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
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
- Mass
- 268.125
Show 4 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
via Wikidata · CC0
~8 min read
Article
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.