Isonipecotic acid
Names
IUPAC name
4-Piperidinecarboxylic acid
Identifiers
498-94-2 Y
3D model (Jmol )
Interactive image
ChEMBL
ChEMBL279998 N
ChemSpider
3641 N
ECHA InfoCard
100.007.158
EC Number
207-872-3
4227
PubChem
3773
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
Properties
C6 H11 NO2
Molar mass
129.16 g/mol
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is Y N ?)
Infobox references
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").
A known use of isonipecotic acid is to prepare 4-(4-Chlorobenzoyl)-piperidine,[2] which in-turn finds an application in the synthesis of Cloroperone (Cloperone ).
An alternative use in in the preparation of (4-bromophenyl)(4-piperidyl)methanone-(Z)—O-ethyloxime.[3]
The 4-(p-fluorobenzoyl)piperidine moiety[4] [5] is known to have application in the synthesis of Ketanserin, Setoperone, Lidanserin, Pirenperone, altanserin & Duoperone.
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 .
^ Cavallini et al. Farmaco, Edizione Scientifica, 1957 , vol. 12, p. 853,862.
^ George S. K. Wong, Jeonghan Park, Weidong Tong, Ramani Raghavan, U.S. Patent 6,914,142 (2005 to Schering Corporation).
^ Chumpradit, S.; Choi, S. R.; Hou, C.; Acton, P. D.; Kung, H. F. (2001). "Novel TC-99M N2S2 derivatives for imaging 5HT2A receptors". Journal of Labelled Compounds and Radiopharmaceuticals . 44 (S1): S524–S526. doi :10.1002/jlcr.25804401186 . ISSN 0362-4803 .
^ Journal of Medicinal Chemistry, vol. 46, # 25 p. 5512 - 5532. doi :10.1021/jm0309349
Receptor
(ligands )
Agonists
PAMs
(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 , cholesterol )
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 , diethyl ether , paraldehyde , sevoflurane )
Antagonists
NAMs
1,3M1B
3M2B
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
Bilobalide
CHEB
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
Iomazenil (123 I)
Isoallopregnanolone
Isopregnanolone (sepranolone)
L-655,708
Laudanosine
Leptazol
Lindane
MaxiPost
Morphine
Morphine-3-glucuronide
MRK-016
Naloxone
Naltrexone
Nicardipine
Non-steroidal antiandrogens (e.g., apalutamide , bicalutamide , enzalutamide , flutamide , nilutamide )
Oenanthotoxin
Pentetrazol (metrazol)
Phenylsilatrane
Picrotoxin (i.e., picrotin and picrotoxinin )
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
Agonists
PAMs
Antagonists
NAMs
Agonists
Antagonists
NAMs
PAMs
Transporter
(blockers )
Enzyme
(inhibitors )
Others
Precursors
Analogues
Others
Receptor
(ligands )
PAMs: Alcohols (e.g., brometone , chlorobutanol (chloretone) , ethanol , 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
Antagonists: 2-Aminostrychnine
2-Nitrostrychnine
4-Phenyl-4-formyl-N-methylpiperidine
αEMBTL
Bicuculline
Brucine
Cacotheline
Caffeine
Colchicine
Colubrine
Cyanotriphenylborate
Dendrobine
Diaboline
Endocannabinoids (e.g., 2-AG , anandamide (AEA) )
Gaboxadol (THIP)
Gelsemine
iso-THAZ
Isobutyric acid
Isonipecotic acid
Isostrychnine
Laudanosine
N-Methylbicuculline
N-Methylstrychnine
N,N-Dimethylmuscimol
Nipecotic acid
Pitrazepin
Pseudostrychnine
Quinolines (e.g., 4-hydroxyquinoline , 4-hydroxyquinoline-3-carboxylic acid , 5,7-CIQA , 7-CIQ , 7-TFQ , 7-TFQA )
RU-5135
Sinomenine
Strychnine
Thiocolchicoside
Tutin
NAMs: 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 and picrotoxinin )
PMBA
Riluzole
Tropeines (e.g., bemesetron , LY-278584 , tropisetron , zatosetron )
Verapamil
Zinc
Transporter
(blockers )
Others