N-Alkyl derivatives of (.+-.)-.alpha.-methyldopamine

A series of N-alkylated alpha-methyldopamine derivatives has been prepared for comparison of their biological effects with those of semirigid dopamine congeners derived from 2-aminotetralin systems. All of the alpha-methyldopamine derivatives were inert as dopaminergic agonists in a variety of anima...

Full description

Saved in:
Bibliographic Details
Published in:Journal of medicinal chemistry 1979-08, Vol.22 (8), p.901-907
Main Authors: Cannon, Joseph G, Perez, Zurilma, Long, John Paul, Rusterholz, David B, Flynn, Jan R, Costall, Brenda, Fortune, David H, Naylor, Robert J
Format: Article
Language:English
Subjects:
Animals
Cats
Deoxyepinephrine - analogs & derivatives
Deoxyepinephrine - chemical synthesis
Deoxyepinephrine - pharmacology
Dogs
Dopamine - analogs & derivatives
Heart Rate - drug effects
Humans
In Vitro Techniques
Injections
Mice
Motor Activity - drug effects
Myocardial Contraction - drug effects
Nucleus Accumbens
Rats
Stereotyped Behavior - drug effects
Citations: Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-a353t-e9eb871e9cea556b5e24fb8118a6e15e89446a33e13f4347d356b2b2a7107a163
cites
container_end_page 907
container_issue 8
container_start_page 901
container_title Journal of medicinal chemistry
container_volume 22
creator Cannon, Joseph G
Perez, Zurilma
Long, John Paul
Rusterholz, David B
Flynn, Jan R
Costall, Brenda
Fortune, David H
Naylor, Robert J
description A series of N-alkylated alpha-methyldopamine derivatives has been prepared for comparison of their biological effects with those of semirigid dopamine congeners derived from 2-aminotetralin systems. All of the alpha-methyldopamine derivatives were inert as dopaminergic agonists in a variety of animal assays, both centrally and peripherally, although certain compounds produced powerful and prolonged locomotor hyperactivity on intra-accumbens injection in mice, by indirect mechanism(s). A rationalization, based upon conformational analysis, is presented for the lack of direct dopaminergic agonist activity of alpha-methyldopamine derivatives.
doi_str_mv 10.1021/jm00194a003
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_74742531</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>74742531</sourcerecordid><originalsourceid>FETCH-LOGICAL-a353t-e9eb871e9cea556b5e24fb8118a6e15e89446a33e13f4347d356b2b2a7107a163</originalsourceid><addsrcrecordid>eNpt0EtLw0AUBeBBfNXqyq2LrnwgE-eZSZa1-MJWBSu4GybJDU2bNHEmKfbfG0kpLlzdxfk4Fw5Cp5R4lDB6My8IoaEwhPAd1KOSESwCInZRjxDGMPMZP0RHzs1JKyjjB2hfKq7CoIfECx7mi3U-SMBmK1NnK3CDMh1cetfYu8KeyauZ8XAB9WydJ2VlimwJx2gvNbmDk83to4_7u-noEY9fH55GwzE2XPIaQwhRoCiEMRgp_UgCE2kUUBoYH6iEIBTCN5wD5angQiW8RSxiRlGiDPV5H513vZUtvxpwtS4yF0OemyWUjdNKKMEkpy287mBsS-cspLqyWWHsWlOifyfSfyZq9dmmtokKSLa226SNcRdnrobvbWrsQvutkHr69q4ncjr55M9C37b-ovMmdnpeNnbZbvLv4x8vxXlP</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>74742531</pqid></control><display><type>article</type><title>N-Alkyl derivatives of (.+-.)-.alpha.-methyldopamine</title><source>American Chemical Society</source><creator>Cannon, Joseph G ; Perez, Zurilma ; Long, John Paul ; Rusterholz, David B ; Flynn, Jan R ; Costall, Brenda ; Fortune, David H ; Naylor, Robert J</creator><creatorcontrib>Cannon, Joseph G ; Perez, Zurilma ; Long, John Paul ; Rusterholz, David B ; Flynn, Jan R ; Costall, Brenda ; Fortune, David H ; Naylor, Robert J</creatorcontrib><description>A series of N-alkylated alpha-methyldopamine derivatives has been prepared for comparison of their biological effects with those of semirigid dopamine congeners derived from 2-aminotetralin systems. All of the alpha-methyldopamine derivatives were inert as dopaminergic agonists in a variety of animal assays, both centrally and peripherally, although certain compounds produced powerful and prolonged locomotor hyperactivity on intra-accumbens injection in mice, by indirect mechanism(s). A rationalization, based upon conformational analysis, is presented for the lack of direct dopaminergic agonist activity of alpha-methyldopamine derivatives.