(1R,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine hydrochloride

• ChemBase ID: 177749
• Molecular Formular: C17H18Cl3N
• Molecular Mass: 342.69052
• Monoisotopic Mass: 341.05048262
• SMILES: c1(ccc(cc1Cl)[C@@H]1CC[C@H](c2c1cccc2)NC)Cl.Cl
• Canonical SMILES: CN[C@@H]1CC[C@H](c2c1cccc2)c1ccc(c(c1)Cl)Cl.Cl
• InChI: InChI=1S/C17H17Cl2N.ClH/c1-20-17-9-7-12(13-4-2-3-5-14(13)17)11-6-8-15(18)16(19)10-11;/h2-6,8,10,12,17,20H,7,9H2,1H3;1H/t12-,17+;/m0./s1
• InChIKey: BLFQGGGGFNSJKA-LWHGMNCYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine hydrochloride
• IUPAC Traditional name: (1R,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine hydrochloride
• Synonyms: (1R,4R)-rel-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine Hydrochloride; cis-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine Hydrochloride; (+/-)-Sertraline Hydrochloride; rac-cis-Sertraline Hydrochloride; (1S,4S)-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine, Hydrochloride; Sertraline Hydrochloride; (1R,4S)-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine Hydrochloride; (1R-trans)-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1--naphthalenamine Hydrochloride; (1R,4S)-Sertraline Hydrochloride

Database IDs

• CAS Number: 79559-97-0; 79617-95-1; 79896-32-5
• PubChem SID: 164233659
• PubChem CID: 18600608

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.9396342
• LogD (pH = 7.4): 2.759919
• Log P: 5.1493
• Molar Refractivity: 85.741 cm^3
• Polarizability: 33.5986 Å^3
• Polar Surface Area: 12.03 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid; White Solid; White solid
• Melting Point: 248-250°C; 260-262°C; 270-273°C

Safety Information

• Storage Condition: -20°C Freezer; -20°C Freezer, Under Inert Atmosphere; Refrigerator
• Storage Warning: Store in Freezer

DETAILS

Toronto Research Chemicals - S280000

A selective serotonin reuptake inhibitor. Used as an antidepressant.

Toronto Research Chemicals - S279975

Potent and selective inhibitors of serotonin uptake.

Toronto Research Chemicals - S280010

Enantiomer 1R,4S of Sertraline. Antidepressant.

REFERENCES

• Brady, K., et al.: J. Am. Med. Accoc., 283, 1837 (2000)
• Welch, W.M., et al.: J. Med. Chem., 27, 1508 (1984).
• Wozniak, T., et al.: J. Pharm. Biomed. Anal., 9, 363 (1991)
• Kudo, K., et al.: Enantiomer, 5, 369 (1991)
• Adams, A., et al.: J. Pharm. Biomed. Anal., 26, 505 (1991)