Synthesis of enantiomerically pure (+)- and (-)-18-methoxycoronaridine hydrochloride and their preliminary assessment as anti-addictive agents.
Chemical resolution of racemic 18-methoxycoronaridine (18-MC) was achieved by the formation of its diastereomeric sulfonamides with either (R)-(-)- or (S)-(+)-camphorsulfonyl chloride. Preliminary assessment of (+)-, (-)-, and (+/-)-18-MC x HCl showed similar effects on morphine self-administration in a rat model, and similar affinities at the kappa opioid receptors.
King
C H
CH
Albany Molecular Research, Inc., NY 12203, USA.
Meckler
H
H
Herr
R J
RJ
Trova
M P
MP
Glick
S D
SD
Maisonneuve
I M
IM
D000818:Animals; D007050:Ibogaine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D009020:Morphine / Q000494:pharmacology; D009021:Morphine Dependence / Q000188:drug therapy*; D009294:Narcotics / Q000494:pharmacology; D051381:Rats; D017465:Receptors, Opioid, delta / Q000187:drug effects; D017473:Receptors, Opioid, kappa / Q000187:drug effects; D017450:Receptors, Opioid, mu / Q000187:drug effects; D012646:Self Administration
D009294:Narcotics; D017465:Receptors, Opioid, delta; D017473:Receptors, Opioid, kappa; D017450:Receptors, Opioid, mu; D007050:Ibogaine; D009020:Morphine; C103345:18-methoxycoronaridine