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This is a list of agonists of the serotonin receptor subtype 5-HT2A (and other 5-HT2 subtypes to a varying extent) which fall outside the common structural classes. Most agonists at this receptor are either substituted phenethylamine derivatives from the 2C, DOx and 25-NB groups, or substituted tryptamines and related compounds along with more complex derivatives of these such as lysergamides and iboga-type alkaloids. [1] There are however numerous 5-HT2A receptor agonists which do not fall within any of these groups, some representative examples of which are listed below. Ki and EC50 values vary depending on the assay conditions used and so may not be directly comparable between sources. Many of these compounds have been designed to be non-psychoactive derivatives for medical applications, and it should not be assumed that a compound which acts as a 5-HT2A agonist will necessarily be psychedelic in nature. [2]

Structure Name Chemical name h5-HT2A Ki (EC50) (nM) PubChem CAS number Reference
Compound 11a 11-chloro-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole 6.5 20726100 599173-28-1 [3]
Compound 23 9-Chloro-7-(2-ethoxy-phenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole 32 44315398 599173-25-8 [3]
Compound 10d 7-Benzyloxy-8-bromo-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine 22 10472780 616201-60-6 [4]
Example 22.67 4-(6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepin-2-yl)thiomorpholine 21 44124494 [5]
Compound 3d (N-Bn-THAZ) 2-benzyl-5,6,7,8-tetrahydro-4H-[1,2]oxazolo[4,5-d]azepin-3-one (549) 14515725 125115-66-4 [6]
Compound 11 (3R)-N,N-diethyl-5-(1H-indol-4-yl)-1-methyl-3,6-dihydro-2H-pyridine-3-carboxamide (<10) 156278040 [7]
Compound 106 6-chloro-1-(2,4,5-trimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 4376990 528525-37-3 [8]
Compound 6c (6S)-2,3-dichloro-7,8,9,10-tetrahydro-6H-6,9-epiminocyclohepta[b]quinoxaline (400) [9]
Compound 70 3-(4-bromo-2-methylpyrazol-3-yl)-N-(4-chlorophenyl)-4-methoxyaniline 1.77 9952456 [10]
Compound 22 7-(trifluoromethoxy)-2,3,4,10b-tetrahydro-1H-pyrazino[1,2-b]isoindol-6-one 67 (87) 11448649 [10]
Example 1 ( ZC-B) 3-(4-bromo-2,5-dimethoxyphenyl)azetidine (1.6) 156337249 2641630-65-9 [11]
2C-B-aminorex 5-(4-bromo-2,5-dimethoxyphenyl)-4,5-dihydro-1,3-oxazol-2-amine 165360199 [12]
2-(2,5-dimethoxy-4-bromophenyl)morpholine 2-(2,5-dimethoxy-4-bromophenyl)morpholine 20.6 11429275 [13]
LPH-5 (3S)-3-[2,5-dimethoxy-4-(trifluoromethyl)phenyl]piperidine (3.2) 156337168 2641630-97-7 [14]
2C-B-PP 1-(2,5-dimethoxy-4-bromophenyl)piperazine 4738744 100939-87-5 [15]
cis-urocanic acid (cis-UCA) (Z)-3-(1H-imidazol-5-yl)prop-2-enoic acid 4.6 1549103 7699-35-6 [16] [17] [18]
CPD-1 (3S)-3-Methyl-1-[4-(trifluoromethyl)-1-benzofuran-7-yl]piperazine 9925822 325145-37-7 [19]
Efavirenz (4S)-6-Chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one 64139 154598-52-4 [20]
IHCH-7079 (6bR,10aS)-8-(2-Methoxyphenethyl)-3-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline 169488014 2957888-63-8 [21]
IHCH-7113 (6bR,10aS)-3-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline 21302499 313368-85-3 [21]
NDTDI N,N-diethyl-3-[methyl(1,3,4,5-tetrahydrobenzo[cd]indol-4-yl)amino]propanamide 163192742 [22]
Mefloquine 2,8-bis(trifluoromethyl)quinolin-4-yl-(2-piperidyl)methanol 40692 53230-10-7 [23]
ORG-12962 1-(5-trifluoromethyl-6-chloropyridin-2-yl)piperazine 9796408 210821-63-9 [24]
ORG-37684 (3S)-3-[(2,3-dihydro-5-methoxy-1H-inden-4-yl)oxy]pyrrolidine 9794656 213007-95-5 [25]
OSU-6162 (3S)-3-[3-(methylsulfonyl)phenyl]-1-propylpiperidine 9795741 156907-84-5 [26]
PHA-57378 2,7,8,9,10,11-hexahydro-1H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole 4.1 10198481 303798-94-9 [3]
P-54 2-(5-methoxypyrazolo[1,5-a]pyridin-3-yl)-N,N-dimethylethanamine 168946740 [27]
I-28 N-[2-(8-methoxynaphthalen-1-yl)ethyl]-N-methylpropan-2-amine 170604481 [28]
(R)-69 3-[(5R)-5-methyl-1,2,5,6-tetrahydropyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine 164513426 [29]
RS134-49 4-methyl-3-(1,2,3,6-tetrahydropyridin-5-yl)-1H-indole 168941768 [30] [31]
RH-34 3-[2-(2-methoxybenzylamino)ethyl]-1H-quinazoline-2,4-dione 10041987 1028307-48-3 [32]
SCHEMBL5334361 7-[(3-methoxyphenoxy)methyl]-2,3,4,5-tetrahydro-1H-3-benzazepine (0.4) 59027940 959867-47-1 [33]
Tabernanthalog 8-methoxy-3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole 146026994 2483829-59-8 [34]
TKU-II-100 [(1S,2S)-2-(2-fluorophenyl)cyclopropyl]methanamine 0.62 44572747 [35]
WAY-470 1,16-diazatetracyclo[8.8.1.02,9.014,19]nonadeca-2(9),10,12,14(19)-tetraene 36 10037962 [36]
WXVL_BT0793LQ2118 6-fluoro-4-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)-1H-indole [37]
Z2825713589 (4-amino-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl)-(6-methoxypyrazin-2-yl)methanone 167788805 [37]
Z2876442907 ethyl 2-[[2-(4-methyl-1H-indol-3-yl)ethylamino]methyl]-1,3-thiazole-5-carboxylate 167850865 [37]
Z3517967757 4-[1-(1-pyrimidin-2-ylethyl)piperidin-3-yl]phenol 167949972 [37]
Z3881312504 2-bromo-4-[2-[methyl-[2-(1,3-thiazol-2-yl)ethyl]amino]ethyl]phenol 167904469 [37]
Z4154032166 2,2,2-trifluoro-1-[6-(1,2,3,6-tetrahydropyridin-5-yl)pyridin-2-yl]ethanol 167878716 [37]
Z5247692566 4-[(3,3-dimethyloxolan-2-yl)methyl]-3-[(1H-indol-3-yl)methyl]morpholine [37]
Z5247692629 1-(1-bicyclo[1.1.1]pentanyl)-4-[[5-(4-chlorophenyl)-1H-pyrazol-4-yl]methyl]piperazine 166358273 [37]

See also

References

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Retrieved from " https://en.wikipedia.org/?title=List_of_miscellaneous_5HT2A_agonists&oldid=1232640054"
From Wikipedia, the free encyclopedia

This is a list of agonists of the serotonin receptor subtype 5-HT2A (and other 5-HT2 subtypes to a varying extent) which fall outside the common structural classes. Most agonists at this receptor are either substituted phenethylamine derivatives from the 2C, DOx and 25-NB groups, or substituted tryptamines and related compounds along with more complex derivatives of these such as lysergamides and iboga-type alkaloids. [1] There are however numerous 5-HT2A receptor agonists which do not fall within any of these groups, some representative examples of which are listed below. Ki and EC50 values vary depending on the assay conditions used and so may not be directly comparable between sources. Many of these compounds have been designed to be non-psychoactive derivatives for medical applications, and it should not be assumed that a compound which acts as a 5-HT2A agonist will necessarily be psychedelic in nature. [2]

Structure Name Chemical name h5-HT2A Ki (EC50) (nM) PubChem CAS number Reference
Compound 11a 11-chloro-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole 6.5 20726100 599173-28-1 [3]
Compound 23 9-Chloro-7-(2-ethoxy-phenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole 32 44315398 599173-25-8 [3]
Compound 10d 7-Benzyloxy-8-bromo-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine 22 10472780 616201-60-6 [4]
Example 22.67 4-(6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepin-2-yl)thiomorpholine 21 44124494 [5]
Compound 3d (N-Bn-THAZ) 2-benzyl-5,6,7,8-tetrahydro-4H-[1,2]oxazolo[4,5-d]azepin-3-one (549) 14515725 125115-66-4 [6]
Compound 11 (3R)-N,N-diethyl-5-(1H-indol-4-yl)-1-methyl-3,6-dihydro-2H-pyridine-3-carboxamide (<10) 156278040 [7]
Compound 106 6-chloro-1-(2,4,5-trimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 4376990 528525-37-3 [8]
Compound 6c (6S)-2,3-dichloro-7,8,9,10-tetrahydro-6H-6,9-epiminocyclohepta[b]quinoxaline (400) [9]
Compound 70 3-(4-bromo-2-methylpyrazol-3-yl)-N-(4-chlorophenyl)-4-methoxyaniline 1.77 9952456 [10]
Compound 22 7-(trifluoromethoxy)-2,3,4,10b-tetrahydro-1H-pyrazino[1,2-b]isoindol-6-one 67 (87) 11448649 [10]
Example 1 ( ZC-B) 3-(4-bromo-2,5-dimethoxyphenyl)azetidine (1.6) 156337249 2641630-65-9 [11]
2C-B-aminorex 5-(4-bromo-2,5-dimethoxyphenyl)-4,5-dihydro-1,3-oxazol-2-amine 165360199 [12]
2-(2,5-dimethoxy-4-bromophenyl)morpholine 2-(2,5-dimethoxy-4-bromophenyl)morpholine 20.6 11429275 [13]
LPH-5 (3S)-3-[2,5-dimethoxy-4-(trifluoromethyl)phenyl]piperidine (3.2) 156337168 2641630-97-7 [14]
2C-B-PP 1-(2,5-dimethoxy-4-bromophenyl)piperazine 4738744 100939-87-5 [15]
cis-urocanic acid (cis-UCA) (Z)-3-(1H-imidazol-5-yl)prop-2-enoic acid 4.6 1549103 7699-35-6 [16] [17] [18]
CPD-1 (3S)-3-Methyl-1-[4-(trifluoromethyl)-1-benzofuran-7-yl]piperazine 9925822 325145-37-7 [19]
Efavirenz (4S)-6-Chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one 64139 154598-52-4 [20]
IHCH-7079 (6bR,10aS)-8-(2-Methoxyphenethyl)-3-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline 169488014 2957888-63-8 [21]
IHCH-7113 (6bR,10aS)-3-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline 21302499 313368-85-3 [21]
NDTDI N,N-diethyl-3-[methyl(1,3,4,5-tetrahydrobenzo[cd]indol-4-yl)amino]propanamide 163192742 [22]
Mefloquine 2,8-bis(trifluoromethyl)quinolin-4-yl-(2-piperidyl)methanol 40692 53230-10-7 [23]
ORG-12962 1-(5-trifluoromethyl-6-chloropyridin-2-yl)piperazine 9796408 210821-63-9 [24]
ORG-37684 (3S)-3-[(2,3-dihydro-5-methoxy-1H-inden-4-yl)oxy]pyrrolidine 9794656 213007-95-5 [25]
OSU-6162 (3S)-3-[3-(methylsulfonyl)phenyl]-1-propylpiperidine 9795741 156907-84-5 [26]
PHA-57378 2,7,8,9,10,11-hexahydro-1H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole 4.1 10198481 303798-94-9 [3]
P-54 2-(5-methoxypyrazolo[1,5-a]pyridin-3-yl)-N,N-dimethylethanamine 168946740 [27]
I-28 N-[2-(8-methoxynaphthalen-1-yl)ethyl]-N-methylpropan-2-amine 170604481 [28]
(R)-69 3-[(5R)-5-methyl-1,2,5,6-tetrahydropyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine 164513426 [29]
RS134-49 4-methyl-3-(1,2,3,6-tetrahydropyridin-5-yl)-1H-indole 168941768 [30] [31]
RH-34 3-[2-(2-methoxybenzylamino)ethyl]-1H-quinazoline-2,4-dione 10041987 1028307-48-3 [32]
SCHEMBL5334361 7-[(3-methoxyphenoxy)methyl]-2,3,4,5-tetrahydro-1H-3-benzazepine (0.4) 59027940 959867-47-1 [33]
Tabernanthalog 8-methoxy-3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole 146026994 2483829-59-8 [34]
TKU-II-100 [(1S,2S)-2-(2-fluorophenyl)cyclopropyl]methanamine 0.62 44572747 [35]
WAY-470 1,16-diazatetracyclo[8.8.1.02,9.014,19]nonadeca-2(9),10,12,14(19)-tetraene 36 10037962 [36]
WXVL_BT0793LQ2118 6-fluoro-4-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)-1H-indole [37]
Z2825713589 (4-amino-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl)-(6-methoxypyrazin-2-yl)methanone 167788805 [37]
Z2876442907 ethyl 2-[[2-(4-methyl-1H-indol-3-yl)ethylamino]methyl]-1,3-thiazole-5-carboxylate 167850865 [37]
Z3517967757 4-[1-(1-pyrimidin-2-ylethyl)piperidin-3-yl]phenol 167949972 [37]
Z3881312504 2-bromo-4-[2-[methyl-[2-(1,3-thiazol-2-yl)ethyl]amino]ethyl]phenol 167904469 [37]
Z4154032166 2,2,2-trifluoro-1-[6-(1,2,3,6-tetrahydropyridin-5-yl)pyridin-2-yl]ethanol 167878716 [37]
Z5247692566 4-[(3,3-dimethyloxolan-2-yl)methyl]-3-[(1H-indol-3-yl)methyl]morpholine [37]
Z5247692629 1-(1-bicyclo[1.1.1]pentanyl)-4-[[5-(4-chlorophenyl)-1H-pyrazol-4-yl]methyl]piperazine 166358273 [37]

See also

References

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