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Natural cannabinoids: Templates for drug discovery
Recent studies have elucidated the biosynthetic pathway of cannabinoids and have highlighted the preference for a C-3 n-pentyl side chain in the most prominently represented cannabinoids from Cannabis sativa and their medicinally important decarboxylation products. The corresponding C-3 n-propyl sid...
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| Published in: | Life sciences (1973) 2005-12, Vol.78 (5), p.454-466 |
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| Main Authors: | , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c417t-56d7d9fbb47e0600ddeaeeaa24a642a9346ab7488af484cc358a032129cb1cd83 |
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| cites | cdi_FETCH-LOGICAL-c417t-56d7d9fbb47e0600ddeaeeaa24a642a9346ab7488af484cc358a032129cb1cd83 |
| container_end_page | 466 |
| container_issue | 5 |
| container_start_page | 454 |
| container_title | Life sciences (1973) |
| container_volume | 78 |
| creator | Thakur, Ganesh A. Duclos, Richard I. Makriyannis, Alexandros |
| description | Recent studies have elucidated the biosynthetic pathway of cannabinoids and have highlighted the preference for a C-3
n-pentyl side chain in the most prominently represented cannabinoids from
Cannabis sativa and their medicinally important decarboxylation products. The corresponding C-3
n-propyl side chain containing cannabinoids are also found, although in lesser quantities. Structure–activity relationship (SAR) studies performed on Δ
9-tetrahydrocannabinol (Δ
9-THC), the key psychoactive ingredient of
Cannabis, and its synthetic analogues have identified the C-3 side chain as the key pharmacophore for ligand affinity and selectivity for the known cannabinoid receptors and for pharmacological potency. Interestingly, the terminal
n-pentyl saturated hydrocarbon side chain of endocannabinoids also plays a corresponding crucial role in conferring similar properties. This review briefly summarizes the biosynthesis of cannabinoids and endocannabinoids and focuses on their side chain SAR. |
| doi_str_mv | 10.1016/j.lfs.2005.09.014 |
| format | article |
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n-pentyl side chain in the most prominently represented cannabinoids from
Cannabis sativa and their medicinally important decarboxylation products. The corresponding C-3
n-propyl side chain containing cannabinoids are also found, although in lesser quantities. Structure–activity relationship (SAR) studies performed on Δ
9-tetrahydrocannabinol (Δ
9-THC), the key psychoactive ingredient of
Cannabis, and its synthetic analogues have identified the C-3 side chain as the key pharmacophore for ligand affinity and selectivity for the known cannabinoid receptors and for pharmacological potency. Interestingly, the terminal
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n-pentyl side chain in the most prominently represented cannabinoids from
Cannabis sativa and their medicinally important decarboxylation products. The corresponding C-3
n-propyl side chain containing cannabinoids are also found, although in lesser quantities. Structure–activity relationship (SAR) studies performed on Δ
9-tetrahydrocannabinol (Δ
9-THC), the key psychoactive ingredient of
Cannabis, and its synthetic analogues have identified the C-3 side chain as the key pharmacophore for ligand affinity and selectivity for the known cannabinoid receptors and for pharmacological potency. Interestingly, the terminal
n-pentyl saturated hydrocarbon side chain of endocannabinoids also plays a corresponding crucial role in conferring similar properties. This review briefly summarizes the biosynthesis of cannabinoids and endocannabinoids and focuses on their side chain SAR.