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

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H17NO3
Molecular Weight 271.3111
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORMORPHINE

SMILES

[H][C@@]12OC3=C4C(C[C@@]5([H])NCC[C@@]14[C@@]5([H])C=C[C@@H]2O)=CC=C3O

InChI

InChIKey=ONBWJWYUHXVEJS-ZTYRTETDSA-N
InChI=1S/C16H17NO3/c18-11-3-1-8-7-10-9-2-4-12(19)15-16(9,5-6-17-10)13(8)14(11)20-15/h1-4,9-10,12,15,17-19H,5-7H2/t9-,10+,12-,15-,16-/m0/s1

HIDE SMILES / InChI
Normorphine is an opiate analog, specifically the N-demethylated derivative of morphine. It was first described in the 1953 as part of an effort to characterize N-substituted morphine analogs. Normorphine has relatively little opioid activity, but it is a useful intermediate for the production of more potent morphine analogs. It is also a major metabolite of morphine.

Originator

Curator's Comment: # Merck

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P35372|||G8XRH8|||Q5TDA1|||Q9UN57
Gene ID: 4988.0
Gene Symbol: OPRM1
Target Organism: Homo sapiens (Human)
0.061 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

Normorphine hydrochloride was administered as a subcutaneous injection to male adult white volunteers as either a single 30 mg/kg dose or seven doses of 9 or 10 mg
Route of Administration: Parenteral
μ-Opioid receptor (MOR) expressing 293T cells were homogenized in 5 mM Tris, 2 mM EDTA, pH 7.4 and centrifuged to extract the cell pellet. The pellet was resuspended in 50 mM of potassium phosphate buffer, pH 7.4. 20 micro-g of membrane protein was mixed with 0.1 - 1 nM of 3H-naloxone, 100 micro-M GTP and various concentrations of normorphine. Samples were incubated for 3 hours, then filtered through a glass fiber filter before liquid scintillation counting. The radioligand binding assay determined the initial affinity of normorphine for the μ-opioid receptor; a Ki of 0.063 μM was reported.
Name Type Language
NORMORPHINE
INN   MI  
INN  
Official Name English
normorphine [INN]
Common Name English
(-)-NORMORPHINE
Common Name English
IDS-NN-008
Code English
N-DEMETHYLMORPHINE
Common Name English
DEA NO. 9313
Code English
4,5-EPOXY-3,6-DIHYDROXYMORPHIN-7-ENE
Systematic Name English
NORMORPHINE [MI]
Common Name English
MORPHINAN-3,6.ALPHA.-DIOL, 7,8-DIDEHYDRO-4,5.ALPHA.-EPOXY-
Systematic Name English
NSC-270042
Code English
Classification Tree Code System Code
DEA NO. 9313
Created by admin on Fri Dec 15 15:53:42 GMT 2023 , Edited by admin on Fri Dec 15 15:53:42 GMT 2023
Code System Code Type Description
SMS_ID
100000083601
Created by admin on Fri Dec 15 15:53:42 GMT 2023 , Edited by admin on Fri Dec 15 15:53:42 GMT 2023
PRIMARY
MESH
C010616
Created by admin on Fri Dec 15 15:53:42 GMT 2023 , Edited by admin on Fri Dec 15 15:53:42 GMT 2023
PRIMARY
PUBCHEM
5462508
Created by admin on Fri Dec 15 15:53:42 GMT 2023 , Edited by admin on Fri Dec 15 15:53:42 GMT 2023
PRIMARY
CAS
466-97-7
Created by admin on Fri Dec 15 15:53:42 GMT 2023 , Edited by admin on Fri Dec 15 15:53:42 GMT 2023
PRIMARY
ChEMBL
CHEMBL1227
Created by admin on Fri Dec 15 15:53:42 GMT 2023 , Edited by admin on Fri Dec 15 15:53:42 GMT 2023
PRIMARY
NSC
270042
Created by admin on Fri Dec 15 15:53:42 GMT 2023 , Edited by admin on Fri Dec 15 15:53:42 GMT 2023
PRIMARY
EPA CompTox
DTXSID1049019
Created by admin on Fri Dec 15 15:53:42 GMT 2023 , Edited by admin on Fri Dec 15 15:53:42 GMT 2023
PRIMARY
WIKIPEDIA
NORMORPHINE
Created by admin on Fri Dec 15 15:53:42 GMT 2023 , Edited by admin on Fri Dec 15 15:53:42 GMT 2023
PRIMARY
EVMPD
SUB09377MIG
Created by admin on Fri Dec 15 15:53:42 GMT 2023 , Edited by admin on Fri Dec 15 15:53:42 GMT 2023
PRIMARY
MERCK INDEX
m8070
Created by admin on Fri Dec 15 15:53:42 GMT 2023 , Edited by admin on Fri Dec 15 15:53:42 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
207-381-4
Created by admin on Fri Dec 15 15:53:42 GMT 2023 , Edited by admin on Fri Dec 15 15:53:42 GMT 2023
PRIMARY
NCI_THESAURUS
C170234
Created by admin on Fri Dec 15 15:53:42 GMT 2023 , Edited by admin on Fri Dec 15 15:53:42 GMT 2023
PRIMARY
INN
833
Created by admin on Fri Dec 15 15:53:42 GMT 2023 , Edited by admin on Fri Dec 15 15:53:42 GMT 2023
PRIMARY
FDA UNII
XUI1Y24IMI
Created by admin on Fri Dec 15 15:53:42 GMT 2023 , Edited by admin on Fri Dec 15 15:53:42 GMT 2023
PRIMARY