Compound: Desomorphine
SMILES: O1c2c(O)ccc3c2[C@@]45[C@@H]1CCC[C@H]4[C@H](N(C)CC5)C3
InChIKey: LNNWVNGFPYWNQE-GMIGKAJZSA-N
Synonyms: Desomorphine, Dihydrodeoxymorphine, Permonid, Deoxydihydromorphine D, Dihydrodesoxymorphine D, 427-00-9, Desomorfina, Krokodil, Dihydrodesoxymorphine-D, Desomorphinum, 4,5-Epoxy-3-hydroxy-N-methylmorphinan, 6-Deoxy-7,8-dihydromorphine, Morphine, 6-deoxy-7,8-dihydro-, IDS-ND-002, 7OP86J5E33, IDS-ND-002(SECT.3), DTXSID10195390, RefChem:132272, DTXCID20117881, Morphinan-3-ol, 4,5-epoxy-17-methyl-, (5alpha)-, (1S,5R,13S,17R)-4-methyl-12-oxa-4-azapentacyclo(9.6.1.01,13.0?,1?.0?,1?)octadeca-7,9,11(18)-trien-10-ol, 207-045-7, Desomorfin, Desomorphine (INN), DESOMORPHINE [INN], Desomorfin [Czech], Desomorfina [INN-Spanish], Desomorphinum [INN-Latin], CHEMBL3228684, Desomorphine (1.0 mg/mL in Acetonitrile), Desomorphine [INN:BAN:DCF], EINECS 207-045-7, UNII-7OP86J5E33, DEA No. 9055, HSDB 8070, Krokodil [Street Name], Crocodile [Street Name], DESOMORPHINE [MI], Morphinan-3-ol, 4,5-alpha-epoxy-17-methyl-, SCHEMBL24969, CHEMBL2106274, CHEBI:135119, LNNWVNGFPYWNQE-GMIGKAJZSA-N, Dihydrodeoxymorphine or 4,5-Epoxy-3-hydroxy-N-methylmorphinan, BDBM50496883, Desomorphine, 1mg/ml in Acetonitrile, DB01531, (4R,4aR,7aS,12bS)-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-ol, 17-Methyl-5alpha-4,5-epoxymorphinan-3-ol, NS00015682, D12670, Q422163, Desomorphine (Dihydrodesoxymorphine; Krokodil) 1.0 mg/ml in Acetonitrile
Theoretical properties:
molecular_formula: C17H21NO2
molecular_weight: 271.35 g/mol
exact_mass: 271.157228913 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 0
heavy_atom_count: 20
topological_polar_surface_area: 32.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Rectangular plates from acetone-water
color: Rectangular plates from acetone-water
boiling_point: Sublimes in high vacuum between 140 and 170 °C
solubility: Soluble in acetone, ethyl acetate
Descriptions:
pubchem: Desomorphine is a morphinane alkaloid.
chembl: DESOMORPHINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Desomorphine (or in some formulations known as Krokodil) is a semi-synthetic opioid commercialized by Roche, with powerful, fast-acting effects, such as sedation and analgesia. It was first discovered and patented in Germany by a German team working for Knoll in 1920 but was not generally recognized. It was later synthesized in 1932 by American chemist Lyndon Frederick Small. Small also successfully patented it in 1934 in the United States. Desomorphine was used in Germany, Austria, and Switzerland under the brand name Permonid and was described as having a fast onset and a short duration of action, with relatively little nausea compared to equivalent doses of morphine. Dose for dose it is roughly ten times more potent than morphine, with 1 mg desomorphine being equivalent 10 mg morphine, via the intravenous (IV) or intramuscular (IM) routes.
Desomorphine is a morphine analogue where the 6-hydroxyl group and the 7,8 double bond have been reduced. The traditional synthesis of desomorphine starts from α-chlorocodide, which is itself obtained by treating codeine with thionyl chloride. By catalytic reduction, α-chlorocodide gives dihydrodesoxycodeine, which yields desomorphine on demethylation.
A desomorphine product, usually based on codeine, has been developed as a recreational drug. The product in question is typically a highly impure variant of desomorphine. The scaly sores and necrosis that develop around the injection site has prompted the name krokodil (Russian for crocodile).