Exploring E. To explore a different substance…

PiHKAL#72 E; SI#64 Escaline
Names:
E · Escaline · Escaline · 3,5-Dimethoxy-4-ethoxyphenethylamine · 4-Ethoxy-3,5-dimethoxyphenethylamine
IUPAC name:
2-(4-Ethoxy-3,5-dimethoxyphenyl)ethan-1-amine
ID: 72 · Formula: C12H19NO3 · Molecular weight: 225.284
InChI: InChI=1S/C12H19NO3/c1-4-16-12-10(14-2)7-9(5-6-13)8-11(12)15-3/h7-8H,4-6,13H2,1-3H3

Chapman, SJ; Avanes, AA. PeakAL: Protons I Have Known and Loved — Fifty Shades of Grey-Market Spectra. Supplementary Data. BLOTTER, 1 Aug 2015. 11879 kB. http://dx.doi.org/10.16889/isomerdesign-1-supp Open access DOI

Chapman, SJ; Avanes, AA. PeakAL: Protons I Have Known and Loved — Fifty Shades of Grey-Market Spectra. BLOTTER, 1 Aug 2015. 2608 kB. http://dx.doi.org/10.16889/isomerdesign-1 Open access DOI

Thakur, M; Thakur, A; Khadikar, PV. QSAR studies on psychotomimetic phenylalkylamines. Bioorg. Med. Chem., 15 Feb 2004, 12 (4), 825–831. 323 kB. http://dx.doi.org/10.1016/j.bmc.2003.10.027

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.

Kier, LB; Glennon, RA. Psychotomimetic phenalkylamines as serotonin agonists: An SAR analysis. Life Sci., 8 May 1978, 22 (18), 1589–1593. 238 kB. http://dx.doi.org/10.1016/0024-3205(78)90053-X

Benington, F; Morin, RD; Clarke, LC. Synthesis of 4-hydroxy- and 4-ethoxy-3,5-dimethoxy-β-phenethylamines. J. Am. Chem. Soc., 1 Nov 1954, 76 (21), 5555–5556. 307 kB. http://dx.doi.org/10.1021/ja01650a084

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

Jacob, P; Shulgin, AT. Sulfur analogues of psychotomimetic agents. 3. Ethyl homologues of mescaline and their monothioanalogues. J. Med. Chem., 1 Jan 1984, 27 (7), 881–887. 1213 kB. http://dx.doi.org/10.1021/jm00373a013

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Nichols, DE; Shulgin, AT; Dyer, DC. Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives. Life Sci., 1 Jan 1977, 21 (4), 569–576. 320 kB. http://dx.doi.org/10.1016/0024-3205(77)90099-6

Meyers-Riggs, B. Leminger’s scalines. countyourculture: rational exploration of the underground, 4 May 2012.

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Analysis, 13 Dec 2011. 1038 kB. http://dx.doi.org/10.1002/dta.413

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Nichols, DE; Dyer, DC. Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues. J. Med. Chem., 1 Jan 1977, 20 (2), 299–301. 409 kB. http://dx.doi.org/10.1021/jm00212a022

