Cannabinergic nitrate esters and related analogs

1. A compound of formula (I):

or a pharmaceutically acceptable salt thereof;

wherein:

ring C has zero, one, two or three double bonds;

X is carbon, CH, N, NH, C(CH 2 ) 2 , S, O, SO, SO 2 , or CF 2 ;

R 1 is H, OH, alkyl-OH, ═O, halogen, alkyl, COOH, C(O)Oalkyl, O(CO)alkyl, nitro, ONO 2 , or optionally substituted alkyl, haloalkyl, alkenyl, alkynyl, acyl, aryl, heterocyclyl, heteroaryl, alkoxy, aryloxy, heteroarylalkyl, heteroalkoxy, heteroaryloxy, alkenyl, amino, thio, cyano, thiocynato, isothiocynato, carboxyl, formyl, carbamyl, amino, acylamino, amido, imido, aminoalkyl, aminoaryl, heteroarylamino, heterocyclylamino, sulfonate, sufonamide, sulfonyl, thioalkyl, thioaryl, heteroarylthio, heterocyclylthio, phosphonate, phosphate, or acetate;

W is C(CH 3 ) 2 , CH(CH 3 ), C═O, CF 2 , C═S, C═CH 2 , spirocyclic ring, S, SO, SO 2 , or C[CH 3 (R 4 )];

R 4 is an optionally substituted alkyl, alkenyl, or alkynyl group;

Z is O, S, SO, SO 2 , NH, or N-alkyl;

R 2 is H, OH, SH, NH 2 , CF 3 , COOH, alkoxy, halogen, ONO 2 , alkyl-ONO 2 , or optionally substituted alkyl, haloalkyl, amine, amide, imide, alkoxy, alkoxy thio, phosphate, phosphonate, carboxyl, formyl, carbamyl, amino, acylamino, amido, imido, aminoalkyl, aminoaryl, heteroarylamino, heterocyclylamino, sulfonate, sufonamide, sulfonyl, thioalkyl, thioaryl, heteroarylthio, heterocyclylthio, phosphonate, phosphate, or acetate;

Y is a bond, C(CH 3 ) 2 , CF 2 , C═O, CH(alkyl), C(alkyl) 2 , C(O)O, NHCO, CONH, alkyl, C(O)Oalkyl, OC(O)alkyl, cycloalkyl, heterocyclyl, lactone, lactam, sultam, O, S, SO, SO 2 , OSO 2 , amine, diazine, alkenyl, or alkynyl group;

R 3 is absent, or is O, S, SO 2 , SO 2 NH, NHSO 2 , OSO 2 , OSO 2 alkyl, C(O)Oalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, a carbocyclic, a spirocyclic, heterocyclyl, aryl, heteroaryl, carboxyl, acetate, amine, amide, or imide;

V is V 1 or ONO 2 , wherein when any of rings A, B or C comprises a group comprising ONO 2 , V is V 1 , otherwise V is ONO 2 ; and

V 1 is H, F, Cl, Br, I, haloalkyl, N 3 , NCS, CN, NO 2 , OH, alkoxy, amino, alkylamino, dialkylamino, trialkylamino, aryl, cycloalkyl, alkyl, alkenyl, alkynyl, —C(O)aryl, —C(O)alkyl, C(O)Oalkyl, —C(O)heteroaryl, —C(O)amino, —C(O)(dialkylamino), C(O)(trialkylamino), C(O)(heterocyclyl), C(O)heteroaryl, —OC(O)alkyl, OSO 2 H, OSO 2 (alkyl), OSO 2 (aryl), OSO 2 NO 2 , OSO 2 (alkyl)CN, OSO 2 (alkyl)OH, OSO 2 alkylamino), —SC(O)alkyl, —SO 2 alkyl, —SO-alkyl, —SC(CH 3 ) 2 C(O)Oalkyl, —SC(CH 3 ) 2 C(O)Oaryl, —SC(CH 3 ) 2 C(O)Oheteroaryl, —SC(CH 3 ) 2 C(O)Oheterocyclyl, Si(alkyl) 3 , —OC(O)aryl, NHC(O)alkyl, NHC(O)aryl, —C(O)H, C(O)Oalkyl, SO 2 (amino), SO 2 (heterocyclyl), SO 2 (trialkylamino), SO 2 (dialkylamino), carbocyclic, a spirocyclic ring, heterocyclyl, heteroaryl, alkylthio, alkylamino, dialkylamino, alkylsulfinyl, alkylsulfonyl, boronic acid, boronate ester, BF 3 K, or a biotin group tethered via an amide bond.

2. The compound of claim 1 , wherein V is ONO 2 .

3. The compound of claim 1 , wherein R 1 is ONO 2 , alkyl-ONO 2 , O-alkyl-ONO 2 , O—SO 2 -alkyl-ONO 2 , —C(O)O-alkyl-ONO 2 , alkyl-C(O)O-alkyl-ONO 2 , or alkyl-O-alkyl-ONO 2 .

4. The compound of claim 1 , wherein:

ring C has one, two or three double bonds, and at least one double bond is at the C8-C9 position, the C9-C10 position, or the C6a-C10a position;

W is C(CH 3 ) 2 , CH(CH 3 ), C═O, or CF 2 ;

Z is O or N; and

V is H when R 1 is a group comprising ONO 2 , or V is ONO 2 .

5. The compound of claim 1 , wherein Y—R 3 —V is ONO 2 , alkyl-ONO 2 , O-alkyl-ONO 2 , O—SO 2 -alkyl-ONO 2 , —C(O)O-alkyl-ONO 2 , alkyl-C(O)O-alkyl-ONO 2 , or alkyl-O-alkyl-ONO 2 .

6. The compound of claim 1 , wherein:

ring C is:

ring B is:

and V is ONO 2 .

7. The compound of claim 1 , wherein:

ring C has one double bond at the C8-C9 position or the C9-C10 position;

W is C(CH 3 ) 2 ;

X is carbon;

R 1 is H, alkyl, COOH, alkyl-OH;

R 2 is OH, O-alkyl, SH, O(CO)alkyl, OC(O)NH 2 , OC(O)NHalkyl, or OC(O)N(alkyl) 2 ;

Z is O;

Y is alkyl, C(CH 3 ) 2 , or CF 2 ; and

V is ONO 2 .

8. The compound of claim 1 , wherein:

ring C is saturated;

W is C(CH 3 ) 2 ;

X is CH, R 1 is OH, or X—R 1 is C═O;

R 2 is OH, O-alkyl, SH, O(CO)alkyl, O(CO)N—

Z is O

Y is alkyl, C(CH 3 ) 2 , or CF 2 ;

V is ONO 2 .

