81487-04-9

Basic information

• Product Name: exo-8-Methyl-3-aMino-azabicyclo[3.2.1]octane
• Synonyms: exo-8-Methyl-3-aMino-azabicyclo[3.2.1]octane;exo-8-Methyl-3-aMino-azab...;exo-3-Aminotropane;(3-exo)-8-Methyl-8-azabicyclo[3.2.1]octan-3-amine;exo-8-methyl-8-azabicyclo[3.2.1]octan-3-amine;(1R,3r,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-amine;8-Azabicyclo[3.2.1]octan-3-amine, 8-methyl-, (3-exo)-
• CAS NO: 81487-04-9
• Molecular Formula: C₈H₁₆N₂
• Molecular Weight: 140.22604
• Mol File: 81487-04-9.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: exo-8-Methyl-3-aMino-azabicyclo[3.2.1]octane(CAS DataBase Reference)
• NIST Chemistry Reference: exo-8-Methyl-3-aMino-azabicyclo[3.2.1]octane(81487-04-9)
• EPA Substance Registry System: exo-8-Methyl-3-aMino-azabicyclo[3.2.1]octane(81487-04-9)

Safety Data

• Hazardous Substances Data: 81487-04-9(Hazardous Substances Data)

Usage

General Description

Exo-8-Methyl-3-amino-azabicyclo[3.2.1]octane, also known as isopropyl norantipine, is a chemical compound with a bicyclic structure that is commonly used as a research tool in neuroscience. It acts as a potent and selective antagonist of alpha-1 adrenergic receptors, meaning it blocks the action of these receptors in the central nervous system. This can lead to effects such as reduced blood pressure and heart rate, making it a potential candidate for the treatment of hypertension and other cardiovascular conditions. Additionally, exo-8-Methyl-3-amino-azabicyclo[3.2.1]octane has also been investigated for its potential anti-addictive properties, particularly in the context of opioid addiction. Its unique structure and pharmacological profile make it an important compound for understanding the role of alpha-1 adrenergic receptors in various physiological and pathological processes.

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Relevant articles and documents

Synthesis and biological investigations of 3β-aminotropane arylamide derivatives with atypical antipsychotic profile

This work is a continuation of our previous research, concentrating this time on lead structure modification to increase the 5-HT1A receptor affinity and water solubility of designed compounds. Therefore, the compounds synthesised within the present project included structural analogues of 3β-acylamine derivatives of tropane with the introduction of a methyl substituent in the benzyl ring and a 2-quinoline, 3-quinoline, or 6-quinoline moiety. A series of novel 3β-aminotropane derivatives was evaluated for their affinity for 5-HT1A, 5-HT2A, and D2 receptors, which allowed for the identification of compounds 12e, 12i, and 19a as ligands with highest affinity for the tested receptors; they were then subjected to further evaluation in preliminary in vivo studies. Selected compounds 12i and 19a displayed antipsychotic properties in the d-amphetamine-induced and MK-801-induced hyperlocomotor activity test in mice. Moreover, compound 19a showed significant antidepressant-like activity in the forced swim test in mice.

METHOD FOR PRODUCING N-SUBSTITUTED 3β-AMINONORTROPANES

The invention relates to a method for producing, on the basis of the corresponding 3-oxonortropane or the corresponding 3α-aminonortropane, N-substituted 3β-aminonortropanes of formula (I), wherein R1 is defined as in the claim. According to the inventive method, the starting compounds are converted to the corresponding imines by means of an arylmethylamine or an arylaldehyde, said imines are tautomerized or isomerized and then hydrolyzed. The invention also relates to the novel compounds of formula (V), wherein R1 and Ar are defined as in the claims.

Molecular features associated with polyamine modulation of NMDA receptors

The effect of 1,3-diamines on basal and spermine-stimulated [3H]MK-801 binding was investigated. Systematic variations in the molecular parameters revealed that, in general, lipophilic 1,3-diamines inhibited and hydrophilic 1,3-diamines enhance