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Summary - Bruckner's synthesis, Shulgin's tests and publication, early reports of human use
>Larnaca
Undo revision 166774 by Blackhole (talk)
 
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{{SummarySheet}}
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{{SubstanceBox/TMA-2}}
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'''2,4,5-Trimethoxyamphetamine''' (abbreviated '''TMA-2''') is a synthetic [[psychoactive class::psychedelic]] [[substituted amphetamine|amphetamine]] and the amphetamine homologue of [[TMPEA-2]] known to produce a unique spectrum of [[hallucinogenic]] and [[stimulant]] effects that differ substantially from other psychoactive [[chemical class::phenethylamines]]. 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 [[hallucinogen]]ic, [[stimulant]], [[psychedelic]] and [[entactogen]]ic 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<ref>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</ref>, but was not investigated as a psychoactive chemical until [[Alexander Shulgin]] synthesized and tested it in 1962<ref>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</ref>. 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.<ref>Shulgin, A.T. Experientia (1964) 20: 366. doi:10.1007/BF02147960 | https://erowid.org/archive/rhodium/chemistry/shulgin.meo-34-dialkoxyamphetamines.html</ref>.
'''2,4,5-Trimethoxyamphetamine''' (abbreviated '''TMA-2''') is a synthetic [[psychoactive class::psychedelic]] [[chemical class::substituted amphetamine|amphetamine]]
known to produce a unique spectrum of [[hallucinogenic]] and [[stimulant]] effects that differ substantially from other psychoactive [[phenethylamines]]. 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 [[hallucinogen]]ic, [[stimulant]], [[psychedelic]] and [[entactogen]]ic effects that qualitatively separates it from other psychedelic phenethylamine compounds like members of the [[2C-x]] or [[DOx]] series.  


There are occasional references to the use of TMA-2 in early 1970's counter-culture publications<ref>'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</ref><ref>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</ref>, 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.
TMA-2 was first synthesized by Viktor Bruckner in 1933<ref>{{cite journal | vauthors=((Bruckner, V.)) | journal=Journal für Praktische Chemie | title=Über das Pseudonitrosit des Asarons | volume=138 | issue=9–10 | pages=268–274 | date=24 October 1933 | url=https://onlinelibrary.wiley.com/doi/10.1002/prac.19331380907 | issn=00218383 | doi=10.1002/prac.19331380907}}</ref>, but was not investigated as a psychoactive chemical until [[Alexander Shulgin]] synthesized and tested it in 1962<ref>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</ref>. 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.<ref>{{cite journal | vauthors=((Shulgin, A. T.)) | journal=Experientia | title=Psychotomimetic amphetamines: Methoxy 3,4-dialkoxyamphetamines | volume=20 | issue=7 | pages=366–367 | date= July 1964 | url=http://link.springer.com/10.1007/BF02147960 | issn=0014-4754 | doi=10.1007/BF02147960}}</ref>.
 
There are occasional references to the use of TMA-2 in early 1970's counter-culture publications<ref>'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</ref><ref>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</ref>, 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 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.
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.
Line 16: Line 14:


==Chemistry==
==Chemistry==
TMA-2, or 2,4,5-trimethoxyamphetamine, is a molecule of the [[substituted amphetamine]] class. Amphetamines are substituted phenethylamines, being comprised of a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain and a methyl group bound to the alpha carbon R<sub>α</sub>. TMA-2 contains methoxy functional groups CH<sub>3</sub>O- attached to carbons R<sub>2</sub> and R<sub>4</sub> and R<sub>5</sub> of the amphetamine backbone.<ref>https://www.erowid.org/library/books_online/pihkal/pihkal162.shtml</ref>
TMA-2, or 2,4,5-trimethoxyamphetamine, is a molecule of the [[substituted amphetamine]] class. Amphetamines are substituted phenethylamines, being comprised of a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain and a methyl group bound to the alpha carbon R<sub>α</sub>. TMA-2 contains methoxy functional groups CH<sub>3</sub>O- attached to carbons R<sub>2</sub> and R<sub>4</sub> and R<sub>5</sub> of the amphetamine backbone.<ref>{{Citation | title=Erowid Online Books : “PIHKAL” - #162 TMA-6 | url=https://www.erowid.org/library/books_online/pihkal/pihkal162.shtml}}</ref>


==Pharmacology==
==Pharmacology==
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{{EffectStub}}
{{EffectStub}}
{{Preamble/SubjectiveEffects}}
{{Preamble/SubjectiveEffects}}
 
