Exploring EMM. To explore a different substance…

PiHKAL#76 EMM
Names:
EMM · 4,5-Dimethoxy-2-ethoxyamphetamine · 2-Ethoxy-4,5-dimethoxyamphetamine
IUPAC name:
1-(2-Ethoxy-4,5-dimethoxyphenyl)propan-2-amine
ID: 76 · Formula: C13H21NO3 · Molecular weight: 239.311
InChI: InChI=1S/C13H21NO3/c1-5-17-11-8-13(16-4)12(15-3)7-10(11)6-9(2)14/h7-9H,5-6,14H2,1-4H3

Shulgin, AT. The ethyl homologs of 2,4,5-trimethoxyphenylisopropylamine. J. Med. Chem., 1 Jan 1968, 11 (1), 186–187. 242 kB. http://dx.doi.org/10.1021/jm00307a056

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

Shulgin, AT. Chemistry and structure-activity relationships of the psychotomimetics. In Psychotomimetic Drugs; Efron, DH, Ed., Raven Press, New York, 1 Jan 1970; pp 21–41. 8647 kB.

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.

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. http://dx.doi.org/10.1016/0014-2999(81)90106-0

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
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
o-DOT · ORTHO-DOT
PiHKAL#139 ORTHO-DOT
TMA-2
PiHKAL#158 TMA-2; SI#118 TMA-2
o-DOM · 2-DOM
o-DOM; 4,5-Dimethoxy-2-methylamphetamine
o-DOB · ORTHO-DOB
o-DOB; 2-Bromo-4,5-dimethoxyamphetamine
2-F-4,5-DMA
2-F-4,5-DMA; 1-(2-Fluoro-4,5-dimethoxyphenyl)propan-2-amine
2-NH2-4,5-DMA
2-NH2-4,5-DMA; 2-(2-Aminopropyl)-4,5-dimethoxyaniline
o-DON
o-DON; 1-(4,5-Dimethoxy-2-nitrophenyl)propan-2-amine
2,4,5-DOET
2,4,5-DOET; 1-(2-Ethyl-4,5-dimethoxyphenyl)propan-2-amine
2-I-4,5-DMA
2-I-4,5-DMA; 1-(2-Iodo-4,5-dimethoxyphenyl)propan-2-amine
EEM
PiHKAL#74 EEM
FLORENCE
FLORENCE; 2-Ethoxy-5-methoxy-4-methylamphetamine
532
2-Ethoxy-4-ethyl-5-methoxyamphetamine
EME
PiHKAL#75 EME
EMDA-2
EMDA-2; 2-Ethoxy-4,5-methylenedioxyamphetamine
Propargylpemoline
Propargylpemoline
10846
2-(Dimethylamino)-5-methyl-5-phenyl-1,3-oxazol-4(5H)-one
AEM
PiHKAL#1 AEM; SI#1 AEM
ASB
PiHKAL#9 ASB; SI#8 ASB
3C-E
PiHKAL#25 3C-E
2C-O-4
PiHKAL#35 2C-O-4
IP
PiHKAL#92 IP
MEM
PiHKAL#122 MEM; SI#87 MEM
MME
PiHKAL#136 MME
MP
PiHKAL#137 MP
P
PiHKAL#140 P; SI#104 Proscaline
SB
PiHKAL#144 SB
189
1-(2,5-Dimethoxy-4-methylphenyl)-N-hydroxy-2-aminobutane
4C-TMPEA-6
4C-TMPEA-6; 1-(2,4,6-Trimethoxyphenyl)-2-aminobutane
BOED
BOED; 2,5-Dimethoxy-β-ethoxy-4-methylphenethylamine
Z-7.2
Z-7.2; 4-Methyl-2,3,6-trimethoxyamphetamine
Trichocerine
Trichocerine
N-Me-TMA · METHYL-TMA
N-Me-TMA; N-Methyl-3,4,5-trimethoxyamphetamine
