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696420

Sigma-Aldrich

(R)-Ethyl piperidine-3-carboxylate

97%

Sinónimos:

(R)-Piperidine-3-carboxylic acid ethyl ester, (R)-ethyl nipecotate

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About This Item

Fórmula empírica (notación de Hill):
C8H15NO2
Número de CAS:
25137-01-3
Peso molecular:
157.21
MDL number:
MFCD03093637
UNSPSC Code:
12352100
PubChem Substance ID:
329761827
NACRES:
NA.22

assay

97%

form

liquid

density

1.092 g/mL at 25 °C

SMILES string

CCOC(=O)[C@@H]1CCCNC1

InChI

1S/C8H15NO2/c1-2-11-8(10)7-4-3-5-9-6-7/h7,9H,2-6H2,1H3/t7-/m1/s1

InChI key

XIWBSOUNZWSFKU-SSDOTTSWSA-N

Application

Reactant for synthesis of:
  • DPP-4 inhibitors
  • Dual H1/5-HT2A receptor antagonists for treatment of sleep disorders
  • Serotonin and noradrenaline reuptake inhibitors
  • GABA uptake inhibitors

Reactant for stereocontrolled hydoiodination of alkynes

Used for an orally potent anti-anxiety drug

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

219.2 °F

flash_point_c

104 °C

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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M Potegal
Psychopharmacology, 89(4), 444-448 (1986-01-01)
The GABA uptake inhibitor ethyl (R,S)-nipecotate produces a dose-dependent suppression of aggression in highly aggressive hamsters but not in minimally aggressive ones. This suppression occurs at doses below those producing peripheral cholinergic effects; at the highest dose used it persists
S H Zorn et al.
The Journal of pharmacology and experimental therapeutics, 242(1), 173-178 (1987-07-01)
Previous reports have suggested that the ethyl ester of (R)-nipecotic acid ethyl ester [(R)-NAEE] displays cholinomimetic properties in vivo. The present study was undertaken to characterize more fully this action by examining the effects of (R)-NAEE in a number of
T Andree et al.
Life sciences, 32(19), 2265-2272 (1983-05-09)
THIP (4,5,6,7-tetrahydroisoxazolo (5,4-c) pyridone-3-ol), a direct acting GABA receptor agonist, has been shown to have antinociceptive properties. To determine whether tolerance develops to the analgesic response, mice received multiple injections of THIP for up to 21 days after which analgesia
Jia-Hua Hu et al.
Journal of neuroscience research, 73(4), 565-572 (2003-08-05)
The present study focused on the involvement of gamma-aminobutyric acid transporter I (GAT1) in pain. We found that GABA uptake was increased in mouse spinal cord at 20 min and 120 min after formalin injection and in mouse brain at
Wen-Juan Zhao et al.
Acta pharmacologica Sinica, 24(10), 991-995 (2003-10-09)
The changes of seizure susceptibility of transgenic mice overexpressing GABA transporter-1 (GAT-1) were studied to clarify the possible role of GABAergic transmission in epileptogenesis. Seizures were induced by intraperitoneal administration of pentylenetetrazol (PTZ), picrotoxin (PIC), or kainic acid (KA) respectively.
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