《The action of tertiary and quaternary arecaidine and dihydroarecaidine esters on the guinea pig isolated ileum》 was published in British Journal of Pharmacology and Chemotherapy in 1966. These research results belong to Gloge, Holger; Luellmann, Heinz; Mutschler, Erich. Application of 1690-72-8 The article mentions the following:
A homologous series of tertiary and quaternary arecaidine esters (methyl to isobutyl), as well as the corresponding dihydrocompds., were investigated quant. on the isolated ileum of the guinea pig. The tertiary arecaidine esters are agonists. Highest activities (effective doses) are observed for the Et ester (E.D.50 = 1.5 × 10-4M) and for arecoline, the Me ester (E.D.50 = 5.8 × 10-8M). Esters with a longer side-chain show considerably lower activity. The intrinsic activities of arecaidine Et ester, arecoline, and dimethylaminoethyl acetate are higher than that of acetylcholine. Hydrogenation of the double bond in the ring markedly reduces the affinity and intrinsic activity of the tertiary arecaidine esters. Hydrogenated esters with a longer side-chain act as inhibitors. Quaternization by means of iodomethylation exerts varying influences on the intrinsic activities of arecaidine esters. In the case of the Me ester the intrinsic activity is somewhat reduced whereas that of the Et ester considerably decreases upon iodomethylation, thus yielding a partial antagonist. Similar transformation of esters with a longer side-chain leads to a complete loss of intrinsic activity. The quaternized compounds thus obtained are inhibitors with atropine-like action. Iodoethylation and iodopropylation even abolish the intrinsic activities of esters with a short side-chain. Hydrogenation of the double bond in the ring of the quaternary compounds similarly diminishes the activity as observed for the tertiary compounds For aliphatic N atoms, quaternization is essential in order to enable a reaction with the acetylcholine receptors of the muscarine type. In the case of ring N atoms, the tertiary protonated form is necessary for obtaining a high intrinsic activity upon combination with the receptor mol. In arecaidine esters, quaternization of the ring N atom reduces or even destroys intrinsic activity, in proportion to the length of the ester side-chain. The experimental process involved the reaction of Methyl 1-methylpiperidine-3-carboxylate(cas: 1690-72-8Application of 1690-72-8)
Methyl 1-methylpiperidine-3-carboxylate(cas: 1690-72-8) is a member of piperidine. Piperidine is ubiquitous structural motif widely occurred in diverse synthetically and naturally occurring bioactive molecules. Piperidines are an immensely important class of compounds medicinally: the piperidine ring is the most common heterocyclic subunit among FDA approved drugs.Application of 1690-72-8
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem