Dihydromorphine
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| Systematic (IUPAC) name | |
| 3,6-Dihydroxy-(5α,6α)-4,5-epoxy-17-methylmorphinan | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | Schedule I (US) |
| Routes | Oral, Intravenous, Intranasally, Sublingually |
| Identifiers | |
| CAS number | 1421-28-9  |
| ATC code | None |
| PubChem | CID 5359421 |
| IUPHAR ligand | 1616 |
| DrugBank | DB01565 |
| ChemSpider | 4514282 |
| KEGG | C11782 |
| ChEMBL | CHEMBL1500 |
| Synonyms | Dihydromorphine, Paramorphan |
| Chemical data | |
| Formula | C17H21NO3 |
| Mol. mass | 287.354 g/mol |
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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.[1] 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.[2][3][4]
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Uses [edit]
Medical [edit]
Dihydromorphine is an opioid that is used for the management of moderate to severe pain such as cancer, although its less effective in treating things such as neuropathic pain and is generally considered inappropriate and ineffective for psychological pain.[2][5]
Research [edit]
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.[6][7]
Strength [edit]
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.[8]
Pharmacology [edit]
Dihydromorphine acts as an agonist at the μ-opioid (mu), δ-opioid (delta) and κ-opioid (kappa) receptors.[3][2] Agonism 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.[9][10]
Pharmacokinetics [edit]
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.[citation needed]
Legality [edit]
Under the 1961 international Single Convention on Narcotic Drugs treaty dihydromorphine is a Schedule I narcotic subject to control, and other countries' laws may vary.[11]
United States of America [edit]
Under the Controlled Substances Act, dihydromorphine is listed as a Schedule I substance along with heroin.[12] In the United States, its role in the production of dihydrocodeine makes it the Schedule I substance with one of the higher annual manufacturing quotas granted by the US Drug Enforcement Administration.[citation needed]
Sweden [edit]
Under Sweden's drug control laws, dihydromorphine is listed as a Schedule II substance which recognizes a controlled substance has medicinal value and allows for its medical usage with restrictions.[13]
See also [edit]
References [edit]
- ^ Rama Rao Nadendla. Principles Of Organic Medicinal Chemistry pp. 215
- ^ a b c DrugBank: Dihydromorphine (DB01565)
- ^ a b Dihydromorphine - PubChem
- ^ Susanne Ammon, Ute Hofmann, Ernst-Ulrich Griese, Nadja Gugeler, and Gerd Mikus (1999). "Pharmacokinetics of dihydrocodeine and its active metabolite after single and multiple oral dosing". British Journal of Clinical Pharmacology 48 (3): 317–322. PMC 2014322.
- ^ Dureja. Handbook Of Pain Management pp. 67
- ^ Antkiewicz-Michaluk L, Vetulani J, Havemann U, Kuschinsky K (1982). "3H-dihydromorphine binding sites in subcellular fractions of rat striatum.". Pol J Pharmacol Pharm 34 (1-3): 73–78. PMID 6300816.
- ^ Savage DD, Mills SA, Jobe PC, Reigel CE (1988). "Elevation of naloxone-sensitive 3H-dihydromorphine binding in hippocampal formation of genetically epilepsy-prone rats.". Life Sci. 43 (3): 239–246. PMID 2840539.
- ^ Rama Rao Nedendla. Principles Of Organic Medicinal Chemistry pp. 216
- ^ Costantino CM, Gomes I, Stockton SD, Lim MP, Devi LA (2012). "Opioid receptor heteromers in analgesia.". Expert Rev Mol Med 14 (9). PMID 22490239.
- ^ Varga EV, Navratilova E, Stropova D, Jambrosic J, Roeske WR, Yamamura HI (2004). "Agonist-specific regulation of the delta-opioid receptor". Life Sci. 76 (6): 599–612. doi:10.1016/j.lfs.2004.07.020. PMID 15567186.
- ^ Single Convention on Narcotic Drugs, 1961 - Page 40 of 44
- ^ Controlled Substances (in alphabetical order) - Page 5 of 12
- ^ Läkemedelsverkets föreskrifter (LVFS 1997:12) om förteckningar över narkotika - Drug Administration regulations; list of drugs (Swedish)
External links [edit]
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