N-Me-TMA-2 · METHYL-TMA-2
N-Me-TMA-2; N-Methyl-2,4,5-trimethoxyamphetamine
N-Me-TMA-6 · METHYL-TMA-6
N-Me-TMA-6; N-Methyl-2,4,6-trimethoxyamphetamine
2C-O-7
2C-O-7; 2,5-Dimethoxy-4-n-propoxyphenethylamine
Salbutamol
Salbutamol
homo-TMA-2
homo-TMA-2; 4-(2,4,5-Trimethoxyphenyl)butan-2-amine
homo-TMA-3
homo-TMA-3; 4-(2,3,4-Trimethoxyphenyl)butan-2-amine
homo-TMA-6
homo-TMA-6; 4-(2,4,6-Trimethoxyphenyl)butan-2-amine
N,N-Me-β,3,4-TMPEA
N,N-Me-β,3,4-TMPEA; 2-(3,4-Dimethoxyphenyl)-2-methoxy-N,N-dimethylethan-1-amine
β-HO-β,N,N-Me-2,5-DMPEA
β-HO-β,N,N-Me-2,5-DMPEA; 2-(2,5-Dimethoxyphenyl)-1-(dimethylamino)propan-2-ol
β-HO-N,N-Me-2,5-DMA
β-HO-N,N-Me-2,5-DMA; 1-(2,5-Dimethoxyphenyl)-2-(dimethylamino)propan-1-ol
β-HO-N-Me-2,5-DEPEA
β-HO-N-Me-2,5-DEPEA; 1-(2,5-Diethoxyphenyl)-2-(methylamino)ethanol
β-HO-2,5-DEA
β-HO-2,5-DEA; 2-Amino-1-(2,5-diethoxyphenyl)propan-1-ol
N-Me-TMA-3
N-Me-TMA-3; N-Methyl-1-(2,3,4-trimethoxyphenyl)propan-2-amine
4C-TMPEA-3
4C-TMPEA-3; 1-(2,3,4-Trimethoxyphenyl)butan-2-amine
4C-HM
4C-HM; 4-(2-Aminobutyl)-2,5-dimethoxybenzaldehyde
BOE
BOE; 2-(4-Ethyl-2,5-dimethoxyphenyl)-2-methoxyethan-1-amine
DOEH
DOEH; 2-[4-(2-Aminopropyl)-2,5-dimethoxyphenyl]ethanol
4C-MeO
4C-MeO; 1-(2,4,5-Trimethoxyphenyl)butan-2-amine
DESMETHYL-iPr
DESMETHYL-iPr; 2,6-Dimethoxy-4-[2-(propan-2-ylamino)ethyl]phenol
α-MM-M
α-MM-M; 2-Methyl-1-(3,4,5-trimethoxyphenyl)propan-2-amine
DOMOM
DOMOM; 1-[2,5-Dimethoxy-4-(methoxymethyl)phenyl]propan-2-amine
10453
2-(2,4,5-Trimethoxy-3,6-dimethylphenyl)ethan-1-amine
DMe-M
DMe-M; 2-(3,4,5-Trimethoxy-2,6-dimethylphenyl)ethan-1-amine
10404
2-(2-Ethyl-3,4,5-trimethoxyphenyl)ethan-1-amine
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
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
o-DOT · ORTHO-DOT
PiHKAL#139 ORTHO-DOT
TMA-2
PiHKAL#158 TMA-2; SI#118 TMA-2
o-DOM · 2-DOM
o-DOM; 4,5-Dimethoxy-2-methylamphetamine
o-DOB · ORTHO-DOB
o-DOB; 2-Bromo-4,5-dimethoxyamphetamine
2-F-4,5-DMA
2-F-4,5-DMA; 1-(2-Fluoro-4,5-dimethoxyphenyl)propan-2-amine
2-NH2-4,5-DMA
2-NH2-4,5-DMA; 2-(2-Aminopropyl)-4,5-dimethoxyaniline
o-DON
o-DON; 1-(4,5-Dimethoxy-2-nitrophenyl)propan-2-amine
2,4,5-DOET
2,4,5-DOET; 1-(2-Ethyl-4,5-dimethoxyphenyl)propan-2-amine
2-I-4,5-DMA
2-I-4,5-DMA; 1-(2-Iodo-4,5-dimethoxyphenyl)propan-2-amine
EEM
PiHKAL#74 EEM
FLORENCE
FLORENCE; 2-Ethoxy-5-methoxy-4-methylamphetamine
532
2-Ethoxy-4-ethyl-5-methoxyamphetamine
EME
