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Description

TMA-2 Also known as:

  • 1-(2,4,5-Trimethoxyphenyl)-2-aminopropane
  • 1-(2,4,5-Trimethoxyphenyl)-2-propanamin[German][ACD/IUPAC Name]
  • 1-(2,4,5-Trimethoxyphenyl)-2-propanamine[ACD/IUPAC Name]
  • 1-(2,4,5-Triméthoxyphényl)-2-propanamine[French][ACD/IUPAC Name]
  • 1-(2,4,5-trimethoxyphenyl)propan-2-amine
  • 2,4,5-trimethoxyamphetamine
  • Benzeneethanamine, 2,4,5-trimethoxy-α-methyl-[ACD/Index Name]
  • Benzeneethanamine, 2,4,5-trimethoxy-α-methyl-, (±)-
  • Phenethylamine, 2,4,5-trimethoxy-α-methyl-
  • Phenethylamine, α-methyl-2,4,5-trimethoxy-
  • (±)1-Methyl-2-(2,4,5-trimethoxy-phenyl)-ethylamine
  • 1-Methyl-2-(2,4,5-trimethoxyphenyl)ethylamine
  • 1-Methyl-2-(2,4,5-trimethoxy-phenyl)-ethylamine
  • 1-Methyl-2-(2,4,5-trimethoxy-phenyl)-ethylamine(2,4,5-TMA)
  • 2,4,5-trimethoxy-?-methyl-benzeneethanamine
  • 2,4,5-TRIMETHOXYAMPHETAMIN
  • 2,4,5-TRIMETHOXYAMPHETAMIN, >99% (HPLC)
  • 2,4,5-TRIMETHOXYAMPHETAMINE, DL-
  • 2,4,5-trimethoxy-α-methyl-benzeneethanamine
  • 2,4,5-trimethoxy-α-methyl-benzeneethanamine
  • 2,4,5-Trimethoxy-α-methylbenzeneethanamine
  • 2,4,5-Trimethoxy-α-methylphenethylamine
  • 2,4,5-Trimethoxy-α-methylphenethylamine
  • amphetamine, 2,4,5-trimethoxy-
  • BENZENEETHANAMINE,2,4,5-TRIMETHOXY-A-METHYL-
  • Benzeneethanamine,2,4,5-trimethoxy-a-methyl-,hydrochloride (1:1)
  • Benzeneethanamine,2,4,5-trimethoxy-α-methyl-(±)-
  • MFCD01707971
  • Phenethylamine, 2,4,5-trimethoxy-α-methyl-
  • Phenethylamine, α-methyl-2,4,5-trimethoxy-
  • TMA-2

Trimethoxyamphetamine-2, a psychedelic amphetamine and stimulant first synthesised by Alexander Shulgin. An uncommon compound of similar activity to other psychedelic amphetamines. Short history of human use.

Summary

TMA-2 along with TMA-6 and others are members of the trimethoxylated family of phenethylamines. Members in this family been observed to produce a complex mixture of hallucinogenic, stimulant, psychedelic and entactogenic effects that qualitatively separates it from other psychedelic phenethylamine compounds like members of the 2C-x or DOx series. TMA-2 was first synthesized by Viktor Bruckner in 1933, but was not investigated as a psychoactive chemical until Alexander Shulgin synthesized and tested it in 1962.

Shulgin published his synthesis and initial research findings in a 1964 paper, describing the effects as similar to mescaline, though lacking in color effects, producing less nausea and prone to causing anxiety and restlessness. . There are occasional references to the use of TMA-2 in early 1970’s counter-culture publications, describing the drug as being rarely produced for sale and expensive in comparison to LSD.

This suggests that there was only very limited human usage of TMA-2 between its invention and the publication of its synthesis and pharmacology in Shulgin’s 1991 book PiHKAL (“Phenethylamines I Have Known And Loved”). Since then it has been regarded as an oddball and a novelty in the psychedelics community and is only occasionally sought after intentionally. In terms of its subjective effects, it is known for its lack of classic psychedelic visuals compared to its parent compound (mescaline) and is known instead for its instead a unique stimulating body-high and altered headspace that ranges from euphoric to dysphoric variably.

