U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H21NO3.C6H3N3O7
Molecular Weight 516.4575
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIHYDROMORPHINE PICRATE

SMILES

OC1=C(C=C(C=C1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O.[H][C@@]23OC4=C5C(C[C@@]6([H])N(C)CC[C@@]25[C@@]6([H])CC[C@@H]3O)=CC=C4O

InChI

InChIKey=RIEAKNQPZCQWTP-VYKNHSEDSA-N
InChI=1S/C17H21NO3.C6H3N3O7/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;10-6-4(8(13)14)1-3(7(11)12)2-5(6)9(15)16/h2,4,10-11,13,16,19-20H,3,5-8H2,1H3;1-2,10H/t10-,11+,13-,16-,17-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C17H21NO3
Molecular Weight 287.3535
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C6H3N3O7
Molecular Weight 229.1039
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Dihydromorphine is a semi-synthetic opioid derived from morphine. dihydromorphine is a moderately strong analgesic and is used clinically in the treatment of pain and is also the active metabolite of dihydrocodeine. Dihydromorphine acts as an agonist at the μ-opioid (mu), δ-opioid (delta) and κ-opioid (kappa) receptors. Dihydromorphone is approved for clinical use in the United States, Europe, and Japan; and sold under the brand name Dilaudid. Similar to morphine, and other morphine derivatives, hydromorphone has a high potential for addiction and abuse and is listed as a Schedule II drug in the United States Controlled Substances Act of 1970 (and similarly regulated in other countries).

Originator

Curator's Comment: now Abott Laboratories

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P35372|||G8XRH8|||Q5TDA1|||Q9UN57
Gene ID: 4988.0
Gene Symbol: OPRM1
Target Organism: Homo sapiens (Human)
0.23 nM [Ki]
Target ID: P41143
Gene ID: 4985.0
Gene Symbol: OPRD1
Target Organism: Homo sapiens (Human)
Target ID: P41145
Gene ID: 4986.0
Gene Symbol: OPRK1
Target Organism: Homo sapiens (Human)
183.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
dilaudid

Approved Use

Dihydromorphine is approved for the treatment of pain and to be administered as an injection, oral tablet or oral solution. The usual starting injection dose is 1-2 mg subcutaneously or intramuscularly every 4 to 6 hours as necessary for pain control. The usual adult oral dosage of DILAUDID ORAL LIQUID is one-half (2.5 mL) to two teaspoonfuls (10 mL) corresponding to 2.5 mg - 10 mg every 3 to 6 hours as directed by the clinical situation. The usual starting dose for DILAUDID tablets is 2 mg to 4 mg, orally, every 4 to 6 hours.

Launch Date

4.42627195E11
PubMed

PubMed

TitleDatePubMed
Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications.
1998 Mar
Contribution of dihydrocodeine and dihydromorphine to analgesia following dihydrocodeine administration in man: a PK-PD modelling analysis.
2001 Jul
Evaluation of urinary dihydrocodeine excretion in human by gas chromatography-mass spectrometry.
2001 Mar 5
Capillary electrophoresis and capillary electrophoresis-ion trap multiple-stage mass spectrometry for the differentiation and identification of oxycodone and its major metabolites in human urine.
2002 Apr 25
Affinities of dihydrocodeine and its metabolites to opioid receptors.
2002 Aug
LC-MS-MS analysis of hydromorphone and hydromorphone metabolites with application to a pharmacokinetic study in the male Sprague-Dawley rat.
2002 Feb
Morphine 6 glucuronide stimulates nitric oxide release in mussel neural tissues: evidence for a morphine 6 glucuronide opiate receptor subtype.
2002 Mar
Hydromorphone metabolites: isolation and identification from pooled urine samples of a cancer patient.
2002 May
The role of active metabolites in dihydrocodeine effects.
2003 Mar
Practical and high-yield syntheses of dihydromorphine from tetrahydrothebaine and efficient syntheses of (8S)-8-bromomorphide.
2003 Mar 7
Pharmacological characterization of dihydromorphine, 6-acetyldihydromorphine and dihydroheroin analgesia and their differentiation from morphine.
2004 May 25
Capillary electrophoresis contributions to the hydromorphone metabolism in man.
2006 Jun
Acupuncture treatment for pain: systematic review of randomised clinical trials with acupuncture, placebo acupuncture, and no acupuncture groups.
2009 Jan 27
Recent advances in the use of opioids for cancer pain.
2009 Sep 23
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
The role of dihydrocodeine (DHC) metabolites in dihydrocodeine-related deaths.
2010 Oct
In vitro and in vivo pharmacological profile of the 5-benzyl analogue of 14-methoxymetopon, a novel mu opioid analgesic with reduced propensity to alter motor function.
2010 Sep 11
Patents

Sample Use Guides

Dihydromorphine is approved for the treatment of pain and to be administered as an injection, oral tablet or oral solution. The usual starting injection dose is 1-2 mg subcutaneously or intramuscularly every 4 to 6 hours as necessary for pain control. The usual adult oral dosage of DILAUDID ORAL LIQUID is one-half (2.5 mL) to two teaspoonfuls (10 mL) corresponding to 2.5 mg - 10 mg every 3 to 6 hours as directed by the clinical situation. The usual starting dose for DILAUDID tablets is 2 mg to 4 mg, orally, every 4 to 6 hours.
Route of Administration: Other
Human Embryonic Kidney 293 cells (HEK293) were transfected with mouse delta-opioid receptor and maintained in D-MEM/F-12 medium, supplemented with 10% (v/v)fetal calf serum (FCS), and 200 micro-g/mL G-418 in an atmosphere of 5% CO2 at 37 deg-C. Cells were re-plated once per week. Agonistic activity of opioid ligands was assessed by measuring the inhibitory effect of the ligands on forskolin-stimulated cAMP accumulation. Hydromorphone demonstrated an IC50 of 54 nM for the activation of HEK-delta cells.
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:15:08 UTC 2023
Edited
by admin
on Sat Dec 16 10:15:08 UTC 2023
Record UNII
S6V722J7YS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIHYDROMORPHINE PICRATE
Common Name English
MORPHINAN-3,6-DIOL, 4,5-EPOXY-17-METHYL-, (5.ALPHA.,6.BETA.)-, COMPD. WITH 2,4,6-TRINITROPHENOL
Systematic Name English
Code System Code Type Description
PUBCHEM
126961346
Created by admin on Sat Dec 16 10:15:08 UTC 2023 , Edited by admin on Sat Dec 16 10:15:08 UTC 2023
PRIMARY
CAS
5988-18-1
Created by admin on Sat Dec 16 10:15:08 UTC 2023 , Edited by admin on Sat Dec 16 10:15:08 UTC 2023
PRIMARY
FDA UNII
S6V722J7YS
Created by admin on Sat Dec 16 10:15:08 UTC 2023 , Edited by admin on Sat Dec 16 10:15:08 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE