Dihydromorphine

Not to be confused with dihydromorphinone (Dilaudid, etc.) or dehydromorphine.
Dihydromorphine
Skeletal formula of dihydromorphine
Ball-and-stick model of the dihydromorphine molecule
Clinical data
Other namesDihydromorphine, Paramorphan
Dependence
liability		High
Addiction
liability		High
Routes of
administration		Oral, Intravenous, Intranasally, Sublingually
ATC code
  • none
Legal status
Legal status
Identifiers
  • 3,6-dihydroxy-(5α,6α)-4,5-epoxy-17-methylmorphinan
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.007.365 Edit this at Wikidata
Chemical and physical data
FormulaC17H21NO3
Molar mass287.359 g·mol−1
3D model (JSmol)
  • O[C@@H]4[C@@H]5Oc1c2c(ccc1O)C[C@H]3N(CC[C@]25[C@H]3CC4)C
  • InChI=1S/C17H21NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2,4,10-11,13,16,19-20H,3,5-8H2,1H3/t10-,11+,13-,16-,17-/m0/s1 checkY
  • Key:IJVCSMSMFSCRME-KBQPJGBKSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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.[2] 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.[3][4][5] 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.[6]

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ Nadendla R (2005). Principles of Organic Medicinal Chemistry. pp. 215–216. OCLC 938923816.
  3. ^ "Dihydromorphine". DrugBank. DB01565.
  4. ^ "Dihydromorphine". PubChem. U.S. National Library of Medicine.
  5. ^ Ammon S, Hofmann U, Griese EU, Gugeler N, Mikus G (September 1999). "Pharmacokinetics of dihydrocodeine and its active metabolite after single and multiple oral dosing". British Journal of Clinical Pharmacology. 48 (3): 317–322. doi:10.1046/j.1365-2125.1999.00042.x. PMC 2014322. PMID 10510141.
  6. ^ Przybyl AK, Flippen-Anderson JL, Jacobson AE, Rice KC (March 2003). "Practical and high-yield syntheses of dihydromorphine from tetrahydrothebaine and efficient syntheses of (8S)-8-bromomorphide". The Journal of Organic Chemistry. 68 (5): 2010–3. doi:10.1021/jo0206871. PMID 12608825.