Antagonism of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane stimulus with a newly identified 5-HT2- versus 5-HT1C-selective antagonist was written by Ismaiel, Abd M.;De Los Angeles, Joseph;Teitler, Milt;Ingher, Stacy;Glennon, Richard A.. And the article was included in Journal of Medicinal Chemistry in 1993.Synthetic Route of C12H14ClFO2 This article mentions the following:
DOM [i.e., 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane] is a 5-HT1C/2 serotonin agonist that exerts stimulus control of behavior in animals. In order to determine if the discriminative stimulus effect of DOM is 5-HT1C– or 5-HT2-mediated, it would be informative to conduct tests of stimulus antagonism with a 5-HT1C or 5-HT2-selective antagonist. To date, no such agents exist. Although the neuroleptic agent spiperone binds at D2 dopamine receptors and 5-HT1A serotonin receptors, (a) it displays about a 1000-fold selectivity for 5-HT2 vs. 5-HT1C sites and (b) it has been used as a “5-HT2-selective” antagonist. Because spiperone is a behaviorally disruptive agent, it is not suitable for use in drug-discrimination studies. Using the spiperone mol. as a starting point, a limited structure-affinity investigation was conducted in order to identify a suitable antagonist with high affinity and selectivity for 5-HT2 receptors, and yet an antagonist that might lack the disruptive actions of spiperone. Various modifications of the spiperone mol. were examined, but most resulted in decreased 5-HT2 affinity or in loss of selectivity. One compound, 8-[3-(4-fluorophenoxy)propyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (I), was shown to bind at 5-HT2 sites with high affinity (Ki = 2 nM) and >2,000-fold selectivity vs. 5-HT1C sites. In tests of stimulus antagonism using rats trained to discriminate 1 mg/kg of DOM from saline vehicle, I behaved as a potent antagonist (ED50 = 0/003 mg/kg) and lacked the disruptive effects associated with spiperone. As such, (a) it would appear that the DOM stimulus is primarily a 5-HT2-mediated, and not 5-HT1C-mediated, phenomenon, and (b) compound I may find application in other pharmacol. investigations where spiperone may not be a suitable antagonist. In the experiment, the researchers used many compounds, for example, 2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (cas: 3308-94-9Synthetic Route of C12H14ClFO2).
2-(3-Chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane (cas: 3308-94-9) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. Dioxole functionalized metal-organic frameworks have also been recently reported.Synthetic Route of C12H14ClFO2
Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem