An investigation of the N-demethylation of 3-deoxymorphine and the affinity of the alkylation products to mu, delta, and kappa receptors.
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.
Csutoras
Csaba
C
Alcohol and Drug Abuse Research Center, McLean Hospital, Harvard Medical School, 115 Mill Street, Belmont, MA 02478, USA.
Zhang
Ao
A
Bidlack
Jean M
JM
Neumeyer
John L
JL
D000818:Animals; D016466:CHO Cells; D002462:Cell Membrane / Q000737:chemistry; D006224:Cricetinae; D003412:Cricetulus; D005561:Formates / Q000737:chemistry; D008745:Methylation; D009020:Morphine / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D009022:Morphine Derivatives; D009294:Narcotics / Q000737:chemistry* / Q000494:pharmacology; D011957:Receptors, Opioid / Q000378:metabolism*; D017465:Receptors, Opioid, delta / Q000378:metabolism; D017473:Receptors, Opioid, kappa / Q000378:metabolism; D017450:Receptors, Opioid, mu / Q000378:metabolism
C493775:3-deoxymorphine; D005561:Formates; D009022:Morphine Derivatives; D009294:Narcotics; D011957:Receptors, Opioid; D017465:Receptors, Opioid, delta; D017473:Receptors, Opioid, kappa; D017450:Receptors, Opioid, mu; D009020:Morphine; C014667:methyl chloroformate