| Record Information |
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| Version | 1.0 |
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| Created at | 2020-04-27 17:10:29 UTC |
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| Updated at | 2021-01-06 19:06:59 UTC |
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| CannabisDB ID | CDB005927 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | dibenz[a,c]anthracene |
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| Description | Dibenz[a,c]anthracene also known as 1,2:3,4-Dibenzanthracene or Db(a,c)A, belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. Dibenzo[a,c]anthracene is possibly neutral. Dibenz[a,c]anthracene is an organic compound with the chemical formula C22H14. It is a polycyclic aromatic hydrocarbon made of five fused benzene rings. It is one ingredient of cigarettes. Dibenz[a,c]anthracene is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI > Ref:DOI ). Dibenzo(a,c)anthracene is one of over 100 different polycyclic aromatic hydrocarbons (PAHs). PAHs are chemicals that are formed during the incomplete burning organic substances, such as fossil fuels. They are usually found as a mixture containing two or more of these compounds. PAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates (T3DB). Dibenz[a,c]anthracene is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI > Ref:DOI ). |
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| Structure | |
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| Synonyms | | Value | Source |
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| Benzo[b]triphenylene | Kegg | | Benzotriphenylene | Kegg | | 1,2,3,4-Dibenzanthracene | MeSH | | Benzo(b)triphenylene | MeSH | | Dibenz(a,c)anthracene | MeSH | | Dibenzo(a,c)anthracene | MeSH |
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| Chemical Formula | C22H14 |
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| Average Molecular Weight | 278.35 |
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| Monoisotopic Molecular Weight | 278.1096 |
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| IUPAC Name | pentacyclo[12.8.0.0^{2,7}.0^{8,13}.0^{16,21}]docosa-1(22),2,4,6,8,10,12,14,16,18,20-undecaene |
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| Traditional Name | pentacyclo[12.8.0.0^{2,7}.0^{8,13}.0^{16,21}]docosa-1(22),2,4,6,8,10,12,14,16,18,20-undecaene |
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| CAS Registry Number | 414-29-9 |
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| SMILES | C1=CC=C2C=C3C4=CC=CC=C4C4=CC=CC=C4C3=CC2=C1 |
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| InChI Identifier | InChI=1S/C22H14/c1-2-8-16-14-22-20-12-6-4-10-18(20)17-9-3-5-11-19(17)21(22)13-15(16)7-1/h1-14H |
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| InChI Key | RAASUWZPTOJQAY-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as triphenylenes. Triphenylenes are compounds containing a triphenylene moiety, which consists of four fused benzene rings forming a 9,10-benzo[l]phenanthrene. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Phenanthrenes and derivatives |
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| Sub Class | Triphenylenes |
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| Direct Parent | Triphenylenes |
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| Alternative Parents | |
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| Substituents | - Triphenylene
- Anthracene
- Aromatic hydrocarbon
- Polycyclic hydrocarbon
- Unsaturated hydrocarbon
- Hydrocarbon
- Aromatic homopolycyclic compound
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| Molecular Framework | Aromatic homopolycyclic compounds |
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| External Descriptors | |
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| Ontology |
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|
Not Available | | Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | logP | Not Available | Not Available |
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| Predicted Properties | [] |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | dibenz[a,c]anthracene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-004i-0090000000-e1ce3386049e9597145f | Spectrum | | Predicted GC-MS | dibenz[a,c]anthracene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0090000000-a1fad70bc82276bcac28 | 2016-08-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-0090000000-a5edc66a6ad5477b71b1 | 2016-08-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fb9-0090000000-5b78c4ace1ea24809066 | 2016-08-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0090000000-b378317029404ab7883e | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-0090000000-b378317029404ab7883e | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-0090000000-3acb0c13ce12682559d2 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0090000000-3ca26a652eff5433f50a | 2021-10-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-0090000000-3ca26a652eff5433f50a | 2021-10-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004i-0090000000-90f642c5a50b3a056759 | 2021-10-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0090000000-f1f000ca3cb2151d263d | 2021-10-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-0090000000-f1f000ca3cb2151d263d | 2021-10-12 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-0090000000-f1f000ca3cb2151d263d | 2021-10-12 | View Spectrum |
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