Desomorphine

Title: Desomorphine
CAS Registry Number: 427-00-9
CAS Name: 4,5a-Epoxy-17-methylmorphinan-3-ol
Additional Names: dihydrodesoxymorphine-D
Trademarks: Permonid (Roche)
Molecular Formula: C17H21NO2
Molecular Weight: 271.35
Percent Composition: C 75.25%, H 7.80%, N 5.16%, O 11.79%
Literature References: Synthesis, physical data: L. F. Small et al., J. Am. Chem. Soc. 55, 3863 (1933).
Properties: Rectangular plates from acetone-water. Sublimes in high vacuum between 140° and 170°. Anhydr base, mp 189°. [a]D28 -77° (c = 1.6 in methanol). Sol in acetone, ethyl acetate. Alcoholic solns darken and acquire a reddish color.
Melting point: mp 189°
Optical Rotation: [a]D28 -77° (c = 1.6 in methanol)
Derivative Type: Hemihydrate
Properties: Crystals from ethyl acetate, mp 162-164°. [a]D28 -79° (c = 1.08 in ethyl acetate).
Melting point: mp 162-164°
Optical Rotation: [a]D28 -79° (c = 1.08 in ethyl acetate)
Derivative Type: Hydrochloride
Molecular Formula: C17H21NO2.HCl
Molecular Weight: 307.82
Percent Composition: C 66.33%, H 7.20%, N 4.55%, O 10.40%, Cl 11.52%
Properties: Crystals from alcohol, [a]D27 -67° (c = 0.90). Very sol in water.
Optical Rotation: [a]D27 -67° (c = 0.90)
Derivative Type: Hydrogen sulfate dihydrate
Molecular Formula: (C17H21NO2)2.H2SO4.2H2O
Molecular Weight: 676.82
Percent Composition: C 60.34%, H 7.15%, N 4.14%, O 23.64%, S 4.74%
Properties: Scales, plates from water, brown at 210°, unmelted at 230°. Sol in 40 parts water; freely sol in hot water. Soln is stable to boiling. [a]D29 -60° (c = 1.43).
Optical Rotation: [a]D29 -60° (c = 1.43)
NOTE: This is a controlled substance (opium derivative): 21 CFR, 1308.11.
Therap-Cat: Analgesic (narcotic).
Keywords: Analgesic (Narcotic).
Desonide Desosamine Desoximetasone Dess-Martin Periodinane Desthiobiotin

Desomorphine
Permonid.svg
Systematic (IUPAC) name
4,5-α-Epoxy-17-methylmorphinan-3-ol
Clinical data
Legal status Prohibited (S9) (AU) Schedule I (US)
Dependence liability Very High
Identifiers
CAS number 427-00-9 N
ATC code None
PubChem CID 5362456
ChemSpider 4515044 YesY
UNII 7OP86J5E33 YesY
ChEMBL CHEMBL2106274 N
Synonyms Desomorphine, Dihydrodesoxymorphine, Permonid
Chemical data
Formula C17H21NO2 
Mol. mass 271.354 g/mol
 N (what is this?)  (verify)

Desomorphine (dihydrodesoxymorphine, Permonid, street name krokodil) is a derivative from morphine (an opioid) with powerful, fast-acting sedative and analgesic effects.[1][2][3][4] Patented in 1932,[5] Desomorphine was used in Switzerland under the brand name Permonid[6] and was described as having a fast onset and a short duration of action, with relatively little nausea or respiratory depression compared to equivalent doses of morphine.

Desomorphine is derived from morphine where the 6-hydroxyl group and the 7,8 double bond have been reduced.[5] The traditional synthesis of desomorphine starts from α-chlorocodide, which is itself obtained by reacting thionyl chloride with codeine. By catalytic reduction, α-chlorocodide gives dihydrodesoxycodeine, which yields desomorphine on demethylation.[7][8]