MORPHINONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H17NO3
Molecular Weight	283.3218
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12OC3=C4C(C[C@H]5N(C)CC[C@@]14[C@@]5([H])C=CC2=O)=CC=C3O

InChI

InChIKey=PFBSOANQDDTNGJ-YNHQPCIGSA-N

InChI=1S/C17H17NO3/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/h2-5,10-11,16,19H,6-8H2,1H3/t10-,11+,16-,17-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C17H17NO3
Molecular Weight	283.3218
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7078349
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17094451 | https://www.ncbi.nlm.nih.gov/pubmed/1688995 | https://www.ncbi.nlm.nih.gov/pubmed/6135574 | https://www.ncbi.nlm.nih.gov/pubmed/7078349

Morphinone is an oxidation product of morphine with weak agonistic activity toward mu opioid receptor. Morphinone is the intermediate when morphine is being converted to hydromorphone. Morphinone is toxic compound, subcutaneous administration of morphinone produced a reduction of hepatic non-protein sulfhydryl concentration. Glutathione or cysteine significantly decrease Morphinone toxicity.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mu opioid receptor 221 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17616524	Agonist 2678		146.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7078349	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effects of environment on flavin reactivity in morphinone reductase: analysis of enzymes displaying differential charge near the N-1 atom and C-2 carbonyl region of the active-site flavin.	2001 Oct 15	11583577
Deep tunneling dominates the biologically important hydride transfer reaction from NADH to FMN in morphinone reductase.	2008 Jun 4	18470990

Patents

Sample Use Guides

In Vivo Use Guide

The analgesic effects of morphinone and morphine in mice were determined by the acetic acid writhing test. Each group of I0 male mice was subcutaneously administered a solution of morphine or morphinone (0.25, 0.5, 1.0 and 1.5 mg/kg) in a volume of I0 ml solution per kg, 30 min prior to the intraperltoneal injection of I0 ml/kg of 0.7% acetic acid in the saline.

Route of Administration: Other

In Vitro Use Guide

HL-60 cells were inoculated at 1.0x10^6 cells/well in 96-microwell (Becton Dickinson Labware, NJ, USA), unless otherwise stated. After 24 h, the medium was removed with an aspirator and replaced with 0.1 mL of fresh medium containing the 0-100mkM of morphinone. Cells were incubated for another 24 h and the relative viable cell number was then determined by the MTT method.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:39:31 UTC 2023` Edited by `admin` on `Fri Dec 15 18:39:31 UTC 2023`
Record UNII	28MBK63MAW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MORPHINONE

Common Name

English

HYDROMORPHONE RELATED COMPOUND A [USP-RS]

Common Name

English

MORPHINAN-6-ONE, 7,8-DIDEHYDRO-4,5-EPOXY-3-HYDROXY-17-METHYL-, (5-.ALPHA.)-

Common Name

English

HYDROMORPHONE RELATED COMPOUND A [USP IMPURITY]

Common Name

English

HYDROMORPHONE RELATED COMPOUND A

Common Name

English

MORPHINE SULFATE IMPURITY E [EP IMPURITY]

Common Name

English

HYDROMORPHONE RELATED COMPOUND A CII

Common Name

English

MORPHINE HYDROCHLORIDE IMPURITY E [EP IMPURITY]

Common Name

English

(5.ALPHA.)-7,8-DIDEHYDRO-4,5-EPOXY-3-HYDROXY-17-METHYLMORPHINAN-6-ONE

Systematic Name

English

Code System Code Type Description

CHEBI

57728