Tbps

TBPS^[1]
Names
	Preferred IUPAC name 4-tert-Butyl-2,6,7-trioxa-1λ5-phosphabicyclo[2.2.2]octane-1-thione
Identifiers
CAS Number	70636-86-1;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL485673;
ChemSpider	94586;
KEGG	C19930;
PubChem CID	104781;
	InChI InChI=1S/C8H15O3PS/c1-7(2,3)8-4-9-12(13,10-5-8)11-6-8/h4-6H2,1-3H3 Key: VTBHBNXGFPTBJL-UHFFFAOYSA-N;
	SMILES CC(C)(C)C12COP(=S)(OC1)OC2;
Properties
Chemical formula	C8H15O3PS
Molar mass	222.24 g·mol−1
Hazards
Main hazards	Extremely toxic
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	53 μg/kg (mice)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

TBPS (tert-butylbicyclophosphorothionate) is a bicyclic phosphate convulsant.^[3] It is an extremely potent GABA receptor antagonist.^[4]^[5]

References

↑ "tert-Butyl bicyclo[2.2.2phosphorothionate"]. https://www.sigmaaldrich.com/catalog/product/sigma/b104?lang=en.
↑ Milbrath, Dean S.; Engel, Judith L.; Verkade, John G.; Casida, John E. (February 1979). "Structure-toxicity relationships of 1-substituted-4-alkyl-2,6,7-trioxabicyclo[2.2.2.]octanes". Toxicology and Applied Pharmacology 47 (2): 287–293. doi:10.1016/0041-008x(79)90323-5. PMID 452023.
↑ Trifiletti, Rosario R; Snowman, Adele M; Snyder, Solomon H (1984). "Solubilization and anionic regulation of cerebral sedative and convulsant receptors labeled with [³⁵S] tert-butylbicyclophosphorothionate (TBPS)". Biochemical and Biophysical Research Communications 120 (2): 692–9. doi:10.1016/0006-291x(84)91311-1. PMID 6329179.
↑ Atack, J R; Ohashi, Y; McKernan, R M (2009). "Characterization of [35St-butylbicyclophosphorothionate ([35S]TBPS) binding to GABAA receptors in postmortem human brain"]. British Journal of Pharmacology 150 (8): 1066–74. doi:10.1038/sj.bjp.0707186. PMID 17339834.
↑ Im, Wha Bin; Pregenzer, Jeffrey F; Thomsen, Darrel R (1994). "Effects of GABA and various allosteric ligands on TBPS binding to cloned rat GABAA receptor subtypes". British Journal of Pharmacology 112 (4): 1025–30. doi:10.1111/j.1476-5381.1994.tb13185.x. PMID 7952860.

{{Navbox | name = GABA receptor modulators | title = GABA receptor modulators | state = collapsed | bodyclass = hlist | groupstyle = text-align:center;

 | group1 = Ionotropic
 |  list1 = {{Navbox|subgroup
 | groupstyle = text-align:center
 | groupwidth = 5em

   | group1 = GABA_A
   | list1  =

Agonists: (+)-Catechin
Bamaluzole
Barbiturates (e.g., phenobarbital)
BL-1020
DAVA
Dihydromuscimol
GABA
Gabamide
GABOB
Gaboxadol (THIP)
Homotaurine (tramiprosate, 3-APS)
Ibotenic acid
iso-THAZ
iso-THIP
Isoguvacine
Isomuscimol
Isonipecotic acid
Kojic amine
Lignans (e.g., honokiol)
Methylglyoxal
Monastrol
Muscimol
Nefiracetam
Neuroactive steroids (e.g., allopregnanolone)
Org 20599
PF-6372865
Phenibut
Picamilon
P4S
Progabide
Propofol
Quisqualamine
SL-75102
TACA
TAMP
Terpenoids (e.g., borneol)
Thiomuscimol
Tolgabide
ZAPA

Positive modulators (abridged; see here for a full list): α-EMTBL
Alcohols (e.g., ethanol)
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, [[Chemistry:Cholecholesterol]], THDOC)
Niacin
Nicotinamide (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, [[Chemistry:Diethyl diethyl ether, Parparaldehyde]], sevoflurane)

Antagonists: Bicuculline
Coriamyrtin
Dihydrosecurinine
Gabazine (SR-95531)
Hydrastine
Hyenachin (mellitoxin)
PHP-501
Pitrazepin
Securinine
Sinomenine
SR-42641
SR-95103
Thiocolchicoside
Tutin

Negative modulators: 1,3M1B
3M2B
11-Ketoprogesterone
17-Phenylandrostenol
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 (¹²³I)
IPTBO
Isopregnanolone (sepranolone)
L-655,708
Laudanosine
Leptazol
Lindane
MaxiPost
Morphine
Morphine-3-glucuronide
MRK-016
Naloxone
Naltrexone
Nicardipine
Nonsteroidal antiandrogens (e.g., [[apalutamide, [[Chemistry:Bicalutbicalutamide, Enzalutenzalutamide, Chemistry:Flutamide|flut]]amide]], 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

   | group2 = GABA_A-ρ
   | list2  =

Agonists: BL-1020
CACA
CAMP
Homohypotaurine
GABA
GABOB
Ibotenic acid
Isoguvacine
Muscimol
N⁴-Chloroacetylcytosine arabinoside
Picamilon
Progabide
TACA
TAMP
Thiomuscimol
Tolgabide