Anecdotal reports suggest that TMA-2 is a highly unpredictable and dose-sensitive substance that can produce uncomfortable amounts of body load, nausea, overstimulation, and inconsistencies between experiences. In modern times, TMA-2 is used as an obscure recreational drug and a occasional entheogen. It is rarely sold on the streets and is almost exclusively obtainable as a grey area research chemical through the use of online vendors.

Chemistry

Amphetamines are substituted phenethylamines, being comprised of a phenyl ring bound to an amino (NH2) group through an ethyl chain and a methyl group bound to the alpha carbon Rα.

TMA-2 contains methoxy functional groups CH3O- attached to carbons R2 and R4 and R5 of the amphetamine backbone.

Common Name2,4,5-trimethoxyamphetamine
Systematic name2,4,5-trimethoxyamphetamine
FormulaC_{12}H_{19}NO_{3}
SMILESCC(Cc1cc(c(cc1OC)OC)OC)N
Std. InChiInChI=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
Std. InChiKeyTVSIMAWGATVNGK-UHFFFAOYSA-N
Avg. Mass225.2842 Da
Molecular Weight225.2842
Monoisotopic Mass225.13649 Da
Nominal Mass225
ChemSpider ID28773

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Dose Chart

Oral
Threshold5-10mg
Light10-20mg
Common20-40mg
Strong40-60mg+

Duration Chart

TMA-2 Duration Data
Onset20-120 minutes
Duration6-12 hours
After-effectsPossibility hours

Legal Status

  • Austria: TMA-2 is illegal to possess, produce and sell under the SMG (Suchtmittelgesetz Österreich).
  • Germany: TMA-2 is controlled under Anlage I BtMG (Narcotics Act, Schedule I) as of October 10, 1999. It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.
  • Switzerland: TMA-2 is a controlled substance in Switzerland.

    • Sources

    References

    1. Bruckner, V. (1933), Über das Pseudonitrosit des Asarons. J. Prakt. Chem., 138: 268–274. doi:10.1002/prac.19331380907 | http://onlinelibrary.wiley.com/doi/10.1002/prac.19331380907/abstract
    2. Shulgin, Alexander. "Pharmacology Lab Notes #1". Lafayette, CA. (1960-1976). p54 (Erowid.org) | https://erowid.org/library/books_online/shulgin_labbooks/shulgin_labbook1_searchable.pdf
    3. Shulgin, A.T. Experientia (1964) 20: 366. doi:10.1007/BF02147960 | https://erowid.org/archive/rhodium/chemistry/shulgin.meo-34-dialkoxyamphetamines.html
    4. 'Acidman'. "Straight Dope". Berkeley Tribe, December 18-25, 1970 p23 (Independent Voices) | http://voices.revealdigital.com/cgi-bin/independentvoices?a=d&d=BFBJFGJ19701218.1.23
    5. Lampe, Matt. "Dope-O-Scope". Ann Arbor Sun, November 12-25, 1971, p16 (Independent Voices) | http://voices.revealdigital.com/cgi-bin/independentvoices?a=d&d=BFBJFGJ19701218.1.23
    6. https://www.erowid.org/library/books_online/pihkal/pihkal162.shtml
    7. "Dreizehnte Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften" (in German). Bundesanzeiger Verlag. Retrieved December 11, 2019.
    8. "Anlage I BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 11, 2019.
    9. "§ 29 BtMG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 11, 2019.
    10. https://www.admin.ch/opc/de/classified-compilation/20101220/index.html

    Information made possible with:

    1. PsychonautWiki is a community-driven online encyclopedia that aims to document the field of psychonautics in a comprehensive, scientifically-grounded manner.
    2. Erowid is a non-profit educational & harm-reduction resource with 60 thousand pages of online information about psychoactive drugs
    3. PubChem National Center for Bio Informatics
    4. Chemspider is a free chemical structure database providing fast access to over 34 million structures, properties and associated information.
    5. Wikipedia

    Additional APIs were used to construct this information. Thanks to ChemSpider, NCBI, PubChem etc.

    Data is constantly updated so please check back later to see if there is any more available information on this substance.