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Disclosed are novel C 4 -carbonothioate-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 method for treating a brain neurological disorder, the method comprising administering to a subject in need thereof a chemical compound having chemical formula (I):
wherein R 4 is a carbonothioate 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 carbonothioate moiety or derivative thereof has the chemical formula (III):
wherein R 4b is an optionally substituted alkyl group, wherein the chemical compound is administered in an effective amount to treat the brain neurological disorder in the subject,
wherein the brain neurological disorder is a stress disorder, a sleep disorder, a depressive disorder, a substance-related disorder, and/or headache disorder.
2. A method according to claim 1 , wherein R 4b is a C 1 -C 6 alkyl substituted with an aryl group.
3. A method according to claim 1 , wherein R 4b is C 1 -C 3 alkyl substituted with an aryl group.
4. A method according to claim 1 , wherein R 4b is a methylene (—CH 2 —) substituted with an aryl group.
5. A method according to claim 4 , wherein the aryl group is a phenyl group.
6. A method according to claim 5 , wherein the aryl group is a phenyl group.
7. A method according to claim 1 , wherein R 3a and R 3b are independently a C 1 -C 6 alkyl group.
8. A method according to claim 1 , wherein R 3a and R 3b are independently a C 1 -C 3 alkyl group.
9. A method according to claim 1 , wherein R 3a and R 3b are a methyl group.
10. A method 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.
11. A method according to claim 1 , wherein R 4 is a carbonothioate moiety or derivative thereof, and wherein the compound is E(VI):
12. A method according to claim 1 , 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.
13. A method according to claim 12 , 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.
14. A method according to claim 13 , 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, a CHRM1 receptor, a CHRM2 receptor, a CNR1 receptor, a DRD1 receptor, a DRD2S receptor, an OPRD1 receptor, a GABAA receptor, or a NMDAR receptor.
15. A method according to claim 12 , wherein upon administration the compound having formula (I) interacts with a transmembrane transport protein in the subject to thereby modulate the transmembrane transport protein and exert a pharmacological effect.
16. A method according to claim 15 , wherein the transmembrane transport protein is a dopamine active transporter (DAT), a norephedrine transporter (NET), or a serotonin transporter (SERT) transmembrane transport protein.
17. A method according to claim 12 , 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.
18. A method according to claim 17 , 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, a CHRM1 receptor, a CHRM2 receptor, a CNR1 receptor, a DRD1 receptor, a DRD2S receptor, an OPRD1 receptor, a GABAA receptor, or a NMDAR receptor.
19. A method according to claim 12 , 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, an OPRD1 receptor-mediated disorder, a GABAA receptor-mediated disorder, or a NMDAR receptor-mediated disorder.
20. A method according to claim 12 , wherein a dose is administered of about 0.001 mg to about 5,000 mg.
21. A method according to claim 1 , wherein a pharmaceutical formulation comprising the chemical compound is administered to the subject in need thereof.
22. A method according to claim 21 , wherein the pharmaceutical formulation further comprises a diluent, excipient, or carrier.
23. A method according to claim 21 , wherein a dose of about 0.001 mg to about 5,000 mg is administered to the subject in need thereof.