6-Methylenedihydrodesoxymorphine (6-MDDM) is an opiate

Opiate

In medicine, the term opiate describes any of the narcotic opioid alkaloids found as natural products in the opium poppy plant.-Overview:Opiates are so named because they are constituents or derivatives of constituents found in opium, which is processed from the latex sap of the opium poppy,...

 analogue that is a derivative of hydromorphone

Hydromorphone

Hydromorphone, a more common synonym for dihydromorphinone, commonly a hydrochloride is a very potent centrally-acting analgesic drug of the opioid class. It is a derivative of morphine, to be specific, a hydrogenated ketone thereof and, therefore, a semi-synthetic drug...

, where the 6-ketone

Ketone

In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...

 group has been replaced by methylene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 ....

. It has sedative

Sedative

A sedative or tranquilizer is a substance that induces sedation by reducing irritability or excitement....

 and analgesic

Analgesic

An analgesic is any member of the group of drugs used to relieve pain . The word analgesic derives from Greek an- and algos ....

 effects.

6-Methylenedihydrodesoxymorphine is a potent μ-opioid

Mu Opioid receptor

The μ-opioid receptors are a class of opioid receptors with high affinity for enkephalins and beta-endorphin but low affinity for dynorphins. They are also referred to as μ opioid peptide receptors. The prototypical μ receptor agonist is the opium alkaloid morphine; μ refers to morphine...

 agonist

Agonist

An agonist is a chemical that binds to a receptor of a cell and triggers a response by that cell. Agonists often mimic the action of a naturally occurring substance...

, 80x stronger than morphine

Morphine

Morphine is a potent opiate analgesic medication and is considered to be the prototypical opioid. It was first isolated in 1804 by Friedrich Sertürner, first distributed by same in 1817, and first commercially sold by Merck in 1827, which at the time was a single small chemists' shop. It was more...

. Compared to morphine it has a faster onset of action and similar duration of effects. It produces around the same degree of respiratory depression as morphine, but less inhibition of gastrointestinal motility

Constipation

Constipation refers to bowel movements that are infrequent or hard to pass. Constipation is a common cause of painful defecation...

. Animal studies show it to be a potent analgesic which produces significant analgesic effects even at low doses which produce comparatively few side effects, however it has never been developed for medical use in humans.

6-Methylenedihydrodesoxymorphine is synthesised in two steps; first a Wittig reaction

Wittig reaction

The Wittig reaction is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide to give an alkene and triphenylphosphine oxide....

 is used, reacting hydrocodone

Hydrocodone

Hydrocodone or dihydrocodeinone is a semi-synthetic opioid derived from either of two naturally occurring opiates: codeine and thebaine. It is an orally active narcotic analgesic and antitussive...

 with methylenetriphenylphosphorane and an alkyl lithium reagent in diethyl ether

Diethyl ether

Diethyl ether, also known as ethyl ether, simply ether, or ethoxyethane, is an organic compound in the ether class with the formula . It is a colorless, highly volatile flammable liquid with a characteristic odor...

 to form 6-Methylenedihydrodesoxycodeine. The 3-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...

 group is then cleaved to hydroxy

Hydroxyl

A hydroxyl is a chemical group containing an oxygen atom covalently bonded with a hydrogen atom. In inorganic chemistry, the hydroxyl group is known as the hydroxide ion, and scientists and reference works generally use these different terms though they refer to the same chemical structure in...

, by reaction with pyridine

Pyridine

Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N. It is structurally related to benzene, with one C-H group replaced by a nitrogen atom...

. The second step tends to be incomplete and often gives fairly low yields, but these can be improved by changing the reaction conditions.