dimethyl({3-[(2E)-9-oxatricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaen-2-ylidene]propyl})amine hydrochloride

• ChemBase ID: 131062
• Molecular Formular: C19H22ClNO
• Molecular Mass: 315.83708
• Monoisotopic Mass: 315.13899201
• SMILES: CN(C)CC/C=C/1\c2ccccc2COc2c1cccc2.Cl
• Canonical SMILES: CN(CC/C=C\1/c2ccccc2OCc2c1cccc2)C.Cl
• InChI: InChI=1S/C19H21NO.ClH/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19;/h3-6,8-12H,7,13-14H2,1-2H3;1H/b17-11+
• InChIKey: MHNSPTUQQIYJOT-SJDTYFKWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dimethyl({3-[(2E)-9-oxatricyclo[9.4.0.0^3,^8]pentadeca-1(15),3(8),4,6,11,13-hexaen-2-ylidene]propyl})amine hydrochloride
• IUPAC Traditional name: dimethyl({3-[(2E)-9-oxatricyclo[9.4.0.0^3,^8]pentadeca-1(15),3(8),4,6,11,13-hexaen-2-ylidene]propyl})amine hydrochloride
• Synonyms: 11-(3-Dimethylaminopropylidene)-6,11-dihydrodibenz[b,e]oxepine hydrochloride; Doxepin hydrochloride; 多虑平 盐酸盐

Database IDs

• CAS Number: 1668-19-5; 1229-29-4
• EC Number: 214-966-8
• MDL Number: MFCD00079135
• PubChem SID: 24278093; 162225340
• PubChem CID: 6419921

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.40824065
• LogD (pH = 7.4): 1.5076776
• Log P: 3.8399742
• Molar Refractivity: 98.2448 cm^3
• Polarizability: 34.1806 Å^3
• Polar Surface Area: 12.47 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 1 M HCl: soluble50 mg/mL; H2O: soluble
• Apperance: white to off-white powder

Safety Information

• RTECS: HQ4375000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Gene Information: human ... ADRA1A(148), ADRA1B(147), ADRA1D(146), CHRM1(1128), CHRM2(1129), CHRM3(1131), CHRM4(1132), CHRM5(1133), HRH1(3269), 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: ~85% E-isomer basis; ≥98% (GC); 15% Z-isomer basis

DETAILS

Sigma Aldrich - D4526

Other Notes
Mixture of cis- and trans-isomers
Biochem/physiol Actions
Tricyclic antidepressant that is a more potent inhibitor of norepinephrine uptake than of serotonin uptake; antagonist at H1 histamine, muscarinic cholinergic, and α-adrenoreceptors.