DESOXYSCALINE DERIVATIVES WITH MODIFIED MESCALINE-LIKE ACTION

1 . A composition comprising a compound represented by FIG. 1 ,

characterized in that R alpha1 and, independently and in any combination, R alpha2 is chosen from the group consisting of hydrogen, deuteron, methyl, ethyl, deuterated methyl (D 1 -D 3 ), or deuterated ethyl (D 1 -D 5 ), and further characterized in that R′ is one of the following substituents:

C 1 -C 6 branched or unbranched alkyl with the alkyl optionally substituted with F 1 -F 11 fluorine and/or D 1 -D 11 deuteron substituents up to a fully fluorinated and/or deuterated alkyl,

C 3 -C 6 cycloalkyl optionally and independently substituted with one or more substituents chosen from the group consisting of F 1 -F 15 fluorine, D 1 -D 15 deuteron, C 1 -C 2 alkyl, and combinations thereof,

(C 3 -C 6 cycloalkyl)-C 1 -C 2 branched or unbranched alkyl optionally substituted with one or more substituents chosen from the group consisting of F 1 -F 15 fluorine, D 1 -D 15 deuteron, C 1 -C 2 alkyl, and combinations thereof,

C 2 -C 5 branched or unbranched alkenyl with E or Z or cis or trans double bond configuration, where any of the carbons of the branched or unbranched alkenyl substituent is substituted with a substituent chosen from the group consisting of C 1 -C 2 alkyl, F 1 -F 13 fluorine, D 1 -D 13 deuteron, C 2 alkenyl, aryl or heteroaryl bearing zero up to any number of ether, thioether, halogen, alkyl, fluorinated alkyl, alkenyl, alkynyl or nitrogen-containing substituents, and combinations thereof,

C 2 -C 5 branched or unbranched alkynyl where any of the carbons of the branched or unbranched alkynyl substituent is substituted with a substituent chosen from the group consisting of one or more C 1 -C 2 alkyl, F 1 -F 11 fluorine, D 1 -D 11 deuteron, C 2 alkenyl, aryl or heteroaryl bearing zero up to any number of ether, thioether, halogen, alkyl, fluorinated alkyl, alkenyl, alkynyl or nitrogen-containing substituents, and combinations thereof,

any halogen or

a nitrogen-containing substituent of CN or NO 2 .

2 . The composition of claim 1 , wherein said compound is a free base.

3 . The composition of claim 1 , wherein said compound is a salt thereof.

4 . The composition of claim 3 , wherein said compound is a hydrochloride salt thereof.

5 . The composition of claim 4 , wherein said compound is a pharmacologically acceptable acid addition salt thereof chosen from the group consisting of sulfate, pyrosulfate, bisulfate, sulfite, bisulfite, phosphate, monohydrogen-phosphate, dihydrogenphosphate, metaphosphate, pyro-phosphate, chloride, bromide, iodide, formate, acetate, propionate, decanoate, caprylate, acrylate, isobutyrate, caproate, heptanoate, oxalate, malonate, succinate, suberate, sebacate, fumarate, maleate, benzoate, phthalate, sulfonate, phenylacetate, citrate, lactate, glycollate, tartrate, methanesulfonate, propanesulfonate, and mandelate.

6 . The composition of claim 1 , wherein said compound is chosen from the group consisting of a racemate, a single enantiomer, a diastereomer, and a mixture of enantiomers or diastereomers in any ratio, a single and a mixture E or Z configurational isomer in any ratio, a single and a mixture cis or trans configurational isomer in any ratio, and any combination thereof.

