Methods, compounds, and compositions for reducing body fat and modulating fatty acid metabolism

1. A method of reducing body weight in a mammal in need thereof, said method comprising administering to said mammal a fatty acid alkanolamide in an effective amount to reduce body weight in said mammal, wherein the fatty acid alkanolamide is a compound of the formula:

or a pharmaceutically acceptable salt thereof, wherein n is an integer from 1 to 5; a and b are each an integer wherein the sum of a and b is from 0 to 4; and R 1 is hydrogen and R 2 is selected from the group consisting of hydrogen, unsubstituted (C 1 -C 6 ) alkyl, and unsubstituted (C 2 -C 6 ) acyl, and wherein optionally up to four hydrogen atoms of the fatty acid portion and alkanolamide portion of the formula are substituted by methyl or a double bond joining adjacent carbons of the formula, and additionally the bond between carbons c and d may be unsaturated or saturated.

2. The method according to claim 1 , wherein the fatty acid alkanolamide is oleoylethanolamide.

3. The method of claim 1 , wherein n is 1.

4. The method of claim 1 , wherein the fatty acid portion is monounsaturated.

5. The method of claim 1 , wherein the administering is via a dermal patch.

6. The method of claim 4 , wherein the fatty acid portion is oleic acid.

7. The method of claim 3 , wherein the fatty acid portion is selected from the group consisting of elaidic acid, palmitoleic acid, palmitic acid, linoleic acid, alpha- linolenic acid, and gamma-linolenic acid.

8. The method of claim 3 , wherein n is 1 and R 2 is a lower (C 1 -C 3 ) alkyl.

9. The method of claim 3 , wherein n is 1 and R 2 is straight or branched (C 2 -C 6 ) acyl.

10. The method according to claim 1 , wherein the mammal is human.

11. The method according to claim 1 , wherein the fatty acid alkanolamide is palmitoylethanolamide.

12. The method according to claim 1 , wherein said fatty acid alkanolamide is administered with a pharmaceutically acceptable carrier by an oral, rectal, topical, or parenteral route.

13. The method of claim 1 , wherein a dose of the fatty acid alkanolamide in an amount from about 10 mg to 1000 mg of the fatty acid alkanolamide is administered.

14. The method of claim 1 , wherein a dose of about 1 mg to 100 mg of the fatty acid alkanolamide is administered.

15. The method of claim 1 , wherein a dose of about 100 mg to 500 mg of the fatty acid alkanolamide is administered.

16. The method of claim 1 , wherein the fatty acid alkanolamide is administered in a unit dose format.

17. The method of claim 1 , wherein the fatty acid alkanolamide is administered orally.

18. The method of claim 1 , wherein the fatty acid alkanolamide is orally administered in a tablet, pill, or capsule form.

19. The method of claim 1 , wherein the administering is topical.

20. The method of claim 1 , wherein one of the hydrogen atoms of the fatty acid portion and alkanolamide portion of the compound is substituted by methyl.

21. The method of claim 20 , wherein the compound is selected from the group consisting of (R)1′-methyloleoylethanolamide, (S)1′-methyloleoylethanolamide, (R)2′-methyloleoylethanolamide, (S)2′-methyloleoylethanolamide, (R)1-methyloleoylethanolamide, (S)1-methyloleoylethanolamide and the pharmaceutically acceptable salts thereof.

22. The method of claim 12 , wherein R 2 is —C(O)CH 2 CH 3, —C(O)CH 2 CH 2 CH 3, or —C(O)CH 3.

23. The method of claim 1 , wherein n is 1 and R 2 is hydrogen.

24. The method of claim 1 , wherein the fatty acid alkanolamide is elaidylethanolamide.

25. The method of claim 1 , wherein there is a double bond between carbons c and d.

26. The method of claim 1 , wherein a=1, b=1, and n=1.

27. The method of claim 1 , wherein the stereochemistry of the compound about the double bond is E.

28. The method of claim 1 , wherein the stereochemistry of the compound about the double bond is Z.