Collect. Czech. Chem. Commun. 1994, 59, 2472-2480

The Molecular and Crystal Structure of Buprenorphine Hydrochloride, a Morphine Analogue

Bohumil Kratochvíla, Michal Hušáka, Petr Bulejb and Alexandr Jegorovc

a Department of Solid State Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6, Czech Republic
b Galena Co., R. & D., 747 70 Opava-Komárov, Czech Republic
c Galena Co., Research Unit, Branišovská 31, 370 05 České Budějovice, Czech Republic


The structure of buprenorphine hydrochloride {(6R,7R,14S)-17-cyclopropylmethyl-7,8-dihydro- 7-[(1S)-1-hydroxy-1,2,2-trimethylpropyl]- 6-O-methyl-6,14-ethano-17-normorphine hydrochloride} was solved by direct methods and refined anisotropically to the R value of 0.062 for 3 049 observed reflections. The substance crystallizes in the tetragonal space group P43212, a = b = 11.513(2) Å, c = 42.054(8) Å, V = 5 574(2) Å3, Z = 8, Dcalc = 1.201 g cm-3, μ(MoKα) = 0.17 mm-1. The compound is the first morphine derivative with a 6,14-ethano bridge whose molecular structure has been solved.