Structure via PubChem · Public domain (PubChem)
methylcholanthrene
Sign in to saveAlso known as 3-Methylcholanthrene
Methylcholanthrene is a highly carcinogenic polycyclic aromatic hydrocarbon produced by burning organic compounds at very high temperatures. Methylcholanthrene is also known as 3-methylcholanthrene, 20-methylcholanthrene or the IUPAC name 3-methyl-1,2-dyhydrobenzo[j]aceanthrylene. The short notation often used is 3-MC or MCA. This compound forms pale yellow solid crystals when crystallized from benzene and ether. It has a melting point around 180 °C and its boiling point is around 280 °C at a pressure of 80 mmHg. Methylcholanthrene is used in laboratory studies of chemical carcinogen
In the Vinony graph
Vinony's link graph records 42 inbound references to methylcholanthrene, and connects out to mass density, halogens and cholesterol.
It is catalogued under topics including Carcinogens, ECHA InfoCard ID from Wikidata and Hepatotoxins.
Vinony links it to 10 Wikipedia language editions.
Chemical data
- Formula
- C21H16
- Molecular weight
- 268.4 g/mol
- IUPAC name
- 3-methyl-1,2-dihydrobenzo[j]aceanthrylene
- SMILES
- CC1=C2CCC3=C2C(=CC4=C3C=CC5=CC=CC=C54)C=C1
- InChIKey
- PPQNQXQZIWHJRB-UHFFFAOYSA-N
- XLogP
- 6.4
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
9,765 papers- Role of glutathione S-transferases in detoxification of a polycyclic aromatic hydrocarbon, methylcholanthrene.Chemico-biological interactions · 2018
- Immunity to methylcholanthrene-induced sarcomas.Journal of the National Cancer Institute · 1957
- The metabolism of 3-methylcholanthrene and some related compounds by rat-liver homogenates.The Biochemical journal · 1966
- 3-Methylcholanthrene uptake and metabolism in organ culture.British journal of cancer · 1975
- Potentiation of 3-methylcholanthrene induction of rat hepatic cytochrome P450IA1 by dexamethasone in vivo.The Journal of pharmacology and experimental therapeutics · 1989
via PubMed
Wikidata facts
- Subclass of
- polycyclic aromatic hydrocarbons
- Has part
- carbon
- Mass
- 268.125
Show 5 more facts
- melting point
- 180
- canonical SMILES
- CC1=C2CCC3=C2C(=CC4=C3C=CC5=CC=CC=C54)C=C1
- chemical formula
- C₂₁H₁₆
- Commons category
- 3-Methylcholanthrene
- subject has role
- carcinogen
via Wikidata · CC0
~8 min read
Encyclopedic overview
11 sectionsContents
- History
- Synthesis
- Mechanism
- Metabolism
- Efficacy
- Toxicity
- Effects on animals
- Effects on human
- Non-human toxicity studies
- References
- External links
Methylcholanthrene is a highly carcinogenic polycyclic aromatic hydrocarbon produced by burning organic compounds at very high temperatures. Methylcholanthrene is also known as 3-methylcholanthrene, 20-methylcholanthrene or the IUPAC name 3-methyl-1,2-dyhydrobenzo[j]aceanthrylene. The short notation often used is 3-MC or MCA. This compound forms pale yellow solid crystals when crystallized from benzene and ether. It has a melting point around 180 °C and its boiling point is around 280 °C at a pressure of 80 mmHg. Methylcholanthrene is used in laboratory studies of chemical carcinogenesis. It is an alkylated derivative of [[benz(a)anthracene|benz[a]anthracene]] and has a similar UV spectrum. The most common isomer is 3-methylcholanthrene, although the methyl group can occur in other places.
3-Methylcholanthrene, a known carcinogen which builds up in the prostate due to cholesterol breakdown, is implicated in prostate cancer. It "readily produces" primary sarcomas in mice.
Excerpted from Wikipedia’s “methylcholanthrene” article, available under the CC BY-SA 4.0 licence.