CBD-DMH (original) (raw)
Cannabidiol-dimethylheptyl (CBD-DMH or DMH-CBD) is a synthetic homologue of cannabidiol where the pentyl chain has been replaced by a dimethylheptyl chain. Several isomers of this compound are known. The most commonly used isomer in research is (−)-CBD-DMH, which has the same stereochemistry as natural cannabidiol, and a 1,1-dimethylheptyl side chain. This compound is not psychoactive and acts primarily as an anandamide reuptake inhibitor, but is more potent than cannabidiol as an anticonvulsant and has around the same potency as an antiinflammatory. Unexpectedly the “unnatural” enantiomer (+)-CBD-DMH, which has reversed stereochemistry from cannabidiol, was found to be a directly acting cannabinoid receptor agonist with a Ki of 17.4nM at CB1 and 211nM at CB2, and produces typical cannabin
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| dbo:abstract | Cannabidiol-dimethylheptyl (CBD-DMH or DMH-CBD) is a synthetic homologue of cannabidiol where the pentyl chain has been replaced by a dimethylheptyl chain. Several isomers of this compound are known. The most commonly used isomer in research is (−)-CBD-DMH, which has the same stereochemistry as natural cannabidiol, and a 1,1-dimethylheptyl side chain. This compound is not psychoactive and acts primarily as an anandamide reuptake inhibitor, but is more potent than cannabidiol as an anticonvulsant and has around the same potency as an antiinflammatory. Unexpectedly the “unnatural” enantiomer (+)-CBD-DMH, which has reversed stereochemistry from cannabidiol, was found to be a directly acting cannabinoid receptor agonist with a Ki of 17.4nM at CB1 and 211nM at CB2, and produces typical cannabinoid effects in animal studies, as does its 7-OH derivative. Another closely analogous compound has also been described, with the double bond in the cyclohexene ring shifted to between the 1,6-positions rather than the 2,3-positions (i.e. analogous to synthetic THC analogues such as parahexyl), the isopropenyl group saturated to isopropyl, and a 1,2-dimethylheptyl side chain. It is synthesized by Birch reduction from the 1,2-dimethylheptyl analogue of cannabidiol. This compound also produces potent cannabinoid-like effects in animals, but has three chiral centers and is composed of a mixture of eight stereoisomers, which have not been studied individually, so it is not known which stereoisomers are active. (en) |
| dbo:casNumber | (−)-enantiomer 97452-63-6 |
| dbo:fdaUniiCode | P28FSD6QS7 |
| dbo:pubchem | 126670 |
| dbo:thumbnail | wiki-commons:Special:FilePath/CBD-DMH_structure.png?width=300 |
| dbo:wikiPageID | 53052196 (xsd:integer) |
| dbo:wikiPageLength | 6217 (xsd:nonNegativeInteger) |
| dbo:wikiPageRevisionID | 1095231013 (xsd:integer) |
