Journal article
(R)-(-)-10-Methyl-11-hydroxyaporphine: a highly selective serotonergic agonist
Journal of medicinal chemistry, Vol.31(2), pp.313-318
02/01/1988
DOI: 10.1021/jm00397a007
PMID: 3339604
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aporphine ring system to give a congener of the dopaminergic agonist apomorphine in which the position 10 OH group has been replaced by methyl.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.
Details
- Title: Subtitle
- (R)-(-)-10-Methyl-11-hydroxyaporphine: a highly selective serotonergic agonist
- Creators
- Joseph G CannonPrem MohanJacek BojarskiJohn Paul LongRanbir K BhatnagarPaul A LeonardJan R FlynnTapan K Chatterjee
- Resource Type
- Journal article
- Publication Details
- Journal of medicinal chemistry, Vol.31(2), pp.313-318
- Publisher
- American Chemical Society
- DOI
- 10.1021/jm00397a007
- PMID
- 3339604
- ISSN
- 0022-2623
- eISSN
- 1520-4804
- Language
- English
- Date published
- 02/01/1988
- Academic Unit
- Anesthesia; Neuroscience and Pharmacology
- Record Identifier
- 9984007193702771
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