Norcyclobenzaprine

HCID 9918

Notes Reactions

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Basic information

CAS: 303-50-4
Standard SMILES: CNCCC=C1c2ccccc2C=Cc2ccccc21
InChIKey: XECQQDXTQRYYBH-UHFFFAOYSA-N
Molecular formula: C19H19N
Average molar mass: 261.4 g/mol
Monoisotopic mass: 261.15174961

Overview

3-(11-dibenzo[1,2-a:1',2'-e][7]annulenylidene)-N-methyl-1-propanamine is an organic tricyclic compound.

Names & identifiers

Preferred name: Norcyclobenzaprine
IUPAC: N-methyl-3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaenylidene)propan-1-amine
English name: Norcyclobenzaprine
Molecular formula: C19H19N
Molecular weight: 261.36

Names & synonyms

Norcyclobenzaprine303-50-4DesmethylcyclobenzaprineNorproheptatrien10,11-DehydronortriptylineT6X8KQ83F41-Propanamine, 3-(5H-dibenzo(a,d)cyclohepten-5-ylidene)-N-methyl-G-381885H-Dibenzo(a,d)cycloheptene-DELTA5,gamma-propylamine, N-methyl-RefChem:10925783-(5H-Dibenzo[a,d][7]annulen-5-ylidene)-N-methylpropan-1-amineN-methyl-3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaenylidene)propan-1-amine

Show more names

Nortriptyline ImpurityityNortriptyline Impurity 245-[3-(methylamino)propylidene]-5H-dibenzo[a,d]cycloheptene3-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine1-Propanamine, 3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-3-(5H-dibenzo[a,d][7]annulen-5-ylidene)-N-methylpropan-1-amine (norcyclobenzaprine)

UNII-T6X8KQ83F43-(5H-Dibenzo(a,d)cyclohepten-5-ylidene)-N-methyl-1-propanamineDehydronortriptylinePrestwick_807Norcyclobenzaprine CRSN-DesmethylcyclobenzaprinePrestwick0_000513Prestwick1_000513

Database identifiers

CAS: 303-50-4
PubChem CID: 9918
DTXSID: DTXSID30952664
ChEMBL: CHEMBL1557167
ChEBI: CHEBI:93101
UNII: T6X8KQ83F4
EC Number: 172-189-9
Nikkaji: J747.857G

Properties

Computed structural properties

XLogP: 4.7
Topological polar surface area: 12 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 1
Rotatable bonds: 3
Heavy atoms: 20
Formal charge: 0
Complexity: 340

Physicochemical properties

Boiling point: 150 °C · 150 °C(Press: 0.1 Torr)
Density: 1.106 · 1.106±0.06 g/cm3(Predicted)
storage temp.: 2 · 2-8°C
solubility: Chloroform
pka: 9.97 · 9.97±0.10(Predicted)
color: White
Major Application: pharmaceutical (small molecule)
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
InChIKey: XECQQDXTQRYYBH-UHFFFAOYSA-N
SMILES: N(CCC=C1c2c(cccc2)C=Cc3c1cccc3)C
FDA UNII: 6 X8KQ83F4 · T6X8KQ83F4
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302+H312+H332 (100%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Chemistry & industry

Pharmacology

Metabolism/MetabolitesN-Desmethylcyclobenzaprine is a known human metabolite of cyclobenzaprine.

Tissue LocationsKidney

Cellular LocationsCytoplasm

Applications

UsesNorcyclobenzaprine is an intermediate in the synthesis of Cyclobenzaprine N-β-D-Glucuronide (C987755). Cyclobenzaprine N-β-D-Glucuronide is a metabolite of Cyclobenzaprine.