9. A compound that is:

10. The compound of claim 1 that is: 4-(nitrooxy)butyl 2-((1′S,2′S)-5′-(acetoxymethyl)-2,6-dihydroxy-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-4-yl)-2-methylpropanoate; 5-(nitrooxy)pentyl 2-((1′S,2′S)-5′-(acetoxymethyl)-2,6-dihydroxy-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-4-yl)-2-methylpropanoate; 6-(nitrooxy)hexyl 2-((1′S,2′S)-5′-(acetoxymethyl)-2,6-dihydroxy-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-4-yl)-2-methylpropanoate; (E)-4-(((1′R,2′R)-6-hydroxy-5′-methyl-4-(2-methyl-1-(4-(nitrooxy)butoxy)-1-oxopropan-2-yl)-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)-4-oxobut-2-enoic acid; (1′R,2′R)-6-hydroxy-5′-methyl-4-(2-methyl-1-(4-(nitrooxy)butoxy)-1-oxopropan-2-yl)-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl 4-(nitrooxy)butanoate; (1′R,2′R)-6-hydroxy-5′-methyl-4-(2-methyl-1-(4-(nitrooxy)butoxy)-1-oxopropan-2-yl)-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl 2,5,8,11,14,17,20-heptaoxadocosan-22-oate; (1′S,2′S)-5′-(acetoxymethyl)-6-hydroxy-4-(2-methyl-1-oxo-1-propoxypropan-2-yl)-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl 4-(nitrooxy)butanoate; (1′S,2′S)-5′-(acetoxymethyl)-6-hydroxy-4-(2-methyl-1-(3-(nitrooxy)propoxy)-1-oxopropan-2-yl)-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl 2-propylpentanoate; 4,4′-(((1′S,2′S)-5′-(acetoxymethyl)-4-(2-methyl-1-(4-(nitrooxy)butoxy)-1-oxopropan-2-yl)-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(4-oxobutanoic acid); (1′S,2′S)-5′-(acetoxymethyl)-4-(1-(hexyloxy)-2-methyl-1-oxopropan-2-yl)-6-hydroxy-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl 4-(nitrooxy)butanoate; 2-(((1′S,2′S)-5′-(acetoxymethyl)-6-hydroxy-4-(2-methyl-1-((6-(nitrooxy)hexyl)oxy)-1-oxopropan-2-yl)-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)-N,N,N-trimethyl-2-oxoethanaminium iodide; 2-(nitrooxy)ethyl 2-((1′R,2′R)-2,6-dihydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-4-yl)-2,2-difluoroacetate; 3-(nitrooxy)propyl 2-((1′R,2′R)-2,6-dihydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-4-yl)-2,2-difluoroacetate; 4-(nitrooxy)butyl 2-((1′R,2′R)-2,6-dihydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-4-yl)-2,2-difluoroacetate; 5-(nitrooxy)pentyl 2-((1′R,2′R)-2,6-dihydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-4-yl)-2,2-difluoroacetate; 6-(nitrooxy)hexyl 2-((1′R,2′R)-2,6-dihydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-4-yl)-2,2-difluoroacetate; 2-(nitrooxy)ethyl 2-((1′S,2′S)-5′-(acetoxymethyl)-2,6-dihydroxy-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-4-yl)-2,2-difluoroacetate; 3-(nitrooxy)propyl 2-((1′S,2′S)-5′-(acetoxymethyl)-2,6-dihydroxy-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-4-yl)-2,2-difluoroacetate; 4-(nitrooxy)butyl 2-((1′S,2′S)-5′-(acetoxymethyl)-2,6-dihydroxy-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-4-yl)-2,2-difluoroacetate; 5-(nitrooxy)pentyl 2-((1′S,2′S)-5′-(acetoxymethyl)-2,6-dihydroxy-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-4-yl)-2,2-difluoroacetate; 6-(nitrooxy)hexyl 2-((1′S,2′S)-5′-(acetoxymethyl)-2,6-dihydroxy-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-4-yl)-2,2-difluoroacetate; (1′R,2R)-4-(1,1-difluoro-2-(4-(nitrooxy)butoxy)-2-oxoethyl)-6-hydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl 4-(nitrooxy)butanoate; (1′R,2′R)-4-(1,1-difluoro-2-(4-(nitrooxy)butoxy)-2-oxoethyl)-6-hydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl 2,5,8,11,14,17,20-heptaoxadocosan-22-oate; (E)-4-(((1′R,2′R)-4-(1,1-difluoro-2-(4-(nitrooxy)butoxy)-2-oxoethyl)-6-hydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)-4-oxobut-2-enoic