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(1,2,5,6-Tetrahydropyridin-4-yl)methylphosphinic acid

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(1,2,5,6-Tetrahydropyridin-4-yl)methylphosphinic acid
Names

Preferred IUPAC name Methyl(1,2,3,6-tetrahydropyridin-4-yl)phosphinic acid
Other names TPMPA
Identifiers
CAS Number	182485-36-5^Y
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL397209^Y
ChemSpider	5319^Y
IUPHAR/BPS	4328
PubChem CID	5521
UNII	TR7I0800L2^Y
CompTox Dashboard(EPA)	DTXSID801017153
InChI InChI=1S/C6H12NO2P/c1-10(8,9)6-2-4-7-5-3-6/h2,7H,3-5H2,1H3,(H,8,9)^Y Key: MFUKVPOVVKKLRQ-UHFFFAOYSA-N^Y InChI=1/C6H12NO2P/c1-10(8,9)6-2-4-7-5-3-6/h2,7H,3-5H2,1H3,(H,8,9) Key: MFUKVPOVVKKLRQ-UHFFFAOYAY
SMILES CP(=O)(C1=CCNCC1)O O=P([O-])(/C1=C/C[NH2+]CC1)C
Properties
Chemical formula	C₆H₁₂NO₂P
Molar mass	161.141 g·mol⁻¹
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

(1,2,5,6-Tetrahydropyridin-4-yl)methylphosphinic acid (TPMPA) is aGABA antagonist selective for theGABA_A-ρ (previously known as GABA_C) subtype.^[1]

References

^Li, Shifeng; Zhang, Yunbin; Liu, Haixiong; Yan, Yuanchang; Li, Yiping (2008). "Identification and expression of GABACreceptor in rat testis and spermatozoa".Acta Biochimica et Biophysica Sinica.40 (8):761–7.doi:10.1111/j.1745-7270.2008.00453.x.PMID 18685793.

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GABA receptor modulators

GABA_ATooltip γ-Aminobutyric acid A receptor

Positive modulators (abridged; seehere 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)

GABA_A-ρTooltip γ-Aminobutyric acid A-rho receptor

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

GABA_BTooltip γ-Aminobutyric acid B receptor

Negative modulators:Compound 14

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

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