Escaline-NBOMe
Escaline-NBOMe; 2-(4-Ethoxy-3,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethan-1-amine
3C-E
PiHKAL#25 3C-E
ASB
PiHKAL#9 ASB; SI#8 ASB
3-TASB
PiHKAL#146 3-TASB
AL
PiHKAL#2 AL; SI#2 AL
B
PiHKAL#10 B
CPM
PiHKAL#37 CPM
4-D
PiHKAL#50 4-D
DESOXY
PiHKAL#52 DESOXY; SI#31 DESOXY
IP
PiHKAL#92 IP
Mescaline · M
PiHKAL#96 M; SI#91 Mescaline
MAL
PiHKAL#99 MAL
P
PiHKAL#140 P; SI#104 Proscaline
PE
PiHKAL#141 PE
PROPYNYL
PiHKAL#143 PROPYNYL
TB
PiHKAL#149 TB
4-TE
PiHKAL#151 4-TE
4-TM
PiHKAL#156 4-TM
TP
PiHKAL#174 TP
BZ
BZ; 4-Benzyloxy-3,5-dimethoxyphenethylamine
A
A; 4-n-Amyloxy-3,5-dimethoxyphenethylamine
H
H; 4-n-Hexyloxy-3,5-dimethoxyphenethylamine
S
S; 4-n-Heptyloxy-3,5-dimethoxyphenethylamine
FE
FE; Fluoroescaline
DFE
DFE; 4-(2,2-Difluoroethoxy)-3,5-dimethoxyphenethylamine
TFE
TFE; 3,5-Dimethoxy-4-(2,2,2-trifluoroethoxy)phenethylamine
FP
FP; Fluoroproscaline
IB
IB; 4-Isobutoxy-3,5-dimethoxyphenethylamine
341
3,5-Dimethoxy-4-(2-methoxyethoxy)phenethylamine
3,4,5-MBM · 4-Br-3,5-DMPEA
3,4,5-MBM; 4-Bromo-3,5-dimethoxyphenethylamine
DESMETHYL
DESMETHYL; 4-(2-Aminoethyl)-2,6-dimethoxyphenol
3,5-DMPEA
3,5-DMPEA; 2-(3,5-Dimethoxyphenyl)ethan-1-amine
3C-DFM
3C-DFM; 1-[4-(Difluoromethoxy)-3,5-dimethoxyphenyl]propan-2-amine
DFIP
DFIP; Difluoroisoproscaline
TFP
TFP; Trifluoroproscaline
TFM
TFM; Trifluoromescaline
DFM
DFM; Difluoromescaline
MEPEA
PiHKAL#123 MEPEA; SI#90 MEPEA
3-TE
PiHKAL#150 3-TE
BOD
PiHKAL#14 BOD; SI#13 BOD
ME
PiHKAL#119 ME
TMA
PiHKAL#157 TMA; SI#117 TMA
TMA-2
PiHKAL#158 TMA-2; SI#118 TMA-2
TMA-3
PiHKAL#159 TMA-3; SI#119 TMA-3
TMA-4
PiHKAL#160 TMA-4; SI#120 TMA-4
TMA-5
PiHKAL#161 TMA-5; SI#121 TMA-5
TMA-6
PiHKAL#162 TMA-6; SI#122 TMA-6
METHYL-MESCALINE
METHYL-MESCALINE; N-Methyl-3,4,5-trimethoxyphenethylamine
2C-O-2
2C-O-2; 2,5-Dimethoxy-4-ethoxyphenethylamine
N,N-Me-3-DESMETHYL
N,N-Me-3-DESMETHYL; N,N-Dimethyl-3-demethylmescaline
N,N-Me-DME · Macromerine
N,N-Me-DME; Macromerine
4C-HO
4C-HO; 1-(4-Hydroxy-2,5-dimethoxyphenyl)-2-aminobutane
homo-Mescaline
homo-Mescaline; 3-(3,4,5-Trimethoxyphenyl)propan-1-amine
β-HO-N-iPr-GEA
β-HO-N-iPr-GEA; 4-[1-Hydroxy-2-(propan-2-ylamino)ethyl]-2-methoxyphenol
N-Me-β,3,4-TMPEA
