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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

Molecular Formula C16H17NO3
Molecular Weight 271.3111
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Normorphine, a neurotoxic metabolite?
1990 Mar 24
Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications.
1998 Mar
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:53:42 GMT 2023
Edited
by admin
on Fri Dec 15 15:53:42 GMT 2023
Record UNII
XUI1Y24IMI
Record Status Validated (UNII)
Record Version
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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
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