List of miscellaneous 5HT2A agonists

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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
File:11a from Bioorg Med Chem Lett 2003, 13, 2369 structure.png Compound 11a 11-chloro-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole 6.5 20726100 599173-28-1 [3]
File:23 from Bioorg Med Chem Lett 2003, 13, 2369 structure.png 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]
File:10d from Bioorg Med Chem Lett 2005, 15, 1467 structure.png Compound 10d 7-Benzyloxy-8-bromo-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine 22 10472780 616201-60-6 [4]
File:22.67 from WO 2009-079765 structure.png Example 22.67 4-(6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepin-2-yl)thiomorpholine 21 44124494 [5]
File:3d from J Med Chem 2013, 56, 1211 structure.png 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]
File:11 from WO 2021-076572 structure.png Compound 11 (3R)-N,N-diethyl-5-(1H-indol-4-yl)-1-methyl-3,6-dihydro-2H-pyridine-3-carboxamide (<10) 156278040 [7]
File:106 from ACS Med Chem Lett 2022, 13, 4, 648 structure.png 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]
File:6c from J Med Chem 2023, 66, 11536 structure.png Compound 6c (6S)-2,3-dichloro-7,8,9,10-tetrahydro-6H-6,9-epiminocyclohepta[b]quinoxaline (400) [9]
File:WO2004-058722-ex70 structure.png Compound 70 3-(4-bromo-2-methylpyrazol-3-yl)-N-(4-chlorophenyl)-4-methoxyaniline 1.77 9952456 [10]
File:22jmedchem2007-50-1367 structure.png Compound 22 7-(trifluoromethoxy)-2,3,4,10b-tetrahydro-1H-pyrazino[1,2-b]isoindol-6-one 67 (87) 11448649 [10]
File:WO2021-0137908-1 structure.png Example 1 (ZC-B) 3-(4-bromo-2,5-dimethoxyphenyl)azetidine (1.6) 156337249 2641630-65-9 [11]
File:2CB-AR structure.png 2C-B-aminorex 5-(4-bromo-2,5-dimethoxyphenyl)-4,5-dihydro-1,3-oxazol-2-amine 165360199 [12]
File:2CB-norphenmetrazine structure.png 2-(2,5-dimethoxy-4-bromophenyl)morpholine 2-(2,5-dimethoxy-4-bromophenyl)morpholine 20.6 11429275 [13]
File:Ibogaminalog.svg DM-506 (ibogaminalog) 3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole 24183 7546-66-9 [14]
File:LPH-5 structure.png LPH-5 (3S)-3-[2,5-dimethoxy-4-(trifluoromethyl)phenyl]piperidine (3.2) 156337168 2641630-97-7 [15]
File:2C-B-PP Structure.svg 2C-B-PP 1-(2,5-dimethoxy-4-bromophenyl)piperazine 4738744 100939-87-5 [16]
File:Cis-urocanic-acid structure.png cis-urocanic acid (cis-UCA) (Z)-3-(1H-imidazol-5-yl)prop-2-enoic acid 4.6 1549103 7699-35-6 [17][18][19]
File:CPD-1 Structure.svg CPD-1 (3S)-3-Methyl-1-[4-(trifluoromethyl)-1-benzofuran-7-yl]piperazine 9925822 325145-37-7 [20]
File:Efavirenz.svg Efavirenz (4S)-6-Chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one 64139 154598-52-4 [21]
GM-2505 [22]
File:IHCH-7079 structure.png 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 [23]
File:IHCH-7113.svg 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 [23]
? ITI-1549 ? 10.2 ? ? [24]
File:NDTDI structure.png NDTDI N,N-diethyl-3-[methyl(1,3,4,5-tetrahydrobenzo[cd]indol-4-yl)amino]propanamide 163192742 [25]
File:Mefloquine structure without stereochemistry.svg Mefloquine 2,8-bis(trifluoromethyl)quinolin-4-yl-(2-piperidyl)methanol 40692 53230-10-7 [26]
File:Org12962 structure.png ORG-12962 1-(5-trifluoromethyl-6-chloropyridin-2-yl)piperazine 9796408 210821-63-9 [27]
File:ORG-37684.svg ORG-37684 (3S)-3-[(2,3-dihydro-5-methoxy-1H-inden-4-yl)oxy]pyrrolidine 9794656 213007-95-5 [28]
File:OSU-6162.svg OSU-6162 (3S)-3-[3-(methylsulfonyl)phenyl]-1-propylpiperidine 9795741 156907-84-5 [29]
File:PHA-57378.svg 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]
File:P-54 structure.png P-54 2-(5-methoxypyrazolo[1,5-a]pyridin-3-yl)-N,N-dimethylethanamine 168946740 [30]
File:I-28 structure.png I-28 N-[2-(8-methoxynaphthalen-1-yl)ethyl]-N-methylpropan-2-amine 170604481 [31]
File:R69 structure.png (R)-69 3-[(5R)-5-methyl-1,2,5,6-tetrahydropyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine 164513426 [32]
File:RS134-49 structure.png RS134-49 4-methyl-3-(1,2,3,6-tetrahydropyridin-5-yl)-1H-indole 168941768 [33][34]
File:RH-34 structure.png RH-34 3-[2-(2-methoxybenzylamino)ethyl]-1H-quinazoline-2,4-dione 10041987 1028307-48-3 [35]
File:SCHEMBL5334361.svg SCHEMBL5334361 7-[(3-methoxyphenoxy)methyl]-2,3,4,5-tetrahydro-1H-3-benzazepine (0.4) 59027940 959867-47-1 [36]
File:Tabernanthalog.svg Tabernanthalog 8-methoxy-3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole 146026994 2483829-59-8 [37]
File:TKU-II-100 structure.png TKU-II-100 [(1S,2S)-2-(2-fluorophenyl)cyclopropyl]methanamine 0.62 44572747 [38]
File:WAY-470 structure.png WAY-470 1,16-diazatetracyclo[8.8.1.02,9.014,19]nonadeca-2(9),10,12,14(19)-tetraene 36 10037962 [39]
File:WXVL BT0793LQ2118 structure.png WXVL_BT0793LQ2118 6-fluoro-4-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)-1H-indole [40]
File:Z2825713589 structure.png Z2825713589 (4-amino-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl)-(6-methoxypyrazin-2-yl)methanone 167788805 [40]
File:Z2876442907 structure.png Z2876442907 ethyl 2-[[2-(4-methyl-1H-indol-3-yl)ethylamino]methyl]-1,3-thiazole-5-carboxylate 167850865 [40]
File:Z3517967757 structure.png Z3517967757 4-[1-(1-pyrimidin-2-ylethyl)piperidin-3-yl]phenol 167949972 [40]
File:Z3881312504 structure.png Z3881312504 2-bromo-4-[2-[methyl-[2-(1,3-thiazol-2-yl)ethyl]amino]ethyl]phenol 167904469 [40]
File:Z4154032166 structure.png Z4154032166 2,2,2-trifluoro-1-[6-(1,2,3,6-tetrahydropyridin-5-yl)pyridin-2-yl]ethanol 167878716 [40]
File:Z5247692566 structure.png Z5247692566 4-[(3,3-dimethyloxolan-2-yl)methyl]-3-[(1H-indol-3-yl)methyl]morpholine [40]
File:Z5247692629 structure.png Z5247692629 1-(1-bicyclo[1.1.1]pentanyl)-4-[[5-(4-chlorophenyl)-1H-pyrazol-4-yl]methyl]piperazine 166358273 [40]

See also

References

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  2. ↑ Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chemical Reviews. 124 (1): 124–163. doi:10.1021/acs.chemrev.3c00375. PMID 38033123. S2CID 265512698.
  3. ↑ 3.0 3.1 3.2 Ennis MD, Hoffman RL, Ghazal NB, Olson RM, Knauer CS, Chio CL, et al. (July 2003). "2,3,4,5-tetrahydro- and 2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indoles: new templates for 5-HT(2C) agonists". Bioorganic & Medicinal Chemistry Letters. 13 (14): 2369–2372. doi:10.1016/s0960-894x(03)00403-7. PMID 12824036.
  4. ↑ Smith BM, Smith JM, Tsai JH, Schultz JA, Gilson CA, Estrada SA, et al. (March 2005). "Discovery and SAR of new benzazepines as potent and selective 5-HT(2C) receptor agonists for the treatment of obesity". Bioorganic & Medicinal Chemistry Letters. 15 (5): 1467–1470. doi:10.1016/j.bmcl.2004.12.080. PMID 15713408.
  5. ↑ WO 2009/079765, Slassi A, Isaac M, Xin T, Higgins G, He Z, Sun G, Quach T, "Compounds with activity at the 5-ht2c receptor", published 2 July 2009, assigned to Cascade Therapeutics Inc. 
  6. ↑ Jensen AA, Plath N, Pedersen MH, Isberg V, Krall J, Wellendorph P, et al. (February 2013). "Design, synthesis, and pharmacological characterization of N- and O-substituted 5,6,7,8-tetrahydro-4H-isoxazolo[4,5-d]azepin-3-ol analogues: novel 5-HT(2A)/5-HT(2C) receptor agonists with pro-cognitive properties". Journal of Medicinal Chemistry. 56 (3): 1211–1227. doi:10.1021/jm301656h. PMID 23301527.
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  8. ↑ Orr MJ, Cao AB, Wang CT, Gaisin A, Csakai A, Friswold AP, et al. (April 2022). "Discovery of Highly Potent Serotonin 5-HT2 Receptor Agonists Inspired by Heteroyohimbine Natural Products". ACS Medicinal Chemistry Letters. 13 (4): 648–657. doi:10.1021/acsmedchemlett.1c00694. PMC 9014500. PMID 35450369.
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  30. ↑ WO 2023115165, Banister S, Jorgensen W, Jinlong T, "Compounds", published 29 June 2023, assigned to Psylo Pty Ltd. 
  31. ↑ WO 2023230649, Banister S, Jorgensen W, Jinlong T, Whish L, "Compounds", published 7 December 2023, assigned to Psylo Pty Ltd. 
  32. ↑ Kaplan AL, Confair DN, Kim K, Barros-Álvarez X, Rodriguiz RM, Yang Y, et al. (October 2022). "Bespoke library docking for 5-HT2A receptor agonists with antidepressant activity". Nature. 610 (7932): 582–591. Bibcode:2022Natur.610..582K. doi:10.1038/s41586-022-05258-z. PMC 9996387. PMID 36171289. S2CID 252598838.
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  34. ↑ WO 2023114472, Manish J, Slocum S, Skiniotis G, Barros X, Jin J, Kaniskan HU, Sun N, Xiong Y, Shen Y, Xu Z, Qui X, Qian C, Song X, Deng Z, Roth B, Biberto J, Kuglae K, Suomivuori CM, Daemgen MA, Dror R, Shoichet B, Kaplan AL, "Heterocyclic compounds as 5ht2a biased agonists.", published 22 June 2023, assigned to Icahn School of Medicine at Mount Sinai, The University of North Carolina at Chapel Hill, The Board of Trustees of The Leland Stanford Junior University, The Regents of The University of California 
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  36. ↑ WO 2007149728, Mohapatra S, Hellberg MR, Feng Z, "Aryl and heteroaryl tetrahydrobenzazepine derivatives and their use for treating glaucoma", assigned to Alcon Manufacturing, Ltd. 
  37. ↑ Cameron LP, Tombari RJ, Lu J, Pell AJ, Hurley ZQ, Ehinger Y, et al. (January 2021). "A non-hallucinogenic psychedelic analogue with therapeutic potential". Nature. 589 (7842): 474–479. Bibcode:2021Natur.589..474C. doi:10.1038/s41586-020-3008-z. PMC 7874389. PMID 33299186.
  38. ↑ WO 2007/025144, Kozikowski A, Kurome T, Setola V, Roth B, "5-ht2c receptor agonists as anorectic agents", published 1 March 2007, assigned to University Of Illinois - Chicago 
  39. ↑ Sabb AL, Vogel RL, Welmaker GS, Sabalski JE, Coupet J, Dunlop J, et al. (May 2004). "Cycloalkyl[b][1,4]benzodiazepinoindoles are agonists at the human 5-HT2C receptor". Bioorganic & Medicinal Chemistry Letters. 14 (10): 2603–7. doi:10.1016/j.bmcl.2004.02.100. PMID 15109661.
  40. ↑ 40.0 40.1 40.2 40.3 40.4 40.5 40.6 40.7 Lyu J, Kapolka N, Gumpper R, Alon A, Wang L, Jain MK, et al. (December 2023). "AlphaFold2 structures template ligand discovery". bioRxiv. doi:10.1101/2023.12.20.572662. PMC 10769324. PMID 38187536.
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