Dihydromorphine
Identification
- Generic Name
- Dihydromorphine
- DrugBank Accession Number
- DB01565
- Background
A semisynthetic analgesic used in the study of narcotic receptors. It has abuse potential. [PubChem]
- Type
- Small Molecule
- Groups
- Experimental, Illicit
- Structure
Structure for Dihydromorphine (DB01565)
- Weight
- Average: 287.3535
Monoisotopic: 287.152143543 - Chemical Formula
- C17H21NO3
- Synonyms
- Dihydromorphine
- External IDs
- IDS-ND-009
- NSC-117865
Pharmacology
- Indication
Dihydromorphine is an opioid analgesic used for moderate to severe pain relief.
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AMu-type opioid receptor agonistHumans UDelta-type opioid receptor agonistHumans UKappa-type opioid receptor agonistHumans UE3 ubiquitin-protein ligase TRIM13 agonistHumans UPro-opiomelanocortin agonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Dihydromorphine Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Dihydromorphine is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Dihydromorphine. Acetophenazine The risk or severity of hypotension and CNS depression can be increased when Acetophenazine is combined with Dihydromorphine. Aclidinium The risk or severity of adverse effects can be increased when Aclidinium is combined with Dihydromorphine. Agomelatine The risk or severity of adverse effects can be increased when Dihydromorphine is combined with Agomelatine. Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Dihydromorphine. Alimemazine The risk or severity of hypotension and CNS depression can be increased when Alimemazine is combined with Dihydromorphine. Alloin The therapeutic efficacy of Alloin can be decreased when used in combination with Dihydromorphine. Almotriptan The risk or severity of adverse effects can be increased when Almotriptan is combined with Dihydromorphine. Alosetron The risk or severity of adverse effects can be increased when Alosetron is combined with Dihydromorphine. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Categories
- Drug Categories
- Alkaloids
- Analgesics
- Central Nervous System Agents
- Central Nervous System Depressants
- Heterocyclic Compounds, Fused-Ring
- Morphinans
- Morphine Derivatives
- Narcotics
- Opiate Alkaloids
- Opioids
- Peripheral Nervous System Agents
- Phenanthrenes
- Semi-synthetic Opioids
- Sensory System Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
- Kingdom
- Organic compounds
- Super Class
- Alkaloids and derivatives
- Class
- Morphinans
- Sub Class
- Not Available
- Direct Parent
- Morphinans
- Alternative Parents
- Phenanthrenes and derivatives / Tetralins / Coumarans / Aralkylamines / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Piperidines / Trialkylamines / Secondary alcohols / Cyclic alcohols and derivatives show 4 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / Alcohol / Alkyl aryl ether / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Coumaran / Cyclic alcohol show 16 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- morphinane alkaloid (CHEBI:4575)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- C3S5FRP6JW
- CAS number
- 509-60-4
- InChI Key
- IJVCSMSMFSCRME-KBQPJGBKSA-N
- 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
- IUPAC Name
- (1S,5R,13R,14S,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-triene-10,14-diol
- SMILES
- [H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])CC[C@@H]2O
References
- Synthesis Reference
Herbert Merz, Ingrid Wiedemann, Helmut Ensinger, Klaus Stockhaus, Matthias Grauert, "14-hydroxy-N-(2-methoxyethyl)-7,8-dihydromorphine and -norisomorphine, processes for the preparation thereof and the use thereof as pharmaceutical compositions." U.S. Patent US5240933, issued August 31, 1993.
US5240933- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0060548
- KEGG Compound
- C11782
- PubChem Compound
- 5359421
- PubChem Substance
- 46506587
- ChemSpider
- 4514282
- BindingDB
- 50452273
- ChEBI
- 4575
- ChEMBL
- CHEMBL1500
- ZINC
- ZINC000004102205
- Wikipedia
- Dihydromorphine
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 157 dec °C PhysProp - Predicted Properties
Property Value Source logP 1.08 ChemAxon pKa (Strongest Acidic) 10.29 ChemAxon pKa (Strongest Basic) 9.24 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 52.93 Å2 ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 79.16 m3·mol-1 ChemAxon Polarizability 30.68 Å3 ChemAxon Number of Rings 5 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.995 Blood Brain Barrier + 0.985 Caco-2 permeable + 0.8356 P-glycoprotein substrate Substrate 0.8896 P-glycoprotein inhibitor I Non-inhibitor 0.8653 P-glycoprotein inhibitor II Non-inhibitor 0.9868 Renal organic cation transporter Inhibitor 0.5516 CYP450 2C9 substrate Non-substrate 0.8115 CYP450 2D6 substrate Substrate 0.8647 CYP450 3A4 substrate Substrate 0.7582 CYP450 1A2 substrate Non-inhibitor 0.797 CYP450 2C9 inhibitor Non-inhibitor 0.9309 CYP450 2D6 inhibitor Non-inhibitor 0.617 CYP450 2C19 inhibitor Non-inhibitor 0.7678 CYP450 3A4 inhibitor Non-inhibitor 0.8793 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9646 Ames test Non AMES toxic 0.7901 Carcinogenicity Non-carcinogens 0.9598 Biodegradation Not ready biodegradable 0.9846 Rat acute toxicity 2.8928 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8927 hERG inhibition (predictor II) Non-inhibitor 0.8414
