64603-90-3

Basic information

• Product Name: ISOGUVACINE HYDROCHLORIDE
• Synonyms: isoguvacine;C13694;1,2,3,6-tetrahydro-4-Pyridinecarboxylic acid;4-Pyridinecarboxylic acid, 1,2,3,6-tetrahydro-;ISOGUVACINE HCL;ISOGUVACINE HYDROCHLORIDE;1,2,3,6-TETRAHYDRO-PYRIDINE-4-CARBOXYLIC ACIDHYDROCHLORIDE;1,2,3,6-TETRAHYDRO-4-PYRIDINECARBOXYLIC ACID HYDROCHLORIDE
• CAS NO: 64603-90-3
• Molecular Formula: C6H10ClNO2
• Molecular Weight: 163.6
• Product Categories: GABA/Glycine receptor
• Mol File: 64603-90-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 220 °C
• Boiling Point: 280.8°C at 760 mmHg
• Flash Point: 123.6°C
• Appearance: white/solid
• Density: 1.199±0.06 g/cm3(Predicted)
• Vapor Pressure: 0.000983mmHg at 25°C
• Storage Temp.: Store at RT
• Solubility: H2O: refrigerate if not used immediately.soluble
• PKA: pK1:9.07 (25°C)
• Water Solubility: Soluble in water
• CAS DataBase Reference: ISOGUVACINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ISOGUVACINE HYDROCHLORIDE(64603-90-3)
• EPA Substance Registry System: ISOGUVACINE HYDROCHLORIDE(64603-90-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: US5908286
• HazardClass: IRRITANT
• Hazardous Substances Data: 64603-90-3(Hazardous Substances Data)

Usage

Description

ISOGUVACINE HYDROCHLORIDE is an alkaloid that is optically inactive and can be isolated from the nuts of Areca catechu, along with Guvacine. It forms crystalline salts such as the hydrochloride, aurichloride, and platinichloride, with distinct melting points. The alkaloid exhibits faint acidity to litmus and undergoes methylation to produce N-methyl and dimethyl derivatives. Upon distillation with Zn dust, it yields products with the characteristic pyrrole reaction. ISOGUVACINE HYDROCHLORIDE has a boiling point of 195-197°C.

Uses

Used in Pharmaceutical Industry:
ISOGUVACINE HYDROCHLORIDE is used as a GABAA receptor agonist for its anticonvulsant and antiepileptic properties. It plays a crucial role in the treatment of seizures and epilepsy by modulating the activity of the GABAA receptor, which is involved in the regulation of neuronal excitability.
Used in Neurological Applications:
In the field of neurology, ISOGUVACINE HYDROCHLORIDE is utilized for its potential to alleviate symptoms associated with neurological disorders. Its agonistic action on the GABAA receptor can help in managing conditions such as anxiety, insomnia, and muscle relaxation, contributing to the overall well-being of patients suffering from these disorders.
Used in Research and Development:
ISOGUVACINE HYDROCHLORIDE is also employed in research and development for the study of GABAergic systems and the development of new drugs targeting the GABAA receptor. Its unique chemical properties and interactions with the receptor make it a valuable tool in understanding the underlying mechanisms of various neurological conditions and the development of novel therapeutic strategies.

Biological Activity

Specific GABA A receptor agonist.

References

Jahns., Ber., 21,3404 (1888) Jahns., ibid, 23, 2972 (1890) Jahns., ibid, 24,2615 (1891) Jahns., Arch. Pharrn., 229, 669 (1891) Trier., Zeit. Physiol. Chern., 85,372 (1913)

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

Upstream product

• 873190-88-6 C₆H₈F₃NO₃S 
• 124-38-9 carbon dioxide 
• 40240-23-1 ethyl 1,2,3,6-tetrahydropyridine-4-formate 

Downstream Products

• 792136-23-3 methyl 1,2,3,6-tetrahydro-4-pyridinecarboxylate 

Relevant articles and documents

Palladium-Catalyzed Visible-Light-Driven Carboxylation of Aryl and Alkenyl Triflates by Using Photoredox Catalysts

A visible-light-driven carboxylation of aryl and alkenyl triflates with CO2 is developed by using a combination of Pd and photoredox catalysts. This reaction proceeds under mild conditions and can be applied to a wide range of substrates including acyclic alkenyl triflates.

Novel amides useful for treating pain

The present invention relates to compounds of formula (I-VII) or a pharmaceutically acceptable salt or prodrug thereof, in which A, L, R6, R7 and R8 are defined herein. The present invention also relates to methods of trating pain using these compounds and pharmaceutical compositions including these compounds.

GABA agonists. Synthesis and structure-activity studies on analogues of isoguvacine and THIP

A series of analogues of the specific GABA receptor agonists isoguvacine, isonipecotic acid, and THIP (4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-ol) have been synthesized and tested as inhibitors of the binding of 3H-GABA to GABA receptor sites on rat brain membranes in vitro. Introduction of a hydroxy group into the 3- or 4-position of isonipecotic acid results in compounds with considerably reduced receptor affinity. The 7-membered ring analogues of isoguvacine and isonipecotic acid are more than two orders of magnitude weaker than the parent compounds. Replacement of the 3-isoxazolol unit of THIP by related heterocyclic rings also result in dramatic loss of activity. Thus iso-THIP (4,5,6,7-tetrahydroisoxazolo[3,4-c]pyridin-3-ol) is a weak inhibitor of 3H-GABA binding, whereas the 3-pyrazolol THIP analogues are inactive.