Trimethoxyamphetamines (TMAs) are a family of isomeric psychedelic

hallucinogenic Hallucinogens are a large, diverse class of psychoactive drugs that can produce altered states of consciousness characterized by major alterations in thought, mood, and perception as well as other changes. Most hallucinogens can be categorized ...

drugs. There exist six different TMAs that differ only in the position of the three

methoxy In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position a ...

groups A group is a number of persons or things that are located, gathered, or classed together. Groups of people * Cultural group, a group whose members share the same cultural identity * Ethnic group, a group whose members share the same ethnic ide ...

: TMA, TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6. The TMAs are analogs of the phenethylamine

cactus A cactus (, or less commonly, cactus) is a member of the plant family Cactaceae, a family comprising about 127 genera with some 1750 known species of the order Caryophyllales. The word ''cactus'' derives, through Latin, from the Ancient Gree ...

alkaloid Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...

mescaline. The TMAs are substituted amphetamines, however, their mechanism of action is more complex than that of the unsubstituted compound ''amphetamine'', probably involving agonist activity on serotonin receptors such as the 5HT2A receptor in addition to the generalised dopamine receptor agonism typical of most amphetamines. This action on serotonergic receptors likely underlie the psychedelic effects of these compounds. It is reported that some TMAs elicit a range of emotions ranging from sadness to empathy and euphoria. TMA was first synthesized by Hey, in 1947. Synthesis data as well as

human Humans (''Homo sapiens'') are the most abundant and widespread species of primate, characterized by bipedalism and exceptional cognitive skills due to a large and complex brain. This has enabled the development of advanced tools, cultu ...

activity data has been published in the book '' PiHKAL''. The most important TMA compound from a pharmacological standpoint is TMA-2, as this isomer has been much more widely used as a recreational drug and sold on the

grey market A grey market or dark market (sometimes confused with the similar term " parallel market") is the trade of a commodity through distribution channels that are not authorized by the original manufacturer or trade mark proprietor. Grey market pr ...

as a so-called research chemical; TMA (sometimes referred to as "mescalamphetamine" or TMA-1) and TMA-6 have also been used in this way to a lesser extent. These three isomers are significantly more active as hallucinogenic drugs, and have consequently been placed onto the illegal drug schedules in some countries such as the

Netherlands ) , anthem = ( en, "William of Nassau") , image_map = , map_caption = , subdivision_type = Sovereign state , subdivision_name = Kingdom of the Netherlands , established_title = Before independence , established_date = Spanish Netherl ...

and Japan. The other three isomers TMA-3, TMA-4, and TMA-5 are not known to have been used as recreational drugs to any great extent.

TMAs

Note: Because they are isomers, the TMAs have the same

chemical formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbol ...

, C₁₂H₁₉NO₃, and the same

molecular mass The molecular mass (''m'') is the mass of a given molecule: it is measured in daltons (Da or u). Different molecules of the same compound may have different molecular masses because they contain different isotopes of an element. The related quanti ...

, 225.28 g/mol.

Properties

Legality

Sweden

''Sveriges riksdag'' added TMA-2 to schedule I (''"substances, plant materials and fungi which normally do not have medical use"'') as narcotics in Sweden as of Dec 30, 1999, published by ''Medical Products Agency'' in their regulation LVFS 2004:3 listed as 2,4,5-trimetoxiamfetamin (TMA-2).

United Kingdom

Illegal under the

Psychoactive Substances Act 2016 The Psychoactive Substances Act 2016 (c. 2) is an Act of the Parliament of the United Kingdom intended to restrict the production, sale and supply of a new class of psychoactive substances often referred to as "legal highs". The bill was given R ...

United States of America

3,4,5-Trimethoxyamphetamine is listed as a Schedule 1 controlled substance, along with positional isomers 2,4,5-Trimethoxyamphetamine (TMA-5), 2,4,6-Trimethoxyamphetamine (TMA-6) and

Escaline Escaline (3,5-methoxy-4-ethoxyphenethylamine) is a psychedelic drug and entheogen of the phenethylamine class of compounds. Escaline was first synthesized and reported in the scientific literature by Benington, et al., in 1954, but was later re-ex ...

. https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf

TMAs

Properties

Legality

Sweden

United Kingdom

United States of America

See also

References

External links