(1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro(1,2,2,4-2H4)naphthalen-1-amine 6-N-propyl-7-{[6-(propylamino)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]methyl}-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine hydrochloride

• ChemBase ID: 166453
• Molecular Formular: C37H49Cl3N6S2
• Molecular Mass: 748.31416
• Monoisotopic Mass: 746.25257064
• SMILES: c12c(CC(CC1)NCCC)sc(n2)CC1c2c(CCC1NCCC)nc(s2)N.[C@H]1(CC[C@@H](c2c1cccc2)N)c1cc(c(cc1)Cl)Cl.Cl
• Canonical SMILES: Clc1ccc(cc1Cl)[C@@H]1CC[C@@H](c2c1cccc2)N.CCCNC1CCc2c(C1)sc(n2)CC1C(NCCC)CCc2c1sc(n2)N.Cl
• InChI: InChI=1S/C21H33N5S2.C16H15Cl2N.ClH/c1-3-9-23-13-5-6-16-18(11-13)27-19(25-16)12-14-15(24-10-4-2)7-8-17-20(14)28-21(22)26-17;17-14-7-5-10(9-15(14)18)11-6-8-16(19)13-4-2-1-3-12(11)13;/h13-15,23-24H,3-12H2,1-2H3,(H2,22,26);1-5,7,9,11,16H,6,8,19H2;1H/t;11?,16-;/m.0./s1
• InChIKey: IORKQJFGOWEAMT-XTISJKQFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro(1,2,2,4-^2H₄)naphthalen-1-amine 6-N-propyl-7-{[6-(propylamino)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]methyl}-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine hydrochloride
• IUPAC Traditional name: (1S,4S)-4-(3,4-dichlorophenyl)(1,2,2,4-^2H₄)-3H-naphthalen-1-amine 6-N-propyl-7-{[6-(propylamino)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]methyl}-4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine hydrochloride
• Synonyms: cis-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine-d4 Hydrochloride; cis-(+/-)-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine-d4 Hydrochloride; rac-cis-N-Desmethyl Sertraline-d4 Hydrochloride

Database IDs

• PubChem SID: 162260586
• PubChem CID: 71315743

CALCULATED PROPERTIES

• Acid pKa: 17.513279
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.9960659
• LogD (pH = 7.4): -1.9422944
• Log P: 3.5089514
• Molar Refractivity: 117.8405 cm^3
• Polarizability: 45.41721 Å^3
• Polar Surface Area: 75.86 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White to Off-White Solid

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D292103

A labelled metabolite of Sertraline. N-Desmethyl Sertraline is significantly less active analogue as compared to the methylated compound, Sertraline.

REFERENCES

• Welch, W.M., et al.: J. Med. Chem. 27, 1508 (1984)