From Wikipedia, the free encyclopedia
Isonipecotic acid
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Names
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Preferred IUPAC name
Piperidine-4-carboxylic acid
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Identifiers
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ChEMBL
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ChemSpider
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ECHA InfoCard
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100.007.158
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EC Number
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UNII
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InChI=1S/C6H11NO2/c8-6(9)5-1-3-7-4-2-5/h5,7H,1-4H2,(H,8,9) NKey: SRJOCJYGOFTFLH-UHFFFAOYSA-N NInChI=1/C6H11NO2/c8-6(9)5-1-3-7-4-2-5/h5,7H,1-4H2,(H,8,9) Key: SRJOCJYGOFTFLH-UHFFFAOYAD
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Properties
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C6H11NO2
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Molar mass
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129.16 g/mol
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Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
Isonipecotic acid is a
heterocyclic compound which acts as a
GABAA receptor
partial agonist.
[1]
It consists of a
piperidine ring with a
carboxylic acid
moiety in the iso position (and as such is also known as "4-piperidinecarboxylic acid").
References
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Ionotropic |
GABAATooltip γ-Aminobutyric acid A receptor |
- Positive modulators (abridged; see
here for a full list):
α-EMTBL
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Alcohols (e.g.,
drinking alcohol,
2M2B)
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Anabolic steroids
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Avermectins (e.g.,
ivermectin)
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Barbiturates (e.g.,
phenobarbital)
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Benzodiazepines (e.g.,
diazepam)
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Bromide compounds (e.g.,
potassium bromide)
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Carbamates (e.g.,
meprobamate)
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Carbamazepine
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Chloralose
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Chlormezanone
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Clomethiazole
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Dihydroergolines (e.g.,
ergoloid (dihydroergotoxine))
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Etazepine
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Etifoxine
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Fenamates (e.g.,
mefenamic acid)
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Flavonoids (e.g.,
apigenin,
hispidulin)
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Fluoxetine
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Flupirtine
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Imidazoles (e.g.,
etomidate)
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Kava constituents (e.g.,
kavain)
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Lanthanum
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Loreclezole
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Monastrol
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Neuroactive steroids (e.g.,
allopregnanolone,
cholesterol,
THDOC)
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Niacin
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Niacinamide
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Nonbenzodiazepines (e.g.,
β-carbolines (e.g.,
abecarnil),
cyclopyrrolones (e.g.,
zopiclone),
imidazopyridines (e.g.,
zolpidem),
pyrazolopyrimidines (e.g.,
zaleplon))
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Norfluoxetine
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Petrichloral
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Phenols (e.g.,
propofol)
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Phenytoin
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Piperidinediones (e.g.,
glutethimide)
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Propanidid
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Pyrazolopyridines (e.g.,
etazolate)
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Quinazolinones (e.g.,
methaqualone)
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Retigabine (ezogabine)
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ROD-188
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Skullcap constituents (e.g.,
baicalin)
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Stiripentol
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Sulfonylalkanes (e.g.,
sulfonmethane (sulfonal))
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Topiramate
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Valerian constituents (e.g.,
valerenic acid)
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Volatiles/
gases (e.g.,
chloral hydrate,
chloroform,
diethyl ether,
paraldehyde,
sevoflurane)
- Negative modulators:
1,3M1B
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3M2B
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11-Ketoprogesterone
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17-Phenylandrostenol
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α3IA
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α5IA (LS-193,268)
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β-CCB
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β-CCE
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β-CCM
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β-CCP
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β-EMGBL
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Anabolic steroids
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Amiloride
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Anisatin
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β-Lactams (e.g.,
penicillins,
cephalosporins,
carbapenems)
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Basmisanil
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Bemegride
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Bicyclic phosphates (
TBPS,
TBPO,
IPTBO)
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BIDN
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Bilobalide
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Bupropion
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CHEB
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Chlorophenylsilatrane
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Cicutoxin
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Cloflubicyne
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Cyclothiazide
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DHEA
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DHEA-S
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Dieldrin
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(+)-DMBB
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DMCM
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DMPC
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EBOB
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Etbicyphat
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FG-7142 (ZK-31906)
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Fiproles (e.g.,
fipronil)
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Flavonoids (e.g.,
amentoflavone,
oroxylin A)
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Flumazenil
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Fluoroquinolones (e.g.,
ciprofloxacin)
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Flurothyl
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Furosemide
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Golexanolone
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Iomazenil (123I)
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IPTBO
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Isopregnanolone (sepranolone)
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L-655,708
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Laudanosine
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Lindane
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MaxiPost
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Morphine
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Morphine-3-glucuronide
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MRK-016
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Naloxone
