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G002

Sigma-Aldrich

Isoguvacine hydrochloride

solid

Synonym(s):

1,2,3,6-Tetrahydro-4-pyridinecarboxylic acid hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C6H9NO2 · HCl
CAS Number:
68547-97-7
Molecular Weight:
163.60
MDL number:
MFCD00055192
UNSPSC Code:
12352200
PubChem Substance ID:
24278160
NACRES:
NA.77

form

solid

color

white

solubility

H2O: soluble (refrigerate if not used immediately.)
methanol: slightly soluble
neutral and acidic solutions: stable (in basic solutions the free amine can oxidize easily)

SMILES string

Cl[H].OC(=O)C1=CCNCC1

InChI

1S/C6H9NO2.ClH/c8-6(9)5-1-3-7-4-2-5;/h1,7H,2-4H2,(H,8,9);1H

InChI key

SUWREQRNTXCCBL-UHFFFAOYSA-N

Gene Information

human ... GABRA1(2554) , GABRA2(2555) , GABRA3(2556) , GABRA4(2557) , GABRA5(2558) , GABRA6(2559) , GABRB1(2560) , GABRB2(2561) , GABRB3(2562)

Application

Isoguvacine hydrochloride has been used as a γ-aminobutyric acid type A (GABAA) receptor agonist:
  • to study its effects on neuronal activity in rats
  • to study its antiallodynic effect in rats
  • to study its effects on baroreflex gains in rats

Biochem/physiol Actions

Isoguvacine is a strong γ-aminobutyric acid A (GABAA) receptor agonist.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the GABAA Receptors and GABAC Receptors pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Roman Tyzio et al.
Epilepsia, 48 Suppl 5, 96-105 (2007-10-04)
The timing of the developmental switch in the GABA(A) mediated responses from excitatory to inhibitory was studied in Wistar rat CA3 hippocampal pyramidal cells using gramicidin perforated patch-clamp and extracellular recordings. Gramicidin perforated patch recordings revealed a gradual developmental shift
Ke-Zhong Shen et al.
The Journal of physiology, 573(Pt 3), 697-709 (2006-04-15)
The subthalamic nucleus (STN) plays an important role in movement control by exerting its excitatory influence on the substantia nigra pars reticulata (SNR), a major output structure of the basal ganglia. Moreover, excessive burst firing of SNR neurons seen in
Structure-activity studies on the inhibition of GABA binding to rat brain membranes by muscimol and related compounds.
P Krogsgaard-Larsen et al.
Journal of neurochemistry, 30(6), 1377-1382 (1978-06-01)
Tero Viitanen et al.
The Journal of physiology, 588(Pt 9), 1527-1540 (2010-03-10)
GABAergic excitatory [K(+)](o) transients can be readily evoked in the mature rat hippocampus by intense activation of GABA(A) receptors (GABA(A)Rs). Here we show that these [K(+)](o) responses induced by high-frequency stimulation or GABA(A) agonist application are generated by the neuronal
N G Bowery et al.
Experientia, 34(9), 1193-1195 (1978-09-15)
The GABA-mimetic activities of 4 analogues muscimol, isonipecotic acid, isoguvacine and N-methyl isoguvacine have been examined at the GABA receptor in the rat isolated superior cervical ganglion. The depolarizing action of all 4 analogues could be selectively antagonized by bicuculline
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