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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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Laura Lagostena et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 30(3), 885-893 (2010-01-22)
GABA, the main inhibitory transmitter in adulthood, early in postnatal development exerts a depolarizing and excitatory action. This effect, which results from a high intracellular chloride concentration ([Cl(-)](i)), promotes neuronal growth and synaptogenesis. During the second postnatal week, the developmental
Kai Y Fan et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 32(40), 13718-13728 (2012-10-05)
The symptoms of Parkinson's disease (PD) are related to changes in the frequency and pattern of activity in the reciprocally connected GABAergic external globus pallidus (GPe) and glutamatergic subthalamic nucleus (STN). In idiopathic and experimental PD, the GPe and STN
Palakodety Radha Krishna et al.
Journal of combinatorial chemistry, 10(3), 426-435 (2008-04-16)
The preparation of chiral tetrahydropyridine-4-carboxylates as isoguvacine analogues and azasugars with a tertiary stereocenter from L-amino acids via diastereoselective a Baylis-Hillman reaction of N-allyl-Boc alpha-aminal, followed by ring-closing metathesis and dihydroxylation sequences, is reported.
Intracapsular technique of transplant nephrectomy
D E Sutherland, et al.
Surgery, Gynecology & Obstetrics, 146(6), 950-952 (1978)
Jen-Kun Cheng et al.
Anesthesia and analgesia, 102(1), 182-187 (2005-12-22)
Gabapentin is a novel analgesic whose mechanism of action is not known. We investigated in a postoperative pain model whether adenosine triphosphate (ATP)-sensitive K+ (K(ATP)) channels, N-methyl-d-aspartic acid (NMDA) receptors, and Ca2+ channels are involved in the antiallodynic effect of
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