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PiHKAL#168 TMPEA; SI#124 TMPEA-2
Names:
TMPEA · TMPEA-2 · 2C-O · 2,4,5-Trimethoxyphenethylamine
IUPAC name:
2-(2,4,5-Trimethoxyphenyl)ethan-1-amine
ID: 168 · Formula: C11H17NO3 · Molecular weight: 211.258
InChI: InChI=1S/C11H17NO3/c1-13-9-7-11(15-3)10(14-2)6-8(9)4-5-12/h6-7H,4-5,12H2,1-3H3

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Silva, ME. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 26 Aug 2008. 5904 kB.

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. http://dx.doi.org/10.1038/221537a0

Clark, LC; Benington, F; Morin, RD. The effects of ring-methoxyl groups on biological deamination of phenethylamines. J. Med. Chem., 1 May 1965, 8 (3), 353–355. 389 kB. http://dx.doi.org/10.1021/jm00327a016

Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15),. 366 kB. http://dx.doi.org/10.1016/j.bmc.2008.06.009

Altun, A; Golcuk, K; Kumru, M; Jalbout, AF. Electron-conformation study for the structure-hallucinogenic activity relationships of phenylalkylamines. Bioorg. Med. Chem., 1 Dec 2003, 11 (24), 3861–3868. 577 kB. http://dx.doi.org/10.1016/S0968-0896(03)00437-1

Short, JH; Dunnigan, DA; Ours, CW. Synthesis of phenethylamines from phenylacetonitriles obtained by alkylation of cyanide ion with Mannich bases from phenols and other benzylamines. Tetrahedron, 1973, 29 (14), 1931–1939. 791 kB. http://dx.doi.org/10.1016/0040-4020(73)80127-9

Silva, ME; Heim, R; Strasser, A; Elz, S; Dove, S. Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor. J. Comput. Aided Mol. Des., 1 Jan 2011, 25 (1), 51–66. 834 kB. http://dx.doi.org/10.1007/s10822-010-9400-2

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; Vol. 11, pp 243–333. 2584 kB. http://dx.doi.org/10.1007/978-1-4757-0510-2_6 Rhodium.

Jansen, MPJM. β-2,4,5-Trimethoxyphenylethylamine, an isomer of mescaline. Recl. Trav. Chim. Pays-Bas, 1931, 50 (4), 291–312. 1227 kB. http://dx.doi.org/10.1002/recl.19310500403

Bailey, K; Legault, D. 13C NMR spectra and structure of mono-, di- and trimethoxyphenylethylamines and amphetamines. Org. Magn. Resonance, 1 Jun 1983, 21 (6), 391–396. 680 kB. http://dx.doi.org/10.1002/omr.1270210611

Glennon, RA; Kier, LB; Shulgin, AT. Molecular connectivity analysis of hallucinogenic mescaline analogs. J. Pharm. Sci., 1 Jan 1979, 68 (7), 906–907. 252 kB. http://dx.doi.org/10.1002/jps.2600680733

