The N-allyl and N-(cyclopropylmethyl) analogues of (-)-alpha-acetylmethadol and (-)-alpha-methadol have been synthesized and evaluated for opiate agonist and opiate antagonist activity. Both acetylmethadol analogues possessed weak analgesic activity in vivo tests for narcotic analgesia; the N-allyl analogue partially antagonized morphine-induced tail-flick analgesia. All four compounds possessed only opiate agonist-like activity as determined by in vitro studies measuring inhibition of [3H]naloxone binding to opiate receptors.