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Identification
NameDihydromorphine
Accession NumberDB01565
TypeSmall Molecule
GroupsExperimental, Illicit
Description

A semisynthetic analgesic used in the study of narcotic receptors. It has abuse potential. [PubChem]

Structure
Thumb
SynonymsNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number509-60-4
WeightAverage: 287.3535
Monoisotopic: 287.152143543
Chemical FormulaC17H21NO3
InChI KeyIJVCSMSMFSCRME-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[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassMorphinans
Sub ClassNot Available
Direct ParentMorphinans
Alternative Parents
Substituents
  • Morphinan
  • Benzylisoquinoline
  • Phenanthrene
  • Tetralin
  • Benzofuran
  • Aralkylamine
  • Alkyl aryl ether
  • Benzenoid
  • Piperidine
  • Cyclic alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationDihydromorphine is an opioid analgesic used for moderate to severe pain relief.
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Dihydromorphine Action PathwayDrug actionSMP00689
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.995
Blood Brain Barrier+0.985
Caco-2 permeable+0.8356
P-glycoprotein substrateSubstrate0.8896
P-glycoprotein inhibitor INon-inhibitor0.8653
P-glycoprotein inhibitor IINon-inhibitor0.9868
Renal organic cation transporterInhibitor0.5516
CYP450 2C9 substrateNon-substrate0.8115
CYP450 2D6 substrateSubstrate0.8647
CYP450 3A4 substrateSubstrate0.7582
CYP450 1A2 substrateNon-inhibitor0.797
CYP450 2C9 substrateNon-inhibitor0.9309
CYP450 2D6 substrateNon-inhibitor0.617
CYP450 2C19 substrateNon-inhibitor0.7678
CYP450 3A4 substrateNon-inhibitor0.8793
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9646
Ames testNon AMES toxic0.7901
CarcinogenicityNon-carcinogens0.9598
BiodegradationNot ready biodegradable0.9846
Rat acute toxicity2.8928 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8927
hERG inhibition (predictor II)Non-inhibitor0.8414
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point157 dec °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.82 mg/mLALOGPS
logP1.26ALOGPS
logP1.08ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)10.29ChemAxon
pKa (Strongest Basic)9.24ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.93 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.16 m3·mol-1ChemAxon
Polarizability30.66 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
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 ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Mu-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Mu-type opioid receptor P35372 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Delta-type opioid receptor P41143 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Kappa-type opioid receptor P41145 Details

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. E3 ubiquitin-protein ligase TRIM13

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
E3 ubiquitin-protein ligase TRIM13 O60858 Details

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. Pro-opiomelanocortin

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Pro-opiomelanocortin P01189 Details

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

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Drug created on July 31, 2007 07:10 / Updated on September 16, 2013 17:15