An investigation of the N-demethylation of 3-deoxymorphine and the affinity of the alkylation products to μ, δ, and κ receptors

被引：19

作者：

Csutoras, C

Zhang, A

Bidlack, JM

Neumeyer, JL

机构：

[1] Harvard Univ, Sch Med, Alcohol & Drug Abuse Res Ctr, Belmont, MA 02478 USA

[2] Univ Rochester, Sch Med & Dent, Dept Pharmacol & Physiol, Rochester, NY 14642 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2004年 / 12卷 / 10期

关键词：

morphine; codeine; N-demethylation; opioid receptors; binding affinity;

D O I：

10.1016/j.bmc.2004.03.011

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The N-demethylation of 3-deoxymorphine (1) was investigated using methyl chloroformate and hydrazine. 3-Deoxynormorphine (2) was obtained in 70% yield, and 3-deoxydihydronormorphine (3) was also obtained as a side product. The mu, delta, and kappa receptor binding affinity of a series of N-substituted 3-deoxynormorphines 6 and 7 and N-substituted 3-deoxydihydronormorphines 8-11 was also determined. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：2687 / 2690

页数：4

共 20 条

[1] N-DEMETHYLATION OF MORPHINE AND STRUCTURALLY RELATED COMPOUNDS WITH CHLOROFORMATE ESTERS [J].