Further investigations demonstrated that both the rate of the ultraviolet-catalyzed decomposition of dibutylchloroamine and the yield of newly formed pyrrolidine are strongly dependent on the acidity of the reaction medium faster and higher-yielding reaction was observed with increasing sulfuric acid concentration.
32.
"' Pyrrolidine "', also known as "'tetrahydropyrrole "', is an organic compound with the molecular formula ( CH 2 ) 4 NH . It is a cyclic secondary amine, also classified as a saturated heterocycle.
33.
On the other hand, the stereochemical outcome is reversed with ee selectivities of up to 83 % by using the homologue amino acid catalysts, such as ( S )-?-homoproline, [ ( pyrrolidine-( 2S )-yl ) acetic acid ].
34.
The reaction is very versatile, consisting in the condensation of an alpha-amino acid and an aldehyde to generate a reactive 1, 3-dipole that then adds to a double bond of C60 or CNT, giving a pyrrolidine ring fused to the carbon skeleton.
35.
The analog compound with the " N ", " N "-dialkyl substituents constrained into a pyrrolidine ring, is a slightly stronger agonist for the 5-HT 1A receptor and retains the selectivity over the 5-HT 2A / 2C receptors.
36.
It is more potent than the corresponding pyrrolidine and morpholine analogues ( LPD-824 and LSM-775 respectively ), but is still several times less potent than LSD as a psychedelic in humans, though this does not seem to have been confirmed by any more recent work.
37.
This catalyst, developed by Itsuno and Elias James Corey, is generated by heating ( " R " )-( + )-2-( diphenylhydroxymethyl ) pyrrolidine along with chiral oxazaborolidine catalysts has been used in the synthesis of commercial drugs such as ezetimibe and aprepitant.
38.
Phthalimidopropiophenone is not an active stimulant, but is believed to be potentially capable of acting as a prodrug for cathinone when ingested, as similar N-substituted cathinone derivatives have been encountered by law enforcement, and were found to form cathinone " in vivo " by initial hydroxylation of the pyrrolidine ring followed by subsequent dehydrogenation to the corresponding lactam, then by double dealkylation of the pyrrolidine ring to form the primary amine.
39.
Phthalimidopropiophenone is not an active stimulant, but is believed to be potentially capable of acting as a prodrug for cathinone when ingested, as similar N-substituted cathinone derivatives have been encountered by law enforcement, and were found to form cathinone " in vivo " by initial hydroxylation of the pyrrolidine ring followed by subsequent dehydrogenation to the corresponding lactam, then by double dealkylation of the pyrrolidine ring to form the primary amine.
40.
So dextromoramide, with a pyrrolidine ring on the 1-amide position, a " dextro " methyl group on the 3-position of the alkyl chain, a morpholine ring around the 4-amine group, and both phenyl rings unsubstituted, was by far the most potent out of all the compounds in this series and was the only one that became widely used in medicine ( although the racemic mix racemoramide saw some limited use ).
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