2,5-Bis(3,4-dimethoxybenzyl)cyclopentylamine, a peripheral dopamine blocking agent.
2,5-Bis(3,4-dimethoxybenzyl)cyclopentylamine hydrochloride has been synthesized. The intermediate 2,5-bis-(3,4-dimethoxybenzyl)cyclopentanone was formed in 91.8% yield using a sodium methoxide catalyzed aldol condensation and catalytic reduction. The oxime of this ketone was catalytically hydrogenated to the amine which was converted to the hydrochloride (76%). The amine hydrochloride was found to be an effective antagonist to the low-dose hypotensive effect of dopamine; the half-life of this effect was 18 min. At dopamine doses of 3 mg/kg in the atropinized and phenoxybenzamine treated dog, the ED50 for blockade was 4--5 mumol/kg. In direct contrast to its peripheral dopamine blocking activity, the compound potentiates apomorphine-induced stereotypy.
D000588:Amines / Q000138:chemical synthesis / Q000494:pharmacology*; D000818:Animals; D001794:Blood Pressure / Q000187:drug effects; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000494:pharmacology*; D004285:Dogs; D018492:Dopamine Antagonists; D004305:Dose-Response Relationship, Drug; D005260:Female; D006439:Hemodynamics / Q000187:drug effects; D006801:Humans; D008297:Male; D051379:Mice; D013239:Stereotyped Behavior / Q000187:drug effects
C018233:2,5-bis(3,4-dimethoxybenzyl)cyclopentylamine; D000588:Amines; D003517:Cyclopentanes; D018492:Dopamine Antagonists