acid; (1′S,2′S)-5′-(acetoxymethyl)-4-(1,1-difluoro-2-oxo-2-propoxyethyl)-6-hydroxy-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl 4-(nitrooxy)butanoate; (1′S,2′S)-5′-(acetoxymethyl)-4-(1,1-difluoro-2-(3-(nitrooxy)propoxy)-2-oxoethyl)-6-hydroxy-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl 2-propylpentanoate; 4,4′-(((1′S,2′S)-5′-(acetoxymethyl)-4-(1,1-difluoro-2-(4-(nitrooxy)butoxy)-2-oxoethyl)-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(4-oxobutanoic acid); (1′S,2′S)-5′-(acetoxymethyl)-4-(1,1-difluoro-2-(hexyloxy)-2-oxoethyl)-6-hydroxy-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl 4-(nitrooxy)butanoate; 2-(((1′S,2′S)-5′-(acetoxymethyl)-4-(1,1-difluoro-2-((6-(nitrooxy)hexyl)oxy)-2-oxoethyl)-6-hydroxy-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)-N,N,N-timethyl-2-oxoethanaminium iodide; 2-(nitrooxy)ethyl 2-(4-((1S,2S,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)-2-methylpropanoate; 3-(nitrooxy)propyl 2-(4-((1S,2S,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)-2-methylpropanoate; 4-(nitrooxy)butyl 2-(4-((1S,2S,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)-2-methylpropanoate; 5-(nitrooxy)pentyl 2-(4-((1S,2S,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)-2-methylpropanoate; 6-(nitrooxy)hexyl 2-(4-((1S,2S,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)-2-methylpropanoate; 2-(nitrooxy)ethyl 2-(4-((1R,2R,5R)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)-2-methylpropanoate; 3-(nitrooxy)propyl 2-(4-((1R,2R,5R)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)-2-methylpropanoate; 4-(nitrooxy)butyl 2-(4-((1R,2R,5R)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)-2-methylpropanoate; 5-(nitrooxy)pentyl 2-(4-((1R,2R,5R)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)-2-methylpropanoate; 6-(nitrooxy)hexyl 2-(4-((1R,2R,5R)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)-2-methylpropanoate; (E)-4-(2-((1S,2S,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3-hydroxy-5-(2-methyl-1-(4-(nitrooxy)butoxy)-1-oxopropan-2-yl)phenoxy)-4-oxobut-2-enoic acid; 2-((1S,2S,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3-hydroxy-5-(2-methyl-1-(3-(nitrooxy)propoxy)-1-oxopropan-2-yl)phenyl 2-propylpentanoate; 4,4′-((2-((1S,2S,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-5-(2-fluoro-1-(4-(nitrooxy)butoxy)-1-oxopropan-2-yl)-1,3-phenylene)bis(oxy))bis(4-oxobutanoic acid); 2-((1S,2S,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-5-(1-(hexyloxy)-2-methyl-1-oxopropan-2-yl)-3-hydroxyphenyl 4-(nitrooxy)butanoate; 2-(2-((1S,2S,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3-hydroxy-5-(2-methyl-1-((6-(nitrooxy)hexyl)oxy)-1-oxopropan-2-yl)phenoxy)-N,N,N-trimethyl-2-oxoethanaminium iodide; 2-((1R,2R,5R)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3-hydroxy-5-(2-methyl-1-oxo-1-(pentyloxy)propan-2-yl)phenyl 4-(nitrooxy)butanoate; 2-((1R,2R,5R)-6,6-dimethyl-1-oxobicyclo[3.1.1]heptan-2-yl)-3-hydroxy-5-(2-methyl-1-(4-(nitrooxy)butoxy)-1-oxopropan-2-yl)phenyl 2,5,8,11,14,17,20-heptaoxadocosan-22-oate; (E)-4-(2-((1R,2R,5R)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3-hydroxy-5-(2-methyl-1-(4-(nitrooxy)butoxy)-1-oxopropan-2-yl)phenoxy)-4-oxobut-2-enoic acid; 2-(nitrooxy)ethyl 2-(4-((1R,2R,5R)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3-hydroxy-5-(((1-(isobutyryloxy)ethoxy)carbonyl)oxy)phenyl)-2-methylpropanoate; 2-((1S,2S,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3-hydroxy-5-(2-methyl-8-(nitrooxy)octan-2-yl)phenyl 2-propylpentanoate; 3-(nitrooxy)propyl 2-(4-((1S,2S,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)-2,2-difluoroacetate; 4-(nitrooxy)butyl 2-(4-((1S,2S,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)-2,2-difluoroacetate; 