Apex 2 ultra

(+/-)-Vesamicol, (+)-pentazocine and DTG were purchased from Sigma-Aldrich Co. (St. Louis, MO). Radioisotopes were purchased from PerkinElmer, Inc. (Waltham, MA), unless otherwise noted.
The HPLC column (Chiralpak IA, 9.6 mm × 250 mm) was purchased from DAICEL Co. (Osaka, Japan). The reverse phase HPLC column (Zorbax-ODS RX-18, 9.6 mm × 250 mm) was purchased from Agilent Technologies Inc. (Santa Clara, CA). [¹²⁵I]NaI was purchased from PerkinElmer Inc. (Waltham, MA)). [¹²³I]NaI was supplied by Nihon Medi-Physics Co (Nishinomiya Japan). Specific rotation was obtained on a Nippon Bunko DIP-181 digital polarimeter. Sprague-Dawley (SD) rats were purchased from Sankyo Labo Service Co. (Tokyo, Japan). Animal experiments were performed in compliance with the Guidelines for the Care and Use of Laboratory Animals at the Takara-machi Campus of Kanazawa University. The animal experimental protocols used were approved by the Committee on Animal Experimentation of Kanazawa University (Permit Number: AP-153454). In animal studies, the animals were sacrificed by decapitation under ether anesthesia. The structures of the two OIDV optical isomers were determined by X-ray crystallographic analysis (APEX II ULTRA, Bruker AXS K. K. Japan) performed by Bruker AXS K. K. company (Fig 1) (S1 and S2 Files).

Diffraction data were recorded at 293 K on a Bruker single-crystal charge-coupled device x-ray diffractometer (SMART APEX II ULTRA) with Mo Kα radiation (λ = 0.71073 Å) and a graphite monochromator. A total of 3430 reflections were measured with a maximum 2θ angle of 51.0°, of which 1326 were independent reflections. The structure was solved using direct methods [SHELXS-97 (34 )] and was refined by full-matrix least squares on F² [SHELXL-97 (34 )]. All non-hydrogen atoms were refined anisotropically. All hydrogen atoms were placed using AFIX instructions. The crystal data are as follows: C₇H₂₀I₃N₃; formula weight = 526.96, crystal size of 0.13 mm by 0.20 mm by 0.30 mm, trigonal, R3, a = 7.2599(8) Å, α = 84.7570(10)°, V = 378.11(13) ų, Z = 1, and D_c = 2.314 g cm⁻³. The refinement converged to R₁ = 0.0402, wR₂ = 0.1132 [I > 2 s (I)], and the goodness of fit was = 1.353. Crystallographic data have been provided in the Cambridge Crystallographic Data Centre (CCDC) [CCDC-2157903].