N-Me-β,3,4-TMPEA; 2-(3,4-Dimethoxyphenyl)-2-methoxy-N-methylethan-1-amine
DMMAOH
DMMAOH; 1-(3,4-Dimethoxyphenyl)-N-hydroxy-N-methylpropan-2-amine
DEE
DEE; 2-Amino-1-(3,4-diethoxyphenyl)ethanol
β-HO-N,N-Me-2,5-DMPEA
β-HO-N,N-Me-2,5-DMPEA; 1-(2,5-Dimethoxyphenyl)-2-(dimethylamino)ethanol
β-HO-β,N-Me-2,5-DMPEA
β-HO-β,N-Me-2,5-DMPEA; 2-(2,5-Dimethoxyphenyl)-1-(methylamino)propan-2-ol
β-HO-N-Me-2,5-DMA
β-HO-N-Me-2,5-DMA; 1-(2,5-Dimethoxyphenyl)-2-(methylamino)propan-1-ol
β,2-HO-N-Me-5-EA
β,2-HO-N-Me-5-EA; 4-Ethoxy-2-[1-hydroxy-2-(methylamino)propyl]phenol
β-HO-2,5-DEPEA
β-HO-2,5-DEPEA; 2-Amino-1-(2,5-diethoxyphenyl)ethanol
β-HO-N,N-Me-3,5-DMPEA
β-HO-N,N-Me-3,5-DMPEA; 1-(3,5-Dimethoxyphenyl)-2-(dimethylamino)ethanol
N-HO-DOM
N-HO-DOM; 1-(2,5-Dimethoxy-4-methylphenyl)-N-hydroxypropan-2-amine
DESMETHYL-MM
DESMETHYL-MM; 4-[2-(Dimethylamino)ethyl]-2,6-dimethoxyphenol
β-HO-DOM
β-HO-DOM; 2-Amino-1-(2,5-dimethoxy-4-methylphenyl)propan-1-ol
1016
[4-(2-Aminopropyl)-2,5-dimethoxyphenyl]methanol
N-MeO-3,4-DMA
N-MeO-3,4-DMA; N,3,4-Trimethoxyamphetamine
Escaline-NBOMe
Escaline-NBOMe; 2-(4-Ethoxy-3,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethan-1-amine
3C-E
PiHKAL#25 3C-E
ASB
PiHKAL#9 ASB; SI#8 ASB
3-TASB
PiHKAL#146 3-TASB
AL
PiHKAL#2 AL; SI#2 AL
B
PiHKAL#10 B
CPM
PiHKAL#37 CPM
4-D
PiHKAL#50 4-D
DESOXY
PiHKAL#52 DESOXY; SI#31 DESOXY
IP
PiHKAL#92 IP
Mescaline · M
PiHKAL#96 M; SI#91 Mescaline
MAL
PiHKAL#99 MAL
P
PiHKAL#140 P; SI#104 Proscaline
PE
PiHKAL#141 PE
PROPYNYL
PiHKAL#143 PROPYNYL
TB
PiHKAL#149 TB
4-TE
PiHKAL#151 4-TE
4-TM
PiHKAL#156 4-TM
TP
PiHKAL#174 TP
BZ
BZ; 4-Benzyloxy-3,5-dimethoxyphenethylamine
A
A; 4-n-Amyloxy-3,5-dimethoxyphenethylamine
H
H; 4-n-Hexyloxy-3,5-dimethoxyphenethylamine
S
S; 4-n-Heptyloxy-3,5-dimethoxyphenethylamine
FE
FE; Fluoroescaline
DFE
DFE; 4-(2,2-Difluoroethoxy)-3,5-dimethoxyphenethylamine
TFE
TFE; 3,5-Dimethoxy-4-(2,2,2-trifluoroethoxy)phenethylamine
FP
FP; Fluoroproscaline
IB
IB; 4-Isobutoxy-3,5-dimethoxyphenethylamine
341
3,5-Dimethoxy-4-(2-methoxyethoxy)phenethylamine
3,4,5-MBM · 4-Br-3,5-DMPEA
3,4,5-MBM; 4-Bromo-3,5-dimethoxyphenethylamine
DESMETHYL
DESMETHYL; 4-(2-Aminoethyl)-2,6-dimethoxyphenol
