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Related Experiment Videos

Structure-activity relationships among some d-N-alkylated amphetamines

W L Woolverton, G Shybut, C E Johanson

    Pharmacology, Biochemistry, and Behavior
    |December 1, 1980
    PubMed
    Summary

    The potency of d-N-alkylated amphetamines decreases as N-alkyl chain length increases. Shorter chains like d-amphetamine and d-N-methylamphetamine show higher potency in animal models and guinea-pig atria.

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    Area of Science:

    • Pharmacology
    • Neuroscience
    • Medicinal Chemistry

    Background:

    • d-N-Alkylated amphetamines are a class of compounds with potential psychoactive properties.
    • Understanding structure-activity relationships is crucial for drug development and predicting effects.

    Purpose of the Study:

    • To synthesize a series of d-N-alkylated amphetamines up to d-N-butylamphetamine.
    • To compare the potencies of these synthesized compounds across various in vivo and in vitro models.

    Main Methods:

    • Self-administration in rhesus monkeys for intravenous drug infusions.
    • Milk intake measurement in rats as an indicator of drug effects.
    • Assessment of contractile responses in isolated guinea-pig atria.

    Main Results:

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    • d-amphetamine, d-N-methylamphetamine, and d-N-ethylamphetamine were self-administered by monkeys, with maximal rates influenced by prior drug exposure (pentobarbital vs. cocaine).
    • d-N-propylamphetamine and d-N-butylamphetamine showed reduced self-administration and lower maximal response rates compared to shorter-chain analogs.
    • All compounds dose-dependently decreased milk intake in rats, with potency inversely related to N-alkyl chain length.
    • Most compounds increased guinea-pig atrial beating rate, except for d-N-butylamphetamine, indicating varying cardiovascular effects.

    Conclusions:

    • The N-alkyl chain length of d-N-alkylated amphetamines significantly influences their pharmacological potency.
    • Potency generally decreases with increasing N-alkyl chain length, particularly beyond ethyl substitution.
    • These findings provide valuable structure-activity relationship data for this class of amphetamine derivatives.