Synthesis and pharmacology of the enantiomers of cis-7-hydroxy-3-methyl-2-(dipropylamino)tetralin.
The enantiomers of cis-7-hydroxy-3-methyl-2-(dipropylamino)tetralin (3) have been synthesized and evaluated for activity at central dopamine (DA), 5-hydroxytryptamine, and norepinephrine (NE) receptors, by use of biochemical and behavioral tests in rats. In addition, the affinities of the compounds for striatal [3H]spiroperidol and [3H]N-propylnorapomorphine binding sites were determined. The absolute configuration of the enantiomers was determined by X-ray diffraction of (+)-3. The pharmacological effects of both enantiomers are complicated, but (2R,3S)-7-hydroxy-3-methyl-2-(dipropylamino)tetralin [(-)-3] produced biochemical effects in vivo similar to those elicited by classical DA D2-receptor antagonists.
Johansson
A M
AM
Department of Organic Pharmaceutical Chemistry, Uppsala University, Sweden.
Fredriksson
K
K
Hacksell
U
U
Grol
C J
CJ
Svensson
K
K
Carlsson
A
A
Sundell
S
S
D006916:5-Hydroxytryptophan / Q000378:metabolism; D017371:8-Hydroxy-2-(di-n-propylamino)tetralin / Q000031:analogs & derivatives*; D000818:Animals; D001058:Apomorphine / Q000031:analogs & derivatives / Q000378:metabolism; D001667:Binding, Competitive; D002417:Cattle; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D003198:Computer Simulation; D003461:Crystallography; D004295:Dihydroxyphenylalanine / Q000378:metabolism; D018492:Dopamine Antagonists; D066298:In Vitro Techniques; D007536:Isomerism; D008297:Male; D008968:Molecular Conformation; D015394:Molecular Structure; D009043:Motor Activity / Q000187:drug effects; D051381:Rats; D012110:Reserpine / Q000494:pharmacology; D013134:Spiperone / Q000378:metabolism; D013329:Structure-Activity Relationship; D013764:Tetrahydronaphthalenes; D014961:X-Ray Diffraction
D018492:Dopamine Antagonists; D013764:Tetrahydronaphthalenes; C054003:8-hydroxy-1-methyl-2-(di-n-propylamino)tetralin; D013134:Spiperone; C009074:N-n-propylnorapomorphine; D004295:Dihydroxyphenylalanine; D017371:8-Hydroxy-2-(di-n-propylamino)tetralin; D012110:Reserpine; D006916:5-Hydroxytryptophan; D001058:Apomorphine