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Naltrexone
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Nicardipine
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Nonsteroidal antiandrogens (e.g.,
apalutamide,
bicalutamide,
enzalutamide,
flutamide,
nilutamide)
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Oenanthotoxin
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Pentylenetetrazol (pentetrazol)
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Phenylsilatrane
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Picrotoxin (i.e.,
picrotin,
picrotoxinin and
dihydropicrotoxinin)
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Pregnenolone sulfate
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Propybicyphat
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PWZ-029
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Radequinil
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Ro 15-4513
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Ro 19-4603
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RO4882224
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RO4938581
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Sarmazenil
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SCS
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Suritozole
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TB-21007
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TBOB
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TBPS
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TCS-1105
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Terbequinil
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TETS
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Thujone
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U-93631
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Zinc
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ZK-93426
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GABAA-ρTooltip γ-Aminobutyric acid A-rho receptor | |
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Metabotropic |
GABABTooltip γ-Aminobutyric acid B receptor | |
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Receptor (
ligands) |
GlyRTooltip Glycine receptor |
- Positive modulators:
Alcohols (e.g.,
brometone,
chlorobutanol (chloretone),
ethanol (alcohol),
tert-butanol (2M2P),
tribromoethanol,
trichloroethanol,
trifluoroethanol)
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Alkylbenzene sulfonate
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Anandamide
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Barbiturates (e.g.,
pentobarbital,
sodium thiopental)
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Chlormethiazole
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D12-116
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Dihydropyridines (e.g.,
nicardipine)
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Etomidate
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Ginseng constituents (e.g.,
ginsenosides (e.g.,
ginsenoside-Rf))
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Glutamic acid (glutamate)
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Ivermectin
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Ketamine
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Neuroactive steroids (e.g.,
alfaxolone,
pregnenolone (eltanolone),
pregnenolone acetate,
minaxolone,
ORG-20599)
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Nitrous oxide
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Penicillin G
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Propofol
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Tamoxifen
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Tetrahydrocannabinol
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Triclofos
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Tropeines (e.g.,
atropine,
bemesetron,
cocaine,
LY-278584,
tropisetron,
zatosetron)
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Volatiles/
gases (e.g.,
chloral hydrate,
chloroform,
desflurane,
diethyl ether (ether),
enflurane,
halothane,
isoflurane,
methoxyflurane,
sevoflurane,
toluene,
trichloroethane (methyl chloroform),
trichloroethylene)
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Xenon
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Zinc
- Antagonists:
2-Aminostrychnine
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2-Nitrostrychnine
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4-Phenyl-4-formyl-N-methylpiperidine
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αEMBTL
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Bicuculline
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Brucine
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Cacotheline
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Caffeine
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Colchicine
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Colubrine
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Cyanotriphenylborate
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Dendrobine
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Diaboline
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Endocannabinoids (e.g.,
2-AG,
anandamide (AEA))
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Gaboxadol (THIP)
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Gelsemine
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iso-THAZ
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Isobutyric acid
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Isonipecotic acid
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Isostrychnine
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Laudanosine
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N-Methylbicuculline
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N-Methylstrychnine
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N,N-Dimethylmuscimol
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Nipecotic acid
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Pitrazepin
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Pseudostrychnine
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Quinolines (e.g.,
4-hydroxyquinoline,
4-hydroxyquinoline-3-carboxylic acid,
5,7-CIQA,
7-CIQ,
7-TFQ,
7-TFQA)
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RU-5135
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Sinomenine
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Strychnine
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Thiocolchicoside
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Tutin
- Negative modulators:
Amiloride
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Benzodiazepines (e.g.,
bromazepam,
clonazepam,
diazepam,
flunitrazepam,
flurazepam)
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Corymine
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Cyanotriphenylborate
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Daidzein
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Dihydropyridines (e.g.,
nicardipine,
nifedipine,
nitrendipine)
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Furosemide
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Genistein
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Ginkgo constituents (e.g.,
bilobalide,
ginkgolides (e.g.,
ginkgolide A,
ginkgolide B,
ginkgolide C,
ginkgolide J,
ginkgolide M))
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Imipramine
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NBQX
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Neuroactive steroids (e.g.,
3α-androsterone sulfate,
3β-androsterone sulfate,
deoxycorticosterone,
DHEA sulfate,
pregnenolone sulfate,
progesterone)
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Opioids (e.g.,
codeine,
dextromethorphan,
dextrorphan,
levomethadone,
levorphanol,
morphine,
oripavine,
pethidine,
thebaine)
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Picrotoxin (i.e.,
picrotin and
picrotoxinin)
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PMBA
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Riluzole
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Tropeines (e.g.,
bemesetron,
LY-278584,
tropisetron,
zatosetron)
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Verapamil
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Zinc
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NMDARTooltip N-Methyl-D-aspartate receptor | |
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Transporter (
blockers) |
GlyT1Tooltip Glycine transporter 1 | |
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GlyT2Tooltip Glycine transporter 2 | |
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