N-Me-TMA-6
METHYL-TMA-6
N-Methyl-2,4,6-trimethoxyamphetamine

IUPAC: N-Methyl-1-(2,4,6-trimethoxyphenyl)propan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: VSIUFWGLSWJBHU-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14-2)6-11-12(16-4)7-10(15-3)8-13(11)17-5/h7-9,14H,6H2,1-5H3

PubChem CID: 69393054

Shulgin Index: See #122 TMA-6; Table: 5 Page: 353 Row: 27

See also PiHKAL:	#126 METHYL-DMA

N-Benzoyl-TMA-6

IUPAC: N-[1-(2,4,6-Trimethoxyphenyl)propan-2-yl]benzamide

Formula: C19H23NO4 Molecular weight: 329.39022 g/mol InChI Key: QKIRRXZGIIENOO-UHFFFAOYSA-N

InChI=1S/C19H23NO4/c1-13(20-19(21)14-8-6-5-7-9-14)10-16-17(23-3)11-15(22-2)12-18(16)24-4/h5-9,11-13H,10H2,1-4H3,(H,20,21)

White, TJ; Goodman, D; Shulgin, AT; Castagnoli, N; Lee, R; Petrakis, NL. Mutagenic activity of some centrally active aromatic amines in Salmonella typhimurium. Mutat. Res., 1 Jan 1977, 56 (2), 199–202. 256 kB. doi:10.1016/0027-5107(77)90210-X

4C-TMPEA-6
1-(2,4,6-Trimethoxyphenyl)-2-aminobutane

IUPAC: 1-(2,4,6-Trimethoxyphenyl)butan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: RPZWJHJIKUKWKO-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-5-9(14)6-11-12(16-3)7-10(15-2)8-13(11)17-4/h7-9H,5-6,14H2,1-4H3

PubChem CID: 43565966

Shulgin Index: See #122 TMA-6; Table: 5 Page: 353 Row: 28

See also PiHKAL:	#8 ARIADNE

TMPEA-6
2C-TMA-6
2,4,6-TMPEA
Ψ-2C-O
2,4,6-Trimethoxyphenethylamine

IUPAC: 2-(2,4,6-Trimethoxyphenyl)ethanamine

Formula: C11H17NO3 Molecular weight: 211.25758 g/mol InChI Key: CGUNKAXAEZSOFA-UHFFFAOYSA-N

InChI=1S/C11H17NO3/c1-13-8-6-10(14-2)9(4-5-12)11(7-8)15-3/h6-7H,4-5,12H2,1-3H3

PubChem CID: 21679959; ChemSpider: 10296635

Shulgin Index: See #122 TMA-6; Table: 5 Page: 353 Row: 25

See also PiHKAL:	#162 TMA-6

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

2,4,6-DOB

IUPAC: 1-(2-Bromo-4,6-dimethoxyphenyl)propan-2-amine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: QEZQLIBEVDLHCE-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)4-9-10(12)5-8(14-2)6-11(9)15-3/h5-7H,4,13H2,1-3H3

Shulgin Index: See #52 DOB; Table: 5 Page: 353 Row: 22

2,4,6-DOET

IUPAC: 1-(2-Ethyl-4,6-dimethoxyphenyl)propan-2-amine

Formula: C13H21NO2 Molecular weight: 223.31134 g/mol InChI Key: QQJTYGJGZRETQO-UHFFFAOYSA-N

InChI=1S/C13H21NO2/c1-5-10-7-11(15-3)8-13(16-4)12(10)6-9(2)14/h7-9H,5-6,14H2,1-4H3

PubChem CID: 57486957

Shulgin Index: See #56 DOET; Table: 5 Page: 353 Row: 24

2,4,6-DOC
2-Chloro-4,6-dimethoxyamphetamine

IUPAC: 1-(2-Chloro-4,6-dimethoxyphenyl)propan-2-amine

Formula: C11H16ClNO2 Molecular weight: 229.70324 g/mol InChI Key: LETSMZRHUXLNTC-UHFFFAOYSA-N

InChI=1S/C11H16ClNO2/c1-7(13)4-9-10(12)5-8(14-2)6-11(9)15-3/h5-7H,4,13H2,1-3H3

PubChem CID: 11184685; ChemSpider: 9359770

Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. doi:10.1021/jm0493109

TeMA-2

IUPAC: 1-(2,3,4,6-Tetramethoxyphenyl)propan-2-amine

Formula: C13H21NO4 Molecular weight: 255.31014 g/mol InChI Key: DJUKQNSUJQBHFW-UHFFFAOYSA-N

InChI=1S/C13H21NO4/c1-8(14)6-9-10(15-2)7-11(16-3)13(18-5)12(9)17-4/h7-8H,6,14H2,1-5H3

Shulgin Index: See #115 TeMPEA-3; Table: 6 Page: 355 Row: 24

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

Ψ-DOM
Z-7
4-Methyl-2,6-dimethoxyamphetamine
2,6-Dimethoxy-4-methylamphetamine

IUPAC: 1-(2,6-Dimethoxy-4-methylphenyl)propan-2-amine

Formula: C12H19NO2 Molecular weight: 209.28476 g/mol InChI Key: CFFJUEYUTHKVMQ-UHFFFAOYSA-N

InChI=1S/C12H19NO2/c1-8-5-11(14-3)10(7-9(2)13)12(6-8)15-4/h5-6,9H,7,13H2,1-4H3

PubChem CID: 13753734; ChemSpider: 21106372; Wikipedia: psi-DOM

Shulgin Index: See #60 DOM; Table: 5 Page: 353 Row: 18

See also PiHKAL:	#42 Ψ-2C-T-4	#68 DOM	#162 TMA-6

See also Pharmacology notes I:	p. 190, Ψ-DOM

Parker, MA; Kurrasch, DM; Nichols, DE. The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands. Bioorg. Med. Chem., 1 Jan 2008, 16 (8), 4661–4669. 296 kB. doi:10.1016/j.bmc.2008.02.033

Shulgin, AT. 4-Alkyl-dialkoxy-alpha-methyl-phenethylamines and their pharmacologically-acceptable salts. U S. Patent 3,547,999, 15 Dec 1970. 448 kB.