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245-NBOMe
245-NBOMe; N-(2-Methoxybenzyl)-2-(2,4,5-trimethoxyphenyl)ethan-1-amine
M-NBF
M-NBF; N-(2-Fluorobenzyl)-2-(3,4,5-trimethoxyphenyl)ethan-1-amine
TMA-2
PiHKAL#158 TMA-2; SI#118 TMA-2
4C-MeO
4C-MeO; 1-(2,4,5-Trimethoxyphenyl)butan-2-amine
α-Carboxy-TMA-2
α-Carboxy-TMA-2; 2-Amino-3-(2,4,5-trimethoxyphenyl)propanoic acid
10797
3-Methyl-3-phenylbutan-2-amine
10741
3-Methyl-3-phenylbutan-2-amine
10606
1-(4-Bromophenyl)-1,1-difluoropropan-2-amine
10605
1,1-Difluoro-1-(4-fluorophenyl)propan-2-amine
10477
N-[2-(2-Chlorophenyl)ethyl]acetamide
10183
3-(2H-1,3-Benzodioxol-5-yl)-3-methylbutan-2-amine
BOT
BOT; 2-Methoxy-2-(2,4,5-trimethoxyphenyl)ethan-1-amine
10060
4-(2-Amino-2-methylpropyl)-N,N,3-trimethylaniline
α-Ethylamphetamine
α-Ethylamphetamine
10579
1-(4-Iodophenyl)-2-methylpropan-2-amine
10568
3-[(4-Fluorophenyl)methyl]-N-methylpentan-3-amine
10567
3-[(4-Fluorophenyl)methyl]pentan-3-amine
10566
1-(4-Fluorophenyl)-N,2-dimethylpropan-2-amine
10565
1-(4-Fluorophenyl)-2-methylpropan-2-amine
α-Methyltyrosine
α-Methyltyrosine
10515
N-Ethyl-2-methyl-1-[3-(trifluoromethyl)phenyl]propan-2-amine
10502
3-[(3-Fluorophenyl)methyl]-N-methylpentan-3-amine
10501
3-[(3-Fluorophenyl)methyl]pentan-3-amine
10500
1-(3-Fluorophenyl)-N,2-dimethylpropan-2-amine
10499
1-(3-Fluorophenyl)-2-methylpropan-2-amine
739
Ethyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoate
10055
4-(2-Amino-2-methylpropyl)-3-chloro-N,N-dimethylaniline
2,4,5-BMM · 6-Br-DMPEA
2,4,5-BMM; 2-Bromo-4,5-dimethoxyphenethylamine
2-Cl-4,5-DMPEA
2-Cl-4,5-DMPEA; 2-(2-Chloro-4,5-dimethoxyphenyl)ethan-1-amine
4,5,2-2C-T-7
4,5,2-2C-T-7; 2-[4,5-Dimethoxy-2-(propylsulfanyl)phenyl]ethan-1-amine
TeMPEA
TeMPEA; 2-(2,3,4,5-Tetramethoxyphenyl)ethan-1-amine
2C-B
PiHKAL#20 2C-B; SI#18 2C-B
2C-C
PiHKAL#22 2C-C; SI#19 2C-C
2C-D
PiHKAL#23 2C-D; SI#20 2C-D
2C-E
PiHKAL#24 2C-E; SI#21 2C-E
2C-F
PiHKAL#26 2C-F
2C-H
PiHKAL#32 2C-H; SI#22 2C-H
2C-I
PiHKAL#33 2C-I; SI#23 2C-I
2C-N
PiHKAL#34 2C-N
2C-O-4
PiHKAL#35 2C-O-4
2C-P
PiHKAL#36 2C-P
2C-SE
PiHKAL#38 2C-SE
2C-T
PiHKAL#39 2C-T; SI#25 2C-T
2C-T-2
PiHKAL#40 2C-T-2; SI#26 2C-T-2
2C-T-4
PiHKAL#41 2C-T-4
2C-T-7
PiHKAL#43 2C-T-7; SI#27 2C-T-7
2C-T-8
PiHKAL#44 2C-T-8
2C-T-9
PiHKAL#45 2C-T-9
2C-T-13
PiHKAL#46 2C-T-13
2C-T-15
PiHKAL#47 2C-T-15
2C-T-17
PiHKAL#48 2C-T-17
2C-T-21
PiHKAL#49 2C-T-21
2C-CN
2C-CN; 2,5-Dimethoxy-4-cyanophenethylamine
2C-CA · 2C-COOH
2C-CA; 2,5-Dimethoxy-4-carboxyphenethylamine
2C-TFM
2C-TFM; 4-Trifuouromethyl-2,5-dimethoxyphenethylamine
2C-O-2
2C-O-2; 2,5-Dimethoxy-4-ethoxyphenethylamine
2C-O-7
2C-O-7; 2,5-Dimethoxy-4-n-propoxyphenethylamine
2C-O-19
2C-O-19; 2,5-Dimethoxy-4-n-butoxyphenethylamine
2C-SE-2
2C-SE-2; 2,5-Dimethoxy-4-ethylselenophenethylamine
2C-SE-4
2C-SE-4; 2,5-Dimethoxy-4-isopropylselenophenethylamine
2C-SE-7
2C-SE-7; 2,5-Dimethoxy-4-n-propylselenophenethylamine
2C-SE-21
2C-SE-21; 2,5-Dimethoxy-4-(2-fluoroethylseleno)phenethylamine
2C-TE
2C-TE; 2,5-Dimethoxy-4-methyltellurophenethylamine
2C-T-10
2C-T-10; 2,5-Dimethoxy-4-(2-pyridylthio)phenethylamine
2C-T-11
2C-T-11; 4-(4-Bromophenylthio)-2,5-dimethoxyphenethylamine
2C-T-12
2C-T-12; 2,5-Dimethoxy-4-(1-morpholinothio)phenethylamine
2C-T-14
2C-T-14; 2,5-Dimethoxy-4-(2-methylthioethylthio)phenethylamine
2C-T-5
2C-T-5; 4-Cyclohexylthio-2,5-dimethoxyphenethylamine
2C-T-16
2C-T-16; 4-Allylthio-2,5-dimethoxyphenethylamine
2C-T-6
2C-T-6; 2,5-Dimethoxy-4-phenylthiophenethylamine
2C-T-19
2C-T-19; 4-n-Butylthio-2,5-dimethoxyphenethylamine
2C-T-21.5
2C-T-21.5; 4-(2,2-Difluouroethylthio)-2,5-dimethoxyphenethylamine
2C-T-22
2C-T-22; 2,5-Dimethoxy-4-(2,2,2-trifluouroethylthio)phenethylamine
2C-T-18
2C-T-18; 4-Cyclobutylthio-2,5-dimethoxyphenethylamine
2C-T-23
2C-T-23; 4-Cyclopentylthio-2,5-dimethoxyamphetamine
2C-YN
2C-YN; 4-Ethynyl-2,5-dimethoxyphenethylamine
2C-pEtOH
2C-pEtOH; 4-(2-Hydroxyethyl)-2,5-dimethoxyphenethylamine
2C-pKet
2C-pKet; 4-Acetoxy-2,5-dimethoxyphenethylamine
2C-T-3
2C-T-3; 4-Methallylthio-2,5-dimethoxyphenethylamine
2C-T-25
2C-T-25; 4-Isobutylthio-2,5-dimethoxyphenethylamine
2C-T-27
2C-T-27; 4-Benzylthio-2,5-dimethoxyphenethylamine
2C-T-28
2C-T-28; 4-(3-Fluoropropylthio)-2,5-dimethoxyphenethylamine
2C-T-30
2C-T-30; 4-(4-Fluorobutylthio)-2,5-dimethoxyphenethylamine
2C-T-31
2C-T-31; 2,5-Dimethoxy-4-[4-(trifluoromethyl)benzylthio]phenethylamine
2C-T-32
2C-T-32; 2,5-Dimethoxy-4-(2,3,4,5,6-pentafluorobenzylthio)phenethylamine
2C-T-33
