C4-carboxylic acid-substituted tryptamine derivatives and methods of using
Disclosed are novel C 4 -carboxylic acid-substituted tryptamine derivative compounds and pharmaceutical and recreational drug formulations containing the same. The pharmaceutical formulations may be used to treat brain neurological disorders.
1. A chemical compound having chemical formula (I):
wherein R 4 is a carboxylic acid moiety or a derivative thereof;
wherein R 3a and R 3b are each independently a hydrogen atom, an alkyl group, or an aryl group; and
wherein the carboxylic acid moiety or derivative thereof has the chemical formula (II):
wherein R 4a is (i) a substituted phenyl group, wherein the phenyl group is substituted with one or more O-alkyl groups, or (ii) substituted alkyl group, wherein the substituted alkyl group is —CH 2 -cyclopropane.
2. A chemical compound according to claim 1 , wherein the O-alkyl group is a methoxy group, an ethoxy group, a propoxy group, an iso-propoxy group a n-butoxy group, a s-butoxy group or a t-butoxy group.
3. A chemical compound according to claim 1 , wherein the O-alkylated phenyl group is O-alkylated by one or more methoxy groups.
4. A chemical compound according to claim 1 , wherein R 3a and R 3b are each independently a C 1 -C 6 alkyl group.
5. A chemical compound according to claim 1 , wherein each R 3a and R 3b are a methyl group.
6. A chemical compound according to claim 1 , wherein one of R 3a and R 3b is a C 1 -C 6 alkyl group, and the other of R 3a and R 3b is a hydrogen atom.
7. A chemical compound according to claim 1 , wherein in the compound having chemical formula (I) the compound is selected from C(IV) and C(V):
8. A pharmaceutical formulation comprising a chemical compound according to claim 1 , together with a pharmaceutically acceptable excipient, diluent, or carrier.
9. A pharmaceutical formulation comprising a chemical compound according to claim 7 , together with a pharmaceutically acceptable excipient, diluent, or carrier.
10. A pharmaceutical formulation according to claim 8 , wherein the pharmaceutical formulation is a pro-drug pharmaceutical formulation, wherein the compound having formula (I) is in vivo hydrolyzed to form a compound having chemical formula (VI):
wherein R 3a and R 3b are each independently a hydrogen atom, an alkyl group, or an aryl group.
11. A method for treating a brain neurological disorder, the method comprising administering to a subject in need thereof a pharmaceutical formulation comprising a chemical compound according to claim 1 , wherein the pharmaceutical formulation is administered in an effective amount to treat the brain neurological disorder in the subject.
12. A method according to claim 11 , wherein upon administration the compound having formula (I) interacts with a receptor in the subject to thereby modulate the receptor and exert a pharmacological effect.
13. A method according to claim 12 , wherein the receptor is a 5-HT 1A receptor, a 5-HT 2A receptor, a 5-HT 1B receptor, a 5-HT 2B receptor, a 5-HT 3A receptor, an ADRA1A receptor, an ADRA2A receptor, CHRM1 receptor, a CHRM2 receptor, a CNR1 receptor, a DRD1 receptor, a DRD2S receptor, or an OPRD1 receptor.
14. A method according to claim 11 , wherein upon administration the compound having formula (I) interacts with an enzyme or transmembrane transport protein in the subject to thereby modulate the enzyme or transmembrane transport protein and exert a pharmacological effect.
15. A method according to claim 14 , wherein the enzyme is monoamine oxidase A (MOA-A), and the transmembrane transport protein is a dopamine active transporter (DAT), or a norephedrine transporter (NET) or a serotonin transporter (SERT) transmembrane transport protein.
16. A method according to claim 11 , wherein upon administration the compound having formula (I) is in vivo hydrolyzed to form a compound having chemical formula (VI):
wherein R 3a and R 3b are each independently a hydrogen atom, an alkyl group, or an aryl group,
and wherein the compound having chemical formula (VI) interacts with a receptor to thereby modulate the receptor in the subject and exert a pharmacological effect.