Chambers, JJ; Kurrasch-Orbaugh, DM; Nichols, DE. Translocation of the 5-alkoxy substituent of 2,5-dialkoxyarylalkylamines to the 6-position: Effects on 5-HT2A/2C receptor affinity. Bioorg. Med. Chem. Lett., 1 Jan 2002, 12 (15), 1997–1999. 100 kB. doi:10.1016/S0960-894X(02)00306-2

Butterick, JR. Synthesis of O-transmethylated catecholamines and psychodysleptic β-phenylisopropylamines. Ph. D. Thesis, Simon Faser University, Burnaby, BC, Canada, 11 Mar 1975. 6069 kB. External examiner: A. T. Shulgin!.

2,6-DMA
2,6-Dimethoxyamphetamine

IUPAC: 1-(2,6-Dimethoxyphenyl)propan-2-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: OHGNLLDQBKOWJW-UHFFFAOYSA-N

InChI=1S/C11H17NO2/c1-8(12)7-9-10(13-2)5-4-6-11(9)14-3/h4-6,8H,7,12H2,1-3H3

PubChem CID: 141048; ChemSpider: 124412

Shulgin Index: #37 2,6-DMA; Table: 4 Page: 337 Row: 23

See also PiHKAL:	#55 3,4-DMA	#124 META-DOB

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

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

2,6-Dimethoxy-4-phenylpropylamphetamine

IUPAC: 1-[2,6-Dimethoxy-4-(3-phenylpropyl)phenyl]propan-2-amine

Formula: C20H27NO2 Molecular weight: 313.43388 g/mol InChI Key: BLTUEXQAJVYGCR-UHFFFAOYSA-N

InChI=1S/C20H27NO2/c1-15(21)12-18-19(22-2)13-17(14-20(18)23-3)11-7-10-16-8-5-4-6-9-16/h4-6,8-9,13-15H,7,10-12,21H2,1-3H3

PubChem CID: 10064188; ChemSpider: 8239728

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., 10 Aug 2000, 43 (16), 3074–3084. 271 kB. doi:10.1021/jm9906062

Ψ-ALEPH
2,6-Dimethoxy-4-methylthioamphetamine

IUPAC: 1-[2,6-Dimethoxy-4-(methylsulfanyl)phenyl]propan-2-amine

Formula: C12H19NO2S Molecular weight: 241.34976 g/mol InChI Key: OAFDDZCNQLOKNK-UHFFFAOYSA-N

InChI=1S/C12H19NO2S/c1-8(13)5-10-11(14-2)6-9(16-4)7-12(10)15-3/h6-8H,5,13H2,1-4H3

PubChem CID: 11300389; ChemSpider: 9475366

Shulgin Index: See #3 ALEPH; Table: 5 Page: 353 Row: 31

See also PiHKAL:	#162 TMA-6

Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. doi:10.1021/jm0493109

4,2,6-DOB
Ψ-DOB
4-Bromo-2,6-dimethoxyamphetamine

IUPAC: 1-(4-Bromo-2,6-dimethoxyphenyl)propan-2-amine

Formula: C11H16BrNO2 Molecular weight: 274.15424 g/mol InChI Key: LLTVNYHNUJIHOU-UHFFFAOYSA-N

InChI=1S/C11H16BrNO2/c1-7(13)4-9-10(14-2)5-8(12)6-11(9)15-3/h5-7H,4,13H2,1-3H3

PubChem CID: 158251; ChemSpider: 139237

Shulgin Index: See #52 DOB; Table: 5 Page: 353 Row: 15

See also PiHKAL:	#162 TMA-6

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

4,2,6-DOET
Ψ-DOET
4-Ethyl-2,6-dimethoxyamphetamine

IUPAC: 1-(4-Ethyl-2,6-dimethoxyphenyl)propan-2-amine

Formula: C13H21NO2 Molecular weight: 223.31134 g/mol InChI Key: DVBZPPVSVLQDKE-UHFFFAOYSA-N

InChI=1S/C13H21NO2/c1-5-10-7-12(15-3)11(6-9(2)14)13(8-10)16-4/h7-9H,5-6,14H2,1-4H3

PubChem CID: 57498518

Shulgin Index: See #56 DOET; Table: 5 Page: 353 Row: 19

See also PiHKAL:	#162 TMA-6

Shulgin, AT. 4-Alkyl-dialkoxy-alpha-methyl-phenethylamines and their pharmacologically-acceptable salts. U S. Patent 3,547,999, 15 Dec 1970. 448 kB.

Ψ-DOI
4-Iodo-2,6-dimethoxyamphetamine

IUPAC: 1-(4-Iodo-2,6-dimethoxyphenyl)propan-2-amine

Formula: C11H16INO2 Molecular weight: 321.15471 g/mol InChI Key: JKWXVAUZJUBUFC-UHFFFAOYSA-N

InChI=1S/C11H16INO2/c1-7(13)4-9-10(14-2)5-8(12)6-11(9)15-3/h5-7H,4,13H2,1-3H3

See also PiHKAL:	#162 TMA-6

DOTFM-6

IUPAC: 1-[2,6-Dimethoxy-4-(trifluoromethyl)phenyl]propan-2-amine

Formula: C12H16F3NO2 Molecular weight: 263.2561496 g/mol InChI Key: DZZWUCOCRKSNLR-UHFFFAOYSA-N

InChI=1S/C12H16F3NO2/c1-7(16)4-9-10(17-2)5-8(12(13,14)15)6-11(9)18-3/h5-7H,4,16H2,1-3H3

Shulgin Index: See #63 DOTFM; Table: 5 Page: 353 Row: 16

Ψ-ALEPH-2

IUPAC: 1-[4-(Ethylsulfanyl)-2,6-dimethoxyphenyl]propan-2-amine

Formula: C13H21NO2S Molecular weight: 255.37634 g/mol InChI Key: UBJBIUDLAZEZPQ-UHFFFAOYSA-N

