Dihydromorphine

Dihydromorphine
Clinical data
Other names	Dihydromorphine, Paramorphan
Routes of; administration	Oral, Intravenous, Intranasally, Sublingually
ATC code	none;
Legal status
Legal status	AU: S8 (Controlled drug); BR: Class A1 (Narcotic drugs); CA: Schedule I; DE: Anlage II (Authorized trade only, not prescriptible); US: Schedule I;
Identifiers
	IUPAC name 3,6-dihydroxy-(5α,6α)-4,5-epoxy-17-methylmorphinan;
CAS Number	509-60-4 ;
PubChem CID	5359421;
IUPHAR/BPS	1616;
DrugBank	DB01565 ;
ChemSpider	4514282 ;
UNII	C3S5FRP6JW;
KEGG	C11782 ;
ChEMBL	ChEMBL1500 ;
CompTox Dashboard (EPA)	DTXSID7048908 ;
ECHA InfoCard	100.007.365
Chemical and physical data
Formula	C17H21NO3
Molar mass	287.359 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O[C@@H]4[C@@H]5Oc1c2c(ccc1O)C[C@H]3N(CC[C@]25[C@H]3CC4)C;
	InChI 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 ; Key:IJVCSMSMFSCRME-KBQPJGBKSA-N ;
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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.

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