{{effects/base
===Physical effects===
|{{effects/physical|
*'''[[Effect::Spontaneous physical sensations]]''' - The "body high" of TMA-2 is manifested as somewhat intense in comparison to most classical psychedelics such as [[LSD]]. The sensation itself can be described as a constantly present yet somewhat mild energetic pins and needles sensation that encompasses a person’s entire body. It is usually felt over every square inch of the skin, but occasionally manifests itself in the form of a continuously shifting tingling sensation that travels up and down the body in spontaneous waves.
*'''[[Effect::Stimulation]]''' - In terms of its effects on the physical energy levels of the user, TMA-2 is usually considered to be extremely stimulating at levels which do not become overwhelming, resulting in a shakiness and unsteadiness of the hands but encouraging one to move around, run, dance, climb and generally engage in physical activities. In comparison, other more commonly used psychedelics such as [[psilocin]] are generally sedating and relaxed.
*'''[[Effect::Stimulation]]''' - In terms of its effects on the physical energy levels of the tripper, TMA-2 is usually considered to be extremely stimulating at levels which do not become overwhelming, resulting in a shakiness and unsteadiness of the hands but encouraging one to move around, run, dance, climb and generally engage in physical activities. In comparison, other more commonly used psychedelics such as [[psilocin]] are generally sedating and relaxed.
*'''[[Effect::Spontaneous bodily sensations]]''' - The "body high" of TMA-2 is manifested as somewhat intense in comparison to most classical psychedelics such as [[LSD]]. The sensation itself can be described as a constantly present yet somewhat mild energetic pins and needles sensation that encompasses a person’s entire body. It is usually felt over every square inch of the skin, but occasionally manifests itself in the form of a continuously shifting tingling sensation that travels up and down the body in spontaneous waves.
*'''[[Effect::Tactile enhancement]]''' - Feelings of enhanced tactile sensation are consistently present at moderate levels throughout most TMA-2 trips.  
*'''[[Effect::Tactile enhancement]]''' - Feelings of enhanced tactile sensation are consistently present at moderate levels throughout most TMA-2 trips.  
*'''[[Effect::Nausea]]''' -  Mild to extreme nausea is reported when consumed in moderate to high dosages and either passes once the person has vomited or gradually fades by itself as the peak sets in.  
*'''[[Effect::Nausea]]''' -  Mild to extreme nausea is reported when consumed in moderate to high dosages and either passes once the person has vomited or gradually fades by itself as the peak sets in.  
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*'''[[Effect::Increased blood pressure]]'''
*'''[[Effect::Increased blood pressure]]'''


===Cognitive effects===
}}
 
{{effects/visual|
====Enhancements====
*'''[[Effect::Visual acuity enhancement]]'''
*'''[[Effect::Colour enhancement]]'''
*'''[[Effect::Pattern recognition enhancement]]'''
 
====Distortions====
*'''[[Effect::Drifting]]''' ''([[Drifting#Melting|melting]], [[Drifting#Flowing|flowing]], [[Drifting#Breathing|breathing]] and [[Drifting# morphing|morphing]])'' - In comparison to other psychedelics, this effect can be described as highly detailed, slow and smooth in motion, static in appearance and unrealistic/cartoon-like in style.
*'''[[Effect::Tracers]]'''
*'''[[Effect::After images]]'''
*'''[[Effect::Symmetrical texture repetition]]'''
*'''[[Effect::Colour shifting]]'''
*'''[[Effect::Diffraction]]'''
 
}}
 
|{{effects/cognitive|
The cognitive effects of TMA-2 are described as powerful mental stimulation along with undertones of intoxication that can increase the connectivity and rate of conceptual thinking without being overwhelming.
The cognitive effects of TMA-2 are described as powerful mental stimulation along with undertones of intoxication that can increase the connectivity and rate of conceptual thinking without being overwhelming.


The total sum of these cognitive components regardless of the setting generally includes:
The total sum of these cognitive components regardless of the setting generally includes:


*'''[[Effect::Empathy, love, and sociability enhancement]]''' - This component is consistently manifested only in the context of social settings in which one is within the company of others. These feelings of sociability, love and empathy are weaker and sharper than those found on substances such as [[MDMA]] and [[2C-B]], but still can elevate one's mood.  
*'''[[Effect::Empathy, affection, and sociability enhancement]]''' - This component is consistently manifested only in the context of social settings in which one is within the company of others. These feelings of sociability, love and empathy are weaker and sharper than those found on substances such as [[MDMA]] and [[2C-B]], but still can elevate one's mood.  
*'''[[Effect::Analysis enhancement]]'''
*'''[[Effect::Analysis enhancement]]'''
*'''[[Effect::Thought acceleration]]'''
*'''[[Effect::Thought acceleration]]'''
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*'''[[Effect::Increased libido]]'''
*'''[[Effect::Increased libido]]'''