| dbo:wikiPageWikiLink | dbr:Cannabidiol dbr:Cannabidiphorol dbr:Cannabinoid_receptor dbr:Enantiomer dbr:Birch_reduction dbr:Anticonvulsant dbr:Reuptake_inhibitor dbr:O-1656 dbc:Cannabinoids dbc:Cyclohexenes dbr:Stereochemistry dbr:NESS-040C5 dbr:Stereoisomer dbr:Dissociation_constant dbr:Abnormal_cannabidiol dbr:Anandamide dbc:2,6-Dihydroxybiphenyls dbr:Cyclohexene dbr:Parahexyl dbr:Isomer dbr:KLS-13019 dbr:Tetrahydrocannabiphorol dbr:THC dbr:HU-211 dbr:HUF-101 dbr:Antiinflammatory dbr:O-1871 dbr:O-1918 dbr:7-OH-CBD dbr:Homolog dbr:File:1-1-CBD-DMH_structure.png dbr:File:1-2-CBD-DMH_structure.png dbr:File:7-OH-(+)-CBD-DMH_structure.png |
| dbp:c | 25 (xsd:integer) |
| dbp:casNumber | 97452 (xsd:integer) |
| dbp:casSupplemental | -enantiomer (en) |
| dbp:chemspiderid | 112525 (xsd:integer) |
| dbp:h | 38 (xsd:integer) |
| dbp:iupacName | 5 (xsd:integer) |
| dbp:molecularWeight | 370.570000 (xsd:double) |
| dbp:o | 2 (xsd:integer) |
| dbp:pubchem | 126670 (xsd:integer) |
| dbp:smiles | CCCCCCCc1ccO (en) |
| dbp:stdinchi | 1 (xsd:integer) |
| dbp:stdinchikey | MPJURNPNPDQYSY-LEWJYISDSA-N (en) |
| dbp:unii | P28FSD6QS7 (en) |
| dbp:width | 220 (xsd:integer) |
| dbp:wikiPageUsesTemplate | dbt:Cannabinoids dbt:Clear-left dbt:Drugbox dbt:Reflist dbt:Short_description dbt:Cascite dbt:Fdacite |
| dcterms:subject | dbc:Cannabinoids dbc:Cyclohexenes dbc:2,6-Dihydroxybiphenyls |
| rdf:type | owl:Thing dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q8386 dbo:Drug |
| rdfs:comment | Cannabidiol-dimethylheptyl (CBD-DMH or DMH-CBD) is a synthetic homologue of cannabidiol where the pentyl chain has been replaced by a dimethylheptyl chain. Several isomers of this compound are known. The most commonly used isomer in research is (−)-CBD-DMH, which has the same stereochemistry as natural cannabidiol, and a 1,1-dimethylheptyl side chain. This compound is not psychoactive and acts primarily as an anandamide reuptake inhibitor, but is more potent than cannabidiol as an anticonvulsant and has around the same potency as an antiinflammatory. Unexpectedly the “unnatural” enantiomer (+)-CBD-DMH, which has reversed stereochemistry from cannabidiol, was found to be a directly acting cannabinoid receptor agonist with a Ki of 17.4nM at CB1 and 211nM at CB2, and produces typical cannabin (en) |
| rdfs:label | CBD-DMH (en) |
| owl:sameAs | yago-res:CBD-DMH wikidata:CBD-DMH dbpedia-sr:CBD-DMH https://global.dbpedia.org/id/2fM6u |
| prov:wasDerivedFrom | wikipedia-en:CBD-DMH?oldid=1095231013&ns=0 |
| foaf:depiction | wiki-commons:Special:FilePath/1-1-CBD-DMH_structure.png wiki-commons:Special:FilePath/1-2-CBD-DMH_structure.png wiki-commons:Special:FilePath/7-OH-(+)-CBD-DMH_structure.png wiki-commons:Special:FilePath/CBD-DMH_structure.png |
| foaf:isPrimaryTopicOf | wikipedia-en:CBD-DMH |
| is dbo:wikiPageRedirects of | dbr:DMH-CBD dbr:Cannabidiol-dimethylheptyl |
| is dbo:wikiPageWikiLink of | dbr:Cannabidiphorol dbr:C25H38O2 dbr:O-1656 dbr:Mary_Ware_(politician) dbr:2020_NASCAR_Cup_Series dbr:2020_NASCAR_Gander_RV_&_Outdoors_Truck_Series dbr:2020_NASCAR_Xfinity_Series dbr:William_M._(Mac)_Thornberry_National_D...uthorization_Act_for_Fiscal_Year_2021 dbr:Drug_policy_of_South_Korea dbr:Tetrahydrocannabiphorol dbr:DMH-CBD dbr:Cannabis_in_Indonesia dbr:Cannabidiol-dimethylheptyl |
| is foaf:primaryTopic of | wikipedia-en:CBD-DMH |