5-(nitrooxy)pentyl 2-(4-((1S,2S,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)-2,2-difluoroacetate; 6-(nitrooxy)hexyl 2-(4-((1S,2S,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)-2,2-difluoroacetate; 2-(nitrooxy)ethyl 2-(4-((1R,2R,5R)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)-2,2-difluoroacetate; 3-(nitrooxy)propyl 2-(4-((1R,2R,5R)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)-2,2-difluoroacetate; 4-(nitrooxy)butyl 2-(4-((1R,2R,5R)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)-2,2-difluoroacetate; 5-(nitrooxy)pentyl 2-(4-((1R,2R,5R)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)-2,2-difluoroacetate; 6-(nitrooxy)hexyl 2-(4-((1R,2R,5R)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)-2,2-difluoroacetate; (E)-4-(5-(1,1-difluoro-2-(4-(nitrooxy)butoxy)-2-oxoethyl)-2-((1S,2S,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3-hydroxyphenoxy)-4-oxobut-2-enoic acid; 5-(1,1-difluoro-2-(3-(nitrooxy)propoxy)-2-oxoethyl)-2-((1S,2S,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3-hydroxyphenyl 2-propylpentanoate; 4,4′-((5-(1,1-difluoro-2-(4-(nitrooxy)butoxy)-2-oxoethyl)-2-((1S,2S,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-1,3-phenylene)bis(oxy))bis(4-oxobutanoic acid); 5-(1,1-difluoro-2-(hexyloxy)-2-oxoethyl)-2-((1S,2S,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3-hydroxyphenyl 4-(nitrooxy)butanoate; 2-(5-(1,1-difluoro-2-((6-(nitrooxy)hexyl)oxy)-2-oxoethyl)-2-((1S,2S,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3-hydroxyphenoxy)-N,N,N-trimethyl-2-oxoethanaminium iodide; 5-(1,1-difluoro-2-oxo-2-(pentyloxy)ethyl)-2-((1R,2R,5R)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3-hydroxyphenyl 4-(nitrooxy)butanoate; 5-(1,1-difluoro-2-(4-(nitrooxy)butoxy)-2-oxoethyl)-2-((1R,2R,5R)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3-hydroxyphenyl 2,5,8,11,14,17,20-heptaoxadocosan-22-oate; (E)-4-(5-(1,1-difluoro-2-(4-(nitrooxy)butoxy)-2-oxoethyl)-2-((1R,2R,5R)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3-hydroxyphenoxy)-4-oxobut-2-enoic acid; 1-(((5-(1,1-difluoro-2-(2-(nitrooxy)ethoxy)-2-oxoethyl)-2-((1R,2R,5R)-6,6-dimethyl-1-oxobicyclo[3.1.1]heptan-2-yl)-3-hydroxyphenoxy)carbonyl)oxy)ethyl isobutyrate; ((1S,6S)-2′,6′-dihydroxy-4′-(2-methyloctan-2-yl)-6-(prop-1-en-2-yl)-1,4,5,6-tetrahydro-[1,1′-biphenyl]-3-yl)methyl nitrate; ((1R,6R)-2′,6′-dihydroxy-4′-(2-methyloctan-2-yl)-6-(prop-1-en-2-yl)-1,4,5,6-tetrahydro-[1,1′-biphenyl]-3-yl)methyl nitrate; ((1S,6S)-2′,6′-dihydroxy-4′-pentyl-6-(prop-1-en-2-yl)-1,4,5,6-tetrahydro-[1,1′-biphenyl]-3-yl)methyl nitrate; ((1R,6R)-2′,6′-dihydroxy-4′-pentyl-6-(prop-1-en-2-yl)-1,4,5,6-tetrahydro-[1,1′-biphenyl]-3-yl)methyl nitrate; 6-(2,6-dihydroxy-5′-methoxy-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-4-yl)-6-methylheptyl nitrate; 7-(2,6-dihydroxy-5′-methoxy-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-4-yl)-7-methyloctyl nitrate; 7-(2,6-dihydroxy-5′-methoxy-2′-(prop-1-en-2-yl)-[1, 1′-biphenyl]-4-yl)-7,7-difluoroheptyl nitrate; 2-(nitrooxy)ethyl 2-(2,6-dihydroxy-5′-methoxy-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-4-yl)-2-methylpropanoate; (S)-6-hydroxy-5′-methoxy-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2-yl 4-(nitrooxy)butanoate; 4,4-difluoro-4-(1-hydroxy-9-methoxy-6,6-dimethyl-6H-benzo[c]chromen-3-yl)butyl nitrate; 4-(nitrooxy)butyl 2-(1-hydroxy-9-methoxy-6,6-dimethyl-6H-benzo[c]chromen-3-yl)-2-methylpropanoate; 4-(nitrooxy)butyl 2,2-difluoro-2-(1-hydroxy-9-methoxy-6,6-dimethyl-6H-benzo[c]chromen-3-yl)acetate; 7-(4-((1S,2S,5S)-4-(hydroxymethyl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-yl)-3,5-dimethoxyphenyl)-7-methyloctyl nitrate; 5-(4-((1S,2S,5S)-4-(hydroxymethyl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-yl)-3,5-dimethoxyphenyl)pentyl nitrate; 4-(nitrooxy)butyl 2-(4-((1S,2S,5S)-4-(hydroxymethyl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-yl)-3,5-dimethoxyphenyl)-2-methylpropanoate; ((1S,4S,5S)-4-(2,6-dimethoxy-4-(2-methylnonan-2-yl)phenyl)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl nitrate; 7,7-difluoro-7-(4-((1S,2S,5S)-4-(hydroxymethyl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-yl)-3,5-dimethoxyphenyl)heptyl nitrate; pentyl 2-(4-((1S,2S,5S)-6,6-dimethyl-4-((nitrooxy)methyl)bicyclo[3.1.1]hept-3-en-2-yl)-3,5-dimethoxyphenyl)-2-methylpropanoate; ((1S,4S,5S)-4-(4-(1,1-difluorooctyl)-2,6-dimethoxyphenyl)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl nitrate; pentyl 2-(4-((1S,2S,5S)-6,6-dimethyl-4-((nitrooxy)methyl)bicyclo[3.1.1]hept-3-en-2-yl)-3,5-dimethoxyphenyl)-2,2-difluoroacetate; 7-(2,6-dihydroxy-3′,5′-dimethyl-[1,1′-biphenyl]-4-yl)-7-methyloctyl nitrate; 5-(2,6-dihydroxy-3′,5′-dimethyl-[1,1′-biphenyl]-4-yl)-5-methylhexyl nitrate; 7-(2-hydroxy-3′,5′-dimethyl-[1,1′-biphenyl]-4-yl)-7-methyloctyl nitrate; 2′-cyano-3′-(trifluoromethyl)-[1,1′-biphenyl]-3-yl 3-(nitrooxy)propane-1-sulfonate; 2′-cyano-3′-(trifluoromethyl)-[1,1′-biphenyl]-3-yl 5-(nitrooxy)pentane-1-sulfonate; 3-(2-cyano-3-(trifluoromethyl)phenoxy)phenyl 3-(nitrooxy)propane-1-sulfonate; 4-hydroxy-3-((2R)-2-(hydroxymethyl)-2,3-dihydro-1H-inden-1-yl)phenyl 3-(nitrooxy)propane-1-sulfonate; 4-hydroxy-3-((2S)-2-(hydroxymethyl)-2,3-dihydro-1H-inden-1-yl)phenyl 3-(nitrooxy)propane-1-sulfonate; 4-(nitrooxy)butyl 2-(2,6-dihydroxy-3′,5′-dimethyl-[1,1′-biphenyl]-4-yl)-2-methylpropanoate; 4-(nitrooxy)butyl 2-(2,6-dihydroxy-3′,5′-dimethyl-[1,1′-biphenyl]-4-yl)-2,2-difluoroacetate; 5-(3-hydroxy-4-((1S,3R)-3-hydroxycyclohexyl)phenyl)-5-methylhexyl nitrate; 7-(3-hydroxy-4-((1S,3R)-3-hydroxycyclohexyl)phenyl)-7-methyloctyl nitrate; 5-(3-hydroxy-4-((1S,3S)-3-hydroxycyclohexyl)phenyl)-5-methylhexyl nitrate; 7-(3-hydroxy-4-((1S,3S)-3-hydroxycyclohexyl)phenyl)-7-methyloctyl nitrate; 4-(nitrooxy)butyl 2-(3-hydroxy-4-((1S,3R)-3-hydroxycyclohexyl)phenyl)-2-methylpropanoate; 4-(nitrooxy)butyl 2-(3-hydroxy-4-((1S,3S)-3-hydroxycyclohexyl)phenyl)-2-methylpropanoate; 8-(3-hydroxy-4-((1S,3R)-3-hydroxycyclohexyl)phenyl)-8-methylnonyl nitrate; 4-(nitrooxy)butyl 2,2-difluoro-2-(3-hydroxy-4-((1S,3S)-3-hydroxycyclohexyl)phenyl)acetate; 4-(nitrooxy)butyl 2,2-difluoro-2-(3-hydroxy-4-((1S,3R)-3-hydroxycyclohexyl)phenyl)acetate; 8-(3-hydroxy-4-((1S,3S)-3-hydroxycyclohexyl)phenyl)-8-methylnonyl nitrate; 7-(3-hydroxy-4-((1R,2R,5R)-5-hydroxy-2-(3-hydroxypropyl)cyclohexyl)phenyl)-7-methyloctyl nitrate; 7-(3-hydroxy-4-((1R,3R,4aS,7S,8aR)-3-hydroxy-7-(hydroxymethyl)decahydronaphthalen-1-yl)phenyl)-7-methyloctyl nitrate; 2-((1′R,2′R)-4,6-dihydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)ethyl nitrate; 3-((1′R,2′R)-4,6-dihydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)propyl nitrate; 3-((1′R,2′R)-4,6-dihydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)propyl nitrate; 5-((1′R,2′R)-4,6-dihydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)pentyl nitrate; 7-((1′R,2′R)-4,6-dihydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)-7-methyloctyl nitrate; 2-((1′S,2′S)-4,6-dihydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)ethyl nitrate; 3-((1′S,2′S)-4,6-dihydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)propyl nitrate; 3-((1′S,2′S)-4,6-dihydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)propyl nitrate; 5-((1′S,2′S)-4,6-dihydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)pentyl nitrate; 