- •#3 Aleph; dot; para-dot; 2,5-dimethoxy-4-methylthioamphetamine
- •#4 Aleph-2; 2,5-dimethoxy-4-ethylthioamphetamine
- •#5 Aleph-4; 2,5-dimethoxy-4-(I)-propylthioamphetamine
- •#6 Aleph-6 2,5-dimethoxy-4-phenylthioamphetamine
- •#7 Aleph-7; 2,5-dimethoxy-4-(n)-propylthioamphetamine
- •#8 Ariadne; 4c-dom; bl-3912; dimoxamine; 1-(2,5-dimethoxy-4-methylphenyl)-2-aminobutane; 2,5-dimethoxy-a-ethyl-4-methylphenethylamine
- •#9 Asb; asymbescaline; 3,4-diethoxy-5-methoxyphenethylamine
- •#10 B; buscaline; 4-(n)-butoxy-3,5-dimethoxyphenethylamine
- •#11 Beatrice; n-methyl-dom; 2,5-dimethoxy-4,n-dimethylamphetamine
- •#13 Bob; beta-methoxy-2c-b; 4-bromo-2,5-beta-trimethoxyphenethylamine
- •#14 Bod; beta-methoxy-2c-d; 4-methyl-2,5,beta-trimethoxyphenethylamine
- •#15 Boh; beta-methoxy-3,4-methylenedioxyphenethylamine
- •#16 Bohd; 2,5-dimethoxy-beta-hydroxy-4-methylphenethylamine
- •#17 Bom; beta-methoxymescaline; 3,4,5,beta-tetramethoxyphenethylamine
- •#37 Cpm; cyclopropylmescaline;
- •#42 Gamma-2c-t-4; 2,6-dimethoxy-4-(I)-propylthiophenethylamine)
- •#51 Beta-d; 3,4,5-trimethoxy-beta,beta-dideuterophenethylamine
- •#52 Desoxy; 3,5-dimethoxy-4-methylphenethylamine
- •#56 Dmcpa; 2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine
- •#58 Dmmda; 2,5-dimethoxy-3,4-methylenedioxyamphetamine
- •#59 Dmmda-2; 2,3-dimethoxy-4,5-methylenedioxyamphetamine
- •#60 Dmpea; 3,4-dimethoxyphenethylamine
- •#61 Doam; 2,5-dimethoxy-4-(n)-amylamphetamine
- •#63 Dobu; 2,5-dimethoxy-4-(n)-butylamphetamine
- •#65 Doef; 2,5-dimethoxy-4-(2-fluoroethyl)-
- •#66 Doet; hecate; 2,5-dimethoxy-4-ethylamphetamine
- •#68 Dom; stp; 2,5-dimethoxy-4-methylamphetamine
- •#69 Gamma-dom; z-7; 2,6-dimethoxy-4-methylamphetamine
- •#71 Dopr; 2,5-dimethoxy-4-(n)-propylamphetamine
- •#72 E; escaline; 3,5-dimethoxy-4-ethoxyphenethylamine
- •#73 Eee; 2,4,5-triethoxyamphetamine
- •#77 Ethyl-j; 2-ethylamino-1-(3,4-methylenedioxyphenyl)butane; n-ethyl-1-(1,3-benzodioxol-5-yl)-2-butanamine
- •#81 Flea; n-hydroxy-n-methyl-3,4-methylenedioxyamphetamine
- •#85 Ganesha; g; 2,5-dimethoxy-3,4-dimethylamphetamine
- •#90 Idnna; 2,5-dimethoxy-n,n-dimethyl-4-iodoamphetamine
- •#91 Im; isomescaline; 2,3,4-trimethoxyphenethylamine
- •#92 Ip; isoproscaline; 3,5-dimethoxy-4-(I)-propoxyphenethylamine
- •#93 Iris; 5-ethoxy-2-methoxy-4-methylamphetamine
- •#94 J; bdb; 2-amino-1-(3,4-methylenedioxyphenyl)butane;
- •#95 Lophophine; 3-methoxy-4,5-methylenedioxyphenethylamine
- •#96 M; mescaline; 3,4,5-trimethoxyphenethylamine
- •#98 Madam-6; 2,n-dimethyl-4,5-methylenedioxyamphetamine
- •#99 Mal; methallylescaline;
- •#100 Mda; 3,4-methylenedioxyamphetamine
- •#101 Mdal; n-allyl-mda; 3,4-methylenedioxy-n- allylamphetamine
- •#102 Mdbu; n-butyl-mda; 3,4-methylenedioxy-n-butylamphetamine
- •#103 Mdbz; n-benzyl-mda; 3,4-methylenedioxy-n-benzylamphetamine
- •#104 Mdcpm; cyclopropylmethyl-mda;
- •#105 Mddm; n,n-dimethyl-mda;
- •#106 Mde; mdea; eve; n-ethyl-mda;
- •#107 Mdhoet; hydroxyethyl-mda;
- •#109 Mdma; mdm; adam; ecstasy; 3,4-methylenedioxy-n-methylamphetamine
- •#110 Mdmc; edma; 3,4-ethylenedioxy-n-methylamphetamine
- •#111 Mdmeo; n-methoxy-mda; 3,4-methylenedioxy-n-methyoxyamphetamine
- •#112 Mdmeoet; n-methoxyethyl-mda;
- •#114 Mdoh; n-hydroxy-mda; 3,4-methylenedioxy-n-hydroxyamphetamine
- •I would put my money on the likelihood of mda going to mdoh if it
- •#115 Mdpea; 3,4-methylenedioxyphenethylamine; homopiperonylamine
- •#116 Mdph; a,a-dimethyl-3,4-methylenedioxy-
- •In symbolic form this is:
- •#117 Mdpl; n-propargyl-mda; n-propynyl-mda;
- •#118 Mdpr; n-propyl-mda; 3,4-methylenedioxy-n-propylamphetamine
- •#119 Me; metaescaline; 3,4-dimethoxy-5-ethoxyphenethylamine
- •#120 Meda; 3-methoxy-4,5-ethylenedioxyamphetamine
- •#121 Mee; 4,5-diethoxy-2-methoxyamphetamine
- •#122 Mem; 2,5-dimethoxy-4-ethoxyamphetamine
- •#123 Mepea; 3-methoxy-4-ethoxyphenethylamine
- •#124 Meta-dob; 5-bromo-2,4-dimethoxyamphetamine
- •#125 Meta-dot; 2,4-dimethoxy-5-methylthioamphetamine
- •#126 Methyl-dma; dmma; 2,5-dimethoxy-n-methylamphetamine
- •#127 Methyl-dob; 4-bromo-2,5-dimethoxy-n-methylamphetamine
- •#130 Methyl-ma; pmma; doone; 4-mma; 4-methoxy-n-methylamphetamine
- •#131 Methyl-mmda-2; 2-methoxy-n-methyl-4,5-methylenedioxyamphetamine
- •#132 Mmda; 3-methoxy-4,5-methylenedioxyamphetamine
- •#133 Mmda-2; 2-methoxy-4,5-methylenedioxyamphetamine
- •#134 Mmda-3a; 2-methoxy-3,4-methylenedioxyamphetamine
- •#135 Mmda-3b; 4-methoxy-2,3-methylenedioxyamphetamine
- •#136 Mme; 2,4-dimethoxy-5-ethoxyamphetamine
- •#137 Mp; metaproscaline; 3,4-dimethoxy-5-(n)-propoxyphenethylamine
- •#138 Mpm; 2,5-dimethoxy-4-(n)-propoxyamphetamine
- •#139 Ortho-dot; 4,5-dimethoxy-2-methylthioamphetamine
- •#140 P; proscaline; 3,5-dimethoxy-4-(n)-propoxyphenethylamine
- •#141 Pe; phenescaline; 3,5-dimethoxy-4-phenethyloxyphenethylamine
- •#142 Pea; phenethylamine
- •#143 Propynyl; 3,5-dimethoxy-4-(2-propynyloxy)phenethylamine
- •#144 Sb; symbescaline; 3,5-diethoxy-4-methoxyphenethylamine
- •#145 Ta; 2,3,4,5-tetramethoxyamphetamine
- •#146 3-Tasb; 3-thioasymbescaline;
- •#147 4-Tasb; 4-thioasymbescaline;
- •#148 5-Tasb; 5-thioasymbescaline;
- •#149 Tb; 4-thiobuscaline; 3,5-dimethoxy-4-(n)-butylthiophenethylamine
- •#150 3-Te; 3-thioescaline;
- •#151 Te; 4-te; 4-thioescaline; 3,5-dimethoxy-4-ethylthiophenethylamine
- •#153 3-Tim; 3-thiomescaline; 2,4-dimethoxy-3-methylthiophenethylamine
- •#154 4-Tim; 4-thioisomescaline;
- •#155 3-Tm; 3-thiomescaline; 3,4-dimethoxy-5-methylthiophenethylamine
- •#156 Tm; 4-tm; 4-thiomescaline;
- •#157 Tma; 3,4,5-trimethoxyamphetamine
- •#158 Tma-2; 2,4,5-trimethoxyamphetamine
- •#159 Tma-3; 2,3,4-trimethoxyamphetamine
- •#160 Tma-4; 2,3,5-trimethoxyamphetamine
- •#161 Tma-5; 2,3,6-trimethoxyamphetamine
- •#162 Tma-6; 2,4,6-trimethoxyamphetamine
- •#163 3-Tme; 3-thiometaescaline;
- •#164 4-Tme; 4-thiometaescaline;
- •#165 5-Tme; 5-thiometaescaline;
- •#166 2T-mmda-3a; 3,4-methylenedioxy-2-methylthioamphetamine
- •#167 4T-mmda-2; 6-(2-aminopropyl)-5-methoxy-1,3-benzoxathiol;
- •#168 Tmpea; 2,4,5-trimethoxyphenethylamine
- •#169 2-Toet; 4-ethyl-5-methoxy-2-methylthioamphetamine
- •#170 5-Toet; 4-ethyl-2-methoxy-5-methylthioamphetamine
- •#171 2-Tom; 5-methoxy-4-methyl-2-methylthioamphetamine
- •#172 5-Tom; 2-methoxy-4-methyl-5-methylthioamphetamine
- •#173 Tomso; 2-methoxy-4-methyl-5-methylsulfinylamphetamine
- •#174 Tp; thioproscaline; 3,5-dimethoxy-4-(n)-propylthiophenethylamine
- •#175 Tris; trescaline; trisescaline; 3,4,5-triethoxyphenethylamine
- •#176 3-Tsb; 3-thiosymbescaline;
- •#177 4-Tsb; 4-thiosymbescaline;
- •#178 3-T-tris; 3-thiotrescaline; 3-thiotrisescaline;
- •#179 4-T-tris; 4-thiotrescaline; 4-thiotrisescaline;
