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Synthesis and LSD-like Discriminative Stimulus Properties in a Series of N(6)-Alkyl Norlysergic Acid

Synthesis and LSD-like Discriminative Stimulus Properties in a Series of N(6)-Alkyl Norlysergic Acid

  1. candy_flipping
    Hoffman.A et al, J Med. Chem. 1985,28, 1252-1255

    A convenient method for the synthesis of N(G)-alkyl norlysergic acid NJV-diethylamide derivatives was developed.
    A series of these compounds was synthesized and tested for substitution in the two-lever drug discrimination assay,
    in rats trained to discriminate injections of d-LSD tartrate (185.5 nmol/kg, ip) from saline. A dose-response curve
    for each of the compounds in the series was generated. Structure-activity relationships were developed, based on
    comparison of the estimated ED, values from these curves. Of the compounds that substituted for LSD, the N(G)-ethyl
    and -allyl were approximately 2-3 times more potent than LSD itself. The N(G)-propyl was equipotent to LSD,
    while the isopropyl derivative was half as active. The n-butyl compound was 1 order of magnitude less potent than
    LSD, suggesting a similarity to the SAR of certain serotonin and dopamine agonists.