| Record Information |
|---|
| Version | 1.0 |
|---|
| Created at | 2020-04-27 17:27:22 UTC |
|---|
| Updated at | 2021-01-06 19:06:57 UTC |
|---|
| CannabisDB ID | CDB000043 |
|---|
| Secondary Accession Numbers | Not Available |
|---|
| Cannabis Compound Identification |
|---|
| Common Name | 8,9-Dihydrocannabidiol |
|---|
| Description | 8,9-Dihydrocannabidiol belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. 8,9-Dihydrocannabidiol is an extremely weak basic (essentially neutral) compound (based on its pKa). 8,9-Dihydrocannabidiol (H2CBD) is a synthetic cannabinoid that is closely related to cannabidiol (CBD) itself (PMID: 31123271 ). It was shown to have anti-seizure activity essentially identical to that of CBD in tests with rats. It may have certain advantages over CBD, in that it is fully synthetic, inexpensive to produce, and it is not a scheduled drug (cannabis extracts are controlled substances in most parts of the world). In addition, there is no path to synthesize the psychoactive substance tetrahydrocannabinol (THC) from H2CBD. CBD has been shown to convert to some extent to THC in the gastric tract (PMID: 28861485 ), and the deliberate laboratory conversion of CBD to THC is simple ( Ref:DOI ). H2CBD has therefore been studied for its potential use as an alternative to CBD in terms of its lack of abuse liability and absence of psychotropic effects. 8,9-Dihydrocannabidiol is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ). |
|---|
| Structure | |
|---|
| Synonyms | Not Available |
|---|
| Chemical Formula | C21H32O2 |
|---|
| Average Molecular Weight | 316.49 |
|---|
| Monoisotopic Molecular Weight | 316.2402 |
|---|
| IUPAC Name | 2-[(1S,6S)-3-methyl-6-(propan-2-yl)cyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol |
|---|
| Traditional Name | 2-[(1S,6S)-6-isopropyl-3-methylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol |
|---|
| CAS Registry Number | Not Available |
|---|
| SMILES | CCCCCC1=CC(O)=C([C@@H]2C=C(C)CC[C@H]2C(C)C)C(O)=C1 |
|---|
| InChI Identifier | InChI=1S/C21H32O2/c1-5-6-7-8-16-12-19(22)21(20(23)13-16)18-11-15(4)9-10-17(18)14(2)3/h11-14,17-18,22-23H,5-10H2,1-4H3/t17-,18+/m0/s1 |
|---|
| InChI Key | PCXRACLQFPRCBB-ZWKOTPCHSA-N |
|---|
| Chemical Taxonomy |
|---|
| Classification | Not classified |
|---|
| Ontology |
|---|
|
Not Available | | Physical Properties |
|---|
| State | Not Available |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | logP | Not Available | Not Available |
|
|---|
| Predicted Properties | [] |
|---|
| Spectra |
|---|
| EI-MS/GC-MS | | Type | Description | Splash Key | View |
|---|
| Predicted GC-MS | 8,9-Dihydrocannabidiol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
|
|---|
| MS/MS | Not Available |
|---|
| NMR | Not Available |
|---|
| Pathways |
|---|
| Pathways | Not Available |
|---|
| Protein Targets |
|---|
| Enzymes | Not Available |
|---|
| Transporters | Not Available |
|---|
| Metal Bindings | Not Available |
|---|
| Receptors | Not Available |
|---|
| Transcriptional Factors | Not Available |
|---|
| Concentrations Data |
|---|
| Not Available |
|---|
| External Links |
|---|
| HMDB ID | Not Available |
|---|
| DrugBank ID | Not Available |
|---|
| Phenol Explorer Compound ID | Not Available |
|---|
| FoodDB ID | Not Available |
|---|
| KNApSAcK ID | Not Available |
|---|
| Chemspider ID | 9891398 |
|---|
| KEGG Compound ID | Not Available |
|---|
| BioCyc ID | Not Available |
|---|
| BiGG ID | Not Available |
|---|
| Wikipedia Link | Not Available |
|---|
| METLIN ID | Not Available |
|---|
| PubChem Compound | 11716677 |
|---|
| PDB ID | Not Available |
|---|
| ChEBI ID | Not Available |
|---|
| References |
|---|
| General References | - Mascal M, Hafezi N, Wang D, Hu Y, Serra G, Dallas ML, Spencer JPE: Synthetic, non-intoxicating 8,9-dihydrocannabidiol for the mitigation of seizures. Sci Rep. 2019 May 23;9(1):7778. doi: 10.1038/s41598-019-44056-y. [PubMed:31123271 ]
- Merrick J, Lane B, Sebree T, Yaksh T, O'Neill C, Banks SL: Identification of Psychoactive Degradants of Cannabidiol in Simulated Gastric and Physiological Fluid. Cannabis Cannabinoid Res. 2016 Apr 1;1(1):102-112. doi: 10.1089/can.2015.0004. eCollection 2016. [PubMed:28861485 ]
|
|---|