3,5-DMPEA
3,5-DMPEA; 2-(3,5-Dimethoxyphenyl)ethan-1-amine
3C-DFM
3C-DFM; 1-[4-(Difluoromethoxy)-3,5-dimethoxyphenyl]propan-2-amine
DFIP
DFIP; Difluoroisoproscaline
TFP
TFP; Trifluoroproscaline
TFM
TFM; Trifluoromescaline
DFM
DFM; Difluoromescaline
MEPEA
PiHKAL#123 MEPEA; SI#90 MEPEA
3-TE
PiHKAL#150 3-TE
BOD
PiHKAL#14 BOD; SI#13 BOD
ME
PiHKAL#119 ME
TMA
PiHKAL#157 TMA; SI#117 TMA
TMA-2
PiHKAL#158 TMA-2; SI#118 TMA-2
TMA-3
PiHKAL#159 TMA-3; SI#119 TMA-3
TMA-4
PiHKAL#160 TMA-4; SI#120 TMA-4
TMA-5
PiHKAL#161 TMA-5; SI#121 TMA-5
TMA-6
PiHKAL#162 TMA-6; SI#122 TMA-6
METHYL-MESCALINE
METHYL-MESCALINE; N-Methyl-3,4,5-trimethoxyphenethylamine
2C-O-2
2C-O-2; 2,5-Dimethoxy-4-ethoxyphenethylamine
N,N-Me-3-DESMETHYL
N,N-Me-3-DESMETHYL; N,N-Dimethyl-3-demethylmescaline
N,N-Me-DME · Macromerine
N,N-Me-DME; Macromerine
4C-HO
4C-HO; 1-(4-Hydroxy-2,5-dimethoxyphenyl)-2-aminobutane
homo-Mescaline
homo-Mescaline; 3-(3,4,5-Trimethoxyphenyl)propan-1-amine
β-HO-N-iPr-GEA
β-HO-N-iPr-GEA; 4-[1-Hydroxy-2-(propan-2-ylamino)ethyl]-2-methoxyphenol
N-Me-β,3,4-TMPEA
N-Me-β,3,4-TMPEA; 2-(3,4-Dimethoxyphenyl)-2-methoxy-N-methylethan-1-amine
DMMAOH
DMMAOH; 1-(3,4-Dimethoxyphenyl)-N-hydroxy-N-methylpropan-2-amine
DEE
DEE; 2-Amino-1-(3,4-diethoxyphenyl)ethanol
β-HO-N,N-Me-2,5-DMPEA
β-HO-N,N-Me-2,5-DMPEA; 1-(2,5-Dimethoxyphenyl)-2-(dimethylamino)ethanol
β-HO-β,N-Me-2,5-DMPEA
β-HO-β,N-Me-2,5-DMPEA; 2-(2,5-Dimethoxyphenyl)-1-(methylamino)propan-2-ol
β-HO-N-Me-2,5-DMA
β-HO-N-Me-2,5-DMA; 1-(2,5-Dimethoxyphenyl)-2-(methylamino)propan-1-ol
β,2-HO-N-Me-5-EA
β,2-HO-N-Me-5-EA; 4-Ethoxy-2-[1-hydroxy-2-(methylamino)propyl]phenol
β-HO-2,5-DEPEA
β-HO-2,5-DEPEA; 2-Amino-1-(2,5-diethoxyphenyl)ethanol
β-HO-N,N-Me-3,5-DMPEA
β-HO-N,N-Me-3,5-DMPEA; 1-(3,5-Dimethoxyphenyl)-2-(dimethylamino)ethanol
N-HO-DOM
N-HO-DOM; 1-(2,5-Dimethoxy-4-methylphenyl)-N-hydroxypropan-2-amine
DESMETHYL-MM
DESMETHYL-MM; 4-[2-(Dimethylamino)ethyl]-2,6-dimethoxyphenol
β-HO-DOM
β-HO-DOM; 2-Amino-1-(2,5-dimethoxy-4-methylphenyl)propan-1-ol
1016
[4-(2-Aminopropyl)-2,5-dimethoxyphenyl]methanol
N-MeO-3,4-DMA
N-MeO-3,4-DMA; N,3,4-Trimethoxyamphetamine
28 August 2016 · Creative Commons BY-NC-SA ·