2C-T-33; 2,5-Dimethoxy-4-(3-methoxybenzylthio)phenethylamine
2C-VI
2C-VI; 4-Ethenyl-2,5-dimethoxyphenethylamine
2C-BI-1
2C-BI-1; 2,5-Dimethoxy-4-phenylphenethylamine
2C-BI-2
2C-BI-2; 2,5-Dimethoxy-4-(2-methoxyphenyl)phenethylamine
2C-BI-3
2C-BI-3; 2,5-Dimethoxy-4-(2-methylphenyl)phenethylamine
2C-BI-4
2C-BI-4; 2,5-Dimethoxy-4-[2-(trifluoromethyl)phenyl]phenethylamine
2C-BI-5
2C-BI-5; 2,5-Dimethoxy-4-(naphthalen-2-yl)phenethylamine
2C-BI-6
2C-BI-6; 2,5-Dimethoxy-4-(3-methoxyphenyl)phenethylamine
2C-BI-7
2C-BI-7; 2,5-Dimethoxy-4-(3-nitrophenyl)phenethylamine
2C-BI-8
2C-BI-8; 2,5-Dimethoxy-4-(4-methoxyphenyl)phenethylamine
2C-BI-9
2C-BI-9; 4-(4-Butylphenyl)-2,5-dimethoxyphenethylamine
2C-BI-10
2C-BI-10; 2,5-Dimethoxy-4-[4-(trifluoromethyl)phenyl]phenethylamine
2C-BI-11
2C-BI-11; 2,5-Dimethoxy-4-(4-phenylphenyl)phenethylamine
2C-BI-12
2C-BI-12; 2,5-Dimethoxy-4-(3,4-methylenedioxyphenyl)phenethylamine
2326
2,5-Dimethoxy-4-phenylpropylphenethylamine
2324
2,5-Dimethoxy-4-phenethylphenethylamine
2327
2,5-Dimethoxy-4-phenylbutylphenethylamine
2C-IP
2C-IP; Jelena
2C-EF
2C-EF; 4-(2-Fluoroethyl)-2,5-dimethoxyphenethylamine
2C-NH
2C-NH; 4-(2-Aminoethyl)-2,5-dimethoxyaniline
2C-HM
2C-HM; 4-(2-Aminoethyl)-2,5-dimethoxybenzaldehyde
2C-IB
2C-IB; 2-[2,5-Dimethoxy-4-(2-methylpropyl)phenyl]ethan-1-amine
2C-TFE
2C-TFE; 2-[2,5-Dimethoxy-4-(2,2,2-trifluoroethyl)phenyl]ethan-1-amine
2C-O-22
2C-O-22; 2-[2,5-Dimethoxy-4-(2,2,2-trifluoroethoxy)phenyl]ethan-1-amine
2C-O-21.5
2C-O-21.5; 2-[4-(2,2-Difluoroethoxy)-2,5-dimethoxyphenyl]ethan-1-amine
2C-O-21
2C-O-21; 2-[4-(2-Fluoroethoxy)-2,5-dimethoxyphenyl]ethan-1-amine
2C-A
2C-A; 2,5-Dimethoxy-4-astatophenethylamine
24
24; 2,4-Dimethoxyphenethylamine
2,4,5-MMB
2,4,5-MMB; 2-(5-Bromo-2,4-dimethoxyphenyl)ethan-1-amine
5-NH2-2,4-DMPEA
5-NH2-2,4-DMPEA; 5-(2-Aminoethyl)-2,4-dimethoxyaniline
2,4,5-2C-T-7
2,4,5-2C-T-7; 1-[2,4-Dimethoxy-5-(propylsulfanyl)phenyl]propan-2-amine
2C-2 · 2C-MMDA-2
2C-2; 2-Methoxy-4,5-methylenedioxyphenethylamine
γ-Asarone
γ-Asarone
β-Asarone
β-Asarone
α-Asarone
α-Asarone
TMCPA
TMCPA; 2-(2,4,5-Trimethoxyphenyl)cyclopropanamine
TMCBA
TMCBA; 2-(2,4,5-Trimethoxyphenyl)cyclobutanamine
Propargylpemoline
Propargylpemoline
10846
2-(Dimethylamino)-5-methyl-5-phenyl-1,3-oxazol-4(5H)-one