17. A method according to claim 16 , wherein the receptor is 5-HT 1A receptor, a 5-HT 2A receptor, a 5-HT 1B receptor, a 5-HT 2B receptor, a 5-HT 3A receptor, an ADRA1A receptor, an ADRA2A receptor, a CHRM1 receptor, a CHRM2 receptor, a CNR1 receptor, a DRD1 receptor, a DRD2S receptor, or an OPRD1 receptor.
18. A method according to claim 11 , wherein the disorder is a 5-HT 1A receptor-mediated disorder, a 5-HT 2A receptor-mediated disorder, a 5-HT 1B receptor-mediated disorder, a 5-HT 2B receptor-mediated disorder, a 5-HT 3A receptor-mediated disorder, an ADRA1A receptor-mediated disorder, an ADRA2A receptor-mediated disorder, a CHRM1 receptor-mediated disorder, a CHRM2 receptor-mediated disorder, a CNR1 receptor-mediated disorder, a DRD1 receptor-mediated disorder, a DRD2S receptor-mediated disorder, or an OPRD1 receptor-mediated disorder.
19. A method according to claim 11 , wherein a dose is administered of about 0.001 mg to about 5,000 mg.
20. A method for treating a brain neurological disorder, the method comprising administering to a subject in need thereof a pharmaceutical formulation comprising a chemical compound according to claim 7 , wherein the pharmaceutical formulation is administered in an effective amount to treat the brain neurological disorder in the subject.
21. A method according to claim 20 , wherein upon administration the compound having formula (I) interacts with a receptor in the subject to thereby modulate the receptor and exert a pharmacological effect.
22. A method according to claim 21 , wherein the receptor is a 5-HT 1A receptor, a 5-HT 2A receptor, a 5-HT 1B receptor, a 5-HT 2B receptor, a 5-HT 3A receptor, an ADRA1A receptor, an ADRA2A receptor, CHRM1 receptor, a CHRM2 receptor, a CNR1 receptor, a DRD1 receptor, a DRD2S receptor, or an OPRD1 receptor.
23. A method according to claim 20 , wherein upon administration the compound having formula (I) interacts with an enzyme or transmembrane transport protein in the subject to thereby modulate the enzyme or transmembrane transport protein and exert a pharmacological effect.
24. A method according to claim 23 , wherein the enzyme is monoamine oxidase A (MOA-A), and the transmembrane transport protein is a dopamine active transporter (DAT), or a norephedrine transporter (NET) or a serotonin transporter (SERT) transmembrane transport protein.
25. A method according to claim 20 , wherein upon administration the compound having formula (I) is in vivo hydrolyzed to form a compound having chemical formula (VI):
wherein R 3a and R 3b are each independently a hydrogen atom, an alkyl group, or an aryl group,
and wherein the compound having chemical formula (VI) interacts with a receptor to thereby modulate the receptor in the subject and exert a pharmacological effect.
26. A method according to claim 25 , wherein the receptor is 5-HT 1A receptor, a 5-HT 2A receptor, a 5-HT 1B receptor, a 5-HT 2B receptor, a 5-HT 3A receptor, an ADRA1A receptor, an ADRA2A receptor, a CHRM1 receptor, a CHRM2 receptor, a CNR1 receptor, a DRD1 receptor, a DRD2S receptor, or an OPRD1 receptor.
27. A method according to claim 20 , wherein the disorder is a 5-HT 1A receptor-mediated disorder, a 5-HT 2A receptor-mediated disorder, a 5-HT 1B receptor-mediated disorder, a 5-HT 2B receptor-mediated disorder, a 5-HT 3A receptor-mediated disorder, an ADRA1A receptor-mediated disorder, an ADRA2A receptor-mediated disorder, a CHRM1 receptor-mediated disorder, a CHRM2 receptor-mediated disorder, a CNR1 receptor-mediated disorder, a DRD1 receptor-mediated disorder, a DRD2S receptor-mediated disorder, or an OPRD1 receptor-mediated disorder.
28. A method according to claim 20 , wherein a dose is administered of about 0.001 mg to about 5,000 mg.