7 . A method of changing neurotransmission, including the steps of:

administering a pharmaceutically effective amount of composition to a mammal of a compound represented by FIG. 1 , which is characterized in that R alpha1 and, independently and in any combination, R alpha2 is chosen from the group consisting of hydrogen, deuteron, methyl, ethyl, deuterated methyl (D 1 -D 3 ), or deuterated ethyl (D 1 -D 5 ), and further characterized in that R′ is one of the following substituents:

C 1 -C 5 branched or unbranched alkyl with the alkyl optionally substituted with F 1 -F 11 fluorine and/or D 1 -D 11 deuteron substituents up to a fully fluorinated and/or deuterated alkyl,

C 3 -C 6 cycloalkyl optionally and independently substituted with one or more substituents chosen from the group consisting of F 1 -F 15 fluorine, D 1 -D 15 deuteron, C 1 -C 2 alkyl, and combinations thereof,

(C 3 -C 6 cycloalkyl)-C 1 -C 2 branched or unbranched alkyl optionally substituted with one or more substituents chosen from the group consisting of F 1 -F 15 fluorine, D 1 -D 15 deuteron, C 1 -C 2 alkyl, and combinations thereof,

C 2 -C 5 branched or unbranched alkenyl with E or Z or cis or trans double bond configuration, where any of the carbons of the branched or unbranched alkenyl substituent is substituted with a substituent chosen from the group consisting of C 1 -C 2 alkyl, F 1 -F 13 fluorine, D 1 -D 13 deuteron, C 2 alkenyl, aryl or heteroaryl bearing zero up to any number of ether, thioether, halogen, alkyl, fluorinated alkyl, alkenyl, alkynyl or nitrogen-containing substituents, and combinations thereof,

C 2 -C 5 branched or unbranched alkynyl where any of the carbons of the branched or unbranched alkynyl substituent is substituted with a substituent chosen from the group consisting of one or more C 1 -C 2 alkyl, F 1 -F 11 fluorine, D 1 -D 11 deuteron, C 2 alkenyl, aryl or heteroaryl bearing zero up to any number of ether, thioether, halogen, alkyl, fluorinated alkyl, alkenyl, alkynyl or nitrogen-containing substituents, and combinations thereof,

any halogen or

a nitrogen-containing substituent of CN or NO 2 ;

increasing serotonin 5-HT2A and 5-HT2C receptor interaction in the mammal; and

inducing psychoactive effects.

8 . The method of claim 7 , wherein the compound is chosen from the group consisting of a racemate, a single enantiomer, a diastereomer, a mixture of enantiomers or diastereomers in any ratio, a single and a mixture E or Z configurational isomer in any ratio, a single and a mixture cis or trans configurational isomer in any ratio, and any combination thereof.

9 . The method of claim 7 , wherein the psychoactive effects include psychedelic or empathogenic effects having intensity, effect quality, or duration of effect in a mammal in comparison to that of mescaline.

10 . The method of claim 7 , wherein the compound is administered to mammals for substance-assisted psychotherapy.

11 . The method of claim 7 , wherein the compound is administered to allow for changing dose potency in comparison to mescaline.

12 . The method of claim 7 , wherein the compound is administered to allow for tailoring and treatment individualization to the mammal's therapeutic need.

13 . The method of claim 10 , wherein the mammal is a human.

14 . A method of treating a patient having adverse reactions to psychedelics, including the steps of:

administering a desoxyscaline derivative to the patient; and

avoiding adverse effects present with psychedelics.

15 . The method of claim 14 , wherein the adverse effects are chosen from the group consisting of anxiety, cardio-stimulant effects, thermogenesis, adverse effects, nausea, and combinations thereof.

16 . The method of claim 15 , further including the step of providing more positive effects than other psychedelics.

17 . The method of claim 16 , wherein the positive effects are chosen from the group consisting of more overall positive effects, more or less perceptual effects, more emotional effects, and combinations thereof.

18 . The method of claim 14 , further including the step of providing a shorter duration of action of the desoxyscaline derivative than with other psychedelics.

