Synthesis of enantiomerically pure (+)- and (-)-18-methoxycoronaridine hydrochloride and their preliminary assessment as anti-addictive agents

C H King; H Meckler; R J Herr; M P Trova; S D Glick; I M Maisonneuve

doi:10.1016/s0960-894x(00)00033-0

Synthesis of enantiomerically pure (+)- and (-)-18-methoxycoronaridine hydrochloride and their preliminary assessment as anti-addictive agents

Bioorg Med Chem Lett. 2000 Mar 6;10(5):473-6. doi: 10.1016/s0960-894x(00)00033-0.

Authors

C H King¹, H Meckler, R J Herr, M P Trova, S D Glick, I M Maisonneuve

Affiliation

¹ Albany Molecular Research, Inc., NY 12203, USA.

PMID: 10743951
DOI: 10.1016/s0960-894x(00)00033-0

Abstract

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.

MeSH terms

Animals
Ibogaine / analogs & derivatives*
Ibogaine / chemical synthesis
Ibogaine / pharmacology
Morphine / pharmacology
Morphine Dependence / drug therapy*
Narcotics / pharmacology
Rats
Receptors, Opioid, delta / drug effects
Receptors, Opioid, kappa / drug effects
Receptors, Opioid, mu / drug effects
Self Administration

Substances

Narcotics
Receptors, Opioid, delta
Receptors, Opioid, kappa
Receptors, Opioid, mu
Ibogaine
Morphine
18-methoxycoronaridine