6-Methylenedihydrodesoxymorphine

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Image:6-methylenehydromorphone.svg
6-Methylenedihydrodesoxymorphine
Systematic (IUPAC) name
4,5-α-epoxy-17-methyl-6-methylenemorphinan-3-ol
Identifiers
CAS number	3414-84-4
ATC code	?
PubChem	5492874
Chemical data
Formula	C18H21NO2
Mol. mass	283.36 g/mol
Synonyms	6-MDDM, 6-Methylenedihydrodesoxymorphine
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

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6-Methylenedihydrodesoxymorphine (6-MDDM) is an opiate analogue that is a derivative of hydromorphone, where the 6-ketone group has been replaced by methylene. It has sedative and analgesic effects.

6-Methylenedihydrodesoxymorphine is a potent μ-opioid agonist, reportedly up to 80x stronger than morphine.[2] Compared to morphine it has a faster onset of action and similar duration of effects.^[1] It produces around the same degree of respiratory depression 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 which produce comparatively few side effects,^[1] 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.^[1][1]

References

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Acknowledgement and Attribution Regarding Sources of Content

Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .