Dihydromorphine

Dihydromorphine

Clinical data
Routes of administration	Oral, Intravenous, Intranasally, Sublingually
ATC code	none
Legal status
Legal status	AU: S8 (Controlled) CA: Schedule I DE: Anlage II (Prohibited) US: Schedule I
Identifiers
IUPAC name 3,6-dihydroxy-(5α,6α)-4,5-epoxy-17-methylmorphinan
Synonyms	Dihydromorphine, Paramorphan
CAS Number	509-60-4 N
PubChem CID	5359421
IUPHAR/BPS	1616
DrugBank	DB01565 Y
ChemSpider	4514282 Y
UNII	C3S5FRP6JW
KEGG	C11782 Y
ChEMBL	CHEMBL1500 Y
ECHA InfoCard	100.007.365
Chemical and physical data
Formula	C17H21NO3
Molar mass	287.354 g/mol
3D model (Jmol)	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 Y Key:IJVCSMSMFSCRME-KBQPJGBKSA-N Y
NY (what is this?)

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.

Dihydromorphine is an opioid that is used for the management of moderate to severe pain such as cancer, although it's less effective in treating things such as neuropathic pain and is generally considered inappropriate and ineffective for psychological pain.

Dihydromorphine, often labelled with the isotope tritium in the form of [3H]-dihydromorphine, is used in scientific research to study binding of the opioid receptors in the nervous system.

Dihydromorphine is slightly stronger than morphine as an analgesic with a similar side effect profile. The relative potency of dihydromorphine is about 1.2 times that of morphine. In comparison, the relative potency of dihydrocodeine is 1.15 times that of codeine.

Dihydromorphine acts as an agonist at the μ-opioid (mu), δ-opioid (delta) and κ-opioid (kappa) receptors. Agonist of the μ-opioid and δ-opioid receptors is largely responsible for the clinical effects of opioids like dihydromorphine with the μ agonism providing more analgesia than the δ.

Dihydromorphine's onset of action is more rapid than morphine and it also tends to have a longer duration of action, generally 4–7 hours.