19 . The method of claim 14 , wherein the desoxyscaline derivative is further defined as a compound represented by FIG. 1 , which is characterized in that R alpha1 and, independently and in any combination, R alpha2 is chosen from the group consisting of hydrogen, deuteron, methyl, ethyl, deuterated methyl (D 1 -D 3 ), or deuterated ethyl (D 1 -D 5 ), and further characterized in that R′ is one of the following substituents:

C 1 -C 5 branched or unbranched alkyl with the alkyl optionally substituted with F 1 -F 11 fluorine and/or D 1 -D 11 deuteron substituents up to a fully fluorinated and/or deuterated alkyl,

C 3 -C 6 cycloalkyl optionally and independently substituted with one or more substituents chosen from the group consisting of F 1 -F 15 fluorine, D 1 -D 15 deuteron, C 1 -C 2 alkyl, and combinations thereof,

(C 3 -C 6 cycloalkyl)-C 1 -C 2 branched or unbranched alkyl optionally substituted with one or more substituents chosen from the group consisting of F 1 -F 15 fluorine, D 1 -D 15 deuteron, C 1 -C 2 alkyl, and combinations thereof,

C 2 -C 5 branched or unbranched alkenyl with E or Z or cis or trans double bond configuration, where any of the carbons of the branched or unbranched alkenyl substituent is substituted with a substituent chosen from the group consisting of C 1 -C 2 alkyl, F 1 -F 13 fluorine, D 1 -D 13 deuteron, C 2 alkenyl, aryl or heteroaryl bearing zero up to any number of ether, thioether, halogen, alkyl, fluorinated alkyl, alkenyl, alkynyl or nitrogen-containing substituents, and combinations thereof,

C 2 -C 5 branched or unbranched alkynyl where any of the carbons of the branched or unbranched alkynyl substituent is substituted with a substituent chosen from the group consisting of one or more C 1 -C 2 alkyl, F 1 -F 11 fluorine, D 1 -D 11 deuteron, C 2 alkenyl, aryl or heteroaryl bearing zero up to any number of ether, thioether, halogen, alkyl, fluorinated alkyl, alkenyl, alkynyl or nitrogen-containing substituents, and combinations thereof,

any halogen or,

a nitrogen-containing substituent of CN or NO 2 .

20 . A method of changing neurotransmission of an individual, including the steps of:

administering a desoxyscaline derivative; and

changing neurotransmission in the individual.

21 . The method of claim 20 , wherein the desoxyscaline derivative is further defined as a compound represented by FIG. 1 , which is characterized in that R alpha1 and, independently and in any combination, R alpha2 is chosen from the group consisting of hydrogen, deuteron, methyl, ethyl, deuterated methyl (D 1 -D 3 ), or deuterated ethyl (D 1 -D 5 ), and further characterized in that R′ is one of the following substituents:

C 1 -C 5 branched or unbranched alkyl with the alkyl optionally substituted with F 1 -F 11 fluorine and/or D 1 -D 11 deuteron substituents up to a fully fluorinated and/or deuterated alkyl,

C 3 -C 6 cycloalkyl optionally and independently substituted with one or more substituents chosen from the group consisting of F 1 -F 15 fluorine, D 1 -D 15 deuteron, C 1 -C 2 alkyl, and combinations thereof,

(C 3 -C 6 cycloalkyl)-C 1 -C 2 branched or unbranched alkyl optionally substituted with one or more substituents chosen from the group consisting of F 1 -F 15 fluorine, D 1 -D 15 deuteron, C 1 -C 2 alkyl, and combinations thereof,

C 2 -C 5 branched or unbranched alkenyl with E or Z or cis or trans double bond configuration, where any of the carbons of the branched or unbranched alkenyl substituent is substituted with a substituent chosen from the group consisting of C 1 -C 2 alkyl, F 1 -F 13 fluorine, D 1 -D 13 deuteron, C 2 alkenyl, aryl or heteroaryl bearing zero up to any number of ether, thioether, halogen, alkyl, fluorinated alkyl, alkenyl, alkynyl or nitrogen-containing substituents, and combinations thereof,

C 2 -C 5 branched or unbranched alkynyl where any of the carbons of the branched or unbranched alkynyl substituent is substituted with a substituent chosen from the group consisting of one or more C 1 -C 2 alkyl, F 1 -F 11 fluorine, D 1 -D 11 deuteron, C 2 alkenyl, aryl or heteroaryl bearing zero up to any number of ether, thioether, halogen, alkyl, fluorinated alkyl, alkenyl, alkynyl or nitrogen-containing substituents, and combinations thereof,

any halogen or,

a nitrogen-containing substituent of CN or NO 2 .