52601-23-7

Basic information

• Product Name: 1-Azabicyclo[2.2.2]octane-2-carboxylic acid hydrochloride
• Synonyms: 1-Azabicyclo[2.2.2]octane-2-carboxylic acid hydrochloride;2-Quinuclidinecarboxylic acid hydrochloride;1-Azabicyclo[2.2.2]octane-2-carboxylic acid, (Hydrochloride) (1:1);quinuclidine-2-carboxylic acid hydrochloride;7-carboxyquinuclidine-7-carboxylic acid hydrochloride
• CAS NO: 52601-23-7
• Molecular Formula: C₈H₁₃NO₂*ClH
• Molecular Weight: 191.65526
• Mol File: 52601-23-7.mol

Chemical Properties

• Melting Point: 304-307℃ (DEC.)
• Appearance: /
• CAS DataBase Reference: 1-Azabicyclo[2.2.2]octane-2-carboxylic acid hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Azabicyclo[2.2.2]octane-2-carboxylic acid hydrochloride(52601-23-7)
• EPA Substance Registry System: 1-Azabicyclo[2.2.2]octane-2-carboxylic acid hydrochloride(52601-23-7)

Safety Data

• Hazardous Substances Data: 52601-23-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Azabicyclo[2.2.2]octane-2-carboxylic acid hydrochloride is used as a muscle relaxant and antispastic agent for the treatment of conditions such as multiple sclerosis, spinal cord injuries, and cerebral palsy. Its action as a GABA agonist helps in alleviating muscle spasms and improving muscle tone.
Used in Off-Label Treatments:
1-Azabicyclo[2.2.2]octane-2-carboxylic acid hydrochloride is also used off-label for conditions like chronic hiccups and alcohol withdrawal, where its muscle-relaxing properties can provide relief and support the management of these conditions.

Upstream product

• 622-26-4 4-(2-Hydroxyethyl)piperidine 
• 89151-44-0 4-(2-hydroxyethyl)piperidine-1-carboxylic acid tert-butyl ester 
• 142374-19-4 tert-butyl 4-(formylmethyl)piperidine-1-carboxylate 
• 885516-98-3 tert-butyl 4-(2-cyano-2-hydroxyethyl)piperidine-1-carboxylate 
• 90196-91-1 quinuclidine-2-carbonitrile 

Downstream Products

• 66073-49-2 quinuiclidine-2-carbonyl chloride hydrochloride 
• 185223-18-1 (1-Aza-bicyclo[2.2.2]oct-2-yl)-(4-p-tolyl-piperazin-1-yl)-methanone 
• 185223-25-0 (1-Aza-bicyclo[2.2.2]oct-2-yl)-[4-(3-chloro-phenyl)-piperazin-1-yl]-methanone 
• 185223-26-1 (1-Aza-bicyclo[2.2.2]oct-2-yl)-[4-(4-chloro-phenyl)-piperazin-1-yl]-methanone 
• 185223-24-9 (1-Aza-bicyclo[2.2.2]oct-2-yl)-[4-(2-chloro-phenyl)-piperazin-1-yl]-methanone 
• 185223-23-8 (1-Aza-bicyclo[2.2.2]oct-2-yl)-[4-(4-methoxy-phenyl)-piperazin-1-yl]-methanone 
• 185223-21-6 (1-Aza-bicyclo[2.2.2]oct-2-yl)-[4-(3-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone 
• 112176-92-8 (+/-)-ethyl quinuclidine-2-carboxylate 
• 72265-42-0 2-benzoylquinuclidine 
• 72265-61-3 2-quinuclidinyl 4-pyridyl ketone 
• 60999-40-8 (1-aza-bicyclo[2.2.2]oct-2-yl)-diphenyl-methanol 
• 72265-51-1 erythro-2-quinuclidinyl-tert-butylcarbinol 
• 72265-56-6 erythro-2-quinuclidinyl-4-pyridylcarbinol 
• 72265-49-7 erythro-2-quinuclidinyl-4-methylphenylcarbinol 

Relevant articles and documents

Discovery of a Novel, Highly Potent, and Selective Thieno[3,2- d]pyrimidinone-Based Cdc7 Inhibitor with a Quinuclidine Moiety (TAK-931) as an Orally Active Investigational Antitumor Agent

In our pursuit of developing a novel, potent, and selective cell division cycle 7 (Cdc7) inhibitor, we optimized the previously reported thieno[3,2-d]pyrimidinone analogue I showing time-dependent Cdc7 kinase inhibition and slow dissociation kinetics. These medicinal chemistry efforts led to the identification of compound 3d, which exhibited potent cellular activity, excellent kinase selectivity, and antitumor efficacy in a COLO205 xenograft mouse model. However, the issue of formaldehyde adduct formation emerged during a detailed study of 3d, which was deemed an obstacle to further development. A structure-based approach to circumvent the adduct formation culminated in the discovery of compound 11b (TAK-931) possessing a quinuclidine moiety as a preclinical candidate. In this paper, the design, synthesis, and biological evaluation of this series of compounds will be presented.