Positive modulators: Allopregnanolone
Alphaxolone
ATHDOC
Lanthanides

Antagonists: (S)-2-MeGABA
(S)-4-ACPBPA
(S)-4-ACPCA
2-MeTACA
3-APMPA
4-ACPAM
4-GBA
cis-3-ACPBPA
CGP-36742 (SGS-742)
DAVA
Gabazine (SR-95531)
Gaboxadol (THIP)
I4AA
Isonipecotic acid
Loreclezole
P4MPA
P4S
SKF-97541
SR-95318
SR-95813
TPMPA
trans-3-ACPBPA
ZAPA

Negative modulators: 5α-Dihydroprogesterone
Bilobalide
Loreclezole
Picrotoxin (picrotin, picrotoxinin)
Pregnanolone
ROD-188
THDOC
Zinc

}}

 | group2 = Metabotropic

| list2 =

 | below =

See also: Receptor/signaling modulators; GABA_A receptor positive modulators; GABA metabolism/transport modulators

}}

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Original source: https://en.wikipedia.org/wiki/TBPS. Read more

[1] "tert-Butyl bicyclo[2.2.2phosphorothionate"]. https://www.sigmaaldrich.com/catalog/product/sigma/b104?lang=en.

[2] Milbrath, Dean S.; Engel, Judith L.; Verkade, John G.; Casida, John E. (February 1979). "Structure-toxicity relationships of 1-substituted-4-alkyl-2,6,7-trioxabicyclo[2.2.2.]octanes". Toxicology and Applied Pharmacology 47 (2): 287–293. doi:10.1016/0041-008x(79)90323-5. PMID 452023.

[3] Trifiletti, Rosario R; Snowman, Adele M; Snyder, Solomon H (1984). "Solubilization and anionic regulation of cerebral sedative and convulsant receptors labeled with [³⁵S] tert-butylbicyclophosphorothionate (TBPS)". Biochemical and Biophysical Research Communications 120 (2): 692–9. doi:10.1016/0006-291x(84)91311-1. PMID 6329179.

[4] Atack, J R; Ohashi, Y; McKernan, R M (2009). "Characterization of [35St-butylbicyclophosphorothionate ([35S]TBPS) binding to GABAA receptors in postmortem human brain"]. British Journal of Pharmacology 150 (8): 1066–74. doi:10.1038/sj.bjp.0707186. PMID 17339834.

[5] Im, Wha Bin; Pregenzer, Jeffrey F; Thomsen, Darrel R (1994). "Effects of GABA and various allosteric ligands on TBPS binding to cloned rat GABAA receptor subtypes". British Journal of Pharmacology 112 (4): 1025–30. doi:10.1111/j.1476-5381.1994.tb13185.x. PMID 7952860.

v t e Neurotoxins
Animal	Batrachotoxin Bestoxin Birtoxin Bungarotoxin Charybdotoxin Conotoxin Fasciculin Huwentoxin Poneratoxin Saxitoxin Tetrodotoxin Vanillotoxin Spooky toxin (SsTx) Epibatidine Zetekitoxin AB Dendrotoxin
Bacterial	Botulinum toxin Tetanospasmin
Cyanotoxins	Anatoxin-a Anatoxin-a(S) BMAA Saxitoxin
Plant	Bicuculline Penitrem A Picrotoxin Strychnine Tutin Rotenone Ginkgotoxin Cicutoxin Oenanthotoxin Thujone Volkensin
Mycotoxins	Ibotenic acid Muscarine Muscimol
Pesticides	Fenpropathrin Tetramethylenedisulfotetramine Bromethalin Crimidine Methamidophos Endosulfan Fipronil Phenylsilatrane Chlorophenylsilatrane Sulfuryl fluoride Mipafox Schradan Dimefox
Nerve agents	Cyclosarin EA-3148 Novichok agent Sarin Soman Tabun VE VG VM VP VR VX GV EA-3990 EA-4056 T-1123 Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) Fluorotabun Chinese VX EA-2192
Bicyclic phosphates	TBPS TBPO IPTBO
Other	Dimethylmercury Toxopyrimidine IDPN

v t e Convulsants
GABA receptor antagonists	Picrotoxin Gabazine Tetramethylenedisulfotetramine Cicutoxin Phenylsilatrane Tutin Pentylenetetrazol Thujone Endosulfan Bicuculline Oenanthotoxin Fipronil EBOB BIDN Dihydropicrotoxinin DMCM FG-7142 Chlorophenylsilatrane Bicyclic phosphates (TBPS, TBPO, IPTBO)
GABA synthesis inhibitors	Allylglycine Crimidine Ginkgotoxin Toxopyrimidine Isoniazid 3-Mercaptopropionic acid 4-Deoxypyridoxine
Glycine receptor antagonists	Strychnine Tutin Picrotoxin Dendrobine
Glutamate receptor agonists	AMPA NMDA Kainic acid Domoic acid Quisqualic acid Tetrazolylglycine
Other	Methyl fluoroacetate Fluoroethyl fluoroacetate Nitrocyclohexane Methionine sulfoximine

Names


Preferred IUPAC name 4-tert-Butyl-2,6,7-trioxa-1λ⁵-phosphabicyclo[2.2.2]octane-1-thione
Identifiers
CAS Number	70636-86-1
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL485673
ChemSpider	94586
KEGG	C19930
PubChem CID	104781
InChI InChI=1S/C8H15O3PS/c1-7(2,3)8-4-9-12(13,10-5-8)11-6-8/h4-6H2,1-3H3 Key: VTBHBNXGFPTBJL-UHFFFAOYSA-N
SMILES CC(C)(C)C12COP(=S)(OC1)OC2
Properties
Chemical formula	C₈H₁₅O₃PS
Molar mass	222.24 g·mol⁻¹
Hazards
Main hazards	Extremely toxic
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	53 μg/kg (mice)^[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tbps

See also

References