Collect. Czech. Chem. Commun. 1994, 59, 1361-1367

The Crystal and Molecular Structure of Butorphanol Hydrogen Tartrate

Alexandr Jegorova, Roman Sobotíkb, Svetlana Pakhomovac, Jan Ondráčekc, Jiří Novotnýc, Michal Hušákc and Bohumil Kratochvílc

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


The structure of butorphanol hydrogen tartrate {(9R,13S,14S)-(-)-17-(cyclobutylmethyl)morphinan-3,14-diol (2S,3S)-(-)-hydrogen tartrate} (C21H29NO2 .C4H6O6) was solved by direct methods and refined anisotropically to the R value of 0.029 for 2 069 observed reflections. The title morphine analogue crystallizes in the triclinic space group P1 with lattice parameters a = 7.620(1), b = 9.140(1), c = 9.591(1) Å, α = 105.48(1), β = 112.91(1), γ = 84.29(1)°, Z = 1. The butorphanol B ring possesses the 3E envelope conformation with small 3H2 distortion, C and D rings have a regular chair conformation. The intramolecular N17-H17...O2 hydrogen bond is observed in crystal structure of the title compound. The butorphanol and hydrogen tartrate molecules are joined together by means of O2-H(O2)...O7, O1-H(O1)...O7' and O3-H(O3)...O8" hydrogen bonds to form networks.