===Visual effects===
}}
====Enhancements====
*'''[[Effect::Visual acuity enhancement]]'''
*'''[[Effect::Colour enhancement]]'''
*'''[[Effect::Pattern recognition enhancement]]'''
 
====Distortions====
*'''[[Effect::Drifting]]''' ''([[Drifting#Melting|melting]], [[Drifting#Flowing|flowing]], [[Drifting#Breathing|breathing]] and [[Drifting# morphing|morphing]])'' - In comparison to other psychedelics, this effect can be described as highly detailed, slow and smooth in motion, static in appearance and unrealistic/cartoon-like in style.
*'''[[Effect::Tracers]]'''
*'''[[Effect::After images]]'''
*'''[[Effect::Symmetrical texture repetition]]'''
*'''[[Effect::Colour shifting]]'''
*'''[[Effect::Diffraction]]'''


===Auditory effects===
{{effects/auditory|
*'''[[Effect::Auditory enhancement|Enhancements]]'''
*'''[[Effect::Auditory enhancement|Enhancements]]'''
*'''[[Effect::Auditory distortion|Distortions]]'''
*'''[[Effect::Auditory distortion|Distortions]]'''
*'''[[Effect::Auditory hallucinations|Hallucinations]]'''
*'''[[Effect::Auditory hallucinations|Hallucinations]]'''
}}


}}
===Experience reports===
===Experience reports===
Anecdotal reports which describe the effects of this compound within our [[experience index]] include:
Anecdotal reports which describe the effects of this compound within our [[experience index]] include:
{{#ask: [[Category:TMA-2]][[Category:Experience]]|format=ul|Columns=1}}
{{#ask: [[Category:TMA-2]][[Category:Experience]]|format=ul|Columns=1}}
Additional experience reports can be found here:
Additional experience reports can be found here:
* [https://erowid.org/experiences/subs/exp_TMA-2.shtml Erowid Experience Vaults: TMA-2]
 
*[https://erowid.org/experiences/subs/exp_TMA-2.shtml Erowid Experience Vaults: TMA-2]


==Toxicity and harm potential==
==Toxicity and harm potential==
{{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}}
{{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}}
Toxicity studies in rats have been showed TMA-2 doses of 80 mg/kg induced frequent clonic convulsions. A dose of 120 mg/kg was associated with fatal toxic effects. It was estimated that the LD50 of mice to be 180mg/kg.<ref>{{cite book | veditors=((European Monitoring Centre for Drugs and Drug Addiction)) | date= 2004 | title=Report on the risk assessment of TMA-2 in the framework of the joint action on new synthetic drugs | publisher=Office for Official Publications of the European Communities | series=EMCDDA risk assessments | isbn=9789291681822}}</ref>
The toxicity and long-term health effects of recreational TMA-2 use do not seem to have been studied in any scientific context and the exact [[Toxicity::toxic dose is unknown]]. This is because TMA-2 has very little history of human usage. Anecdotal evidence from people within the psychonaut community who have tried TMA-2 suggests that there are no negative health effects attributed to simply trying the drug by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption.
The toxicity and long-term health effects of recreational TMA-2 use do not seem to have been studied in any scientific context and the exact [[Toxicity::toxic dose is unknown]]. This is because TMA-2 has very little history of human usage. Anecdotal evidence from people within the psychonaut community who have tried TMA-2 suggests that there are no negative health effects attributed to simply trying the drug by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption.


Line 93: Line 102:
Tolerance to the effects of TMA-2 are built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::3 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::7 days]] to be back at baseline (in the absence of further consumption). TMA-2 presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of TMA-2 all psychedelics will have a reduced effect.
Tolerance to the effects of TMA-2 are built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::3 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::7 days]] to be back at baseline (in the absence of further consumption). TMA-2 presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of TMA-2 all psychedelics will have a reduced effect.


