6-Methylenedihydrodesoxymorphine (6-MDDM) is an
opiate
An opiate, in classical pharmacology, is a substance derived from opium. In more modern usage, the term ''opioid'' is used to designate all substances, both natural and synthetic, that bind to opioid receptors in the brain (including antagonis ...
analogue structurally related to
desomorphine that is a derivative of
hydromorphone, where the 6-
ketone
In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...
group has been replaced by a
methylene group. It has
sedative
A sedative or tranquilliser is a substance that induces sedation by reducing irritability or excitement. They are CNS depressants and interact with brain activity causing its deceleration. Various kinds of sedatives can be distinguished, but t ...
and
analgesic
An analgesic drug, also called simply an analgesic (American English), analgaesic (British English), pain reliever, or painkiller, is any member of the group of drugs used to achieve relief from pain (that is, analgesia or pain management). It ...
effects.
6-Methylenedihydrodesoxymorphine is a potent
μ-opioid agonist
An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ago ...
, 80x stronger than
morphine. Compared to morphine it has a faster onset of action and similar duration of effects.
It produces around the same degree of
respiratory depression
Hypoventilation (also known as respiratory depression) occurs when ventilation is inadequate (''hypo'' meaning "below") to perform needed respiratory gas exchange. By definition it causes an increased concentration of carbon dioxide (hypercapnia ...
as morphine, but less
inhibition of gastrointestinal motility. Animal studies show it to be a potent analgesic which produces significant analgesic effects even at low doses while inducing 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 is used, reacting
hydrocodone with methylenetriphenylphosphorane and an alkyl lithium reagent in
diethyl ether to form 6-Methylenedihydrodesoxycodeine. The 3-
methoxy group is then cleaved to
hydroxy, by reaction with
pyridine. The second step tends to be incomplete and often gives fairly low yields, but these can be improved by changing the reaction conditions.
See also
*
Desomorphine
*
Methyldesorphine
Methyldesorphine is an opioid analgesic. First synthesized in Germany in 1940 and patented in the US in 1952, it has a high potential for abuse as with any potent opioid agonist, and is sometimes found along with desomorphine
Desomorphine is ...
*
Nalmefene
Nalmefene is an opioid antagonist medication used in the management of opioid overdose and alcohol dependence. It is taken by mouth.
Nalmefene is an opiate derivative similar in both structure and activity to the opioid antagonist naltrexone. ...
*
Xorphanol
Xorphanol ( INN) (developmental code name TR-5379 or TR-5379M), also known as xorphanol mesylate ( USAN), is an opioid analgesic of the morphinan family that was never marketed.
Xorphanol is a mixed agonist–antagonist of opioid receptors, a ...
References
{{DEFAULTSORT:Methylenedihydrodesoxymorphine, 6-
4,5-Epoxymorphinans
Mu-opioid receptor agonists
Phenols
Semisynthetic opioids