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00194a003</identifier><identifier>PMID: 573798</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Animals ; Cats ; Deoxyepinephrine - analogs &amp; derivatives ; Deoxyepinephrine - chemical synthesis ; Deoxyepinephrine - pharmacology ; Dogs ; Dopamine - analogs &amp; derivatives ; Heart Rate - drug effects ; Humans ; In Vitro Techniques ; Injections ; Mice ; Motor Activity - drug effects ; Myocardial Contraction - drug effects ; Nucleus Accumbens ; Rats ; Stereotyped Behavior - drug effects</subject><ispartof>Journal of medicinal chemistry, 1979-08, Vol.22 (8), p.901-907</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a353t-e9eb871e9cea556b5e24fb8118a6e15e89446a33e13f4347d356b2b2a7107a163</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm00194a003$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00194a003$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,27064,27924,27925,56766,56816</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/573798$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Cannon, Joseph G</creatorcontrib><creatorcontrib>Perez, Zurilma</creatorcontrib><creatorcontrib>Long, John Paul</creatorcontrib><creatorcontrib>Rusterholz, David B</creatorcontrib><creatorcontrib>Flynn, Jan R</creatorcontrib><creatorcontrib>Costall, Brenda</creatorcontrib><creatorcontrib>Fortune, David H</creatorcontrib><creatorcontrib>Naylor, Robert J</creatorcontrib><title>N-Alkyl derivatives of (.+-.)-.alpha.-methyldopamine</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>A series of N-alkylated alpha-methyldopamine derivatives has been prepared for comparison of their biological effects with those of semirigid dopamine congeners derived from 2-aminotetralin systems. All of the alpha-methyldopamine derivatives were inert as dopaminergic agonists in a variety of animal assays, both centrally and peripherally, although certain compounds produced powerful and prolonged locomotor hyperactivity on intra-accumbens injection in mice, by indirect mechanism(s). A rationalization, based upon conformational analysis, is presented for the lack of direct dopaminergic agonist activity of alpha-methyldopamine derivatives.</description><subject>Animals</subject><subject>Cats</subject><subject>Deoxyepinephrine - analogs &amp; derivatives</subject><subject>Deoxyepinephrine - chemical synthesis</subject><subject>Deoxyepinephrine - pharmacology</subject><subject>Dogs</subject><subject>Dopamine - analogs &amp; derivatives</subject><subject>Heart Rate - drug effects</subject><subject>Humans</subject><subject>In Vitro Techniques</subject><subject>Injections</subject><subject>Mice</subject><subject>Motor Activity - drug effects</subject><subject>Myocardial Contraction - drug effects</subject><subject>Nucleus Accumbens</subject><subject>Rats</subject><subject>Stereotyped Behavior - drug effects</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1979</creationdate><recordtype>article</recordtype><recordid>eNpt0EtLw0AUBeBBfNXqyq2LrnwgE-eZSZa1-MJWBSu4GybJDU2bNHEmKfbfG0kpLlzdxfk4Fw5Cp5R4lDB6My8IoaEwhPAd1KOSESwCInZRjxDGMPMZP0RHzs1JKyjjB2hfKq7CoIfECx7mi3U-SMBmK1NnK3CDMh1cetfYu8KeyauZ8XAB9WydJ2VlimwJx2gvNbmDk83to4_7u-noEY9fH55GwzE2XPIaQwhRoCiEMRgp_UgCE2kUUBoYH6iEIBTCN5wD5angQiW8RSxiRlGiDPV5H513vZUtvxpwtS4yF0OemyWUjdNKKMEkpy287mBsS-cspLqyWWHsWlOifyfSfyZq9dmmtokKSLa226SNcRdnrobvbWrsQvutkHr69q4ncjr55M9C37b-ovMmdnpeNnbZbvLv4x8vxXlP</recordid><startdate>197908</startdate><enddate>197908</enddate><creator>Cannon, Joseph G</creator><creator>Perez, Zurilma</creator><creator>Long, John Paul</creator><creator>Rusterholz, David B</creator><creator>Flynn, Jan R</creator><creator>Costall, Brenda</creator><creator>Fortune, David H</creator><creator>Naylor, Robert J</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>197908</creationdate><title>N-Alkyl derivatives of (.+-.)-.alpha.