InChI=1S/C13H21NO2S/c1-5-17-10-7-12(15-3)11(6-9(2)14)13(8-10)16-4/h7-9H,5-6,14H2,1-4H3

PubChem CID: 11335306; ChemSpider: 9510252

Shulgin Index: See #3 ALEPH; Table: 5 Page: 353 Row: 32

Gallardo-Godoy, A; Fierro, A; McLean, TH; Castillo, M; Cassels, BK; Reyes-Parada, M; Nichols, DE. Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAOA inhibitors: Biological activities, CoMFA analysis, and active site modeling. J. Med. Chem., 1 Jan 2005, 48 (7), 2407–2419. 901 kB. doi:10.1021/jm0493109

Ψ-DODFMO

IUPAC: 1-[4-(2,2-Difluoroethyl)-2,6-dimethoxyphenyl]propan-2-amine

Formula: C13H19F2NO2 Molecular weight: 259.2922664 g/mol InChI Key: QVTWZVXRAGWKCV-UHFFFAOYSA-N

InChI=1S/C13H19F2NO2/c1-8(16)4-10-11(17-2)5-9(7-13(14)15)6-12(10)18-3/h5-6,8,13H,4,7,16H2,1-3H3

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

Ψ-MTFEM

IUPAC: 1-[2,6-Dimethoxy-4-(2,2,2-trifluoroethoxy)phenyl]propan-2-amine

Formula: C13H18F3NO3 Molecular weight: 293.2821296 g/mol InChI Key: PGMSUWCSIAGHKB-UHFFFAOYSA-N

InChI=1S/C13H18F3NO3/c1-8(17)4-10-11(18-2)5-9(6-12(10)19-3)20-7-13(14,15)16/h5-6,8H,4,7,17H2,1-3H3

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

Ψ-MDFEM

IUPAC: 1-[4-(2,2-Difluoroethoxy)-2,6-dimethoxyphenyl]propan-2-amine

Formula: C13H19F2NO3 Molecular weight: 275.2916664 g/mol InChI Key: NBJZLMLXGXIWJW-UHFFFAOYSA-N

InChI=1S/C13H19F2NO3/c1-8(16)4-10-11(17-2)5-9(6-12(10)18-3)19-7-13(14)15/h5-6,8,13H,4,7,16H2,1-3H3

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

Ψ-MFEM

IUPAC: 1-[4-(2-Fluoroethoxy)-2,6-dimethoxyphenyl]propan-2-amine

Formula: C13H20FNO3 Molecular weight: 257.3012032 g/mol InChI Key: ZWTSZKWQJSFARQ-UHFFFAOYSA-N

InChI=1S/C13H20FNO3/c1-9(15)6-11-12(16-2)7-10(18-5-4-14)8-13(11)17-3/h7-9H,4-6,15H2,1-3H3

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

2,4-DMA
2,4-Dimethoxyamphetamine

IUPAC: 1-(2,4-Dimethoxyphenyl)propan-2-amine

Formula: C11H17NO2 Molecular weight: 195.25818 g/mol InChI Key: DQWOZMUBHQPFFF-UHFFFAOYSA-N Properties: Essential amphetamine

InChI=1S/C11H17NO2/c1-8(12)6-9-4-5-10(13-2)7-11(9)14-3/h4-5,7-8H,6,12H2,1-3H3

PubChem CID: 417604; ChemSpider: 124411; Wikipedia: Dimethoxyamphetamine

Shulgin Index: #35 2,4-DMA; Table: 4 Page: 327 Row: 11

See also PiHKAL:	#55 3,4-DMA	#124 META-DOB	#157 TMA

See also Pharmacology notes I:	p. 144, 2,4-DMA

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

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. doi:10.1016/S0968-0896(03)00437-1

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

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

6-Me-2,4-DOM
Z-7.1
2,4-Dimethoxy-6-methylamphetamine

IUPAC: 1-(2,4-Dimethoxy-6-methylphenyl)propan-2-amine

Formula: C12H19NO2 Molecular weight: 209.28476 g/mol InChI Key: NSHTXYRSVXGYPK-UHFFFAOYSA-N

InChI=1S/C12H19NO2/c1-8-5-10(14-3)7-12(15-4)11(8)6-9(2)13/h5,7,9H,6,13H2,1-4H3

Shulgin Index: See #60 DOM; Table: 5 Page: 353 Row: 23

See also PiHKAL:	#69 Ψ-DOM

homo-TMA-6

IUPAC: 4-(2,4,6-Trimethoxyphenyl)butan-2-amine

Formula: C13H21NO3 Molecular weight: 239.31074 g/mol InChI Key: XCOSLSXZEMZDEY-UHFFFAOYSA-N

InChI=1S/C13H21NO3/c1-9(14)5-6-11-12(16-3)7-10(15-2)8-13(11)17-4/h7-9H,5-6,14H2,1-4H3

PubChem CID: 3041180; ChemSpider: 2304485

Shulgin Index: See #91 Mescaline; Table: 10 Page: 358 Row: 30

BOD
β-Methoxy-2C-D
2,5,β-Trimethoxy-4-methylphenethylamine
4-Methyl-2,5,β-trimethoxyphenethylamine

IUPAC: 2-(2,5-Dimethoxy-4-methylphenyl)-2-methoxyethanamine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: VTEIFHQUZWABDE-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-8-5-11(15-3)9(6-10(8)14-2)12(7-13)16-4/h5-6,12H,7,13H2,1-4H3

PubChem CID: 44719486; ChemSpider: 21106262; Wikipedia: BOD (psychedelic)

Shulgin Index: #14 BOB; Table: 5 Page: 342 Row: 29

See also PiHKAL:	#13 BOB #15 BOH	#16 BOHD #17 BOM

Torres, MA; Cassels, B; Rezende, MC. The preparation of potentially psychoactive β-alkoxyphenethylamines. Synth. Commun., 1 Jan 1995, 25 (8), 1239–1247. 415 kB. doi:10.1080/00397919508012687

Lemaire, D; Jacob, P; Shulgin, AT. Ring substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man. J. Pharm. Pharmacol., 1 Jan 1985, 37 (8), 575–7. 1767 kB.

