):
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
(e.g., sulfonmethane (sulfonal) )
Topiramate
Valerian constituents (e.g., valerenic acid )
Volatiles /gases (e.g., chloral hydrate , chloroform , diethyl ether , paraldehyde , sevoflurane )
Negative modulators:
11-Ketoprogesterone
17-Phenylandrostenol
α5IA (LS-193,268)
Anabolic steroids
Amiloride
Anisatin
β-Lactams (e.g., penicillins , cephalosporins , carbapenems )
Basmisanil
Bemegride
Bicyclic phosphates (TBPS , TBPO , IPTBO )
BIDN
Bilobalide
Bupropion
Chlorophenylsilatrane
Cicutoxin
Cloflubicyne
Cyclothiazide
DHEA
DHEA-S
Dieldrin
DMCM
EBOB
FG-7142 (ZK-31906)
(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
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
PWZ-029
Radequinil
Ro 15-4513
Sarmazenil
Suritozole
TB-21007
TBPS
Terbequinil
TETS
Thujone
Zinc
ZK-93426
GABAA -ρ
Metabotropic
See also
Receptor/signaling modulators
GABAA receptor positive modulators
GABA metabolism/transport modulators
GABA receptor antagonists GABA synthesis inhibitors Glycine receptor antagonists Glutamate receptor agonists Other
Categories :
Convulsants Nitrogen heterocycles Organosilicon compounds Oxygen heterocycles Rodenticides Silicon heterocycles GABAA receptor negative allosteric modulators Phenyl compounds Atranes Heterocyclic compound stubs Hidden categories:
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