7-((1′S,2′S)-4,6-dihydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)-7-methyloctyl nitrate; 7-((1′R,2′R)-4,6-dihydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)-7,7-difluoroheptyl nitrate; 7-((1′S,2′S)-4,6-dihydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)-7,7-difluoroheptyl nitrate; 4-(nitrooxy)butyl 2-((1′R,2′R)-4,6-dihydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)-2-methylpropanoate; 4-(nitrooxy)butyl 2-((1′S,2′S)-4,6-dihydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)-2-methylpropanoate; 4-(nitrooxy)butyl 2-((1′R,2′R)-4,6-dihydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)-2,2-difluoroacetate; 4-(nitrooxy)butyl 2-((1′S,2′S)-4,6-dihydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)-2,2-difluoroacetate; 3-(((1′R,2′R)-2-hydroxy-5′-methyl-6-(5-(nitrooxy)pentyl)-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-4-yl)oxy)-3-oxopropanoic acid; (E)-4-(((1′S,2′S)-2-hydroxy-5′-methyl-6-(5-(nitrooxy)pentyl)-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-4-yl)oxy)-4-oxobut-2-enoic acid; (Z)-4-(((1′S,2′S)-2-hydroxy-5′-methyl-6-(5-(nitrooxy)pentyl)-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-4-yl)oxy)-4-oxobut-2-enoic acid; (1′R,2′R)-2-hydroxy-5′-methyl-6-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-4-yl 4-(nitrooxy)butanoate; 3,5-dihydroxy-2-((1R,2S,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-yl)phenethyl nitrate; 4-(3,5-dihydroxy-2-((1R,2S,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-yl)phenyl)butyl nitrate; 7-(3,5-dihydroxy-2-((1R,2S,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-yl)phenyl)-7-methyloctyl nitrate; (E)-4-(3-hydroxy-5-(4-(nitrooxy)butyl)-4-((1R,2S,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-yl)phenoxy)-4-oxobut-2-enoic acid; 3-hexyl-5-hydroxy-4-((1R,2S,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-yl)phenyl 4-(nitrooxy)butanoate; 4-(nitrooxy)butyl 2-(3,5-dihydroxy-2-((1R,2S,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-yl)phenyl)-2-methylpropanoate; 4-(nitrooxy)butyl 2-(3,5-dihydroxy-2-((1R,2S,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-yl)phenyl)-2,2-difluoroacetate; 5-(3,5-dihydroxy-2-((1R,2R,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-yl)phenyl)pentyl nitrate; 5-(3,5-dihydroxy-2-((1R,2R,5S)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-yl)phenyl)-5,5-difluoropentyl nitrate; 2-(1,4-dimethyl-1,2,5,6-tetrahydropyridin-2-yl)-3,5-dihydroxyphenethyl nitrate; 5-(3,5-dihydroxy-2-(1-isopropyl-4-methyl-1,2,5,6-tetrahydropyridin-2-yl)phenyl)pentyl nitrate; 3-hexyl-5-hydroxy-4-(1-isopropyl-4-methyl-1,2,5,6-tetrahydropyridin-2-yl)phenyl 5-(nitrooxy)pentanoate; 4-(nitrooxy)butyl 2-(3,5-dihydroxy-2-(1-isopropyl-4-methyl-1,2,5,6-tetrahydropyridin-2-yl)phenyl)-2-methylpropanoate; 5-(2-cyclohexyl-3,5-dihydroxyphenyl)pentyl nitrate; 4-cyclohexyl-3-hydroxy-5-pentylphenyl 5-(nitrooxy)pentanoate; 7-(2-cyclohexyl-3,5-dihydroxyphenyl)-7-methyl-6-oxooctyl nitrate; 5-(2-((1S,2S,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)pentyl nitrate; 5-(2-((1R,2R,5R)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)pentyl nitrate; 3-(nitrooxy)propyl 1-(6-ethyl-1-(4-fluorobenzyl)-5-methyl-2-oxo-1,2-dihydropyridine-3-carboxamido)cyclohexanecarboxylate; 4-(nitrooxy)butyl 1-(6-ethyl-1-(4-fluorobenzyl)-5-methyl-2-oxo-1,2-dihydropyridine-3-carboxamido)cyclohexanecarboxylate; 3-(nitrooxy)propyl 1-(6-ethyl-1-(4-fluorobenzyl)-5-methyl-2-oxo-1,2-dihydropyridine-3-carboxamido)cyclopentanecarboxylate; 3-(nitrooxy)propyl 2-(6-ethyl-1-(4-fluorobenzyl)-5-methyl-2-oxo-1,2-dihydropyridine-3-carboxamido)-2-methylpropanoate; 3-(nitrooxy)propyl 