NORMORPHINE

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 Search

SMILES

O[C@H]1C=C[C@H]2[C@H]3CC4=C5C(O[C@@H]1[C@@]25CCN3)=C(O)C=C4

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

Description
Sources: http://pubs.acs.org/doi/abs/10.1021/ja01116a024 | https://www.ncbi.nlm.nih.gov/pubmed/235634 | https://www.ncbi.nlm.nih.gov/pubmed/13539761 | https://www.ncbi.nlm.nih.gov/pubmed/13588540

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mu-type opioid receptor 61 Target ID: P35372\|\|\|G8XRH8\|\|\|Q5TDA1\|\|\|Q9UN57 Gene ID: 4988.0 Gene Symbol: OPRM1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21396918	Agonist 2752		0.061 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13588540	Primary		Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
41 nM CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/1867957/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		NORMORPHINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
65 nM CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/1867957/	50 mg 4 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:		NORMORPHINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
191 nM × h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/1867957/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	NORMORPHINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
9 nM × h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/1867957/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	NORMORPHINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
220 nM × h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/1867957/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	NORMORPHINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
257 nM × h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/1867957/	50 mg 4 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:	NORMORPHINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
8.5 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/1867957/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		NORMORPHINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
9.8 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/1867957/	50 mg 4 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered:		NORMORPHINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Sourcing

Vendor/Aggregator	ID	URL
Compound Cloud	5462508
Sigma Aldrich	N-006	http://www.sigmaaldrich.com/catalog/search?term=N-006&interface=All&N=0&mode=match%20partialmax&lang=en®ion=US&focus=product
Tetrahedron	TS74129	http://www.thsci.com/search.do?q=TS74129
Toronto Research Chemicals	KIT2425	https://www.trc-canada.com/product-detail/?CatNum=KIT2425
Toronto Research Chemicals	N740300	https://www.trc-canada.com/product-detail/?CatNum=N740300

PubMed

Title	Date	PubMed
Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications.	1998-03	9686407
Normorphine, a neurotoxic metabolite?	1990-03-24	1969081

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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

IDS-NN-008

Preferred Name

English

NORMORPHINE

Official Name

English

normorphine [INN]

Common Name

English

(-)-NORMORPHINE

Common Name

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