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List of miscellaneous 5-HT2A receptor agonists

From Wikipedia, the free encyclopedia

This is alist of miscellaneousagonists of theserotoninreceptor subtype5-HT2A (and other 5-HT2 subtypes to a varying extent) that fall outside the common structural classes. Most agonists at this receptor are eithersubstituted phenethylamine derivatives from the2C,DOx and25-NB groups, orsubstituted tryptamines and related compounds along with more complex derivatives of these such aslysergamides andiboga-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 bepsychedelic in nature.[2]

StructureNameChemical nameh5-HT2A Ki (EC50) (nM)PubChemCAS #Ref
Compound 11a11-chloro-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole6.520726100599173-28-1[3]
Compound 239-Chloro-7-(2-ethoxy-phenyl)-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole3244315398599173-25-8[3]
Compound 10d7-Benzyloxy-8-bromo-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine2210472780616201-60-6[4]
Example 22.674-(6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepin-2-yl)thiomorpholine21441244941003589-43-2[5]
N-Bn-THAZ (compound 3d)2-benzyl-5,6,7,8-tetrahydro-4H-[1,2]oxazolo[4,5-d]azepin-3-one(549)14515725125115-66-4[6]
DEIMDHPCA (compound 11 or formula IIa)(3R)-N,N-diethyl-5-(1H-indol-4-yl)-1-methyl-3,6-dihydro-2H-pyridine-3-carboxamide(<10)1562780402640392-28-3[7]
NEtPhOH-THPI (compound 24c)2-{2-[5-(1H-indol-3-yl)-3,6-dihydropyridin-1(2H)-yl]ethyl}phenol(58.43)[8]
Compound 1066-chloro-1-(2,4,5-trimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole4376990528525-37-3[9]
Compound 6c(6S)-2,3-dichloro-7,8,9,10-tetrahydro-6H-6,9-epiminocyclohepta[b]quinoxaline(400)2991367-88-3[10]
Compound 703-(4-bromo-2-methylpyrazol-3-yl)-N-(4-chlorophenyl)-4-methoxyaniline1.779952456720702-40-9[11]
Compound 227-(trifluoromethoxy)-2,3,4,10b-tetrahydro-1H-pyrazino[1,2-b]isoindol-6-one67 (87)11448649850033-15-7[11]
Example 1 (ZC-B)3-(4-bromo-2,5-dimethoxyphenyl)azetidine(1.6)1563372492641630-65-9[12]
2C-B-aminorex5-(4-bromo-2,5-dimethoxyphenyl)-4,5-dihydro-1,3-oxazol-2-amine165360199[13]
2C-B-morpholine2-(2,5-dimethoxy-4-bromophenyl)morpholine20.611429275807631-07-8[14]
Lorcaserin(1R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine(158)11658860616202-92-7[15]
7-Chlorolorcaserin(1R)-7,8-dichloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine(10)24773649?[15]
DM-506 (ibogaminalog)3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole241837546-66-9[16]
LPH-5(3S)-3-[2,5-dimethoxy-4-(trifluoromethyl)phenyl]piperidine(3.2)1563371682641630-97-7[17]
2C-B-PP1-(2,5-dimethoxy-4-bromophenyl)piperazine4738744100939-87-5[18]
ENX-1055-chloro-2-methoxy-N-((2R,3R)-2-methyl-1-(phenylmethyl-d2)pyrrolidin-3-yl)-4-((methyl-d3)amino)benzamide2950168-16-6[19]
cis-urocanic acid (cis-UCA)(Z)-3-(1H-imidazol-5-yl)prop-2-enoic acid4.615491037699-35-6[20][21][22]
CPD-1(3S)-3-Methyl-1-[4-(trifluoromethyl)-1-benzofuran-7-yl]piperazine9925822325145-37-7[23]
Efavirenz(4S)-6-Chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one64139154598-52-4[24]
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]quinoxaline1694880142957888-63-8[25]
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]quinoxaline21302499313368-85-3[25]
ITI-1549?10.2??[26]
NDTDIN,N-diethyl-3-[methyl(1,3,4,5-tetrahydrobenzo[cd]indol-4-yl)amino]propanamide163192742[27]
Mefloquine2,8-bis(trifluoromethyl)quinolin-4-yl-(2-piperidyl)methanol4069253230-10-7[28]
ORG-129621-(5-trifluoromethyl-6-chloropyridin-2-yl)piperazine9796408210821-63-9[29]
ORG-37684(3S)-3-[(2,3-dihydro-5-methoxy-1H-inden-4-yl)oxy]pyrrolidine9794656213007-95-5[30]
OSU-6162(3S)-3-[3-(methylsulfonyl)phenyl]-1-propylpiperidine9795741156907-84-5[31]
PHA-573782,7,8,9,10,11-hexahydro-1H-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole4.110198481303798-94-9[3]
P-542-(5-methoxypyrazolo[1,5-a]pyridin-3-yl)-N,N-dimethylethanamine1689467402943954-59-2[32]
I-28N-[2-(8-methoxynaphthalen-1-yl)ethyl]-N-methylpropan-2-amine1706044813019268-34-6[33]
(R)-693-[(5R)-5-methyl-1,2,5,6-tetrahydropyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine1645134262765652-48-8[34]
(R)-703-[(3R)-1,3-dimethyl-3,6-dihydro-2H-pyridin-5-yl]-1H-pyrrolo[2,3-b]pyridine170328782[34]
RS134-494-methyl-3-(1,2,3,6-tetrahydropyridin-5-yl)-1H-indole1689417682945139-94-4[35][36]
RH-343-[2-(2-methoxybenzylamino)ethyl]-1H-quinazoline-2,4-dione100419871028307-48-3[37]
SCHEMBL53343617-[(3-methoxyphenoxy)methyl]-2,3,4,5-tetrahydro-1H-3-benzazepine(0.4)59027940959867-47-1[38]
Tabernanthalog8-methoxy-3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole1460269942483829-59-8[39]
TKU-II-100[(1S,2S)-2-(2-fluorophenyl)cyclopropyl]methanamine0.62445727471821802-54-3[40]
WAY-4701,16-diazatetracyclo[8.8.1.02,9.014,19]-nonadeca-2(9),10,12,14(19)-tetraene3610037962422318-22-7[41]
WXVL_BT0793LQ21186-fluoro-4-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)-1H-indole171676435[42]
Z2825713589(4-amino-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl)-(6-methoxypyrazin-2-yl)methanone167788805[42]
Z2876442907ethyl 2-[[2-(4-methyl-1H-indol-3-yl)ethylamino]methyl]-1,3-thiazole-5-carboxylate167850865[42]
Z35179677574-[1-(1-pyrimidin-2-ylethyl)piperidin-3-yl]phenol1679499722817502-85-3[42]
Z38813125042-bromo-4-[2-[methyl-[2-(1,3-thiazol-2-yl)ethyl]amino]ethyl]phenol167904469[42]
Z41540321662,2,2-trifluoro-1-[6-(1,2,3,6-tetrahydropyridin-5-yl)pyridin-2-yl]ethanol167878716[42]
Z52476925664-[(3,3-dimethyloxolan-2-yl)methyl]-3-[(1H-indol-3-yl)methyl]morpholine[42]
Z52476926291-(1-bicyclo[1.1.1]pentanyl)-4-[[5-(4-chlorophenyl)-1H-pyrazol-4-yl]methyl]piperazine1663582732728554-00-3[42]
RU-28306N,N-dimethyl-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine314(5-HT2)19452873625-11-3[43]
Barettin2-[3-[(2S,5Z)-5-[(6-bromo-1H-indol-3-yl)methylidene]-3,6-dioxopiperazin-2-yl]propyl]guanidine11177588104311-70-8[44]

Others

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Analogues ofaripiprazole with serotonin 5-HT2A receptor agonism andpsychedelic-like effects have been reported.[45]

See also

[edit]

References

[edit]
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Tryptamines
No ring subs.
4-Hydroxytryptamines
5-Hydroxytryptamines
5-Methoxytryptamines
Other ring subs.
α-Alkyltryptamines
Others
Cyclized
Bioisosteres
Phenethylamines
Scalines
2C-x
3C-x
DOx
4C-x
Ψ-PEA
MDxx
FLY
25x-NB (NBOMes)
Others
Cyclized
Lysergamides
  • Bioisosteres:JRT
Others
Natural sources
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
Stimulants
Depressants
Hallucinogens
Entactogens
Psychiatric drugs
Others
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