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Voltage-gated calcium channel activity
- Specific Function
- Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
- Gene Name
- OPRM1
- Uniprot ID
- P35372
- Uniprot Name
- Mu-type opioid receptor
- Molecular Weight
- 44778.855 Da
References
- Crooks PA, Kottayil SG, Al-Ghananeem AM, Byrn SR, Butterfield DA: Opiate receptor binding properties of morphine-, dihydromorphine-, and codeine 6-O-sulfate ester congeners. Bioorg Med Chem Lett. 2006 Aug 15;16(16):4291-5. Epub 2006 Jun 13. [Article]
- Dietis N, Guerrini R, Calo G, Salvadori S, Rowbotham DJ, Lambert DG: Simultaneous targeting of multiple opioid receptors: a strategy to improve side-effect profile. Br J Anaesth. 2009 Jul;103(1):38-49. doi: 10.1093/bja/aep129. Epub 2009 May 27. [Article]
- Gilbert AK, Hosztafi S, Mahurter L, Pasternak GW: Pharmacological characterization of dihydromorphine, 6-acetyldihydromorphine and dihydroheroin analgesia and their differentiation from morphine. Eur J Pharmacol. 2004 May 25;492(2-3):123-30. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Opioid receptor activity
- Specific Function
- G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
- Gene Name
- OPRD1
- Uniprot ID
- P41143
- Uniprot Name
- Delta-type opioid receptor
- Molecular Weight
- 40368.235 Da
References
- Crooks PA, Kottayil SG, Al-Ghananeem AM, Byrn SR, Butterfield DA: Opiate receptor binding properties of morphine-, dihydromorphine-, and codeine 6-O-sulfate ester congeners. Bioorg Med Chem Lett. 2006 Aug 15;16(16):4291-5. Epub 2006 Jun 13. [Article]
- Dietis N, Guerrini R, Calo G, Salvadori S, Rowbotham DJ, Lambert DG: Simultaneous targeting of multiple opioid receptors: a strategy to improve side-effect profile. Br J Anaesth. 2009 Jul;103(1):38-49. doi: 10.1093/bja/aep129. Epub 2009 May 27. [Article]
- Gilbert AK, Hosztafi S, Mahurter L, Pasternak GW: Pharmacological characterization of dihydromorphine, 6-acetyldihydromorphine and dihydroheroin analgesia and their differentiation from morphine. Eur J Pharmacol. 2004 May 25;492(2-3):123-30. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Opioid receptor activity
- Specific Function
- G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
- Gene Name
- OPRK1
- Uniprot ID
- P41145
- Uniprot Name
- Kappa-type opioid receptor
- Molecular Weight
- 42644.665 Da
References
- Crooks PA, Kottayil SG, Al-Ghananeem AM, Byrn SR, Butterfield DA: Opiate receptor binding properties of morphine-, dihydromorphine-, and codeine 6-O-sulfate ester congeners. Bioorg Med Chem Lett. 2006 Aug 15;16(16):4291-5. Epub 2006 Jun 13. [Article]
- Dietis N, Guerrini R, Calo G, Salvadori S, Rowbotham DJ, Lambert DG: Simultaneous targeting of multiple opioid receptors: a strategy to improve side-effect profile. Br J Anaesth. 2009 Jul;103(1):38-49. doi: 10.1093/bja/aep129. Epub 2009 May 27. [Article]
- Gilbert AK, Hosztafi S, Mahurter L, Pasternak GW: Pharmacological characterization of dihydromorphine, 6-acetyldihydromorphine and dihydroheroin analgesia and their differentiation from morphine. Eur J Pharmacol. 2004 May 25;492(2-3):123-30. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- E3 ubiquitin ligase involved in the retrotranslocation and turnover of membrane and secretory proteins from the ER through a set of processes named ER-associated degradation (ERAD). This process ac...
- Gene Name
- TRIM13
- Uniprot ID
- O60858
- Uniprot Name
- E3 ubiquitin-protein ligase TRIM13
- Molecular Weight
- 46987.08 Da
References
- Liebmann C, Schnittler M, Hartrodt B, Born I, Neubert K: Structure-activity studies of novel casomorphin analogues: binding profiles towards mu 1-, mu 2- and delta -opioid receptors. Pharmazie. 1991 May;46(5):345-8. [Article]
- Maneckjee R, Archer S, Zukin RS: Characterization of a polyclonal antibody to the mu opioid receptor. J Neuroimmunol. 1988 Feb;17(3):199-208. [Article]
- Ishizuka Y, Oka T: Relation of diltiazem binding sites to opioid receptor subtypes in the guinea-pig brain. Tokai J Exp Clin Med. 1987 Mar;12(1):11-7. [Article]
- Koman A, Kolb VM, Terenius L: A naloxone-steroid hybrid azine with selective and long-acting opioid antagonism at delta receptors in vitro. Pharm Res. 1987 Apr;4(2):147-9. [Article]
- Ho CL, Hammonds RG Jr, Li CH: Opiate receptor binding profile in the rabbit cerebellum and brain membranes. Biochem Pharmacol. 1985 Apr 1;34(7):925-31. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Type 4 melanocortin receptor binding
- Specific Function
- ACTH stimulates the adrenal glands to release cortisol.MSH (melanocyte-stimulating hormone) increases the pigmentation of skin by increasing melanin production in melanocytes.Beta-endorphin and Met...
- Gene Name
- POMC
- Uniprot ID
- P01189
- Uniprot Name
- Pro-opiomelanocortin
- Molecular Weight
- 29423.72 Da
References
- Somoza E: Influence of neuroleptics on the binding of met-enkephalin, morphine and dihydromorphine to synaptosome-enriched fractions of rat brain. Neuropharmacology. 1978 Aug;17(8):577-81. [Article]
- Johnson N, Houghten R, Pasternak GW: Binding of 3H-beta-endorphin in rat brain. Life Sci. 1982 Sep 20-27;31(12-13):1381-4. [Article]
Drug created on July 31, 2007 13:10 / Updated on February 21, 2021 18:51