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)[2]

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* SizeSet

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

## See also

* IPTBO
* EBOB

## References

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.

{{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 = GABAA
| 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)<!--PMID: 9776662-->
* 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 = GABAA-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 =

GABAB|

* Agonists: 1,4-Butanediol
* 4-Fluorophenibut
* Aceburic acid
* Arbaclofen
* Arbaclofen placarbil
* Baclofen
* BL-1020
* GABA
* Gabamide
* GABOB
* GBL
* GHB
* GHBAL
* GHV
* GVL
* Isovaline
* Lesogaberan
* Phenibut
* Picamilon
* Progabide
* Sodium oxybate
* SKF-97,541
* SL 75102
* Tolgabide
* Tolibut

* Positive modulators: ADX-71441
* BHF-177
* BHFF
* BSPP
* CGP-7930
* CGP-13501
* GS-39783
* rac-BHFF
* KK-92A

* Antagonists: 2-Hydroxysaclofen
* CGP-35348
* CGP-46381
* CGP-52432
* CGP-54626
* CGP-55845
* CGP-64213
* DAVA
* Homotaurine (tramiprosate, 3-APS)
* Phaclofen
* Saclofen
* SCH-50911
* SKF-97541

* Negative modulators: Compound 14

|

| below =

See also
Receptor/signaling modulators
GABAA receptor positive modulators
GABA metabolism/transport modulators

* 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

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

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*[CID]: Compound ID
*[GABA]: γ-Aminobutyric acid
*[GABAA]: γ-Aminobutyric acid A receptor
*[GABAA-ρ]: γ-Aminobutyric acid A-rho receptor
*[GABAB]: γ-Aminobutyric acid B receptor
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template