6-Methylenedihydrodesoxymorphine

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analogue structurally related to desomorphine that is a derivative of hydromorphone, where the 6-ketone group has been replaced by a methylene group.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

Other names6-MDDM, 6-Methylene- dihydrodesoxymorphine

CAS Number

• 3414-84-4 ^N

PubChem CID

• 5492874

ChemSpider

• 4591200 ^Y

Quick facts Clinical data, Other names ...

6-Methylenedihydrodesoxymorphine

Clinical data
Other names	6-MDDM, 6-Methylene- dihydrodesoxymorphine
Identifiers
IUPAC name 4,5-α-Epoxy-17-methyl-6-methylenemorphinan-3-ol
CAS Number	3414-84-4 N
PubChem CID	5492874
ChemSpider	4591200 Y
CompTox Dashboard (EPA)	DTXSID20187741
Chemical and physical data
Formula	C18H21NO2
Molar mass	283.371 g·mol−1
3D model (JSmol)	Interactive image
SMILES Oc2c1O[C@H]5\C(=C)CC[C@H]4[C@@H]3N(CC[C@@]45c1c(cc2)C3)C
InChI InChI=1S/C18H21NO2/c1-10-3-5-12-13-9-11-4-6-14(20)16-15(11)18(12,17(10)21-16)7-8-19(13)2/h4,6,12-13,17,20H,1,3,5,7-9H2,2H3/t12-,13+,17-,18-/m0/s1 Y Key:LBCZKDPFDXFDTN-GGNLRSJOSA-N Y
NY (what is this?)  (verify)

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6-Methylenedihydrodesoxymorphine is a potent μ-opioid agonist, 80x stronger than morphine.^[1] Compared to morphine it has a faster onset of action and similar duration of effects.^[2] 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 while inducing comparatively few side effects,^[3] however it has never been developed for medical use in humans. Its synthesis typically takes 12 hours to a day.

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.^[4][5]