BOHD
PiHKAL#16 BOHD
4-D
PiHKAL#50 4-D
β-D
PiHKAL#51 β-D
IM
PiHKAL#91 IM; SI#72 IM
Mescaline · M
PiHKAL#96 M; SI#91 Mescaline
TMPEA-5 · 2C-TMA-5
TMPEA-5; 2,3,6-Trimethoxyphenethylamine
TMPEA-6 · 2C-TMA-6
TMPEA-6; 2,4,6-Trimethoxyphenethylamine
3,5-D
3,5-D; 4-Methoxy-3,5-di(trideuteromethoxy)phenethylamine
2,6-D
2,6-D; 2,6-Dideutero-3,4,5-trimethoxyphenethylamine
α-D
α-D; α,α-Dideutero-3,4,5-trimethoxyphenethylamine
N-Me-3-DESMETHYL
N-Me-3-DESMETHYL; N-Methyl-3-demethylmescaline
2C-pEtOH
2C-pEtOH; 4-(2-Hydroxyethyl)-2,5-dimethoxyphenethylamine
DOOH
DOOH; 4-Hydroxy-2,5-dimethoxyamphetamine
β-HO-2,5-DMA
β-HO-2,5-DMA; 2,5-Dimethoxynorephedrine
β,3,4-HO-N-iPr-DHPEA
β,3,4-HO-N-iPr-DHPEA; 4-[1-Hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,2-diol
MHMAOH
MHMAOH; 4-{2-[Hydroxy(methyl)amino]propyl}-2-methoxyphenol
N,N-Me-HME
N,N-Me-HME; 5-[2-(Dimethylamino)-1-hydroxyethyl]-2-methoxyphenol
N-Me-DME
N-Me-DME; 1-(3,4-Dimethoxyphenyl)-2-(methylamino)ethan-1-ol
β,3,4-TMPEA
β,3,4-TMPEA; 2-(3,4-Dimethoxyphenyl)-2-methoxyethan-1-amine
DMAOH
DMAOH; 1-(3,4-Dimethoxyphenyl)-N-hydroxypropan-2-amine
β-HO-DMA
β-HO-DMA; 2-Amino-1-(3,4-dimethoxyphenyl)propan-1-ol
β-HO-4,3-EMPEA
β-HO-4,3-EMPEA; 2-Amino-1-(4-ethoxy-3-methoxyphenyl)ethanol
β,2-HO-N-Me-5-MA
β,2-HO-N-Me-5-MA; 2-[1-Hydroxy-2-(methylamino)propyl]-4-methoxyphenol
β-HO-N-Me-2,5-DMPEA
β-HO-N-Me-2,5-DMPEA; 1-(2,5-Dimethoxyphenyl)-2-(methylamino)ethanol
BODM
BODM; 2-(2,5-Dimethoxyphenyl)-2-methoxyethan-1-amine
β-HO,Me-2,5-DMPEA
β-HO,Me-2,5-DMPEA; 1-Amino-2-(2,5-dimethoxyphenyl)propan-2-ol
β,2-HO-N-Me-5-EPEA
β,2-HO-N-Me-5-EPEA; 4-Ethoxy-2-[1-hydroxy-2-(methylamino)ethyl]phenol
β,2-HO-5-EA
β,2-HO-5-EA; 2-(2-Amino-1-hydroxypropyl)-4-ethoxyphenol
β-HO-N-Me-3,5-DMPEA
β-HO-N-Me-3,5-DMPEA; 1-(3,5-Dimethoxyphenyl)-2-(methylamino)ethanol
β-HO-N-Me-2,6-DMPEA
β-HO-N-Me-2,6-DMPEA; 1-(2,6-Dimethoxyphenyl)-2-(methylamino)ethanol
TMPEA-4
TMPEA-4; 2-(2,3,5-Trimethoxyphenyl)ethan-1-amine
N-HO-2C-D
N-HO-2C-D; 2-(2,5-Dimethoxy-4-methylphenyl)-N-hydroxyethan-1-amine
α-Me-3-DESMETHYL
α-Me-3-DESMETHYL; 5-(2-Aminopropyl)-2,3-dimethoxyphenol
DESMETHYL-M
DESMETHYL-M; 2,6-Dimethoxy-4-[2-(methylamino)ethyl]phenol
α-Me-DESMETHYL
α-Me-DESMETHYL; 4-(2-Aminopropyl)-2,6-dimethoxyphenol