#159 Tma-3; 2,3,4-trimethoxyamphetamine
SYNTHESIS: To a solution of 12.4 g 2,3,4-trimethoxybenzaldehyde in 45 mL glacial acetic acid, there was added 7 mL nitroethane and 4.1 g anhydrous ammonium acetate, and all was held at reflux temperature for 1.5 h. To the cooled and well stirred reaction mixture, H2O was added slowly, dropping out an oily crystalline solid mass. This was separated by filtration, and ground under a quantity of 50% aqueous acetic acid, and re-filtered. The 6.5 g of crude product was recrystallized from boiling MeOH to give, after air drying to constant weight, 5.0 g of 2-nitro-1-(2,3,4-trimethoxyphenyl)propene, with a mp of 56-57 deg C. Anal. (C12H15NO5) C,H.
To a gently refluxing suspension of 3.0 g LAH in 300 mL anhydrous Et2O under a He atmosphere, there was added 3.65 g 2-nitro-1-(2,3,4-trimethoxyphenyl)propene by allowing the condensing Et2O drip into a shunted Soxhlet thimble containing the nitrostyrene and effectively adding a warm saturated solu-tion of it dropwise. Refluxing was maintained for 5 h following the completion of the addition of the nitrostyrene. The milky reaction mixture was cooled and the excess hydride destroyed by the addition of 200 mL 10% H2SO4. When the aqueous and Et2O layers were finally clear, they were separated, and 75 g of potassium sodium tartrate was dissolved in the aqueous fraction. NaOH (25%) was then added until the pH was >9, and this was then extracted with 3x75 mL CH2Cl2. Evaporation of the solvent under vacuum produced 2.5 g of a nearly colorless clear oil that was dissolved in 300 mL anhydrous Et2O which was saturated with anhydrous HCl gas. The product, 2,3,4-trimethoxyamphetamine hydrochloride (TMA-3) separated as a fine white solid. This was removed by filtration, Et2O washed, and air dried to constant weight. The yield was 1.65 g of a product which, after recrystallization from IPA, had a mp of 148-149 deg C. Anal. (C12H20ClNO3) C,H.
DOSAGE: greater than 100 mg.
DURATION: unknown.
QUALITATIVE COMMENTS: (with 100 mg) There were no effects at all. No eye dilation, no believable diversion from complete normalcy. Appetite was normal, as well.
EXTENSIONS AND COMMENTARY: There is a small lesson to be learned from this completely inactive compound. There is no way of saying that it is or is not in-active. All that can be said is that trials were made (in this case using three separate individuals) at an oral level of 100 milligrams. And, at this level, nothing happened. And since a bottom threshold for mescaline would be perhaps 200 milligrams, it can be honestly said that the activity of this compound, if expressed relative to mescaline (using mescaline units) is less than 2 M.U. Had 200 milligrams been inactive, it would have been less than 1.0 M.U. If 2 grams had been inactive, it would have been less than 0.1 M.U. But the actual printed form, activity < 2.0 M.U. was accepted by many readers as indicating that TMA-3 was active, but at dosages greater than 100 milligrams. All that can be said is, if there is activity, then it will be at oral levels greater than 100 milligrams At the moment, as far as I know, this compound is not active in man, but then I know of no trials in excess of 100 milligrams.
This admonition applies to all the published M.U. values that are preceded by the "less than" sign, the "<."