CONFORMATIONAL ANALYSIS OF (S)-6-METHOXY-2-(DIPROPYLAMINO)-TETRALIN. Magnus Brisander,^a Ingeborg Csöregh,^a Johanna M. Jansen,^b Anette M. Johansson^b and Uli Hacksell.^b, ^aDepartment of Structural Chemistry, Arrhenius Laboratory, Stockholm University, S-106 91 Stockholm, Sweden, ^bOrganic Pharmaceutical Chemistry, Uppsala Biomedical

Center, Uppsala University, Box 574, S-751 23 Uppsala, Sweden.

The conformational behavior of (S)-6-methoxy-2-(dipropylamino)-tetralin^.HCl (1) has been studied by X-ray crystallography, ¹H NMR spectroscopy and molecular mechanics calculations (MM2). The X-ray structure was determined using Cu K radiation at 20 ⁰C, and the ¹H NMR spectral data was obtained at 400 MHz in CD₃OD at 30 ⁰C.

The preferred conformations of 1 in the various states (solid, liquid and gas) were compared. In addition, the conformational preference of 1 was compared with recently published preferred conformations of 5-, 7-, and 8-OH-DPAT.¹

(1) A. Karlén, A. Helander, A. M. Johansson, L. Kenne, S. Sundell, and U. Hacksell, J. Chem. Research (M), 1993, 3028-3036.