E
Escaline
Escaline
4-Ethoxy-3,5-dimethoxyphenethylamine
3,5-Dimethoxy-4-ethoxyphenethylamine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: RHOGRSKNWDNCDN-UHFFFAOYSA-N

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

PubChem CID: 38240; ChemSpider: 35053; Wikipedia: Escaline

Shulgin Index: #64 Escaline; Table: 5 Page: 350 Row: 36

See also PiHKAL:	#2 AL #10 B #25 3C-E #50 4-D #51 β-D	#92 IP #93 IRIS #99 MAL #119 ME #123 MEPEA	#140 P #141 PE #143 PROPYNYL #150 3-TE #163 3-TME

See also Pharmacology notes II:	p. 217, Escaline

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

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

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. doi:10.1002/jps.2600680733

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. doi:10.1016/S0968-0896(03)00437-1

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. doi:10.1021/jm00212a022

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. doi:10.1021/jm00373a013

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.

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

ME
Metaescaline
3,4-Dimethoxy-5-ethoxyphenethylamine
3-Ethoxy-4,5-dimethoxyphenethylamine

IUPAC: 2-(3-Ethoxy-4,5-dimethoxyphenyl)ethanamine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: HNBAVLIQFTYMAX-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-4-16-11-8-9(5-6-13)7-10(14-2)12(11)15-3/h7-8H,4-6,13H2,1-3H3

PubChem CID: 44350068; ChemSpider: 21106344; Wikipedia: Metaescaline

Shulgin Index: See #91 Mescaline; Table: 5 Page: 351 Row: 32

See also PiHKAL:	#9 ASB #137 MP	#163 3-TME #165 5-TME	#176 3-TSB

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

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. doi: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. doi:10.1021/jm00373a013

TMA
AMM
EA-1319
3,4,5-Trimethoxyamphetamine

IUPAC: 1-(3,4,5-Trimethoxyphenyl)propan-2-amine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: WGTASENVNYJZBK-UHFFFAOYSA-N Properties: Essential amphetamine

InChI=1S/C12H19NO3/c1-8(13)5-9-6-10(14-2)12(16-4)11(7-9)15-3/h6-8H,5,13H2,1-4H3

PubChem CID: 31016; ChemSpider: 28775; Wikipedia: Trimethoxyamphetamine

Shulgin Index: #117 TMA; Table: 5 Page: 349 Row: 27

See also PiHKAL:	#1 AEM #14 BOD #21 3C-BZ #27 2C-G #42 Ψ-2C-T-4	#50 4-D #72 E #97 4-MA #100 MDA #120 MEDA	#132 MMDA #145 TA #158 TMA-2 #160 TMA-4 #166 2T-MMDA-3a
See also TiHKAL:	#13 Harmaline

See also Pharmacology notes I:

p. 8, TMA: Subacute human in vivo tests p. 9, TMA: Objective response p. 10, TMA: Objective response p. 11, TMA: Objective response p. 12, TMA: Objective response p. 13, TMA: Subjective response p. 14, TMA: Subjective response p. 15, TMA: Subjective response p. 16, TMA: Subjective response p. 17, TMA: Subjective response p. 18, TMA: Subjective response p. 19, TMA: Subjective response p. 72, SARs p. 139, The Pseunut Cocktail

See also Pharmacology notes II:

p. 227, TMA: Subjective response

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

Zaitsu, K; Katagi, M; Kamata, H; Kamata, T; Shima, N; Miki, A; Iwamura, T; Tsuchihashi, H. Discrimination and identification of the six aromatic positional isomers of trimethoxyamphetamine (TMA) by gas chromatography-mass spectrometry (GC-MS). J. Mass Spectrom., 1 Apr 2008, 43 (4), 528–534. 147 kB. doi:10.1002/jms.1347

Shulgin, AT. Psychotomimetic amphetamines: Methoxy 3,4-dialkoxyamphetamines. Experientia, 1 Jan 1964, 20 (7), 366–367. 240 kB. doi:10.1007/BF02147960

Nelson, DL; Lucaites, VL; Wainscott, DB; Glennon, RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S. Arch. Pharmacol., 6 Sep 1998, 359 (1), 1–6. 66 kB. doi:10.1007/PL00005315

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

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. doi:10.1016/S0968-0896(03)00437-1

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines. J. Med. Chem., 1 Oct 1974, 17 (10),1100–1111. 1175 kB. doi:10.1021/jm00256a016

Nichols, DE; Barfknecht, CF; Rusterholz, DB; Benington, F; Morin, RD. Asymmetric synthesis of psychotomimetic phenylisopropylamines. J. Med. Chem., 1 Jan 1973, 16 (5), 480–483. 515 kB. doi:10.1021/jm00263a013

Shulgin, AT. The six trimethoxyphenylisopropylamines (trimethoxyamphetamines). J. Med. Chem., 1 Jan 1966, 9 (3), 445–456. 362 kB. doi:10.1021/jm00321a058

Shulgin, AT; Bunnell, S; Sargent, T. The psychotomimetic properties of 3,4,5-trimethoxyamphetamine. Nature, 1 Jan 1961, 189, 1011–1012. 306 kB. doi:10.1038/1891011a0 Rhodium.

