Pivaloyl esters of N,N-dialkylated dopamine congeners. Central dopamine-receptor stimulating activity

• Published in: Journal of medicinal chemistry Vol. 21; no. 9; pp. 864 - 867
• Main Authors: Wikstrom, Hakan, Lindberg, Per, Martinson, Per, Hjorth, Stephan, Carlsson, Arvid, Hacksell, Uli, Svensson, Uno, Nilsson, J. Lars G
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 01.09.1978
• Subjects: Administration, Oral; Animals; Brain - metabolism; Dihydroxyphenylalanine - metabolism; Dopamine - administration & dosage; Dopamine - analogs & derivatives; Dopamine - chemical synthesis; Dopamine - pharmacology; Dose-Response Relationship, Drug; Injections, Subcutaneous; Male; Motor Activity - drug effects; Rats; Receptors, Dopamine - drug effects; Receptors, Dopamine - metabolism; Valerates - administration & dosage; Valerates - chemical synthesis; Valerates - pharmacology
• DOI: 10.1021/jm00207a005
• ISSN: 0022-2623

In order to test for dopamine-receptor stimulating activity a new, sensitive biochemical screening method was designed. For behavioral studies and for determination of the duration of action on the compounds, motor activity measurements were used. O,O'-Dipivaloyl-N,N-dipropyldopamine (4) was the only derivative of a series of dipivaloyl-N,N-dialkyldopamines studied that showed any significant activity. However, the monopivaloyl ester 2-(3-pivaloyloxyphenyl)-N,N-dipropylethylamine (8) seemed to be more potent. The same relationship was found for the corresponding phenols, N,N-dipropyldopamine (3) and 2-(3-hydroxyphenyl)-N,N-dipropylethylamine (7), although both were more active than their pivaloyl esters.