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Details

Stereochemistry ACHIRAL
Molecular Formula C19H19N
Molecular Weight 261.3609
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORCYCLOBENZAPRINE

SMILES

CNCCC=C1C2=C(C=CC=C2)C=CC3=C1C=CC=C3

InChI

InChIKey=XECQQDXTQRYYBH-UHFFFAOYSA-N
InChI=1S/C19H19N/c1-20-14-6-11-19-17-9-4-2-7-15(17)12-13-16-8-3-5-10-18(16)19/h2-5,7-13,20H,6,14H2,1H3

HIDE SMILES / InChI
Molecular Formula C19H19N
Molecular Weight 261.3609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Norcyclobenzaprine (aka desmethylcyclobenzaprine) is one of the major metabolites of cyclobenzaprine which is a muscle relaxant marketed under the brand name Flexeril. Both cyclobenzaprine and norcyclobenzaprine are known to be potent antagonists of the serotonin 2a receptor.

CNS Activity

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
5-hydroxytryptamine receptor 2A
73
Target ID: P28223
Gene ID: 3356.0
Gene Symbol: HTR2A
Target Organism: Homo sapiens (Human)
Antagonist
2849
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
High-performance liquid chromatography-mass spectrometry for the quantification of nortriptyline and 10-hydroxynortriptyline in plasma.
1998-09-25
Identification of human liver cytochrome P450 isoforms involved in the in vitro metabolism of cyclobenzaprine.
1996-07
Potential interference of cyclobenzaprine and norcyclobenzaprine with HPLC measurement of amitriptyline and nortriptyline: resolution by GC-MS analysis.
1995-07-01
Metabolism of cyclobenzaprine in the dog.
1978-03-01
Patents

Patents

WO2009148623A2
2

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:34:07 GMT 2025
Edited
by admin
on Mon Mar 31 21:34:07 GMT 2025
Record UNII
T6X8KQ83F4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
G-38188
Preferred Name English
NORCYCLOBENZAPRINE
Common Name English
NORTRIPTYLINE HYDROCHLORIDE IMPURITY B [EP IMPURITY]
Common Name English
DESMETHYLCYCLOBENZAPRINE
Common Name English
5H-DIBENZO(A,D)CYCLOHEPTENE-.DELTA.5,.GAMMA.-PROPYLAMINE, N-METHYL-
Systematic Name English
NORPROHEPTATRIEN
Common Name English
10,11-DEHYDRONORTRIPTYLINE
Common Name English
1-PROPANAMINE, 3-(5H-DIBENZO(A,D)CYCLOHEPTEN-5-YLIDENE)-N-METHYL-
Systematic Name English
Code System Code Type Description
FDA UNII
T6X8KQ83F4
Created by admin on Mon Mar 31 21:34:07 GMT 2025 , Edited by admin on Mon Mar 31 21:34:07 GMT 2025
PRIMARY
CAS
303-50-4
Created by admin on Mon Mar 31 21:34:07 GMT 2025 , Edited by admin on Mon Mar 31 21:34:07 GMT 2025
PRIMARY
PUBCHEM
9918
Created by admin on Mon Mar 31 21:34:07 GMT 2025 , Edited by admin on Mon Mar 31 21:34:07 GMT 2025
PRIMARY
EPA CompTox
DTXSID30952664
Created by admin on Mon Mar 31 21:34:07 GMT 2025 , Edited by admin on Mon Mar 31 21:34:07 GMT 2025
PRIMARY
Related Record Type Details
Structure of Norcyclobenzaprine hydrochloride
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of CYCLOBENZAPRINE
PARENT -> METABOLITE
MAJOR
Related Record Type Details
Structure of CYCLOBENZAPRINE HYDROCHLORIDE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of Nortriptyline Hydrochloride
PARENT -> IMPURITY
NIH
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