Alkanolamides Sterically Related to Ergometrine

Abstract

The ethanolamides of 3‐dimethylaminopropionic acid, 1‐methyl‐1,2,5,6‐tetrahydronicotinic acid (arecaidine) and 1‐methylhexahydronicotinic acid, and propanolamides of 3‐dimethylaminopropionic acid and arecaidine have been synthesised. None of these compounds had demonstrable oxytocic activity on the isolated oestrous rat uterus in concentrations up to 1 mg./ml. Arecaidine propanolamide inhibited acetylcholine‐induced contractions in concentrations of 0.075 to 0.3 mg./ml. The 2‐styryl derivatives of 3‐dimethylaminopropionic and 4‐dimethylaminobutyric acids were found to be unstable.

Dissociation Constants of Some Compounds Related to Lysergic Acid

“…2-(3'-Dimethylaminopropionamido)ethanol, ( f)-2-(3'-dimethylaminopropionumido) propanol and 2-(1'-methylhexahydronicotin4mido)ethanol hydrochlorides. The acid oxalates, prepared by the method of Chilton and Stenlake (1962), were converted to hydrochlorides as follows: 0.1 millimole of the oxalate dissolved in water (1 ml.) was treated with a very small excess of solution of calcium chloride (10 per cent).…”

“…2-(l'-Methyl-1',2',5',6'tetrahydronicotinamido)ethanol and ( 5 ) -2 - -methyl-l',2',5',6'-tetrahydronicotinamido)propanol hydrochlorides. Prepared by treatment of aqueous solutions of the dihydrochlorides of 2-aminoethyl 1,2,5,6-tetrahydronicotinate and (&)-2-aminopropyl 1,2,5,6tetrahydronicotinate respectively with a slight excess of sodium hydroxide followed by neutralisation with dilute hydrochloric acid as described by Chilton and Stenlake (1962). The neutralised solution was used directly for titration.…”

Muscarinic Properties of Compounds Related to Arecaidine Propargyl Ester

“…All compounds were synthesized from 1-methyl-1,2,5,6tetrahydro-3-carboxypyridine hydrochloride (CAS 6018-28-6, arecaidine hydrochloride) which was transformed into the acyl chloride [10] and then allowed to react with the following alcohols: 2-propynol, 2-butyne-1-ol, 2,3pentadien-1-ol [11], 2,3-butadien-1-ol [12], E-2-buten-1ol [13], n-butan-1-ol, 2,4-pentadiyn-1-ol [14] and cyclopropanemethanol. The structures of the compounds used in the present study are given in Table 1.…”