| Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives. | |
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MedLine Citation:
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PMID: 4032428 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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A convenient method for the synthesis of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives was developed. A series of these compounds was synthesized and tested for substitution in the two-lever drug discrimination assay, in rats trained to discriminate injections of d-LSD tartrate (185.5 nmol/kg, ip) from saline. A dose-response curve for each of the compounds in the series was generated. Structure-activity relationships were developed, based on comparison of the estimated ED50 values from these curves. Of the compounds that substituted for LSD, the N(6)-ethyl and -allyl were approximately 2-3 times more potent than LSD itself. The N(6)-propyl was equipotent to LSD, while the isopropyl derivative was half as active. The n-butyl compound was 1 order of magnitude less potent than LSD, suggesting a similarity to the SAR of certain serotonin and dopamine agonists. By contrast, no generalization occurred to norlysergic acid N,N-diethylamide and the N(6)-2-phenethyl derivative. |
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Authors:
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A J Hoffman; D E Nichols |
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Publication Detail:
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Type: Comparative Study; Journal Article; Research Support, U.S. Gov't, P.H.S. |
Journal Detail:
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Title: Journal of medicinal chemistry Volume: 28 ISSN: 0022-2623 ISO Abbreviation: J. Med. Chem. Publication Date: 1985 Sep |
Date Detail:
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Created Date: 1985-10-17 Completed Date: 1985-10-17 Revised Date: 2008-11-21 |
Medline Journal Info:
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Nlm Unique ID: 9716531 Medline TA: J Med Chem Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 1252-5 Citation Subset: IM |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Animals Chemical Phenomena Chemistry Discrimination Learning / drug effects* Lysergic Acid Diethylamide / analogs & derivatives*, chemical synthesis, pharmacology Male Rats Structure-Activity Relationship |
| Grant Support | |
ID/Acronym/Agency:
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2-S07-RR05586-15/RR/NCRR NIH HHS; DA-02189/DA/NIDA NIH HHS; RR01077/RR/NCRR NIH HHS |
| Chemical | |
Reg. No./Substance:
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50-37-3/Lysergic Acid Diethylamide |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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