Tetrahydrococannabinolic acid cocrystals
New tetrahydrocannabinolic acid cocrystals are disclosed, in particular, a 1:1 tetrahydrocannabinolic acid L-proline cocrystal, a 1:1 tetrahydrocannabinolic acid D-proline cocrystal, a 1:1 tetrahydrocannabinolic acid D,L-proline cocrystal, a 1:1 tetrahydrocannabinolic acid ethyl maltol cocrystal and a 1:1 tetrahydrocannabinolic acid caffeine cocrystal. The invention also relates to pharmaceutical compositions containing a tetrahydrocannabinolic acid cocrystal of the invention and a pharmaceutically acceptable carrier and methods to treat a disease, disorder or condition by administering to a patient in need thereof a therapeutically effective amount of tetrahydrocannabinolic acid cocrystal or a pharmaceutical composition containing a tetrahydrocannabinolic acid cocrystal.
1 . A tetrahydrocannabinolic acid cocrystal selected from the group of a 1:1 tetrahydrocannabinolic acid L-proline cocrystal, a 1:1 tetrahydrocannabinolic acid D-proline cocrystal, a 1:1 tetrahydrocannabinolic acid D,L-proline cocrystal, a 1:1 tetrahydrocannabinolic acid ethyl maltol cocrystal and a 1:1 tetrahydrocannabinolic acid caffeine cocrystal.
2 . A tetrahydrocannabinolic acid cocrystal of claim 1 , wherein the cocrystal is a 1:1 tetrahydrocannabinolic acid L-proline cocrystal characterized by:
at least two, at least three, at least four or all of the peaks selected from the peaks at 4.5, 10.5, 12.8, 13.5, 15.0 and 19.0° 2θ±0.2° 2 θ;
a monoclinic P2 1 crystal system space group at a temperature of about 100K;
unit cell dimensions of a=12.02010(10) Å, b=5.54740(10) Å, c=19.8543(2) Å, a=90.00°, β=102.54(3)°, and γ=90.00°;
an X-ray powder diffraction pattern substantially similar to FIG. 1 ;
an X-ray powder diffraction pattern substantially similar to FIG. 2 ;
an X-ray powder diffraction pattern substantially similar to FIG. 4 ; or
a differential scanning calorimetry trace substantially similar to FIG. 6 .
3 . A tetrahydrocannabinolic acid cocrystal of claim 1 , wherein the cocrystal is a 1:1 tetrahydrocannabinolic acid D-proline cocrystal characterized by:
an X-ray powder diffraction pattern substantially similar to FIG. 8 ; or
a differential scanning calorimetry trace substantially similar to FIG. 9 .
4 . A tetrahydrocannabinolic acid cocrystal of claim 1 , wherein the cocrystal is a 1:1 tetrahydrocannabinolic acid D,L-proline cocrystal, characterized by:
an X-ray powder diffraction pattern substantially similar to FIG. 10 ; or
a differential scanning calorimetry trace substantially similar to FIG. 11 .
5 . A tetrahydrocannabinolic acid cocrystal of claim 1 , wherein the cocrystal is a 1:1 tetrahydrocannabinolic acid ethyl maltol cocrystal characterized by:
at least two, at least three, at least four or all of the peaks selected from the peaks at 6.3, 7.7, 9.0, 11.8 and 12.7° 2θ±0.2° 2θ;
an X-ray powder diffraction pattern substantially similar to FIG. 12 ;
an X-ray powder diffraction pattern substantially similar to FIG. 13 ; or
a differential scanning calorimetry trace substantially similar to FIG. 14 .
6 . A tetrahydrocannabinolic acid cocrystal of claim 1 , wherein the cocrystal is a 1:1 tetrahydrocannabinolic acid caffeine cocrystal characterized by:
at least two, at least three, at least four or all of the peaks selected from the peaks at 7.6, 8.2, 9.7, 10.4, 13.6 and 18.2° 2θ±0.2° 2θ;
an X-ray powder diffraction pattern substantially similar to FIG. 16 ;
an X-ray powder diffraction pattern substantially similar to FIG. 17 ; or
a differential scanning calorimetry trace substantially similar to FIG. 18 .
7 . A pharmaceutical composition comprising a tetrahydrocannabinolic acid cocrystal according to any one of claims 1-6 and a pharmaceutically acceptable carrier.