Trimethoxyamphetamine
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TMAs, also known as trimethoxyamphetamines, are a family of isomeric psychedelic hallucinogenic drugs. There exist six different TMAs that differ only in the position of the three methoxy groups: TMA, TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6. The TMAs are analogs of the phenethylamine cactus alkaloid mescaline. The TMAs are substituted amphetamines, however, their action does not resemble that of the unsubstituted compound amphetamine, which is a stimulant and not a psychedelic. It is reported that some TMA's exhibit a range of emotions ranging from sadness to empathy and euphoria. Several TMAs were first synthesized by the chemist Alexander Shulgin. Synthesis data as well as human activity data has been published in the book PIHKAL.
Contents |
[edit] TMAs
| TMA | |
|---|---|
| Chemical name | 1-(3,4,5-Trimethoxyphenyl)propan-2-amine, 3,4,5-trimethoxyamphetamine |
| Melting point | 220 - 221 °C (hydrochloride) |
| SMILES | NC(C)CC1=CC(OC)=C(OC)C(OC)=C1 |
| CAS number 1082-88-8 |
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| TMA-2 | |
|---|---|
| Chemical name | 1-(2,4,5-Trimethoxyphenyl)propan-2-amine, 2,4,5-trimethoxyamphetamine |
| Melting point | 188.5 - 189.5 °C (hydrochloride) |
| SMILES | NC(C)CC1=C(OC)C=C(OC)C(OC)=C1 |
| CAS number 1083-09-6 |
 |
| TMA-3 | |
|---|---|
| Chemical name | 1-(2,3,4-Trimethoxyphenyl)propan-2-amine, 2,3,4-trimethoxyamphetamine |
| Melting point | 148 - 149 °C (hydrochloride) |
| SMILES | NC(C)CC1=CC=C(OC)C(OC)=C1OC |
| CAS number 1082-23-1 |
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| TMA-4 | |
|---|---|
| Chemical name | 1-(2,3,5-Trimethoxyphenyl)propan-2-amine, 2,3,5-trimethoxyamphetamine |
| Melting point | 118 - 119 °C (hydrochloride) |
| SMILES | NC(C)CC1=CC(OC)=CC(OC)=C1OC |
| CAS number 23693-14-3 |
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| TMA-5 | |
|---|---|
| Chemical name | 1-(2,3,6-Trimethoxyphenyl)propan-2-amine, 2,3,6-trimethoxyamphetamine |
| Melting point | 124 - 125 °C (hydrochloride) |
| SMILES | NC(C)CC1=C(OC)C=CC(OC)=C1OC |
| CAS number 20513-16-0 |
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| TMA-6 | |
|---|---|
| Chemical name | 1-(2,4,6-Trimethoxyphenyl)propan-2-amine, 2,4,6-trimethoxyamphetamine |
| Melting point | 207 - 208 °C (hydrochloride) |
| SMILES | NC(C)CC1=C(OC)C=C(OC)C=C1OC |
| CAS number 15402-79-6 |
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[edit] Chemical data
As they are isomeres the TMAs have the same totals formula, C12H19NO3, and the same molecular mass, 225.28 g/mol.
[edit] Properties
| Compound | Pattern | Dose | Duration |
|---|---|---|---|
| TMA | 3,4,5 | 100 - 250 mg | 6 - 8 h |
| TMA-2 | 2,4,5 | 20 - 40 mg | 8 - 12 h |
| TMA-3 | 2,3,4 | > 100 mg | unknown |
| TMA-4 | 2,3,5 | 80 mg | ~ 6 h |
| TMA-5 | 2,3,6 | ≥ 30 mg | 8 - 10 h |
| TMA-6 | 2,4,6 | 25 - 50 mg | 12 - 16 h |
[edit] See also
[edit] Categorization
AEM, AL, Aleph, Aleph-2, Aleph-4, Aleph-6, Aleph-7, Ariadne, Asymbescaline, Buscaline, Beatrice, Bis-TOM, BOB, BOD, BOH, BOHD, BOM, 4-bromo-3,5-dimethoxyamphetamine, 2-bromo-4,5-methylenedioxyamphetamine, 2C-B, 3C-BZ, 2C-C, 2C-D, 2C-E, 3C-E, 2C-F, 2C-G, 2C-G-3, 2C-G-4, 2C-G-5, 2C-G-N, 2C-H, 2C-I, 2C-N, 2C-O-4, 2C-P, CPM, 2C-SE, 2C-T, 2C-T-2, 2C-T-4, psi-2C-T-4, 2C-T-7, 2C-T-8, 2C-T-9, 2C-T-13, 2C-T-15, 2C-T-17, 2C-T-21, 4-D, beta-D, DESOXY, 2,4-DMA, 2,5-DMA, 3,4-DMA, DMCPA, DME, DMMDA, DMMDA-2, DMPEA, DOAM, DOB, DOBU, DOC, DOEF, DOET, DOI, DOM, psi-DOM, DON, DOPR, Escaline, EEE, EEM, EME, EMM, Ethyl-J/EBDB, Ethyl-K, F-2, F-22, Flea, 3C-G-3, 3C-G-4, 3C-G-5, 3C-G-N, Ganesha, HOT-2, HOT-7, HOT-17, IDNNA, Isomescaline, Isoproscaline, Iris, J/BDB, Lophophine, Mescaline, 4-MA, Madam-6, Methallylescaline, MDA, MDAL, MDBU, MDBZ, MDCPM, MDDM, MDE, MDHOET, MDIP, MDMA, MDMC/EDMA, MDMEO, MDMEOET, MDMP, MDOH, MDPEA, MDPH, MDPL, MDPR, Metaescaline, MEDA, MEE, MEM, MEPEA, Meta-DOB, Meta-DOT, Methyl-DMA, Methyl-DOB, Methyl-J/MBDB, Methyl-K, Methyl-MA, Methyl-MMDA-2, MMDA, MMDA-2, MMDA-3a, MMDA-3b, MME, MP, MPM, Ortho-DOT Proscaline, Phenescaline, Phenethylamine, Propynyl, Symbescaline, 2,3,4,5-tetramethoxyamphetamine, 3-TASB, 4-TASB, 5-TASB, Thiobuscaline, 3-TE, 4-TE, 3-TIM, 4-TIM, 5-TIM, 3-TM, 4-TM, TMA, TMA-2, TMA-3, TMA-4, TMA-5, TMA-6, 3-TME, 4-TME, 5-TME, 2T-MMDA-3a, 4T-MMDA-2, TMPEA, 2-TOET, 5-TOET, 2-TOM, 5-TOM, TOMSO, Thioproscaline, Trisescaline, 3-TSB, 4-TSB, 3-T-Trisescaline, 4-T-Trisescaline