==Legal issues==
==Legal status==
{{legalStub}}
{{legalStub}}
*'''Switzerland:''' TMA-2 is a controlled substance in Switzerland.<ref>https://www.admin.ch/opc/de/classified-compilation/20101220/index.html</ref>
In November 2003, the European Council decided that TMA-2 shall be subjected by the Member States to control measures and criminal penalties within three months.<ref>{{cite magazine|url=http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2003:321:0064:0065:EN:PDF|title=COUNCIL DECISION 2003/847/JHA|date=November 27, 2003|publication-date=December 6, 2003|work=Official Journal of the European Union|pages=64-65|id=L 321|publisher=Office for Official Publications of the European Communites|oclc=52224955}}</ref>
 
*'''Austria''': TMA-2 is illegal to possess, produce and sell under the SMG (Suchtmittelgesetz Österreich).{{citation needed}}
*'''Germany''': TMA-2 is controlled under Anlage I BtMG (Narcotics Act, Schedule I) as of October 10, 1999.<ref>{{cite web|url=https://www.bgbl.de/xaver/bgbl/start.xav?start=%2F%2F*[%40attr_id%3D%27bgbl109s0049.pdf%27]#__bgbl__%2F%2F*%5B%40attr_id%3D%27bgbl199s1935.pdf%27%5D__1576114019111|title=Dreizehnte Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften|publisher=Bundesanzeiger Verlag|access-date=December 11, 2019|language=de}}</ref><ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html|title=Anlage I BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 11, 2019|language=de}}</ref> It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/__29.html|title=§ 29 BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 11, 2019|language=de}}</ref>
*'''Switzerland''': TMA-2 is a controlled substance specifically named under Verzeichnis D.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref>
*'''Turkey:''' TMA-2 is a classed as drug and is illegal to possess, produce, supply, or import.<ref name="Bakanlar Kurulu Kararı - Karar Sayısı : 2013/5742">https://resmigazete.gov.tr/eskiler/2014/01/20140125-3.htm</ref> <ref name="List of illegal substances for law"> https://resmigazete.gov.tr/eskiler/2014/01/20140125-3-1.pdf</ref>
*'''United Kingdom:''' TMA-2 is a controlled Class A drug under the Misuse of Drugs Act 1977 and is covered by the generic definition (TMA-2 is a positional isomer of the UN controlled drug TMA).{{citation needed}}


==See also==
==See also==
*[[Responsible use]]
*[[Responsible use]]
*[[Research chemicals]]
*[[Research chemicals]]
Line 108: Line 124:


==External links==
==External links==
*[http://www.erowid.org/chemicals/TMA-2/TMA-2.shtml TMA-2 (Erowid)]
 
*[https://en.wikipedia.org/wiki/Trimethoxyamphetamine Trimethoxyamphetamine (Wikipedia)]
*[https://erowid.org/chemicals/tma2/ TMA-2 (Erowid Vault)]
*[https://isomerdesign.com/PiHKAL/read.php?domain=pk&id=158 TMA-2 (PiHKAL / Isomer Design)]
 
===Discussion===
 
*[http://www.bluelight.org/vb/threads/115050-The-Big-amp-Dandy-TMA-Series-Thread The Big & Dandy TMA Series Thread (Bluelight)]
*[http://www.bluelight.org/vb/threads/115050-The-Big-amp-Dandy-TMA-Series-Thread The Big & Dandy TMA Series Thread (Bluelight)]
*[http://factsheet.tripsit.me/TMA-2 TMA-2 (TripSit)]
*[https://en.wikipedia.org/wiki/Trimethoxyamphetamine Trimethoxyamphetamine (Wikipedia)]


==References==
==References==
<references/>
<references />
 
[[Category:Psychoactive substance]]
[[Category:Psychoactive substance]]
[[Category:DOx]]
[[Category:Psychedelic]]
[[Category:Stimulant]]
[[Category:Research chemical]]
[[Category:Research chemical]]
[[Category:Phenethylamine]]
[[Category:Psychedelic]]
[[Category:Amphetamine]]


{{#set:Featured=true
{{#set:Featured=true

Latest revision as of 23:58, 2 May 2025

Summary sheet: TMA-2
TMA-2
Chemical Nomenclature
Common names TMA-2
Substitutive name 2,4,5-Trimethoxyamphetamine
Systematic name 1-(2,4,5-Trimethoxyphenyl)propan-2-amine
Class Membership
Psychoactive class Psychedelic / Stimulant
Chemical class Amphetamine
Routes of Administration

WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.



Oral
Dosage
Threshold 5 mg
Light 10 - 20 mg
Common 20 - 40 mg
Strong 40 - 60 mg
Heavy 60 mg +
Duration
Total 8 - 12 hours
Onset 20 - 120 minutes
Come up 1.5 - 3 hours
Peak 4 - 6 hours
Offset 2 - 4 hours
After effects 4 - 24 hours









DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.

Interactions


2,4,5-Trimethoxyamphetamine (abbreviated TMA-2) is a synthetic psychedelic amphetamine known to produce a unique spectrum of hallucinogenic and stimulant effects that differ substantially from other psychoactive phenethylamines. 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[1], but was not investigated as a psychoactive chemical until Alexander Shulgin synthesized and tested it in 1962[2]. 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.[3].