PiHKAL#75 EME
EMDA-2
EMDA-2; 2-Ethoxy-4,5-methylenedioxyamphetamine
Propargylpemoline
Propargylpemoline
10846
2-(Dimethylamino)-5-methyl-5-phenyl-1,3-oxazol-4(5H)-one
AEM
PiHKAL#1 AEM; SI#1 AEM
ASB
PiHKAL#9 ASB; SI#8 ASB
3C-E
PiHKAL#25 3C-E
2C-O-4
PiHKAL#35 2C-O-4
IP
PiHKAL#92 IP
MEM
PiHKAL#122 MEM; SI#87 MEM
MME
PiHKAL#136 MME
MP
PiHKAL#137 MP
P
PiHKAL#140 P; SI#104 Proscaline
SB
PiHKAL#144 SB
189
1-(2,5-Dimethoxy-4-methylphenyl)-N-hydroxy-2-aminobutane
4C-TMPEA-6
4C-TMPEA-6; 1-(2,4,6-Trimethoxyphenyl)-2-aminobutane
BOED
BOED; 2,5-Dimethoxy-β-ethoxy-4-methylphenethylamine
Z-7.2
Z-7.2; 4-Methyl-2,3,6-trimethoxyamphetamine
Trichocerine
Trichocerine
N-Me-TMA · METHYL-TMA
N-Me-TMA; N-Methyl-3,4,5-trimethoxyamphetamine
N-Me-TMA-2 · METHYL-TMA-2
N-Me-TMA-2; N-Methyl-2,4,5-trimethoxyamphetamine
N-Me-TMA-6 · METHYL-TMA-6
N-Me-TMA-6; N-Methyl-2,4,6-trimethoxyamphetamine
2C-O-7
2C-O-7; 2,5-Dimethoxy-4-n-propoxyphenethylamine
Salbutamol
Salbutamol
homo-TMA-2
homo-TMA-2; 4-(2,4,5-Trimethoxyphenyl)butan-2-amine
homo-TMA-3
homo-TMA-3; 4-(2,3,4-Trimethoxyphenyl)butan-2-amine
homo-TMA-6
homo-TMA-6; 4-(2,4,6-Trimethoxyphenyl)butan-2-amine
N,N-Me-β,3,4-TMPEA
N,N-Me-β,3,4-TMPEA; 2-(3,4-Dimethoxyphenyl)-2-methoxy-N,N-dimethylethan-1-amine
β-HO-β,N,N-Me-2,5-DMPEA
β-HO-β,N,N-Me-2,5-DMPEA; 2-(2,5-Dimethoxyphenyl)-1-(dimethylamino)propan-2-ol
β-HO-N,N-Me-2,5-DMA
β-HO-N,N-Me-2,5-DMA; 1-(2,5-Dimethoxyphenyl)-2-(dimethylamino)propan-1-ol
β-HO-N-Me-2,5-DEPEA
β-HO-N-Me-2,5-DEPEA; 1-(2,5-Diethoxyphenyl)-2-(methylamino)ethanol
β-HO-2,5-DEA
β-HO-2,5-DEA; 2-Amino-1-(2,5-diethoxyphenyl)propan-1-ol
N-Me-TMA-3
N-Me-TMA-3; N-Methyl-1-(2,3,4-trimethoxyphenyl)propan-2-amine
4C-TMPEA-3
4C-TMPEA-3; 1-(2,3,4-Trimethoxyphenyl)butan-2-amine
4C-HM
4C-HM; 4-(2-Aminobutyl)-2,5-dimethoxybenzaldehyde
BOE
BOE; 2-(4-Ethyl-2,5-dimethoxyphenyl)-2-methoxyethan-1-amine
DOEH
DOEH; 2-[4-(2-Aminopropyl)-2,5-dimethoxyphenyl]ethanol
4C-MeO
4C-MeO; 1-(2,4,5-Trimethoxyphenyl)butan-2-amine
DESMETHYL-iPr
DESMETHYL-iPr; 2,6-Dimethoxy-4-[2-(propan-2-ylamino)ethyl]phenol
α-MM-M
α-MM-M; 2-Methyl-1-(3,4,5-trimethoxyphenyl)propan-2-amine
DOMOM
DOMOM; 1-[2,5-Dimethoxy-4-(methoxymethyl)phenyl]propan-2-amine
10453
2-(2,4,5-Trimethoxy-3,6-dimethylphenyl)ethan-1-amine
DMe-M
DMe-M; 2-(3,4,5-Trimethoxy-2,6-dimethylphenyl)ethan-1-amine
10404
2-(2-Ethyl-3,4,5-trimethoxyphenyl)ethan-1-amine
30 September 2016 · Creative Commons BY-NC-SA ·