The preparation of this base was carried out in exactly the same manner as for (+)-N-methylpavine from its bitartrate salt. The product, after recrystallization from aqueous ethanol, possessed a melting point of 130-140" (with effervescence); (a] gB -209" (c 1.0, CzH60H).
On drying the crystals in the same way as for the (+)-rotatory base, the white powder melted at 152-153'.
A mixed melting point determination as well as infrared comparison with authentic dried argemonine base showed them to be completely identical.
Spectra
Nuclear Magnetic Resonance-Spectra were obtained in CDCls on a Varian A-60 spectrometer using tetramethylsilane as the internal standard.
Mass-Spectra were obtained on a C.E.C.-103-C instrument at 200" using a metal inlet a t 70 e.v.
Ultraviolet-N -Methyl -1,2dihydropapaverine (100 mg.) was dissolved in 100 ml. of 10% (w/v) aqueous tartaric acid. At various time intervals over a 72-hr. period the spectrum of the solution was examined over the wavelength range of 220-370 mp to determine whether the characteristic absorption bands for argemonine were appearing in the 275-295-mp region. The analysis was carried
Journal of Pharmaceutical Sciences
out by diluting 1 ml. of the sample solution to 100 ml. with water and placing this solution in the sample cell. The reference cell was filled with a solution obtained by diluting 1 ml. of the 10% aqueous tartaric acid solution (without sample) to 100 ml. The measurements were carried out on a Bausch & Lornb model 505 recording spectrophotometer and showed no absorption in the region mentioned although maxima developed at 250 and 312 mp.
REFERENCES
(1) Schermerhorn, J. W., and Soine, T. O., J . A m . Pharm. Assoc., Sci. E d . , 40, 19(1951).
(
) Kier, L. B., and Soine, T. O . , J . Pharm. Sci., 50, 321(1961). (3) Soine, T. O., and Kier L. B. ibid. 51 1196(1962). (4) Shamma, M., E x p e r i e k o , 18, 64(i96i).
(5) Manske, R.