(R)-(-)-10-Methyl-11-hydroxyaporphine: A Highly Selective Serotonergic Agonist

Joseph G. Cannon, Prem Mohan, Jacek Bojarski, John Paul Long, Ranbir K. Bhatnagar, Paul A. Leonard, Jan R. Flynn, Tapan Kumar Chatterjee

Research output: Contribution to journalArticle

41 Citations (Scopus)

Abstract

Prior work in these laboratories identified (±)-5-hydroxy-6-methyl-2-(di-n-propylamino)tetralin as a dopaminergic agonist prodrug. The ortho methyl hydroxy aromatic substitution pattern in this molecule has now been incorporated into the aporphine ring system to give a congener of the dopaminergic agonist apomorphine in which the position 10 OH group has been replaced by methyl. Preparation of the target compound involved acid-catalyzed rearrangement of the 3-(1-phenyltetrazolyl) ether of morphine and subsequent molecular modification of the product, the 10-(1-phenyltetrazolyl) ether of (R)-(-)-apomorphine. Surprisingly, the target compound elicited no responses in any assays for effects at dopamine receptors, but rather it displayed pharmacological properties consistent with its being a serotonergic agonist with a high degree of selectivity for 5-HT1A receptors similar to the serotonergic agonist 8-hydroxy-2-(di-n-propylamino)tetralin.

Original languageEnglish (US)
Pages (from-to)313-318
Number of pages6
JournalJournal of Medicinal Chemistry
Volume31
Issue number2
DOIs
StatePublished - Dec 1 1988

Fingerprint

Serotonin Receptor Agonists
Apomorphine
Dopamine Agonists
Ether
8-Hydroxy-2-(di-n-propylamino)tetralin
Receptor, Serotonin, 5-HT1A
Dopamine Receptors
Prodrugs
Morphine
Pharmacology
Acids
PM 1000
N,N-dipropyl-2-aminotetralin
aporphine

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

Cite this

Cannon, J. G., Mohan, P., Bojarski, J., Long, J. P., Bhatnagar, R. K., Leonard, P. A., ... Chatterjee, T. K. (1988). (R)-(-)-10-Methyl-11-hydroxyaporphine: A Highly Selective Serotonergic Agonist. Journal of Medicinal Chemistry, 31(2), 313-318. https://doi.org/10.1021/jm00397a007

(R)-(-)-10-Methyl-11-hydroxyaporphine : A Highly Selective Serotonergic Agonist. / Cannon, Joseph G.; Mohan, Prem; Bojarski, Jacek; Long, John Paul; Bhatnagar, Ranbir K.; Leonard, Paul A.; Flynn, Jan R.; Chatterjee, Tapan Kumar.

In: Journal of Medicinal Chemistry, Vol. 31, No. 2, 01.12.1988, p. 313-318.

Research output: Contribution to journalArticle

Cannon, JG, Mohan, P, Bojarski, J, Long, JP, Bhatnagar, RK, Leonard, PA, Flynn, JR & Chatterjee, TK 1988, '(R)-(-)-10-Methyl-11-hydroxyaporphine: A Highly Selective Serotonergic Agonist', Journal of Medicinal Chemistry, vol. 31, no. 2, pp. 313-318. https://doi.org/10.1021/jm00397a007
Cannon JG, Mohan P, Bojarski J, Long JP, Bhatnagar RK, Leonard PA et al. (R)-(-)-10-Methyl-11-hydroxyaporphine: A Highly Selective Serotonergic Agonist. Journal of Medicinal Chemistry. 1988 Dec 1;31(2):313-318. https://doi.org/10.1021/jm00397a007
Cannon, Joseph G. ; Mohan, Prem ; Bojarski, Jacek ; Long, John Paul ; Bhatnagar, Ranbir K. ; Leonard, Paul A. ; Flynn, Jan R. ; Chatterjee, Tapan Kumar. / (R)-(-)-10-Methyl-11-hydroxyaporphine : A Highly Selective Serotonergic Agonist. In: Journal of Medicinal Chemistry. 1988 ; Vol. 31, No. 2. pp. 313-318.
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