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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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P28223
Gene ID: 3356.0
Gene Symbol: HTR2A
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

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

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Thu Jul 06 11:34:31 UTC 2023
Edited
by admin
on Thu Jul 06 11:34:31 UTC 2023
Record UNII
T6X8KQ83F4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
G-38188
Code 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 Thu Jul 06 11:34:31 UTC 2023 , Edited by admin on Thu Jul 06 11:34:31 UTC 2023
PRIMARY
CAS
303-50-4
Created by admin on Thu Jul 06 11:34:31 UTC 2023 , Edited by admin on Thu Jul 06 11:34:31 UTC 2023
PRIMARY
PUBCHEM
9918
Created by admin on Thu Jul 06 11:34:31 UTC 2023 , Edited by admin on Thu Jul 06 11:34:31 UTC 2023
PRIMARY
EPA CompTox
DTXSID30952664
Created by admin on Thu Jul 06 11:34:31 UTC 2023 , Edited by admin on Thu Jul 06 11:34:31 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> METABOLITE
Related Record Type Details
PARENT -> IMPURITY
UNSPECIFIED
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP