methyl({3-[(2E)-tricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propyl})amine hydrochloride

• ChemBase ID: 103915
• Molecular Formular: C19H22ClN
• Molecular Mass: 299.83768
• Monoisotopic Mass: 299.14407739
• SMILES: Cl.CNCC/C=C\1/c2c(CCc3c1cccc3)cccc2
• Canonical SMILES: CNCC/C=C/1\c2ccccc2CCc2c1cccc2.Cl
• InChI: InChI=1S/C19H21N.ClH/c1-20-14-6-11-19-17-9-4-2-7-15(17)12-13-16-8-3-5-10-18(16)19;/h2-5,7-11,20H,6,12-14H2,1H3;1H
• InChIKey: SHAYBENGXDALFF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl({3-[(2E)-tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propyl})amine hydrochloride; methyl(3-{tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3,5,7,12,14-hexaen-2-ylidene}propyl)amine hydrochloride; methyl(3-{tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}propyl)amine hydrochloride; methyl({3-[(2Z)-tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propyl})amine hydrochloride
• IUPAC Traditional name: methyl({3-[(2E)-tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propyl})amine hydrochloride; methyl(3-{tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3,5,7,12,14-hexaen-2-ylidene}propyl)amine hydrochloride; nortriptyline hydrochloride; methyl({3-[(2Z)-tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propyl})amine hydrochloride
• Synonyms: Acetexa; Allegron; Nortrilen; Norzepine; Pamelor; Sensival; Vividyl; Nortriptyline Hydrochloride; 3-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine hydrochloride; Desmethylamitriptyline hydrochloride; Nortriptyline hydrochloride; 3-(10,11-Dihydro-5H-dibenzo[a,d]-cyclohepten-5-ylidene)-N-methyl-1-propanamine; NORTRIPTYLINE; N-[3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)propyl]-N-methylamine hydrochloride

Database IDs

• CAS Number: 894-71-3
• EC Number: 212-973-0
• MDL Number: MFCD00058024
• PubChem SID: 24278107; 162090967
• PubChem CID: 441358

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.1924809
• LogD (pH = 7.4): 1.578639
• Log P: 4.426487
• Molar Refractivity: 96.2125 cm^3
• Polarizability: 33.407597 Å^3
• Polar Surface Area: 12.03 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol; ethanol: soluble100 mg/mL; H2O: soluble
• Apperance: Off-White Solid; white to off-white powder
• Melting Point: 217-220°C; 218°C; 219 - 221°C
• Hydrophobicity(logP): 4.315

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C), Protect from light
• RTECS: HP0175000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; R:22
• Safety Statements: 22-36; S:36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Gene Information: human ... HTR2A(3356), HTR2B(3357), HTR2C(3358)

Product Information

• Purity: ≥98% (TLC); 95%
• Salt Data: HCl
• Empirical Formula (Hill Notation): C19H21N · HCl

DETAILS

MP Biomedicals - 02153555

Hydrochloride
A norepinephrine uptake inhibitor.

Sigma Aldrich - N7261

Features and Benefits
The powder is stable at least 5 years at room temperature.
Biochem/physiol Actions
Tricyclic antidepressant that is a more potent inhibitor of the norepinephrine transporter (Ki = 3.4 nM) than the serotonin transporter (Ki = 161 nM). 5-HT2 serotonin receptor antagonist.

Toronto Research Chemicals - N837000

Tricyclic antidepressant.

REFERENCES

• Hale, J. L., et al.: Anal. Profiles Drug Subs., 1, 233 (1972)
• Rubin, E.H., et al.: J. Clin. Psychiatry, 46, 418 (1972)