Document Detail


Synthesis and evaluation of 2,3-dihydrobenzofuran analogues of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane: drug discrimination studies in rats.
MedLine Citation:
PMID:  3950910     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Two analogues, 6-(2-aminopropyl)-5-methoxy-2,3-dihydrobenzofuran and 6-(2-aminopropyl)-5-methoxy-2-methyl-2,3-dihydrobenzofuran, of the hallucinogenic agent 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) were synthesized and tested in the two-lever drug discrimination paradigm. In rats trained to discriminate saline from LSD tartrate (0.08 mg/kg), stimulus generalization occurred to both of the 2,3-dihydrobenzofuran analogues but at doses more than 10-fold higher than for DOM. A possible explanation for this dramatic attenuation of LSD-like activity could involve a highly directional electrophilic binding site on the receptor that cannot accept the orientation of the unshared electron pairs on the heterocyclic oxygen atom in the benzofurans.
Authors:
D E Nichols; A J Hoffman; R A Oberlender; R M Riggs
Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Journal of medicinal chemistry     Volume:  29     ISSN:  0022-2623     ISO Abbreviation:  J. Med. Chem.     Publication Date:  1986 Feb 
Date Detail:
Created Date:  1986-03-28     Completed Date:  1986-03-28     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  9716531     Medline TA:  J Med Chem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  302-4     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
2,5-Dimethoxy-4-Methylamphetamine / analogs & derivatives,  pharmacology*
Amphetamines / pharmacology*
Animals
Benzofurans / chemical synthesis,  pharmacology*
Discrimination Learning / drug effects*
Hallucinogens / chemical synthesis,  pharmacology*
Lysergic Acid Diethylamide / pharmacology
Male
Molecular Conformation
Rats
Rats, Inbred Strains
Structure-Activity Relationship
Grant Support
ID/Acronym/Agency:
2-S07-RR05586-15/RR/NCRR NIH HHS; DA02189/DA/NIDA NIH HHS; GM 709504/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Amphetamines; 0/Benzofurans; 0/Hallucinogens; 15588-95-1/2,5-Dimethoxy-4-Methylamphetamine; 50-37-3/Lysergic Acid Diethylamide

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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