10030
3-{1-Hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,2-diol
Orciprenaline
Orciprenaline
N-Methyl-3,4,5-trimethoxybenzylamine
N-Methyl-3,4,5-trimethoxybenzylamine
Dichloroisoprenaline
Dichloroisoprenaline
Orciprenaline
Orciprenaline
10066
2-Amino-1-(2,4-dimethoxyphenyl)propan-1-ol
245-NBOMe
245-NBOMe; N-(2-Methoxybenzyl)-2-(2,4,5-trimethoxyphenyl)ethan-1-amine
M-NBF
M-NBF; N-(2-Fluorobenzyl)-2-(3,4,5-trimethoxyphenyl)ethan-1-amine
TMA-2
PiHKAL#158 TMA-2; SI#118 TMA-2
4C-MeO
4C-MeO; 1-(2,4,5-Trimethoxyphenyl)butan-2-amine
α-Carboxy-TMA-2
α-Carboxy-TMA-2; 2-Amino-3-(2,4,5-trimethoxyphenyl)propanoic acid
10797
3-Methyl-3-phenylbutan-2-amine
10741
3-Methyl-3-phenylbutan-2-amine
10606
1-(4-Bromophenyl)-1,1-difluoropropan-2-amine
10605
1,1-Difluoro-1-(4-fluorophenyl)propan-2-amine
10477
N-[2-(2-Chlorophenyl)ethyl]acetamide
10183
3-(2H-1,3-Benzodioxol-5-yl)-3-methylbutan-2-amine
BOT
BOT; 2-Methoxy-2-(2,4,5-trimethoxyphenyl)ethan-1-amine
10060
4-(2-Amino-2-methylpropyl)-N,N,3-trimethylaniline
α-Ethylamphetamine
α-Ethylamphetamine
10579
1-(4-Iodophenyl)-2-methylpropan-2-amine
10568
3-[(4-Fluorophenyl)methyl]-N-methylpentan-3-amine
10567
3-[(4-Fluorophenyl)methyl]pentan-3-amine
10566
1-(4-Fluorophenyl)-N,2-dimethylpropan-2-amine
10565
1-(4-Fluorophenyl)-2-methylpropan-2-amine
α-Methyltyrosine
α-Methyltyrosine
10515
N-Ethyl-2-methyl-1-[3-(trifluoromethyl)phenyl]propan-2-amine
10502
3-[(3-Fluorophenyl)methyl]-N-methylpentan-3-amine
10501
3-[(3-Fluorophenyl)methyl]pentan-3-amine
10500
1-(3-Fluorophenyl)-N,2-dimethylpropan-2-amine
10499
1-(3-Fluorophenyl)-2-methylpropan-2-amine
739
Ethyl (2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoate
10055
4-(2-Amino-2-methylpropyl)-3-chloro-N,N-dimethylaniline
2,4,5-BMM · 6-Br-DMPEA
2,4,5-BMM; 2-Bromo-4,5-dimethoxyphenethylamine
2-Cl-4,5-DMPEA
2-Cl-4,5-DMPEA; 2-(2-Chloro-4,5-dimethoxyphenyl)ethan-1-amine
4,5,2-2C-T-7
4,5,2-2C-T-7; 2-[4,5-Dimethoxy-2-(propylsulfanyl)phenyl]ethan-1-amine
TeMPEA
TeMPEA; 2-(2,3,4,5-Tetramethoxyphenyl)ethan-1-amine
2C-B
PiHKAL#20 2C-B; SI#18 2C-B
2C-C
PiHKAL#22 2C-C; SI#19 2C-C
2C-D
PiHKAL#23 2C-D; SI#20 2C-D
2C-E
PiHKAL#24 2C-E; SI#21 2C-E
2C-F
PiHKAL#26 2C-F
2C-H
PiHKAL#32 2C-H; SI#22 2C-H
2C-I