Shulgin, AT. Possible implication of myristicin as a psychotropic substance. Nature, 1 Jan 1966, 210, 380–384. 707 kB. doi:10.1038/210380a0

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

Moya, PR; Berg, KA; Gutiérrez-Hernandez, MA; Sáez-Briones, P; Reyes-Parada, M; Cassels, BK; Clarke, WP. Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors. J. Pharmacol. Exp. Ther., 1 Jun 2007, 321 (3), 1054–1061. 188 kB. doi:10.1124/jpet.106.117507

Peretz, DI; Smythies, JR; Gibson, WC. A new hallucinogen: 3,4,5-Trimethoxyphenyl-β-aminopropane. With notes on the stroboscopic phenomenon. J. Mental Sci., 1 Jan 1955, 101 (423), 317–329. 1559 kB. doi:10.1192/bjp.101.423.317

Takahashi, M; Nagashima, M; Suzuki, J; Seto, T; Yasuda, I; Yoshida, T. Analysis of phenethylamines and tryptamines in designer drugs using gas chromatography-mass spectrometry. J. Health Sci., 2008, 54 (1), 89–96. 1882 kB. doi:10.1248/jhs.54.89

Ray, TS. Psychedelics and the human receptorome. PLoS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

Guy, M; Freeman, S; Alder, JF; Brandt, SD. The Henry reaction: spectroscopic studies of nitrile and hydroxylamine by-products formed during synthesis of psychoactive phenylalkylamines. Cent. Eur. J. Chem., 1 Dec 2008, 6 (4), 526–534. 982 kB. doi:10.2478/s11532-008-0054-z

Shulgin, AT; Sargent, T; Naranjo, C. The chemistry and psychopharmacology of nutmeg and of several related phenylisopropylamines. In Ethnopharmacologic Search for Psychoactive Drugs; Efron, DH; Holmstedt, B; Kline, NS, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 28 Jan 1967; pp 202–215. 951 kB.

Anderson, GM; Braun, G; Braun, U; Nichols, DE; Shulgin, AT. Absolute configuration and psychotomimetic activity. In QuaSAR: Quantitative Structure Activity Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens. NIDA Research Monograph 22; Barnett, G; Trsic, M; Willette, RE, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1978; pp 8–15. 457 kB.

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.

Lemaire, D; Jacob, P; Shulgin, AT. Ring substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man. J. Pharm. Pharmacol., 1 Jan 1985, 37 (8), 575–7. 1767 kB.

Fenderson5555. The Trimethoxylated Amphetamines (TMA-x). 9 Dec 2012.

TMA-2
2,4,5-Trimethoxyamphetamine

IUPAC: 1-(2,4,5-Trimethoxyphenyl)propan-2-amine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: TVSIMAWGATVNGK-UHFFFAOYSA-N Properties: Essential amphetamine

InChI=1S/C12H19NO3/c1-8(13)5-9-6-11(15-3)12(16-4)7-10(9)14-2/h6-8H,5,13H2,1-4H3

PubChem CID: 31014; ChemSpider: 28773; Drugs Forum: TMA-2; Erowid: TMA-2; Wikipedia: Trimethoxyamphetamine

Shulgin Index: #118 TMA-2; Table: 5 Page: 344 Row: 23

See also PiHKAL:	#35 2C-O-4 #42 Ψ-2C-T-4 #52 DESOXY #69 Ψ-DOM #73 EEE #75 EME #76 EMM	#93 IRIS #120 MEDA #121 MEE #122 MEM #136 MME #138 MPM #139 ORTHO-DOT	#145 TA #157 TMA #162 TMA-6 #167 4T-MMDA-2 #168 TMPEA
See also TiHKAL:	#13 Harmaline	#19 5-HO-DMT	#46 5-MeS-DMT

See also Pharmacology notes I:	p. 54, TMA-2: Subacute evaluation p. 55.1, TMA-2: Subjective response p. 56, TMA-2: Subjective response p. 64, TMA-2: Subjective response p. 65, TMA-2: Subjective response p. 72, SARs p. 108, TMA-2: Subjective response p. 151, TMA-2 p. 160, TMA-2 p. 161, TMA-2 p. 185, TMA-2: Qualitative description
See also Pharmacology notes II:	p. 224, TMA-2

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

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

Zaitsu, K; Katagi, M; Kamata, H; Kamata, T; Shima, N; Miki, A; Iwamura, T; Tsuchihashi, H. Discrimination and identification of the six aromatic positional isomers of trimethoxyamphetamine (TMA) by gas chromatography-mass spectrometry (GC-MS). J. Mass Spectrom., 1 Apr 2008, 43 (4), 528–534. 147 kB. doi:10.1002/jms.1347

White, TJ; Goodman, D; Shulgin, AT; Castagnoli, N; Lee, R; Petrakis, NL. Mutagenic activity of some centrally active aromatic amines in Salmonella typhimurium. Mutat. Res., 1 Jan 1977, 56 (2), 199–202. 256 kB. doi:10.1016/0027-5107(77)90210-X

Scorza, M; Carrau, C; Silveira, R; Zapata-Torres, G; Cassels, BK; Reyes-Parada, M. Monoamine oxidase inhibitory properties of some methoxylated and alkylthio amphetamine derivatives. Biochem. Pharmacol., 15 Dec 1997, 54 (12), 1361–1369. 697 kB. doi:10.1016/S0006-2952(97)00405-X

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

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. doi:10.1016/S0968-0896(03)00437-1

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Glennon, RA; Raghupathi, R; Bartyzel, P; Teitler, M; Leonhardt, S. Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity. J. Med. Chem., 1 Feb 1992, 35 (4), 734–740. 1054 kB. doi:10.1021/jm00082a014

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Seggel, MR; Yousif, MY; Lyon, RA; Titeler, M; Roth, BL; Suba, EA; Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33 (3), 1032–1036. 807 kB. doi:10.1021/jm00165a023

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines. J. Med. Chem., 1 Oct 1974, 17 (10),1100–1111. 1175 kB. doi:10.1021/jm00256a016

Shulgin, AT. The six trimethoxyphenylisopropylamines (trimethoxyamphetamines). J. Med. Chem., 1 Jan 1966, 9 (3), 445–456. 362 kB. doi:10.1021/jm00321a058

