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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C16H17NO3.3H2O
Molecular Weight 596.668
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORMORPHINE SESQUIHYDRATE

SMILES

O.O.O.[H][C@@]12OC3=C4C(C[C@@]5([H])NCC[C@@]14[C@@]5([H])C=C[C@@H]2O)=CC=C3O.[H][C@@]67OC8=C9C(C[C@@]%10([H])NCC[C@@]69[C@@]%10([H])C=C[C@@H]7O)=CC=C8O

InChI

InChIKey=CSKBTWFSQKIQRF-WPAPNCBNSA-N
InChI=1S/2C16H17NO3.3H2O/c2*18-11-3-1-8-7-10-9-2-4-12(19)15-16(9,5-6-17-10)13(8)14(11)20-15;;;/h2*1-4,9-10,12,15,17-19H,5-7H2;3*1H2/t2*9-,10+,12-,15-,16-;;;/m00.../s1

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 Sat Dec 16 08:29:35 UTC 2023
Edited
by admin
on Sat Dec 16 08:29:35 UTC 2023
Record UNII
J6061U34KH
Record Status Validated (UNII)
Record Version
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Name Type Language
NORMORPHINE SESQUIHYDRATE
MI  
Common Name English
NORMORPHINE 1.5 HYDRATE
Common Name English
NORMORPHINE SESQUIHYDRATE [MI]
Common Name English
(5.ALPHA.,6.ALPHA.)-7,8-DIDEHYDRO-4,5-EPOXYMORPHINAN-3,6-DIOL SESQUIHYDRATE
Systematic Name English
MORPHINAN-3,6-DIOL, 7,8-DIDEHYDRO-4,5-EPOXY-, HYDRATE (2:3), (5.ALPHA.,6.ALPHA.)-
Systematic Name English
Code System Code Type Description
MERCK INDEX
m8070
Created by admin on Sat Dec 16 08:29:35 UTC 2023 , Edited by admin on Sat Dec 16 08:29:35 UTC 2023
PRIMARY
EPA CompTox
DTXSID60975760
Created by admin on Sat Dec 16 08:29:35 UTC 2023 , Edited by admin on Sat Dec 16 08:29:35 UTC 2023
PRIMARY
FDA UNII
J6061U34KH
Created by admin on Sat Dec 16 08:29:35 UTC 2023 , Edited by admin on Sat Dec 16 08:29:35 UTC 2023
PRIMARY
PUBCHEM
5492888
Created by admin on Sat Dec 16 08:29:35 UTC 2023 , Edited by admin on Sat Dec 16 08:29:35 UTC 2023
PRIMARY
CAS
6035-32-1
Created by admin on Sat Dec 16 08:29:35 UTC 2023 , Edited by admin on Sat Dec 16 08:29:35 UTC 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE