[en] The synthesis of five 1,2,3,4-tetrahydroisoquinolines, which were either randomly labelled (1,1,3,3,4,4-²H₆), or regioselectively labelled (1,1-²H₂,2c; 3,3-²H₂, 2d; 4,4-²H₂), from isoquinoline, indan-2-one, and phenylacetonitrile is described. These deuterated bases were used in the preparation of labelled analogues of the antihypertensive agent debrisoquine. (author)

[en] Kinetically controlled ¹H/²H exchange at carbon atom 5 of (-)-1,6-dehydrosparteinium monoperchlorate followed by sodium borohydride or sodium borodeuteride reduction of the iminium double bond gave optically active 5,5-(²H₂)-sparteine and 5,5,6-(²H₃)-sparteine, respectively. Under thermodynamic control a third deuterium atom was incorporated into 3 at carbon atom 7. Borohydride reduction or rapid re-exchange followed by reduction lead to the novel sparteine analogues 5,5,7-(²H₃)-sparteine and 7-(²H)-sparteine. The title compounds have been prepared in 76 to 83 % yield and 89 to 97 % isotopic purity. (author)