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

Takahashi, M; Nagashima, M; Suzuki, J; Seto, T; Yasuda, I; Yoshida, T. Analysis of phenethylamines and tryptamines in designer drugs using gas chromatography-mass spectrometry. J. Health Sci., 2008, 54 (1), 89–96. 1882 kB. doi:10.1248/jhs.54.89

Ray, TS. Psychedelics and the human receptorome. PLoS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

Guy, M; Freeman, S; Alder, JF; Brandt, SD. The Henry reaction: spectroscopic studies of nitrile and hydroxylamine by-products formed during synthesis of psychoactive phenylalkylamines. Cent. Eur. J. Chem., 1 Dec 2008, 6 (4), 526–534. 982 kB. doi:10.2478/s11532-008-0054-z

Anderson, GM; Braun, G; Braun, U; Nichols, DE; Shulgin, AT. Absolute configuration and psychotomimetic activity. In QuaSAR: Quantitative Structure Activity Relationships of Analgesics, Narcotic Antagonists, and Hallucinogens. NIDA Research Monograph 22; Barnett, G; Trsic, M; Willette, RE, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1 Jan 1978; pp 8–15. 457 kB.

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.

Anon. Report on the risk assessment of TMA-2 in the framework of the joint action on new synthetic drugs, European Monitoring Centre for Drugs and Drug Addiction, 2004.

Shulgin, AT. Profiles of psychedelic drugs. 2. TMA-2. J. Psychedelic Drugs, 1 Jan 1976, 8 (2), 169. 891 kB.

Sargent, T; Shulgin, AT; Kusubov, N. Quantitative measurement of demethylation of [14]C-methoxyl labeled DMPEA and TMA-2 in rats. Psychopharmacol. Commun., 1 Jan 1976, 2 (3), 199–206. 8643 kB.

Ewald, AH. The 2,5-Dimethoxyamphetamines—A new class of designer drugs. Ph. D. Thesis, Universität des Saarlandes, Saarbrücken, Germany, 1 Jan 2008. 195 kB.

Fenderson5555. The Trimethoxylated Amphetamines (TMA-x). 9 Dec 2012.

TMA-3
2,3,4-Trimethoxyamphetamine

IUPAC: 1-(2,3,4-Trimethoxyphenyl)propan-2-amine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: LWDQPPLPHGXYLG-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-8(13)7-9-5-6-10(14-2)12(16-4)11(9)15-3/h5-6,8H,7,13H2,1-4H3

PubChem CID: 31012; ChemSpider: 28771; Wikipedia: Trimethoxyamphetamine

Shulgin Index: #119 TMA-3; Table: 5 Page: 338 Row: 15

See also PiHKAL:	#42 Ψ-2C-T-4	#152 2-TIM	#158 TMA-2

See also Pharmacology notes I:	p. 72, SARs p. 85.1, Subacute evaluation TMA-3 (XVI-13)

Zaitsu, K; Katagi, M; Kamata, H; Kamata, T; Shima, N; Miki, A; Iwamura, T; Tsuchihashi, H. Discrimination and identification of the six aromatic positional isomers of trimethoxyamphetamine (TMA) by gas chromatography-mass spectrometry (GC-MS). J. Mass Spectrom., 1 Apr 2008, 43 (4), 528–534. 147 kB. doi:10.1002/jms.1347

Shulgin, AT. Psychotomimetic amphetamines: Methoxy 3,4-dialkoxyamphetamines. Experientia, 1 Jan 1964, 20 (7), 366–367. 240 kB. doi:10.1007/BF02147960

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

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. doi:10.1016/S0968-0896(03)00437-1

Domelsmith, LN; Eaton, TA; Houk, KN; Anderson, GM; Glennon, RA; Shulgin, AT; Castagnoli, N; Kollman, PA. Photoelectron spectra of psychotropic drugs. 6. Relationships between physical properties and pharmacological actions of amphetamine analogues. J. Med. Chem., 1 Jan 1981, 24 (12), 1414–1421. 963 kB. doi:10.1021/jm00144a009

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Shulgin, AT. The six trimethoxyphenylisopropylamines (trimethoxyamphetamines). J. Med. Chem., 1 Jan 1966, 9 (3), 445–456. 362 kB. doi:10.1021/jm00321a058

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

Fenderson5555. The Trimethoxylated Amphetamines (TMA-x). 9 Dec 2012.

TMA-4
2,3,5-Trimethoxyamphetamine

IUPAC: 1-(2,3,5-Trimethoxyphenyl)propan-2-amine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: MJIBJXKJBRLSQA-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-8(13)5-9-6-10(14-2)7-11(15-3)12(9)16-4/h6-8H,5,13H2,1-4H3

PubChem CID: 602804; ChemSpider: 523988; Wikipedia: Trimethoxyamphetamine

Shulgin Index: #120 TMA-4; Table: 5 Page: 339 Row: 22

See also PiHKAL:	#42 Ψ-2C-T-4 #135 MMDA-3b	#136 MME #158 TMA-2	#161 TMA-5

See also Pharmacology notes I:	p. 61, TMA-4: Subacute evaluation p. 72, SARs

Zaitsu, K; Katagi, M; Kamata, H; Kamata, T; Shima, N; Miki, A; Iwamura, T; Tsuchihashi, H. Discrimination and identification of the six aromatic positional isomers of trimethoxyamphetamine (TMA) by gas chromatography-mass spectrometry (GC-MS). J. Mass Spectrom., 1 Apr 2008, 43 (4), 528–534. 147 kB. doi:10.1002/jms.1347

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. doi:10.1016/S0968-0896(03)00437-1

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

Shulgin, AT. The six trimethoxyphenylisopropylamines (trimethoxyamphetamines). J. Med. Chem., 1 Jan 1966, 9 (3), 445–456. 362 kB. doi:10.1021/jm00321a058

Shulgin, AT; Sargent, T; Naranjo, C. Structure-activity relationships of one-ring psychotomimetics. Nature, 1 Jan 1969, 221, 537–541. 537 kB. doi: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. MMDA (MMDA-4). Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 11 Apr 2003.

Fenderson5555. The Trimethoxylated Amphetamines (TMA-x). 9 Dec 2012.

TMA-5
2,3,6-Trimethoxyamphetamine

IUPAC: 1-(2,3,6-Trimethoxyphenyl)propan-2-amine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: OASZJWLOOFXASO-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-8(13)7-9-10(14-2)5-6-11(15-3)12(9)16-4/h5-6,8H,7,13H2,1-4H3

PubChem CID: 31013; ChemSpider: 28772; Wikipedia: Trimethoxyamphetamine

Shulgin Index: #121 TMA-5; Table: 5 Page: 353 Row: 2

See also PiHKAL:	#8 ARIADNE	#42 Ψ-2C-T-4	#158 TMA-2

See also Pharmacology notes I:	p. 72, SARs p. 97, TMA-5: Subacute evaluation

Zaitsu, K; Katagi, M; Kamata, H; Kamata, T; Shima, N; Miki, A; Iwamura, T; Tsuchihashi, H. Discrimination and identification of the six aromatic positional isomers of trimethoxyamphetamine (TMA) by gas chromatography-mass spectrometry (GC-MS). J. Mass Spectrom., 1 Apr 2008, 43 (4), 528–534. 147 kB. doi:10.1002/jms.1347

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. doi:10.1016/S0968-0896(03)00437-1

Shulgin, AT. The six trimethoxyphenylisopropylamines (trimethoxyamphetamines). J. Med. Chem., 1 Jan 1966, 9 (3), 445–456. 362 kB. doi:10.1021/jm00321a058

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

Fenderson5555. The Trimethoxylated Amphetamines (TMA-x). 9 Dec 2012.

METHYL-MESCALINE
M-M
N-Methyl-3,4,5-trimethoxyphenethylamine
N-Methylmescaline

IUPAC: N-Methyl-2-(3,4,5-trimethoxyphenyl)ethanamine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: OTXANOLOOUNVSR-UHFFFAOYSA-N Properties: Peyote alkaloid

InChI=1S/C12H19NO3/c1-13-6-5-9-7-10(14-2)12(16-4)11(8-9)15-3/h7-8,13H,5-6H2,1-4H3

PubChem CID: 138365; ChemSpider: 121990

Shulgin Index: #97 MMDA; Table: 5 Page: 350 Row: 24

See also PiHKAL:	#96 M

See also Pharmacology notes I:	p. 142, Methyl-mescaline

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. doi:10.1021/jm00177a017

2C-O-2
2C-O-2
2,5-Dimethoxy-4-ethoxyphenethylamine

IUPAC: 2-(4-Ethoxy-2,5-dimethoxyphenyl)ethanamine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: JFXGDWIZRPHJKN-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-4-16-12-8-10(14-2)9(5-6-13)7-11(12)15-3/h7-8H,4-6,13H2,1-3H3

PubChem CID: 57474251

Shulgin Index: See #124 TMPEA-2; Table: 5 Page: 344 Row: 31

See also PiHKAL:	#35 2C-O-4

N,N-Me-3-DESMETHYL
N,N-Dimethyl-3-demethylmescaline
3-Hydroxy-4,5-dimethoxy-N,N-dimethylphenethylamine

IUPAC: 5-[2-(Dimethylamino)ethyl]-2,3-dimethoxyphenol

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: INYMWXUUZSMPQM-UHFFFAOYSA-N Properties: Peyote alkaloid

InChI=1S/C12H19NO3/c1-13(2)6-5-9-7-10(14)12(16-4)11(8-9)15-3/h7-8,14H,5-6H2,1-4H3

PubChem CID: 57478611

Shulgin Index: See #30 3-DESMETHYL; Table: 5 Page: 349 Row: 7

N,N-Me-DME
Macromerine
β-Hydroxy-3,4-dimethoxy-N,N-dimethylphenethylamine

IUPAC: 1-(3,4-Dimethoxyphenyl)-2-(dimethylamino)ethanol

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: YAIPYAQVBZPSSC-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-13(2)8-10(14)9-5-6-11(15-3)12(7-9)16-4/h5-7,10,14H,8H2,1-4H3

PubChem CID: 165055; ChemSpider: 144706; Wikipedia: Macromerine

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 10

Hodgkins, JE; Brown, SD; Massingill, JL. Two new alkaloids in cacti. Tetrahedron Lett., 1 Jan 1967, 8 (14), 1321–1324. 202 kB. doi:10.1016/S0040-4039(00)90694-4

4C-HO
1-(4-Hydroxy-2,5-dimethoxyphenyl)-2-aminobutane
α-Ethyl-4-hydroxy-2,5-dimethoxyphenethylamine

IUPAC: 4-(2-Aminobutyl)-2,5-dimethoxyphenol

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: ASFOLEVMZYIHRE-VIFPVBQESA-N

InChI=1S/C12H19NO3/c1-4-9(13)5-8-6-12(16-3)10(14)7-11(8)15-2/h6-7,9,14H,4-5,13H2,1-3H3/t9-/m0/s1

ChemSpider: 25045865

Shulgin Index: See #118 TMA-2; Table: 5 Page: 344 Row: 12

Standridge, RT; Howell, HG; Tilson, HA; Chamberlain, JH; Holava, HM; Gylys, JA; Partyka, RA; Shulgin, AT. Phenylalkylamines with potential psychotherapeutic utility. 2. Nuclear substituted 2-amino-1-phenylbutanes. J. Med. Chem., 1 Jan 1980, 23 (2), 154–162. 1125 kB. doi:10.1021/jm00176a010

homo-Mescaline

IUPAC: 3-(3,4,5-Trimethoxyphenyl)propan-1-amine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: LKINXVPAOSIISW-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-14-10-7-9(5-4-6-13)8-11(15-2)12(10)16-3/h7-8H,4-6,13H2,1-3H3