There are occasional references to the use of TMA-2 in early 1970's counter-culture publications[4][5], 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 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

TMA-2, or 2,4,5-trimethoxyamphetamine, is a molecule of the substituted amphetamine class. 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.[6]

Pharmacology

This pharmacology section is incomplete.

You can help by adding to it.

Further information: Serotonergic psychedelic

TMA-2's psychedelic effects are believed to come from its efficacy at the 5-HT2A receptor as a partial agonist. However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive.

Subjective effects

This subjective effects section is a stub.

As such, it is still in progress and may contain incomplete or wrong information.

You can help by expanding or correcting it.

Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWiki contributors. As a result, they should be viewed with a healthy degree of skepticism.

It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.

Physical effects

Visual effects

Cognitive effects

Experience reports

Anecdotal reports which describe the effects of this compound within our experience index include:

Additional experience reports can be found here:

Toxicity and harm potential

Toxicity studies in rats have been showed TMA-2 doses of 80 mg/kg induced frequent clonic convulsions. A dose of 120 mg/kg was associated with fatal toxic effects. It was estimated that the LD50 of mice to be 180mg/kg.[7]

The toxicity and long-term health effects of recreational TMA-2 use do not seem to have been studied in any scientific context and the exact toxic dose is unknown. This is because TMA-2 has very little history of human usage. Anecdotal evidence from people within the psychonaut community who have tried TMA-2 suggests that there are no negative health effects attributed to simply trying the drug by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.

Tolerance and addiction potential

TMA-2 is not habit-forming and the desire to use it can actually decrease with use. It is most often self-regulating.

Tolerance to the effects of TMA-2 are built almost immediately after ingestion. After that, it takes about 3 days for the tolerance to be reduced to half and 7 days to be back at baseline (in the absence of further consumption). TMA-2 presents cross-tolerance with [[Cross-tolerance::all psychedelics]], meaning that after the consumption of TMA-2 all psychedelics will have a reduced effect.

This legality section is a stub.

As such, it may contain incomplete or wrong information. You can help by expanding it.

In November 2003, the European Council decided that TMA-2 shall be subjected by the Member States to control measures and criminal penalties within three months.[8]

  • Austria: TMA-2 is illegal to possess, produce and sell under the SMG (Suchtmittelgesetz Österreich).[citation needed]
  • Germany: TMA-2 is controlled under Anlage I BtMG (Narcotics Act, Schedule I) as of October 10, 1999.[9][10] It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.[11]
  • Switzerland: TMA-2 is a controlled substance specifically named under Verzeichnis D.[12]
  • Turkey: TMA-2 is a classed as drug and is illegal to possess, produce, supply, or import.[13] [14]
  • United Kingdom: TMA-2 is a controlled Class A drug under the Misuse of Drugs Act 1977 and is covered by the generic definition (TMA-2 is a positional isomer of the UN controlled drug TMA).[citation needed]

See also

Discussion

References

  1. Bruckner, V. (24 October 1933). "Über das Pseudonitrosit des Asarons". Journal für Praktische Chemie. 138 (9–10): 268–274. doi:10.1002/prac.19331380907. ISSN 0021-8383. 
  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. (July 1964). "Psychotomimetic amphetamines: Methoxy 3,4-dialkoxyamphetamines". Experientia. 20 (7): 366–367. doi:10.1007/BF02147960. ISSN 0014-4754. 
  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. Erowid Online Books : “PIHKAL” - #162 TMA-6 
  7. European Monitoring Centre for Drugs and Drug Addiction, ed. (2004). Report on the risk assessment of TMA-2 in the framework of the joint action on new synthetic drugs. EMCDDA risk assessments. Office for Official Publications of the European Communities. ISBN 9789291681822. 
  8. "COUNCIL DECISION 2003/847/JHA". Official Journal of the European Union. Office for Official Publications of the European Communites (published December 6, 2003). November 27, 2003. pp. 64–65. OCLC 52224955. L 321. 
  9. "Dreizehnte Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften" (in Deutsch). Bundesanzeiger Verlag. Retrieved December 11, 2019. 
  10. "Anlage I BtMG" (in Deutsch). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 11, 2019. 
  11. "§ 29 BtMG" (in Deutsch). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 11, 2019. 
  12. "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in Deutsch). Bundeskanzlei [Federal Chancellery of Switzerland]. Retrieved January 1, 2020. 
  13. https://resmigazete.gov.tr/eskiler/2014/01/20140125-3.htm
  14. https://resmigazete.gov.tr/eskiler/2014/01/20140125-3-1.pdf