3-(2-(1-(cyclohexylmethyl)-2-oxo-1,2,5,6,7,8,9,10-octahydrocycloocta[b]pyridine-3-carboxamido)thiazol-4-yl)propanoate; ((R)-1-((R)-5-(3,3-dimethylbutanamido)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydrobenzofuran-7-yl)ethoxy)methyl nitrate; 3-(((R)-7-((R)-1-hydroxyethyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydrobenzofuran-5-yl)amino)-3-oxopropyl nitrate; (R)-2-((1-(cyclohexylmethyl)-3-(3,4-dimethylpiperazine-1-carbonyl)-1H-indol-7-yl)oxy)ethyl nitrate; (R)-3-(4-(1-(cyclohexylmethyl)-7-methoxy-1H-indole-3-carbonyl)-2-methylpiperazin-1-yl)propyl nitrate; 1-(cyclohexylmethyl)-3-((3S,5R)-3,4,5-trimethylpiperazine-1-carbonyl)-1H-indol-7-yl nitrate; (R)-5-(3-(3,4-dimethylpiperazine-1-carbonyl)-7-methoxy-1H-indol-1-yl)pentyl nitrate; 5-(3-(1-naphthoyl)-1H-indol-1-yl)pentyl nitrate; 4-((4-(1-naphthoyl)naphthalen-1-yl)oxy)butyl nitrate; 5-(3-(2,2,3,3-tetramethylcyclopropanecarbonyl)-1H-indol-1-yl)pentyl nitrate; 5-(3-((1-cyanocyclopropyl)carbamoyl)-1H-indol-1-yl)pentyl nitrate; 4-(nitrooxy)butyl 1-(3-chlorophenyl)-2,4-dioxopiperidine-3-carboxylate; 4-((2-(2,5-dichlorophenyl)-3-oxo-2,3-dihydropyridazin-4-yl)oxy)butyl nitrate; 5-((2-(4-hydroxyphenethyl)-5-methoxy-1-oxoisoindolin-4-yl)amino)pentyl nitrate; 5-((3-((benzo[d][1,3]dioxol-5-ylmethyl)carbamoyl)-7-methoxy-2-oxo-1,2-dihydroquinolin-8-yl)oxy)pentyl nitrate; 3-(4-((2-((2,4-dichlorophenyl)amino)-4-(trifluoromethyl)pyrimidine-5-carboxamido)methyl)piperidin-1-yl)propyl nitrate; 3-(4-(2-(1-(2,3-dichlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)ethyl)piperazin-1-yl)propyl nitrate; 2-((1-(2,3-dichlorobenzoyl)-2-methyl-3-(2-morpholinoethyl)-1H-indol-5-yl)oxy)ethyl nitrate; 2-((1-(2,3-dichlorobenzoyl)-2-methyl-3-(2-morpholinoethyl)-1H-indol-5-yl)oxy)ethyl nitrate; ((1R,3r)-3-((6aR,10R)-1-hydroxy-6,6-dimethyl-9-oxo-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-3-yl)adamantan-1-yl)methyl nitrate; ((1R,3r)-3-(4-((1S,2R,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)adamantan-1-yl)methyl nitrate; 2-(((1R,3r)-3-((6aR,10aR)-1-hydroxy-6,6-dimethyl-9-oxo-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-3-yl)adamantan-1-yl)methoxy)ethyl nitrate; ((1R,3r)-3-((1′R,2′R)-2,6-dihydroxy-5′-methyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-4-yl)adamantan-1-yl)methyl nitrate; ((1R,3r)-3-((6aR,10aR)-1-hydroxy-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-3-yl)adamantan-1-yl)methyl nitrate; ((1R,3r)-3-((6aR,10aR)-1-hydroxy-6,6,9-trimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-3-yl)adamantan-1-yl)methyl nitrate; ((1S,3r)-3-((1′S,2′S)-2,6-dihydroxy-5′-(hydroxymethyl)-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-4-yl)adamantan-1-yl)methyl nitrate; 2-((1R,3r)-3-((6aR,10aR)-1-hydroxy-6,6-dimethyl-9-oxo-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-3-yl)adamantane-1-carboxamido)ethyl nitrate; 2-((1R,3r)-3-(4-((1S,2R,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)adamantane-1-carboxamido)ethyl nitrate; 2-(((1R,3r)-3-(4-((1S,2R,5S)-6,6-dimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)-3,5-dihydroxyphenyl)adamantan-1-yl)methoxy)ethyl nitrate; 3-(1-(3-(nitrooxy)propyl)-1H-indazole-3-carboxamido)adamantane-1-carboxylic acid; 3-(3-((1-cyanocyclopropyl)carbamoyl)-1H-indazol-1-yl)propyl nitrate; or 2-(3-(adamantan-1-ylcarbamoyl)-1H-indazol-1-yl)ethyl nitrate; or a pharmaceutically acceptable salt of any such compound.

11. A composition comprising a compound of claim 1 and at least one pharmaceutically acceptable excipient.

12. A method of inhibiting, agonizing or antagonizing the activity of a cannabinoid 1 (CB1), cannabinoid 2 (CB2) or GPR55 receptor, the method comprising contacting the cannabinoid 1 (CB1), cannabinoid 2 (CB2) or GPR55 receptor with the compound of claim 1 .