(3-{2-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}propyl)dimethylamine hydrochloride

• ChemBase ID: 105438
• Molecular Formular: C19H25ClN2
• Molecular Mass: 316.8682
• Monoisotopic Mass: 316.17062649
• SMILES: Cl.CN(C)CCCN1c2ccccc2CCc2ccccc12
• Canonical SMILES: CN(CCCN1c2ccccc2CCc2c1cccc2)C.Cl
• InChI: InChI=1S/C19H24N2.ClH/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21;/h3-6,8-11H,7,12-15H2,1-2H3;1H
• InChIKey: XZZXIYZZBJDEEP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3-{2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}propyl)dimethylamine hydrochloride; (3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)dimethylamine hydrochloride; (3-{2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3,5,7,12,14-hexaen-2-yl}propyl)dimethylamine hydrochloride
• IUPAC Traditional name: imipramine hydrochloride; (3-{2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3,5,7,12,14-hexaen-2-yl}propyl)dimethylamine hydrochloride
• Synonyms: Chrytemin; Imiprin; G-22355; Tofranil; 10,11-Dihydro-N,N-dimethyl-dibenz[b,f]azepine-5-propanamine hydrochloride; 5-[3-(Dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,f]azepine hydrochloride; IMIPRAMINE HYDROCHLORIDE; Melipramine HCl; 10,11-Dihydro-N,N-dimethyl-5H-dibenz[b,f]azepine-5-propanamine hydrochloride; Imipramine hydrochloride

Database IDs

• CAS Number: 113-52-0
• EC Number: 204-030-7
• MDL Number: MFCD00012669
• PubChem SID: 24278097; 24895912; 162092508
• PubChem CID: 8228

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.9912437
• LogD (pH = 7.4): 2.4832094
• Log P: 4.2785687
• Molar Refractivity: 90.6056 cm^3
• Polarizability: 34.670334 Å^3
• Polar Surface Area: 6.48 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; H2O: soluble0.5 M, colorless to yellow; H2O: soluble50 mg/mL
• Apperance: white crystalline; White Solid
• Melting Point: 168-170°C; 171-176°C

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C), Protect from light
• RTECS: HO1925000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; R:22
• Safety Statements: S:36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302

Pharmacology Properties

• Target: Others
• Gene Information: human ... HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355), HTR2A(3356), HTR2B(3357), HTR2C(3358), HTR3A(3359), HTR3B(9177), HTR3C(170572), HTR3D(200909), HTR3E(285242), HTR4(3360), HTR5A(3361), HTR5B(645694), HTR6(3362), HTR7(3363)

Product Information

• Purity: ≥99% (TLC)
• Salt Data: hydrochloride
• Ignition Residue: ≤0.1%
• Impurities: ≤0.0005% Phosphorus (P); ≤0.1% Insoluble matter
• Cation Traces: Al: ≤0.0005%; Ca: ≤0.005%; Cu: ≤0.0005%; Fe: ≤0.005%; K: ≤0.005%; Mg: ≤0.0005%; Na: ≤0.005%; NH4+: ≤0.05%; Pb: ≤0.001%; Zn: ≤0.0005%
• Antion Traces: sulfate (SO42-): ≤0.05%
• Product Line: BioXtra
• Empirical Formula (Hill Notation): C19H24N2 · HCl

DETAILS

MP Biomedicals - 02190218

Hydrochloride
Crystalline
A serotonin uptake inhibitor.

Sigma Aldrich - I7379

Biochem/physiol Actions
Tricyclic antidepressant; inhibits the serotonin and norepinephrine transporters with Kis of 7.7 nM and 67 nM, respectively. Has little effect on the dopamine transporter (Ki = 25 μM).

Sigma Aldrich - I0899

Biochem/physiol Actions
Tricyclic antidepressant; inhibits the serotonin and norepinephrine transporters with Kis of 7.7 nM and 67 nM, respectively. Has little effect on the dopamine transporter (Ki = 25 μM).

Toronto Research Chemicals - I465980

Tricyclic antidepressant; inhibits the serotonin and norepinephrine transporters. Has little effect on the dopamine transporter.

REFERENCES

• Wood, M.D., et al.: Neuropharmacology, 26, 1081 (1987)
• Casis, O., et al.: J. Cardiovasc. Pharmacol., 32, 521 (1987)
• Linner, L., et al.: Biol. Psychiatry, 46, 766 (1987)
• Teschemacher, et al.: Br. J. Pharmacol., 128, 479 (1987)