Methylenedioxy in the field of chemistry

Chemistry

Chemistry is the science of matter, especially its chemical reactions, but also its composition, structure and properties. Chemistry is concerned with atoms and their interactions with other atoms, and particularly with the properties of chemical bonds....

, particularly in organic chemistry

Organic chemistry

Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, composition, reactions, and preparation of carbon-based compounds, hydrocarbons, and their derivatives...

, is the name for a functional group

Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...

 with the structural formula

Structural formula

The structural formula of a chemical compound is a graphical representation of the molecular structure, showing how the atoms are arranged. The chemical bonding within the molecule is also shown, either explicitly or implicitly...

 R-O-CH₂-O-R' which is connected to the rest of a molecule

Molecule

A molecule is an electrically neutral group of at least two atoms held together by covalent chemical bonds. Molecules are distinguished from ions by their electrical charge...

 by two chemical bond

Chemical bond

A chemical bond is an attraction between atoms that allows the formation of chemical substances that contain two or more atoms. The bond is caused by the electromagnetic force attraction between opposite charges, either between electrons and nuclei, or as the result of a dipole attraction...

s. The methylenedioxy group consists of two oxygen

Oxygen

Oxygen is the element with atomic number 8 and represented by the symbol O. Its name derives from the Greek roots ὀξύς and -γενής , because at the time of naming, it was mistakenly thought that all acids required oxygen in their composition...

 atom

Atom

The atom is a basic unit of matter that consists of a dense central nucleus surrounded by a cloud of negatively charged electrons. The atomic nucleus contains a mix of positively charged protons and electrically neutral neutrons...

s connected to a methylene

Methylene

Methylene is a chemical species in which a carbon atom is bonded to two hydrogen atoms. Three different possibilities present themselves:* the -CH2- substituent group: e.g., dichloromethane ....

 (CH₂) group. The methylenedioxy group is generally found attached to an aromatic structure such as phenyl where it forms the methylenedioxyphenyl or benzodioxole functional group which is widely found in natural product

Natural product

A natural product is a chemical compound or substance produced by a living organism - found in nature that usually has a pharmacological or biological activity for use in pharmaceutical drug discovery and drug design...

s, including safrole

Safrole

Safrole, also known as shikimol, is a phenylpropene. It is a colorless or slightly yellow oily liquid. It is typically extracted from the root-bark or the fruit of sassafras plants in the form of sassafras oil , or synthesized from other related methylenedioxy...

, and drug

Drug

A drug, broadly speaking, is any substance that, when absorbed into the body of a living organism, alters normal bodily function. There is no single, precise definition, as there are different meanings in drug control law, government regulations, medicine, and colloquial usage.In pharmacology, a...

s and chemicals such as tadalafil

Tadalafil

Tadalafil is a PDE5 inhibitor, currently marketed in pill form for treating erectile dysfunction under the name Cialis; and under the name Adcirca for the treatment of pulmonary arterial hypertension...

, MDMA, and piperonyl butoxide

Piperonyl butoxide

Piperonyl butoxide is an organic compound used as pesticide synergist, especially for pyrethroids and rotenone. It does not by itself have pesticidal properties. However, when added to insecticide mixtures, typically pyrethrin, pyrethroid, and carbamate insecticides, their potency is increased...

.

Enzymes within the Cytochrome 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 are canadine

Canadine

Canadine is a protoberberine alkaloid which can act as a calcium channel blocker....

 and berberine

Berberine

Berberine is a quaternary ammonium salt from the protoberberine group of isoquinoline alkaloids. It is found in such plants as Berberis Berberine is a quaternary ammonium salt from the protoberberine group of isoquinoline alkaloids. It is found in such plants as Berberis Berberine is a quaternary...

. 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, both MDMA and MDA

3,4-Methylenedioxyamphetamine

3,4-Methylenedioxyamphetamine , also known as tenamfetamine , is a psychedelic and entactogenic drug of the phenethylamine and amphetamine chemical classes...

 during their metabolism.

See also

• Methoxy
  Methoxy
  In chemistry , methoxy refers to the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula O–CH3.The word is used in organic nomenclature usually to describe an ether...
  
  
• MDxx
• Ethylenedioxy
  Ethylenedioxy
  Ethylenedioxy, in chemistry, especially organic chemistry, is a functional group with the structural formula R-O-CH2-CH2-O-R'. It is generally attached to an aromatic ring such as a phenyl, in which case it is called ethylenedioxyphenyl or dihydrobenzodioxine. The ethylenedioxy moiety can be found...