Crystalline (1r,4r)-6'-fluoro-N,N-dimethyl-4-phenyl-4',9'-dihydro-3'H-spiro[cyclohexane-1,1'-pyrano[3,4,b]indol]-4-amine

1. A method of treating pain in a patient diagnosed with a pain disorder comprising orally administering to the patient an effective amount of a pharmaceutical composition comprising at least one pharmaceutically acceptable additive or adjuvant and an active ingredient comprising a crystalline form of (1r,4r)-6′-fluoro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine having an X-ray powder diffraction pattern comprising characteristic peaks at about 18.3±0.2 degrees 2θ, at about 26.3±0.2 degrees 2θ, and at one or both of about 7.8±0.2 degrees 2θ and about 31.6±0.2 degrees 2θ.

2. The method of claim 1 , wherein the pain disorder is chronic pain.

3. The method of claim 1 , wherein the pain disorder is a neuropathic pain disorder.

4. The method of claim 1 , wherein the active ingredient comprises at least about 50% of the crystalline form.

5. The method of claim 1 , wherein the active ingredient comprises at least about 70% of the crystalline form.

6. The method of claim 1 , wherein the active ingredient comprises at least about 90% of the crystalline form.

7. The method of claim 1 , wherein the active ingredient comprises at least about 95% of the crystalline form.

8. A pharmaceutical composition comprising at least one pharmaceutically acceptable additive and/or adjuvant and an active ingredient that comprises a crystalline form of (1r,4r)-6′-fluoro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine having an X-ray powder diffraction pattern comprising characteristic peaks at about 18.3±0.2 degrees 2θ, at about 26.3±0.2 degrees 2θ, and at one or both of about 7.8±0.2 degrees 2θ and about 31.6±0.2 degrees 2θ.

9. The pharmaceutical composition of claim 8 , wherein the pharmaceutical composition consists of the at least one additive and/or adjuvant and the active ingredient.

10. The pharmaceutical composition of claim 8 , wherein the active ingredient comprises at least about 50% of the crystalline form.

11. The pharmaceutical composition of claim 8 , wherein the active ingredient comprises at least about 70% of the crystalline form.

12. The pharmaceutical composition of claim 8 , wherein the active ingredient comprises at least about 90% of the crystalline form.

13. The pharmaceutical composition of claim 8 , wherein the pharmaceutical composition further comprises a salt of (1r,4r)-6′-fluoro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine with sulfuric acid.

14. The method of claim 1 , wherein the crystalline form comprises characteristic peaks at about 7.8±0.2 degrees 2θ and at about 31.6±0.2 degrees 2θ.

15. The method of claim 1 , wherein the crystalline form comprises a characteristic peak at about 31.6±0.2 degrees 2θ and further comprises a characteristic peak at about 11.7±0.2 degrees 2θ.

16. The method of claim 1 , wherein the crystalline form further comprises a characteristic peak at about 33.6±0.2 degrees 2θ.

17. The method of claim 14 , wherein the crystalline form further comprises a characteristic peak at about 33.6±0.2 degrees 2θ.

18. The pharmaceutical composition of claim 8 , wherein the crystalline form comprises characteristic peaks at about 7.8±0.2 degrees 2θ and at about 31.6±0.2 degrees 2θ.

19. The method of claim 1 , wherein the pharmaceutical composition comprises 40±20 μg, 100±10 μg, 200±50 μg, 400±50 μg, or 600±50 μg of the active ingredient.

20. The method of claim 1 , wherein the crystalline form has a melting endotherm at about 298-308° C.

21. The method of any of claim 1 , wherein the active ingredient comprises at least about 60% of the crystalline form of (1r,4r)-6′-fluoro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine.

22. The method of claim 20 , wherein the active ingredient comprises at least about 60% of the crystalline form of (1r,4r)-6′-fluoro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro [cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine.

23. The method of claim 1 , wherein the active ingredient comprises at least about 80% relative to other isomers of (1r,4r)-6′-fluoro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro [cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine.

24. The method of claim 20 , wherein the active ingredient comprises at least about 80% relative to other isomers of (1r,4r)-6′-fluoro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro [cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine.

25. The pharmaceutical composition of claim 8 , wherein the active ingredient comprises at least about 60% of the crystalline form of (1r,4r)-6′-fluoro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro [cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine.

26. The pharmaceutical composition of claim 8 , wherein the active ingredient comprises at least about 70% of the crystalline form of (1r,4r)-6′-fluoro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro [cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine.

27. The pharmaceutical composition of claim 8 , wherein the active ingredient comprises at least about 80% relative to other isomers of (1r,4r)-6′-fluoro-N,N-dimethyl-4-phenyl-4′,9′-dihydro-3′H-spiro [cyclohexane-1,1′-pyrano[3,4,b]indol]-4-amine.

28. The pharmaceutical composition of claim 8 , wherein the crystalline form has a melting endotherm at about 298-308° C.

29. The method of claim 26 , wherein the crystalline form has a melting endotherm at about 298-308° C.

30. The pharmaceutical composition of claim 8 , wherein the crystalline form comprises a characteristic peak at about 31.6±0.2 degrees 2θ and further comprises a characteristic peak at about 11.7±0.2 degrees 2θ.

31. The pharmaceutical composition of claim 8 , wherein the crystalline form further comprises a characteristic peak at about 33.6±0.2 degrees 2θ.

32. The pharmaceutical composition of claim 18 , wherein the crystalline form further comprises a characteristic peak at about 33.6±0.2 degrees 2θ.

33. The method of claim 1 , wherein the crystalline form has a Raman peak at about 1569±2 cm-1 and/or at about 1002±2 cm-1.

34. The pharmaceutical composition of claim 8 , wherein the crystalline form has a Raman peak at about 1569±2 cm-1 and/or at about 1002±2 cm-1.

35. The method of claim 19 , wherein the crystalline form comprises characteristic peaks at about 7.8±0.2 degrees 2θ and at about 31.6±0.2 degrees 2θ.

36. The method of claim 23 , wherein the crystalline form comprises characteristic peaks at about 7.8±0.2 degrees 2θ and at about 31.6±0.2 degrees 2θ.

37. The method of claim 35 , wherein the active ingredient comprises at least about 90% of the crystalline form.

38. The method of claim 36 , wherein the active ingredient comprises at least about 95% of the crystalline form.

39. The method of claim 35 , wherein the active ingredient comprises at least about 90% of the crystalline form.

40. The method of claim 36 , wherein the active ingredient comprises at least about 95% of the crystalline form.