Compound: Dihydromorphine
SMILES: O1c2c(O)ccc3c2[C@@]45[C@@H]1[C@@H](O)CC[C@H]4[C@H](N(C)CC5)C3
InChIKey: IJVCSMSMFSCRME-KBQPJGBKSA-N
Synonyms: Dihydromorphine, Paramorphan, 509-60-4, C3S5FRP6JW, DTXSID7048908, IDS-ND-009, DTXCID4028834, NSC-117865, Morphinan-3,6-diol, 4,5-epoxy-17-methyl-, (5alpha,6alpha)-, (4R,4aR,7S,7aR,12bS)-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinoline-7,9-diol, (4R,4aR,7S,7aR,12bS)-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol, RefChem:133883, (1S,5R,13R,14S,17R)-4-methyl-12-oxa-4-azapentacyclo(9.6.1.0^(1,13).0^(5,17).0^(7,18))octadeca-7(18),8,10-triene-10,14-diol, 208-100-8, Paramorfan, Morphine, dihydro-, 6-alpha-Hydromorphol, Dihydromorfin, CHEBI:4575, 7,8-DIHYDROMORPHINE, NSC 117865, Dihydromorfin [Czech], Dihydromorphine (1mg/ml in Methanol), 6.alpha.-Hydromorphol, 7,8-Dihydromorphin, EINECS 208-100-8, UNII-C3S5FRP6JW, dihydromorphin, 7,8-Dihydromorphin [IUPAC], DEA No. 9145, NCGC00247721-01, 7,8 dihydromorphine, Morphinan-3,6alpha-diol, 4,5alpha-epoxy-17-methyl-, O-Desmethyldihydrocodeine, Epitope ID:549274, CHEMBL1500, DIHYDROMORPHINE [MI], SCHEMBL26346, (5.alpha.,6.alpha.)-4,5-Epoxy-17-methylmorphinan-3,6-diol, GTPL1616, DIHYDROMORPHINE [WHO-DD], Morphinan-3,6-alpha-diol, 4,5-alpha-epoxy-17-methyl-, SCHEMBL29394226, HYDROMORPHOL, 6.ALPHA.-, Tox21_112886, BDBM50452273, DIHYDROMORPHINE [USP IMPURITY], DB01565, Dihydromorphine 0.1 mg/ml in Methanol, Dihydromorphine 1.0 mg/ml in Methanol, CAS-509-60-4, Hydromorphone Hydrochloride EP Impurity D, NS00001103, 17-Methyl-5alpha-4,5-epoxymorphinan-3,6alpha-diol, Q4161314, HYDROMORPHONE HYDROCHLORIDE IMPURITY D [EP IMPURITY], 3,6-DIHYDROXY-(5.ALPHA.,6.ALPHA.)-4,5-EPOXY-17-METHYLMORPHINAN, HYDROMORPHONE HYDROCHLORIDE IMPURITY, DIHYDROMORPHINE (DHM)- [USP IMPURITY], (4R,4aR,7S,7aR,12bS)-3-methyl-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol
Theoretical properties:
molecular_formula: C17H21NO3
molecular_weight: 287.35 g/mol
exact_mass: 287.15214353 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 0
heavy_atom_count: 21
topological_polar_surface_area: 52.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Dihydromorphine is a morphinane alkaloid.
chembl: DIHYDROMORPHINE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Dihydromorphine (Paramorfan, Paramorphan) is a semi-synthetic opioid structurally related to and derived from morphine. The 7,8-double bond in morphine is reduced to a single bond to get dihydromorphine. Dihydromorphine is a moderately strong analgesic and is used clinically in the treatment of pain and also is an active metabolite of the analgesic opioid drug dihydrocodeine.  Dihydromorphine occurs in trace quantities in assays of opium on occasion, as does dihydrocodeine, dihydrothebaine, tetrahydrothebaine, etc.  The process for manufacturing dihydromorphine from morphine for pharmaceutical use was developed in Germany in the late 19th century, with the synthesis being published in 1900 and the drug introduced clinically as Paramorfan shortly thereafter.  A high-yield synthesis from tetrahydrothebaine was later developed.