PubChem CID: 614460; ChemSpider: 534098

Shulgin Index: See #91 Mescaline; Table: 10 Page: 358 Row: 26

β-HO-N-iPr-GEA

IUPAC: 4-[1-Hydroxy-2-(propan-2-ylamino)ethyl]-2-methoxyphenol

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: XXCCGRRUBBGZRE-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-8(2)13-7-11(15)9-4-5-10(14)12(6-9)16-3/h4-6,8,11,13-15H,7H2,1-3H3

PubChem CID: 68951; ChemSpider: 62174

Shulgin Index: See #49 DMPEA; Table: 4 Page: 329 Row: 9

N-Me-β,3,4-TMPEA

IUPAC: 2-(3,4-Dimethoxyphenyl)-2-methoxy-N-methylethanamine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: DYEDYZOGYUEUAY-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-13-8-12(16-4)9-5-6-10(14-2)11(7-9)15-3/h5-7,12-13H,8H2,1-4H3

PubChem CID: 15612893; ChemSpider: 26711698

Shulgin Index: See #49 DMPEA; Table: 4 Page: 330 Row: 12

DMMAOH

IUPAC: 1-(3,4-Dimethoxyphenyl)-N-hydroxy-N-methylpropan-2-amine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: LFXAGFFVEBTHIU-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-9(13(2)14)7-10-5-6-11(15-3)12(8-10)16-4/h5-6,8-9,14H,7H2,1-4H3

PubChem CID: 11368108; ChemSpider: 9543025

Shulgin Index: See #38 DMA; Table: 4 Page: 330 Row: 25

DEE

IUPAC: 2-Amino-1-(3,4-diethoxyphenyl)ethanol

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: MHZKJOSBJYJMHA-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-3-15-11-6-5-9(10(14)8-13)7-12(11)16-4-2/h5-7,10,14H,3-4,8,13H2,1-2H3

PubChem CID: 18627975

Shulgin Index: See #49 DMPEA; Table: 4 Page: 331 Row: 5

β-HO-N,N-Me-2,5-DMPEA

IUPAC: 1-(2,5-Dimethoxyphenyl)-2-(dimethylamino)ethanol

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: WIUPSOMVTZKAQS-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-13(2)8-11(14)10-7-9(15-3)5-6-12(10)16-4/h5-7,11,14H,8H2,1-4H3

PubChem CID: 46242; ChemSpider: 42100

Shulgin Index: See #22 2C-H; Table: 4 Page: 335 Row: 16

β-HO-β,N-Me-2,5-DMPEA

IUPAC: 2-(2,5-Dimethoxyphenyl)-1-(methylamino)propan-2-ol

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: BWLTUONQPSGLSS-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-12(14,8-13-2)10-7-9(15-3)5-6-11(10)16-4/h5-7,13-14H,8H2,1-4H3

PubChem CID: 50630; ChemSpider: 45890

Shulgin Index: See #22 2C-H; Table: 4 Page: 335 Row: 19

β-HO-N-Me-2,5-DMA

IUPAC: 1-(2,5-Dimethoxyphenyl)-2-(methylamino)propan-1-ol

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: KOVCQSPGHQJOGZ-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-8(13-2)12(14)10-7-9(15-3)5-6-11(10)16-4/h5-8,12-14H,1-4H3

PubChem CID: 3027653; ChemSpider: 2293151

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 335 Row: 27

β,2-HO-N-Me-5-EA

IUPAC: 4-Ethoxy-2-[1-hydroxy-2-(methylamino)propyl]phenol

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: VZNJLAGGAFRCGE-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-4-16-9-5-6-11(14)10(7-9)12(15)8(2)13-3/h5-8,12-15H,4H2,1-3H3

Shulgin Index: See #36 2,5-DMA; Table: 4 Page: 336 Row: 10

β-HO-2,5-DEPEA

IUPAC: 2-Amino-1-(2,5-diethoxyphenyl)ethanol

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: SILWLGCRESUCBZ-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-3-15-9-5-6-12(16-4-2)10(7-9)11(14)8-13/h5-7,11,14H,3-4,8,13H2,1-2H3

PubChem CID: 18627950

Shulgin Index: See #22 2C-H; Table: 4 Page: 336 Row: 12

β-HO-N,N-Me-3,5-DMPEA

IUPAC: 1-(3,5-Dimethoxyphenyl)-2-(dimethylamino)ethanol

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: HXDFCVFYHGYJBF-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-13(2)8-12(14)9-5-10(15-3)7-11(6-9)16-4/h5-7,12,14H,8H2,1-4H3

Shulgin Index: See #50 3,5-DMPEA; Table: 4 Page: 336 Row: 27

N-HO-DOM

IUPAC: 1-(2,5-Dimethoxy-4-methylphenyl)-N-hydroxypropan-2-amine

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: JAIPYOTXVGSAEO-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-8-5-12(16-4)10(6-9(2)13-14)7-11(8)15-3/h5,7,9,13-14H,6H2,1-4H3

PubChem CID: 597107; ChemSpider: 519067

Shulgin Index: See #60 DOM; Table: 5 Page: 342 Row: 17

White, TJ; Goodman, D; Shulgin, AT; Castagnoli, N; Lee, R; Petrakis, NL. Mutagenic activity of some centrally active aromatic amines in Salmonella typhimurium. Mutat. Res., 1 Jan 1977, 56 (2), 199–202. 256 kB. doi:10.1016/0027-5107(77)90210-X

DESMETHYL-MM

IUPAC: 4-[2-(Dimethylamino)ethyl]-2,6-dimethoxyphenol

Formula: C12H19NO3 Molecular weight: 225.28416 g/mol InChI Key: KCJSOMKZGOMQCA-UHFFFAOYSA-N

InChI=1S/C12H19NO3/c1-13(2)6-5-9-7-10(15-3)12(14)11(8-9)16-4/h7-8,14H,5-6H2,1-4H3

PubChem CID: 24971842; ChemSpider: 21404060

Shulgin Index: See #29 DESMETHYL; Table: 5 Page: 349 Row: 19