-methyldopamine</title><author>Cannon, Joseph G ; Perez, Zurilma ; Long, John Paul ; Rusterholz, David B ; Flynn, Jan R ; Costall, Brenda ; Fortune, David H ; Naylor, Robert J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a353t-e9eb871e9cea556b5e24fb8118a6e15e89446a33e13f4347d356b2b2a7107a163</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1979</creationdate><topic>Animals</topic><topic>Cats</topic><topic>Deoxyepinephrine - analogs &amp; derivatives</topic><topic>Deoxyepinephrine - chemical synthesis</topic><topic>Deoxyepinephrine - pharmacology</topic><topic>Dogs</topic><topic>Dopamine - analogs &amp; derivatives</topic><topic>Heart Rate - drug effects</topic><topic>Humans</topic><topic>In Vitro Techniques</topic><topic>Injections</topic><topic>Mice</topic><topic>Motor Activity - drug effects</topic><topic>Myocardial Contraction - drug effects</topic><topic>Nucleus Accumbens</topic><topic>Rats</topic><topic>Stereotyped Behavior - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cannon, Joseph G</creatorcontrib><creatorcontrib>Perez, Zurilma</creatorcontrib><creatorcontrib>Long, John Paul</creatorcontrib><creatorcontrib>Rusterholz, David B</creatorcontrib><creatorcontrib>Flynn, Jan R</creatorcontrib><creatorcontrib>Costall, Brenda</creatorcontrib><creatorcontrib>Fortune, David H</creatorcontrib><creatorcontrib>Naylor, Robert J</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Cannon, Joseph G</au><au>Perez, Zurilma</au><au>Long, John Paul</au><au>Rusterholz, David B</au><au>Flynn, Jan R</au><au>Costall, Brenda</au><au>Fortune, David H</au><au>Naylor, Robert J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>N-Alkyl derivatives of (.+-.)-.alpha.-methyldopamine</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1979-08</date><risdate>1979</risdate><volume>22</volume><issue>8</issue><spage>901</spage><epage>907</epage><pages>901-907</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>A series of N-alkylated alpha-methyldopamine derivatives has been prepared for comparison of their biological effects with those of semirigid dopamine congeners derived from 2-aminotetralin systems. All of the alpha-methyldopamine derivatives were inert as dopaminergic agonists in a variety of animal assays, both centrally and peripherally, although certain compounds produced powerful and prolonged locomotor hyperactivity on intra-accumbens injection in mice, by indirect mechanism(s). A rationalization, based upon conformational analysis, is presented for the lack of direct dopaminergic agonist activity of alpha-methyldopamine derivatives.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>573798</pmid><doi>10.1021/jm00194a003</doi><tpages>7</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0022-2623
ispartof Journal of medicinal chemistry, 1979-08, Vol.22 (8), p.901-907
issn 0022-2623
1520-4804
language eng
recordid cdi_proquest_miscellaneous_74742531
source American Chemical Society
subjects Animals
Cats
Deoxyepinephrine - analogs & derivatives
Deoxyepinephrine - chemical synthesis
Deoxyepinephrine - pharmacology
Dogs
Dopamine - analogs & derivatives
Heart Rate - drug effects
Humans
In Vitro Techniques
Injections
Mice
Motor Activity - drug effects
Myocardial Contraction - drug effects
Nucleus Accumbens
Rats
Stereotyped Behavior - drug effects
title N-Alkyl derivatives of (.+-.)-.alpha.-methyldopamine
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T10%3A57%3A56IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=N-Alkyl%20derivatives%20of%20(.+-.)-.alpha.-methyldopamine&rft.jtitle=Journal%20of%20medicinal%20chemistry&rft.au=Cannon,%20Joseph%20G&rft.date=1979-08&rft.volume=22&rft.issue=8&rft.spage=901&rft.epage=907&rft.pages=901-907&rft.issn=0022-2623&rft.eissn=1520-4804&rft_id=info:doi/10.1021/jm00194a003&rft_dat=%3Cproquest_cross%3E74742531%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a353t-e9eb871e9cea556b5e24fb8118a6e15e89446a33e13f4347d356b2b2a7107a163%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=74742531&rft_id=info:pmid/573798&rfr_iscdi=true