</description><subject>Anandamide</subject><subject>Animals</subject><subject>Biosynthesis</subject><subject>Cannabinoid Receptor Modulators - biosynthesis</subject><subject>Cannabinoid Receptor Modulators - chemistry</subject><subject>Cannabinoid Receptor Modulators - pharmacology</subject><subject>Cannabinoids - biosynthesis</subject><subject>Cannabinoids - chemistry</subject><subject>Cannabinoids - pharmacology</subject><subject>Endocannabinoids</subject><subject>Humans</subject><subject>Molecular Conformation</subject><subject>Pharmacology</subject><subject>Side chain SAR</subject><subject>Structure-Activity Relationship</subject><subject>Δ 9-Tetrahydrocannabinol</subject><issn>0024-3205</issn><issn>1879-0631</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNp9kDtPwzAUhS0EoqXwA1hQJraEa8dxHJhQxUuqYCmz5dg3yFUexU6Q-u9x1UpsTHf5ztG5HyHXFDIKVNxtsrYJGQMoMqgyoPyEzKksqxRETk_JHIDxNGdQzMhFCBuIYFHm52RGBeOMFuWcsHc9Tl63idF9r2vXD86G-2SN3bbVI4akGXxi_fSVWBfM8IN-d0nOGt0GvDreBfl8flovX9PVx8vb8nGVGk7LMS2ELW3V1DUvEQSAtagRtWZcC850lXOh65JLqRsuuTF5ITXkjLLK1NRYmS_I7aF364fvCcOoujgB21b3OExBCSlpIQVEkB5A44cQPDZq612n_U5RUHtRaqOiKLUXpaBSUVTM3BzLp7pD-5c4monAwwHA-OKPQ6-CcdgbtM6jGZUd3D_1vyx4eI0</recordid><startdate>20051222</startdate><enddate>20051222</enddate><creator>Thakur, Ganesh A.</creator><creator>Duclos, Richard I.</creator><creator>Makriyannis, Alexandros</creator><general>Elsevier Inc</general><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>20051222</creationdate><title>Natural cannabinoids: Templates for drug discovery</title><author>Thakur, Ganesh A. ; Duclos, Richard I. ; Makriyannis, Alexandros</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c417t-56d7d9fbb47e0600ddeaeeaa24a642a9346ab7488af484cc358a032129cb1cd83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Anandamide</topic><topic>Animals</topic><topic>Biosynthesis</topic><topic>Cannabinoid Receptor Modulators - biosynthesis</topic><topic>Cannabinoid Receptor Modulators - chemistry</topic><topic>Cannabinoid Receptor Modulators - pharmacology</topic><topic>Cannabinoids - biosynthesis</topic><topic>Cannabinoids - chemistry</topic><topic>Cannabinoids - pharmacology</topic><topic>Endocannabinoids</topic><topic>Humans</topic><topic>Molecular Conformation</topic><topic>Pharmacology</topic><topic>Side chain SAR</topic><topic>Structure-Activity Relationship</topic><topic>Δ 9-Tetrahydrocannabinol</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Thakur, Ganesh A.</creatorcontrib><creatorcontrib>Duclos, Richard I.</creatorcontrib><creatorcontrib>Makriyannis, Alexandros</creatorcontrib><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>Life sciences (1973)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Thakur, Ganesh A.</au><au>Duclos, Richard I.</au><au>Makriyannis, Alexandros</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Natural cannabinoids: Templates for drug discovery</atitle><jtitle>Life sciences (1973)</jtitle><addtitle>Life Sci</addtitle><date>2005-12-22</date><risdate>2005</risdate><volume>78</volume><issue>5</issue><spage>454</spage><epage>466</epage><pages>454-466</pages><issn>0024-3205</issn><eissn>1879-0631</eissn><abstract>Recent studies have elucidated the biosynthetic pathway of cannabinoids and have highlighted the preference for a C-3
n-pentyl side chain in the most prominently represented cannabinoids from
Cannabis sativa and their medicinally important decarboxylation products. The corresponding C-3
n-propyl side chain containing cannabinoids are also found, although in lesser quantities. Structure–activity relationship (SAR) studies performed on Δ
9-tetrahydrocannabinol (Δ
9-THC), the key psychoactive ingredient of
Cannabis, and its synthetic analogues have identified the C-3 side chain as the key pharmacophore for ligand affinity and selectivity for the known cannabinoid receptors and for pharmacological potency. Interestingly, the terminal
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| fulltext | fulltext |
| identifier | ISSN: 0024-3205 |
| ispartof | Life sciences (1973), 2005-12, Vol.78 (5), p.454-466 |
| issn | 0024-3205 1879-0631 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_68815860 |
| source | Elsevier |
| subjects | Anandamide Animals Biosynthesis Cannabinoid Receptor Modulators - biosynthesis Cannabinoid Receptor Modulators - chemistry Cannabinoid Receptor Modulators - pharmacology Cannabinoids - biosynthesis Cannabinoids - chemistry Cannabinoids - pharmacology Endocannabinoids Humans Molecular Conformation Pharmacology Side chain SAR Structure-Activity Relationship Δ 9-Tetrahydrocannabinol |
| title | Natural cannabinoids: Templates for drug discovery |
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