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Methylenedioxy is the term used in the field ofchemistry, particularly inorganic chemistry, for afunctional group with thestructural formulaR−O−CH2−O−R′ which is connected to the rest of amolecule by twochemical bonds. The methylenedioxy group consists of twooxygenatoms connected to amethylene bridge (−CH2− unit). The methylenedioxy group is generally found attached to anaromatic structure such asphenyl where it forms themethylenedioxyphenyl orbenzodioxole functional group which is widely found innatural products, includingsafrole, anddrugs and chemicals such astadalafil,MDMA, paroxetine andpiperonyl butoxide.
Enzymes within thecytochrome P450 superfamily are able to form methylenedioxy bridges by closure of an open, adjacent phenol and methoxy group. Examples of products formed by this process arecanadine andberberine. Similarly,ortho-demethylenation can be carried out by other members of the superfamily to open a bridge; a process which is applied to, as examples, bothMDMA andMDA during their metabolism.
MDPV andMDPHP, both belonging to the class of pyrrolidinophenones, share the street name "monkey dust,"[1][2][3] a play on the chemical term "methylenedioxy" present in both substances.