The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: (S)-1-(Dimethylamino)propan-2-ol(SMILESS: C[C@H](O)CN(C)C,cas:53636-17-2) is researched.Category: piperazines. The article 《Relative potencies of the stereoisomers of bethanechol on muscarinic receptors》 in relation to this compound, is published in Farmaco, Edizione Scientifica. Let’s take a look at the latest research on this compound (cas:53636-17-2).
The stereoisomers S(+)-bethanechol iodide [86941-71-1] and R(-)-bethanechol iodide [86941-72-2], as well as the racemate [86919-69-9], were prepared from the corresponding S(+)-, R(-)-, or RS-forms of 1-amino-2-propranol by refluxing the primary amine with a mixture of HCO2H and H2CO to produce the corresponding tertiary amines, which in turn were reacted with ClSO2NCO, the product being hydrolyzed with aqueous K2CO3 and the quaternary ammonium salts isolated by reacting the tertiary amines with excess MeI. The resulting bethanechol enantiomers and racemate were tested for their muscarinic receptor affinity (pD2) in an isolated rat ileum preparation As was previously reported for the enantiomers of acetyl-β-methylcholine, the highest activity was associated with the S configuration. The more active enantiomer had twice the affinity of the racemate, as would be the case if the R form had almost no affinity at all. It is concluded that acetyl-β-methylcholine and bethanechol satisfy the steric requirements of a common receptor site.
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Reference:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics