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Code Chemical name h5-HT2A Ki / EC50 (nM) Dose (mg) PubChem CAS number Reference
AEM 1-(3,4,5-trimethoxyphenyl)butan-2-amine 204932 17097-73-3 [1]
BOH 1-(3,4-methylenedioxyphenyl)-1-methoxy-2-aminoethane 44719487 73304-06-0 PIHKAL
BOM 2-methoxy-2-(3,4,5-trimethoxyphenyl)ethanamine 98537-40-7 PIHKAL
BOD 2-(2,5-dimethoxy-4-methylphenyl)-2-methoxyethanamine 98537-41-8 PIHKAL
BOB 2-(4-bromo-2,5-dimethoxyphenyl)-2-methoxyethanamine 98537-42-9 PIHKAL
Mescaline 2-(3,4,5-trimethoxyphenyl)ethanamine 551 (vs 125I DOI) 180-360 4076 54-04-6 PIHKAL
Escaline 2-(4-ethoxy-3,5-dimethoxyphenyl)ethanamine 215 40-60 38240 39201-82-6 PIHKAL
Proscaline 2-(3,5-dimethoxy-4-propoxyphenyl)ethanamine 30-60 39201-78-0 PIHKAL
Alscaline 2-(4-allyloxy-3,5-dimethoxyphenyl)ethanamine 20-35 39201-75-7 PIHKAL
Isoproscaline 2-(4-isopropoxy-3,5-dimethoxyphenyl)ethanamine 465 40-80 64778-72-9 PIHKAL
Buscaline 2-(3,5-dimethoxy-4-butoxyphenyl)ethanamine 150+ 64778-75-2 PIHKAL
Methallylescaline 2-(3,5-dimethoxy-4-[(2-methylprop-2-en-1-yl)oxy]phenyl)ethanamine 40-65 207740-41-8 PIHKAL
Metaescaline 2-(3-ethoxy-4,5-dimethoxyphenyl)ethanamine 90132-31-3 PIHKAL
Lophophine 2-(3-methoxy-4,5-methylenedioxyphenyl)ethanamine 90239 23693-38-1 PIHKAL
Macromerine 1-(3,4-dimethoxyphenyl)-2-(dimethylamino)ethanol 165055 2970-95-8
Difluoromescaline 2-[4-(difluoromethoxy)-3,5-dimethoxyphenyl]ethanamine 50-100 1178367-63-9 [2]
Difluoroescaline 1-[4-(2,2-difluoroethoxy)-3,5-dimethoxyphenyl]-2-aminoethane 40-80 501700-02-3 Phenethylamine Von der Struktur zur Funktion
Trifluoroescaline 1-[4-(2,2,2-trifluoroethoxy)-3,5-dimethoxyphenyl]-2-aminoethane 35-65 501700-03-4 Phenethylamine Von der Struktur zur Funktion
Fluoroproscaline 1-[4-(3-fluoropropoxy)-3,5-dimethoxyphenyl]-2-aminoethane 60-150 501700-04-5 Phenethylamine Von der Struktur zur Funktion
Jimscaline (R)-(2,3-dihydro-4,5,6-trimethoxy-1H-inden-1-yl)aminomethane 69 (rat) / 3200 11673493 890309-57-6 [3]
Juncosamine (2S,6S)-2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine 1391499-52-7 [4]
3TM 2-(3-methylthio-4,5-dimethoxyphenyl)ethanamine 60-100 PIHKAL
4TM 2-(3,5-dimethoxy-4-methylthiophenyl)ethanamine 20-40 71539-35-0 PIHKAL
3TE 2-(3-methylthio-4-ethoxy-5-methoxyphenyl)ethanamine 60-80 PIHKAL
4TE 2-(3,5-dimethoxy-4-ethylthiophenyl)ethanamine 20-30 90109-49-2 PIHKAL
4TP 2-(3,5-dimethoxy-4-propylthiophenyl)ethanamine 20-25 90109-55-0 PIHKAL
4TB 2-(4-butylthio-3,5-dimethoxyphenyl)ethanamine 60-120 90109-57-2 PIHKAL
2,5-DMA 2,5-dimethoxyamphetamine 2801-68-5
3,4-DMA 3,4-dimethoxyamphetamine 120-26-3
2,4-DMA 2,4-dimethoxyamphetamine 23690-13-3
3,5-DMA 3,5-dimethoxyamphetamine 15402-82-1
2,6-DMA 2,6-dimethoxyamphetamine 23690-14-4
4-EtO-2,5-DMA 4-ethoxy-2,5-dimethoxyamphetamine 16128-88-4
2-EtO-4,5-DMA 2-ethoxy-4,5-dimethoxyamphetamine 23693-30-3
5-EtO-2,4-DMA 5-ethoxy-2,4-dimethoxyamphetamine 23693-32-5
2,4-diEtO-5-MeO-amphetamine 2,4-diethoxy-5-methoxyamphetamine 23693-33-6
2,5-diEtO-4-MeO-amphetamine 2,5-diethoxy-4-methoxyamphetamine 23693-34-7
2-MeO-4,5-diEtO-amphetamine 2-methoxy-4,5-diethoxyamphetamine 23693-35-8
2,4,5-triEtO-amphetamine 2,4,5-triethoxyamphetamine 23693-42-7
2,3,4-TMA 2,3,4-trimethoxyamphetamine 1082-23-1
2,4,5-TMA 2,4,5-trimethoxyamphetamine 1083-09-6
3,4,5-TMA 3,4,5-trimethoxyamphetamine 1082-88-8
2,4,6-TMA 2,4,6-trimethoxyamphetamine 15402-79-6
2,3,5-TMA 2,3,5-trimethoxyamphetamine 23693-14-3
2,3,6-TMA 2,3,6-trimethoxyamphetamine 20513-16-0
1-(5,8-dimethoxy-3,4-dihydro-1H-isochromen-7-yl)isopropanamine 774538-38-4
AOMA 3-methoxy-4-allyloxyamphetamine 1178502-18-5
BOMA 3-methoxy-4-benzyloxyamphetamine 114963-05-2
POMA 3-methoxy-4-propoxyamphetamine 910407-76-0
DOM 2,5-dimethoxy-4-methylamphetamine 15588-95-1
Ψ-DOM 2,6-dimethoxy-4-methylamphetamine 80888-36-4
DOET 2,5-dimethoxy-4-ethylamphetamine 22004-32-6
DOEF 2,5-dimethoxy-4-(2-fluoroethyl)amphetamine 121649-01-2
DOPR 2,5-dimethoxy-4-propylamphetamine 63779-88-4
DOBU 2,5-dimethoxy-4-butylamphetamine 63779-89-5
DOF 2,5-dimethoxy-4-fluoroamphetamine 125903-69-7
DOC 2,5-dimethoxy-4-chloroamphetamine 123431-31-2
DOB 2,5-dimethoxy-4-bromoamphetamine 32156-26-6 or 64638-07-9
N-Me-DOB N-methyl-2,5-dimethoxy-4-bromoamphetamine 155638-80-5
4C-DOB 1-(2,5-dimethoxy-4-bromophenyl)butan-2-amine 69294-23-1
4C-DOM 1-(2,5-dimethoxy-4-methylphenyl)butan-2-amine 52663-86-2 or 52842-59-8 or 52842-58-7
4C-DOC 1-(2,5-dimethoxy-4-chlorophenyl)butan-2-amine 791010-74-7
4C-DOI 1-(2,5-dimethoxy-4-iodophenyl)butan-2-amine 758631-75-3
4C-DON 1-(2,5-dimethoxy-4-nitrophenyl)butan-2-amine 775234-58-7
4-Br-3,5-DMA 3,5-dimethoxy-4-bromoamphetamine 32156-34-6 or 64778-79-6 (R)
4-PP-3,5-DMA 3,5-dimethoxy-4-(3-phenylpropyl)amphetamine 785765-10-8 [5]
DOI 2,5-dimethoxy-4-iodoamphetamine 64584-34-5 or 82830-44-2 or 82830-53-3
DON 2,5-dimethoxy-4-nitroamphetamine 67460-68-8
DOTFM 2,5-dimethoxy-4-(trifluoromethyl)amphetamine 159277-07-3
DOYN 2,5-dimethoxy-4-ethynylamphetamine 633290-70-7
DODC 2,5-dimethoxy-3,4-dichloroamphetamine 1373918-65-0
DOBn 2,5-dimethoxy-4-benzylamphetamine 125903-73-3
DOTh 2,5-dimethoxy-4-[(thiophen-2-yl)methyl]amphetamine 930776-29-7
DO(3-MeOBn) 2,5-dimethoxy-4-(3-methoxybenzyl)amphetamine 930836-90-1
DOMOM 2,5-dimethoxy-4-(methoxymethyl)amphetamine 260810-10-4
DOMOE 2,5-dimethoxy-4-(ethoxymethyl)amphetamine 930836-81-0
DOTHFM 2,5-dimethoxy-4-[(tetrahydrofuran-2-yl)methyl]amphetamine 930776-12-8
ALEPH 2,5-dimethoxy-4-(methylthio)amphetamine 61638-07-1
ALEPH-2 2,5-dimethoxy-4-(ethylthio)amphetamine 185562-00-9
ALEPH-4 2,5-dimethoxy-4-(isopropylthio)amphetamine 123643-26-5
ALEPH-7 2,5-dimethoxy-4-(propylthio)amphetamine 207740-16-7
TOM-2 2-methylthio-4-methyl-5-methoxyamphetamine 60-100 207740-44-1
TOM-5 2-methoxy-4-methyl-5-methylthioamphetamine 30-50 207740-45-2
TOET-2 2-methylthio-4-ethyl-5-methoxyamphetamine 84910-91-8
TOET-5 2-methoxy-4-ethyl-5-methylthioamphetamine 12-25 207740-43-0
TOMSO 2-methoxy-4-methyl-5-methylsulfinylamphetamine 100-150 84910-95-2
2C-B 2,5-dimethoxy-4-bromophenethylamine 66142-81-2 PIHKAL
β-Methyl-2CB 2-(2,5-dimethoxy-4-bromophenyl)-1-aminopropane 52432-70-9 Phenethylamine Von der Struktur zur Funktion

References

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  1. ^ Alexander Shulgin, Ann Shulgin. PiHKAL: A Chemical Love Story. Transform Press 1991. ISBN 0963009605
  2. ^ Daniel Trachsel, David Lehmann and Christoph Enzensperger. Phenethylamine Von der Struktur zur Funktion. Nachtschatten Verlag AG, 2013. ISBN 9783037887004
  3. ^ Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007
  4. ^ Juncosa JI, Hansen M, et al. Extensive rigid analogue design maps the binding conformation of potent N-benzylphenethylamine 5-HT2A serotonin receptor agonist ligands. ACS Chemical Neuroscience 2012. 4: 120717095020003. doi:10.1021/cn3000668
  5. ^ Dowd CS, Herrick-Davis K, Egan C, DuPre A, Smith C, Teitler M, Glennon RA. 1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT2A Partial Agonists. J Med Chem. 2000 Aug 10;43(16):3074-84. PMID 10956215

Miscellaneous 5HT2A agonists

[edit]
Structure Name Chemical name h5-HT2A Ki (EC50) (nM) PubChem CAS number Reference
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 [1]
Compound 10d 7-Benzyloxy-8-bromo-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine 22 10472780 616201-60-6 [2]
Example 22.67 4-(6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepin-2-yl)thiomorpholine 21 44124494 [3]
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 [4]
Example 1 (ZC-B) 3-(4-bromo-2,5-dimethoxyphenyl)azetidine (1.6) 156337249 2641630-65-9 [5]
Compound 11 (3R)-N,N-diethyl-5-(1H-indol-4-yl)-1-methyl-3,6-dihydro-2H-pyridine-3-carboxamide (<10) 156278040 [6]
Compound 106 6-chloro-1-(2,4,5-trimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 4376990 528525-37-3 [7]
Compound 6c (6S)-2,3-dichloro-7,8,9,10-tetrahydro-6H-6,9-epiminocyclohepta[b]quinoxaline (400) [8]
Efavirenz (4S)-6-Chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one 64139 154598-52-4 [9]
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 [10]
Mefloquine 2,8-bis(trifluoromethyl)quinolin-4-yl-(2-piperidyl)methanol 40692 53230-10-7 [11]
ORG-37684 (3S)-3-[(2,3-dihydro-5-methoxy-1H-inden-4-yl)oxy]pyrrolidine 9794656 213007-95-5 [12]
P-54 2-(5-methoxypyrazolo[1,5-a]pyridin-3-yl)-N,N-dimethylethanamine 168946740 [13]
(R)-69 3-[(5R)-5-methyl-1,2,5,6-tetrahydropyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine 164513426 [14]
RH-34 3-[2-(2-methoxybenzylamino)ethyl]-1H-quinazoline-2,4-dione 10041987 1028307-48-3 [15]
SCHEMBL5334361 7-[(3-methoxyphenoxy)methyl]-2,3,4,5-tetrahydro-1H-3-benzazepine (0.4) 59027940 959867-47-1 [16]
WXVL_BT0793LQ2118 6-fluoro-4-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)-1H-indole [17]
Z2825713589 (4-amino-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl)-(6-methoxypyrazin-2-yl)methanone 167788805 [17]
Z2876442907 ethyl 2-[[2-(4-methyl-1H-indol-3-yl)ethylamino]methyl]-1,3-thiazole-5-carboxylate 167850865 [17]
Z3517967757 4-[1-(1-pyrimidin-2-ylethyl)piperidin-3-yl]phenol 167949972 [17]
Z3881312504 2-bromo-4-[2-[methyl-[2-(1,3-thiazol-2-yl)ethyl]amino]ethyl]phenol 167904469 [17]
Z4154032166 2,2,2-trifluoro-1-[6-(1,2,3,6-tetrahydropyridin-5-yl)pyridin-2-yl]ethanol 167878716 [17]
Z5247692566 4-[(3,3-dimethyloxolan-2-yl)methyl]-3-[(1H-indol-3-yl)methyl]morpholine [17]
Z5247692629 1-(1-bicyclo[1.1.1]pentanyl)-4-[[5-(4-chlorophenyl)-1H-pyrazol-4-yl]methyl]piperazine 166358273 [17]
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