Description

Buy 3-4-5-Trimethoxyamphetamine (TMA- TMA-1) Cas 1082-88-8

3,4,5-Trimethoxyamphetamine (TMA, TMA-1, or 3,4,5-TMA), also known as α-methylmescaline (3C-mescaline or 3C-M) or mescalamphetamine, is a psychedelic drug of the phenethylamine and amphetamine families.^[1]^[2] It is one of the trimethoxyamphetamine (TMA) series of positional isomers.^[1]^[2] The drug is notable in being the amphetamine (α-methylated) analogue of mescaline (3,4,5-trimethoxyphenethylamine).^[1]^[2]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists TMA's dose as 100 to 250 mg orally and its duration as 6 to 8 hours.^[1]^[2]^[4]^[5] For comparison, mescaline is typically used at doses of 200 to 500 mg orally and is said to have a duration of 10 to 12 hours or longer.^[6] TMA's positional isomer 2,4,5-trimethoxyamphetamine (2,4,5-TMA or TMA-2) is much more potent than TMA, with a dose of 20 to 40 mg orally and a duration of 8 to 12 hours.^[7] The effects of TMA have been reported to include closed-eye imagery, introspection, music enhancement, emotional volatility, annoyance and irritability, feeling violent, lightheadedness, giddiness, and nausea, among others.^[1] It is said to lack mescaline's color changes and to have a "thread of negativity" at higher doses and a possible "antisocial nature" that has limited interest in the drug.^[1]

Interactions

Pharmacology

Pharmacodynamics

TMA activities
Target	Affinity (K_i, nM)
5-HT_1A	1,678–>5,600
5-HT_1B	2,855
5-HT_1D	3,035
5-HT_1E	3,369
5-HT_1F	ND
5-HT_2A	>10,000 (K_i) 41.3–1,700 (EC₅₀Tooltip half-maximal effective concentration) 40–96% (E_maxTooltip maximal efficacy)
5-HT_2B	477 (K_i) >10,000 (EC₅₀)
5-HT_2C	4,600–>10,000 (K_i) 47.4 (EC₅₀) 92% (E_max)
5-HT₃	>10,000
5-HT₄	ND
5-HT_5A	>10,000
5-HT₆	>10,000
5-HT₇	749
α_1A, α_1B	>10,000
α_1D	ND
α_2A	2,071–4,030
α_2B	>10,000
α_2C	5,014
β₁, β₂	>10,000
D₁–D₅	>10,000
H₁–H₄	>10,000
M₁, M₃, M₄	ND
M₂, M₅	>10,000
nACh	260–>10,000
TAAR₁	1,800 (K_i) (mouse) 3,200 (K_i) (rat) >10,000 (EC₅₀) (human)
I₁	>10,000
σ₁	537
σ₂	537
SERTTooltip Serotonin transporter	>10,000 (K_i) >100,000 (IC₅₀Tooltip half-maximal inhibitory concentration) 16,000 (EC₅₀) (rat)
NETTooltip Norepinephrine transporter	>10,000 (K_i) >100,000 (IC₅₀) >100,000 (EC₅₀) (rat)
DATTooltip Dopamine transporter	>10,000 (K_i) >100,000 (IC₅₀) >100,000 (EC₅₀) (rat)
MAO-ATooltip Monoamine oxidase A	>200,000 (IC₅₀)
MAO-BTooltip Monoamine oxidase B	>200,000 (IC₅₀)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: ^[8]^[9]^[10]^[11]^[12]^[13]^[14]^[15]

TMA is a low-potency serotonin 5-HT_2A receptor partial agonist, with an affinity (K_i) of >12,000 nM, an EC₅₀ of 1,700 nM, and an E_max of 40%.^[11] Conversely, it was inactive at the serotonin 5-HT_1A, 5-HT_2B and 5-HT_2C receptors and at several other receptors, at least at the assessed concentrations (up to 10,000 nM).^[11] It showed affinity for the mouse and rat trace amine-associated receptor 1 (TAAR1) (K_i = 1,800 nM and 3,200 nM, respectively), whereas it was inactive at the human TAAR1 (EC₅₀ > 10,000 nM).^[11] TMA is also a very low-potency serotonin releasing agent (SRA), with an EC₅₀ value of 16,000 nM.^[12] In contrast, it is inactive as a releasing agent and reuptake inhibitor of dopamine and norepinephrine (EC₅₀ > 100,000 nM).^[12] Despite its apparent SRA activity in vitro, TMA did not increase brain serotonin or dopamine levels in rodents in vivo.^[15] TMA is similarly inactive as a monoamine oxidase inhibitor (MAOI), including of both monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B) (IC₅₀ > 200,000 nM).^[14]^[15] The low potency of TMA as a serotonin 5-HT_2A receptor agonist is analogous to the case of mescaline, which is a well-known and widely used psychedelic but is likewise a very low-potency agonist of this receptor, showing an affinity (K_i) of 9,400 nM, an EC₅₀ of 10,000 nM, and an E_max of 56% in the same study.^[11] For comparison, DOM has shown an affinity (K_i) of 88 nM and an EC₅₀ of 4 to 24 nM.^[16]

Chemistry

Synthesis

The chemical synthesis of TMA has been described.^[1]

Derivatives

A variety of derivatives of TMA, known as the 3C series, have been studied and described.^[1]^[2]^[11]

History

TMA was first synthesized by Gordon Alles around 1937.^[17]^[18] He assessed it in both animal studies and self-experiments and documented its effects, but these were not reported until 1959.^[17]^[18] The drug was first described in the scientific literature in 1947 and its psychedelic effects were first described in 1955.^[19]^[20]^[21]^[22] TMA was studied at Edgewood Arsenal under the code name EA‐1319 in 1953 and 1954.^[17] The drug was further characterized by Alexander Shulgin and described in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).^[1]^[2]

Society and culture

Legal status

Canada

TMA is a controlled substance in Canada.^[23]

United States

TMA is a Schedule I controlled substance in the United States.^[2]^[3]

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Buy 3-4-5-Trimethoxyamphetamine (TMA- TMA-1) Cas 1082-88-8

Description

Buy 3-4-5-Trimethoxyamphetamine (TMA- TMA-1) Cas 1082-88-8

Use and effects

Interactions