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Isonipecotic acid

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Isonipecotic acid

Names

Preferred IUPAC name

Piperidine-4-carboxylic acid

Identifiers

CAS Number

498-94-2^Y

3D model (JSmol)

Interactive image

ChEMBL

ChEMBL279998^N

ChemSpider

3641^N

ECHA InfoCard

100.007.158

EC Number

207-872-3

IUPHAR/BPS

4227

PubChem CID

3773

UNII

M5TZP1RWIE^Y

CompTox Dashboard(EPA)

DTXSID9060100

InChI

InChI=1S/C6H11NO2/c8-6(9)5-1-3-7-4-2-5/h5,7H,1-4H2,(H,8,9)^N
Key: SRJOCJYGOFTFLH-UHFFFAOYSA-N^N
InChI=1/C6H11NO2/c8-6(9)5-1-3-7-4-2-5/h5,7H,1-4H2,(H,8,9)
Key: SRJOCJYGOFTFLH-UHFFFAOYAD

SMILES

C1CNCCC1C(=O)O

Properties

Chemical formula

C₆H₁₁NO₂

Molar mass

129.16 g/mol

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

Isonipecotic acid is aheterocyclic compound which acts as aGABA_A receptor partial agonist.^[1]

It consists of apiperidine ring with acarboxylic acid moiety in theiso position (and as such is also known as "4-piperidinecarboxylic acid").

References

[edit]

^Mortensen M, Kristiansen U, Ebert B, Frølund B, Krogsgaard-Larsen P, Smart TG (June 2004)."Activation of single heteromeric GABA(A) receptor ion channels by full and partial agonists".The Journal of Physiology.557 (Pt 2):389–413.doi:10.1113/jphysiol.2003.054734.PMC 1665090.PMID 14990676.

Hypnotics/sedatives (N05C)

GABA_A

Alcohols	2M2B Chloralodol Ethanol (alcohol) Diethylpropanediol Ethchlorvynol Methylpentynol Trichloroethanol
Barbiturates	Allobarbital Amobarbital Aprobarbital Barbital Butabarbital Butobarbital Cyclobarbital Ethallobarbital Heptabarb Hexobarbital Mephobarbital Methohexital Narcobarbital Pentobarbital Phenallymal Phenobarbital Propylbarbital Proxibarbal Reposal Secobarbital Talbutal Thiamylal Thiopental Thiotetrabarbital Vinbarbital Vinylbital
Benzodiazepines	Brotizolam Cinolazepam Climazolam Clonazolam Doxefazepam Estazolam Flubromazolam Flunitrazolam Flunitrazepam Flurazepam Flutemazepam Flutoprazepam Loprazolam Lormetazepam Midazolam Nimetazepam Nitemazepam Nitrazepam Nitrazolam Quazepam Temazepam Triazolam
Carbamates	Carisoprodol Emylcamate Ethinamate Hexapropymate Meprobamate Methocarbamol Phenprobamate Procymate Tybamate
Imidazoles	Etomidate Metomidate Propoxate
Monoureides	Acecarbromal Apronal (apronalide) Bromisoval Capuride Carbromal Ectylurea
Neuroactive steroids	Acebrochol Allopregnanolone Alphadolone Alphaxolone Eltanolone Hydroxydione Minaxolone Progesterone
Nonbenzodiazepines	Eszopiclone Indiplon Lirequinil Necopidem Pagoclone Pazinaclone Saripidem Suproclone Suriclone Zaleplon Zolpidem Zopiclone
Phenols	Propofol
Piperidinediones	Glutethimide Methyprylon Pyrithyldione Piperidione
Quinazolinones	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164
Others	Acetophenone Acetylglycinamide chloral hydrate Bromide compounds Lithium bromide Potassium bromide Sodium bromide Centalun Chloral betaine Chloral hydrate Chloralose Clomethiazole Dichloralphenazone Gaboxadol Kavalactones Loreclezole Paraldehyde Petrichloral Sulfonylalkanes Sulfonmethane (sulfonal) Tetronal Trional Triclofos Sesquiterpene Isovaleramide Isovaleric acid Valerenic acid

GABA_B

H₁

Antihistamines	Captodiame Cyproheptadine Diphenhydramine Doxylamine Hydroxyzine Methapyrilene Perlapine Pheniramine Promethazine Propiomazine
Antidepressants	Serotonin antagonists and reuptake inhibitors Etoperidone Nefazodone Trazodone Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin Mirtazapine, etc.
Antipsychotics	Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc.

