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targets (5)
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Identification
Name Dihydromorphine
Accession Number DB01565
Type small molecule
Groups illicit, experimental
Description

A semisynthetic analgesic used in the study of narcotic receptors. It has abuse potential. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names Not Available
Brand mixtures Not Available
Categories
  • Narcotics
  • Analgesics, Opioid
CAS number 509-60-4
Weight Average: 287.3535
Monoisotopic: 287.152143543
Chemical Formula C17H21NO3
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication Dihydromorphine is an opioid analgesic used for moderate to severe pain relief.
Pharmacodynamics Not Available
Mechanism of action Not Available
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
Toxicity Not Available
Affected organisms Not Available
Pathways Not Available
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 157 dec °C PhysProp
Predicted Properties
Property Value Source
water solubility 1.82e+00 g/l ALOGPS
logP 1.26 ALOGPS
logP 1.08 ChemAxon
logS -2.2 ALOGPS
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 ChemAxon
rotatable bond count 0 ChemAxon
refractivity 79.16 ChemAxon
polarizability 30.66 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C11782 Link_out
PubChem Compound 5359421 Link_out
PubChem Substance 46506587 Link_out
ChemSpider 4514282 Link_out
Wikipedia http://en.wikipedia.org/wiki/Dihydromorphine Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Mu-type opioid receptor

Pharmacological action: yes
Actions: agonist

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin

Organism class: human
UniProt ID: P35372 Link_out
Gene: OPRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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. Pubmed
  2. 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. Epub 2009 May 27. Pubmed
  3. 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. Pubmed

2. Delta-type opioid receptor

Pharmacological action: unknown
Actions: agonist

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Highly stereoselective. receptor for enkephalins

Organism class: human
UniProt ID: P41143 Link_out
Gene: OPRD1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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. Pubmed
  2. 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. Epub 2009 May 27. Pubmed
  3. 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. Pubmed

3. Kappa-type opioid receptor

Pharmacological action: unknown
Actions: agonist

Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions

Organism class: human
UniProt ID: P41145 Link_out
Gene: OPRK1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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. Pubmed
  2. 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. Epub 2009 May 27. Pubmed
  3. 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. Pubmed

4. Tripartite motif-containing protein 13

Pharmacological action: unknown
Actions: agonist

May act as a tumor suppressor

Organism class: human
UniProt ID: O60858 Link_out
Gene: TRIM13 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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. Pubmed
  2. Maneckjee R, Archer S, Zukin RS: Characterization of a polyclonal antibody to the mu opioid receptor. J Neuroimmunol. 1988 Feb;17(3):199-208. Pubmed
  3. 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. Pubmed
  4. 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. Pubmed
  5. 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. Pubmed

5. Corticotropin-lipotropin

Pharmacological action: unknown
Actions: agonist

Beta-endorphin and Met-enkephalin are endogenous opiates

Organism class: human
UniProt ID: P01189 Link_out
Gene: POMC Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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. Pubmed
  2. 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. Pubmed
Comments
Drug created on July 31, 2007 07:10 / Updated on February 08, 2013 16:20