Add time:08/05/2019 Source:sciencedirect.com
2,5-Dimethyl-2′-hydroxy-9α-(3-methylbutyl)-6,7-benzomorphan, the 9β-analogue, and 9α-N-substituted (N-ethyl, propyl, butyl, pentyl, hexyl, phenylethyl, allyl, and cyclopropylmethyl) compounds were synthesized and evaluated biochemically and pharmacologically. The 9β N-methyl compound was found to be as potent as morphine in the mouse hot plate assay and had one-seventh the affinity of morphine for the opioid receptor. The N-alkyl and N-phenethyl 9α-substituted compounds were either inactive or relatively ineffective as antinociceptive agents. None of the examined compounds substituted for morphine in single-dose suppression studies in the rhesus monkey. The N-cyclopropylmethyl compound in the 9α series had half the narcotic antagonist potency of nalorphine and one-eighth of its affinity for the opioid receptor. The 9α-(3-methylbutyl) moiety, unlike bulky substituents in the 9β position of 6,7-benzomorphans, generally lowers affinity for the μ opioid receptor and diminishes their in vivo activity as agonists or antagonists.
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