Structure via PubChem · Public domain (PubChem)
dihydromorphine
Sign in to saveAlso known as paramorphan
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 u
Chemical data
- Formula
- C17H21NO3
- Molecular weight
- 287.35 g/mol
- IUPAC name
- (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
- SMILES
- CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)O)O[C@H]3[C@H](CC4)O
- InChIKey
- IJVCSMSMFSCRME-KBQPJGBKSA-N
- XLogP
- 1.8
- Polar surface area
- 52.9 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
426 papers- Intranasal analgesia for acute moderate to severe pain in children - a systematic review and meta-analysis.BMC pediatrics · 2023
- Dihydrocodeine: safety concerns.Expert review of clinical pharmacology · 2016
- Development of a Sensitive and Rapid HPLC-MS Method for Dihydrocodeine and Dihydromorphine: Application to Bioequivalence Studies.Journal of chromatographic science · 2022
- Pharmacological characterization of dihydromorphine, 6-acetyldihydromorphine and dihydroheroin analgesia and their differentiation from morphine.European journal of pharmacology · 2004
- DIHYDROMORPHINE IN PERIPHERAL NERVOUS TISSUE.Nature · 1964
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 287.152144
Show 6 more facts
- chemical formula
- C₁₇H₂₁NO₃
- isomeric SMILES
- CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)O)O[C@H]3[C@H](CC4)O
- canonical SMILES
- CN1CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(CC4)O
- subject has role
- narcotic
- found in taxon
- Papaver somniferum
- Commons category
- Dihydromorphine
Sources (2)
via Wikidata · CC0
~5 min read
Encyclopedic overview
13 sectionsContents
- Uses
- Medical
- Research
- Strength
- Pharmacology
- Pharmacokinetics
- Legality
- United States
- Europe
- Japan
- See also
- References
- External links
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.
==Uses==
Excerpted from Wikipedia’s “dihydromorphine” article, available under the CC BY-SA 4.0 licence.