125-70-2Relevant articles and documents
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Schnider,Gruessner
, p. 2211,2217 (1951)
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Bien,S.,Ginsburg,D.
, p. 2065 - 2068 (1963)
Synthesis and opioid receptor affinity of morphinan and benzomorphan derivatives: Mixed κ agonists and μ agonists/antagonists as potential pharmacotherapeutics for cocaine dependence
Neumeyer, John L.,Bidlack, Jean M.,Zong, Rushi,Bakthavachalam, Venkatesalu,Gao, Peng,Cohen, Dana J.,Negus, S. Stevens,Mello, Nancy K.
, p. 114 - 122 (2000)
This report concerns the synthesis and preliminary pharmacological evaluation of a novel series of K agonists related to the morphinan (-)- cyclorphan (3a) and the benzomorphan (-)cyclazocine (2) as potential agents for the pharmacotherapy of cocaine abuse. Recent evidence suggests that agonists acting at κ opioid receptors may modulate the activity of dopaminergic neurons and alter the neurochemical and behavioral effects of cocaine. We describe the synthesis and chemical characterization of a series of morphinans 3a-c, structural analogues of cyclorphan [(-)-3-hydroxy-N- cyclopropylmethylmorphinan S(+)-mandelate, 3a], the 10-ketomorphinans 4a,b, and the 8-ketobenzomorphan 1b. Binding experiments demonstrated that the cyclobutyl analogue 3b [(-)-3-hydroxy-N-cyclobutylmethylmorphinan S(+)- mandelate, 3b, MCL-101] of cyclorphan (3a) had a high affinity for μ, δ, and κ opioid receptors in guinea pig brain membranes. Both 3a,b were approximately 2-fold more selective for the κ receptor than for the μ receptor. However 3b (the cyclobutyl analogue) was 18-fold more selective for the κ receptor in comparison to the δ receptor, while cyclorphan (3a) had only 4-fold greater affinity for the κ receptor in comparison to the δ receptor. These findings were confirmed in the antinociceptive tests (tail- flick and acetic acid writhing) in mice, which demonstrated that cyclorphan (3a) produced antinociception that was mediated by the δ receptor while 3b did not produce agonist or antagonist effects at the δ receptor. Both 3a,b had comparable κ agonist properties 3a,b had opposing effects at the μ receptor: 3b was a μ agonist whereas 3a was a μ antagonist.
METHODS FOR PREPARING LEVORPHANOL AND RELATED COMPOUNDS, AND COMPOSITIONS THEREOF
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Paragraph 0177-0182, (2020/04/29)
A method for producing substantially pure levorphanol and related compounds, when compared to the conventional process, is provided. In particular, a method for producing substantially pure levorphanol tartrate dihydrate is described. Also described are compositions comprising levorphanol and related compounds, particularly compositions comprising levorphanol tartrate dihydrate, levomethorphan, and norlevorphanol in which the levomethorphan and norlevorphanol are present in the composition in reduced levels.
Selective catalytic hydrogenations and hydrogenolyses, VI: An improved synthesis of 1-benzyl-2-methyloctahydroisoquinolines
Reimann,Hoglmuller
, p. 685 - 690 (2007/10/02)
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