α₂-Adrenergic

5-HT_2A

Antidepressants	Trazodone Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin Mirtazapine, etc.
Antipsychotics	Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc.
Others	Niaprazine

Melatonin

Orexin

α₂δ VDCC

Others

GABA receptor modulators

Ionotropic

GABA_ATooltip γ-Aminobutyric acid A receptor

Agonists:(+)-Catechin
Bamaluzole
Barbiturates (e.g.,phenobarbital)
Beta-Alanine
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
L-838,417
Lignans (e.g.,honokiol)
Methylglyoxal
Monastrol
Muscimol
Nefiracetam
Neuroactive steroids (e.g.,allopregnanolone)
Org 20599
PF-6372865
Phenibut
Picamilon
4-PIOL
P4S
Progabide
Propofol
Quisqualamine
SL-75102
Taurine
TACA
TAMP
Terpenoids (e.g.,borneol)
Thiomuscimol
Tolgabide
ZAPA

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

Metabotropic

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

Glycine receptor modulators

Receptor
(ligands)

GlyRTooltip Glycine receptor

Positive modulators:Alcohols (e.g.,brometone,chlorobutanol (chloretone),ethanol (alcohol),tert-butanol (2M2P),tribromoethanol,trichloroethanol,trifluoroethanol)
Alkylbenzene sulfonate
Anandamide
Barbiturates (e.g.,pentobarbital,sodium thiopental)
Chlormethiazole
D12-116
Dihydropyridines (e.g.,nicardipine)
Etomidate
Ginseng constituents (e.g.,ginsenosides (e.g.,ginsenoside-Rf))
Glutamic acid (glutamate)
Ivermectin
Ketamine
Neuroactive steroids (e.g.,alfaxolone,pregnenolone (eltanolone),pregnenolone acetate,minaxolone,ORG-20599)
Nitrous oxide
Penicillin G
Propofol
Tamoxifen
Tetrahydrocannabinol
Triclofos
Tropeines (e.g.,atropine,bemesetron,cocaine,LY-278584,tropisetron,zatosetron)
Volatiles/gases (e.g.,chloral hydrate,chloroform,desflurane,diethyl ether (ether),enflurane,halothane,isoflurane,methoxyflurane,sevoflurane,toluene,trichloroethane (methyl chloroform),trichloroethylene)
Xenon
Zinc

Negative modulators:Amiloride
Benzodiazepines (e.g.,bromazepam,clonazepam,diazepam,flunitrazepam,flurazepam)
Corymine
Cyanotriphenylborate
Daidzein
Dihydropyridines (e.g.,nicardipine,nifedipine,nitrendipine)
Furosemide
Genistein
Ginkgo constituents (e.g.,bilobalide,ginkgolides (e.g.,ginkgolide A,ginkgolide B,ginkgolide C,ginkgolide J,ginkgolide M))
Imipramine
NBQX
Neuroactive steroids (e.g.,3α-androsterone sulfate,3β-androsterone sulfate,deoxycorticosterone,DHEA sulfate,pregnenolone sulfate,progesterone)
Opioids (e.g.,codeine,dextromethorphan,dextrorphan,levomethadone,levorphanol,morphine,oripavine,pethidine,thebaine)
Picrotoxin (i.e.,picrotin andpicrotoxinin)
PMBA
Riluzole
Tropeines (e.g.,bemesetron,LY-278584,tropisetron,zatosetron)
Verapamil
Zinc

NMDARTooltip N-Methyl-D-aspartate receptor

Seehere instead.

Transporter
(blockers)

GlyT1Tooltip Glycine transporter 1	ACPPB ALX-5407 (NFPS) ASP2535 Bitopertin (RG1678/RO4917838) CP-802079 Ethanol (alcohol) Glycyldodecylamide GSK1018921 Iclepertin LY-2365109 Mardepodect ORG-24598 ORG-25935 (SCH-900435) Pesampator (BIIB-104, PF-04958242) PF-03463275 Sarcosine SNG-12 (Synapsinae) SSR-103,800 SSR-504,734 Tilapertin
GlyT2Tooltip Glycine transporter 2	ALX-1393 Amoxapine Ethanol (alcohol) NAGly Opiranserin (VVZ-149) ORG-25543 VVZ-368

See also: Receptor/signaling modulators; GABA receptor modulators; GABA_A receptor positive modulators; Ionotropic glutamate receptor modulators

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