2,4,5-Trimethoxyamphetamine

Last updated
2,4,5-Trimethoxyamphetamine
Trimethoxyamphetamine-2.svg
Clinical data
Other namesTMA-2; 2,4,5-TMA; 2,4,5-Trimethoxy-α-methylphenethylamine; 2,5-Dimethoxy-4-methoxyamphetamine; 4-Methoxy-2,5-dimethoxyamphetamine; DOMeO; DOOMe; DOO
Drug class Serotonergic psychedelic; Hallucinogen
Identifiers
  • 1-(2,4,5-trimethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
Formula C12H19NO3
Molar mass 225.288 g·mol−1
3D model (JSmol)
  • CC(CC1=CC(=C(C=C1OC)OC)OC)N
  • InChI=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
  • Key:TVSIMAWGATVNGK-UHFFFAOYSA-N

2,4,5-Trimethoxyamphetamine (2,4,5-TMA), also known as TMA-2 or as 2,5-dimethoxy-4-methoxyamphetamine (DOMeO), 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 also notable in being the 4-methoxylated member of the DOx (i.e., 4-substituted-2,5-dimethoxyamphetamine) series of drugs. [1] [2]

TMA-2 is said to be active at doses of 20 to 40 mg and to have a duration of 8 to 12 hours. [1] It is much more potent than its positional isomer 3,4,5-trimethoxyamphetamine (3,4,5-TMA, TMA, or TMA-1), which is said to be active at doses of 100 to 250 mg and to have a duration of 6 to 8 hours. [3] However, DOM (2,5-dimethoxy-4-methylamphetamine), the analogue of TMA-2 in which its 4-methoxy group has been replaced with a more lipophilic 4-methyl group, is about 10 times more potent than TMA-2. [4]

The drug's affinity (Ki) for the serotonin 5-HT2A receptor has been found to be 1,300 nM. [5] Its EC50 Tooltip half-maximal effective concentration at the receptor was 190 nM and its Emax Tooltip maximal efficacy was 84%. [5] The drug was also active at the serotonin 5-HT2B receptor and, to a much lesser extent, at the serotonin 5-HT2C receptor. [5] TMA-2 is inactive at the monoamine transporters. [5] It was inactive at the mouse trace amine-associated receptor 1 (TAAR1), whereas it bound to the rat TAAR1 with an affinity (Ki) of 3,100 nM and was not assessed at the human TAAR1. [5]

See also

Related Research Articles

<i>PiHKAL</i> 1991 book by Alexander Shulgin and Ann Shulgin

PiHKAL: A Chemical Love Story is a book by Alexander Shulgin and Ann Shulgin, published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens. The main title, PiHKAL, is an acronym that stands for "Phenethylamines I Have Known and Loved".

<span class="mw-page-title-main">2,5-Dimethoxy-4-methylamphetamine</span> Chemical compound

2,5-Dimethoxy-4-methylamphetamine is a psychedelic and a substituted amphetamine. It was first synthesized by Alexander Shulgin, and later reported in his book PiHKAL: A Chemical Love Story. DOM is classified as a Schedule I substance in the United States, and is similarly controlled in other parts of the world. Internationally, it is a Schedule I drug under the Convention on Psychotropic Substances. It is generally taken orally.

<span class="mw-page-title-main">2,5-Dimethoxy-4-bromoamphetamine</span> Chemical compound

Dimethoxybromoamphetamine (DOB), also known as brolamfetamine and bromo-DMA, is a psychedelic drug and substituted amphetamine of the phenethylamine class of compounds. DOB was first synthesized by Alexander Shulgin in 1967. Its synthesis and effects are documented in Shulgin's book PiHKAL: A Chemical Love Story.

<span class="mw-page-title-main">3,4,5-Trimethoxyamphetamine</span> Pharmaceutical compound

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

Trimethoxyamphetamines (TMAs) are a family of positionally isomeric psychedelic hallucinogenic drugs. There exist six different TMAs that differ only in the positions of the three methoxy groups: TMA (TMA-1), TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6. The TMAs are substituted amphetamines and are analogues of the phenethylamine cactus alkaloid mescaline and the DOx drugs.

<span class="mw-page-title-main">2C-T</span> Chemical compound

2C-T is a psychedelic and hallucinogenic drug of the 2C family. It is used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs mescaline and 2C-T-2.

<span class="mw-page-title-main">2,4,5-Trimethoxyphenethylamine</span> Chemical compound

2,4,5-Trimethoxyphenethylamine or is a phenethylamine of the 2C family and was first synthesized by Jansen in 1931. It is a positional isomer of the drug mescaline (3,4,5-trimethoxy).

<span class="mw-page-title-main">2,5-Dimethoxy-4-ethylamphetamine</span> Psychedelic drug

2,5-Dimethoxy-4-ethylamphetamine is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin, and was described in his book PiHKAL.

<span class="mw-page-title-main">2C (psychedelics)</span> Family of phenethylamine psychedelics

2C (2C-x) is a general name for the family of psychedelic phenethylamines containing methoxy groups on the 2 and 5 positions of a benzene ring. Most of these compounds also carry lipophilic substituents at the 4 position, usually resulting in more potent and more metabolically stable and longer acting compounds.

<span class="mw-page-title-main">Aleph (psychedelic)</span> Chemical compound

Aleph is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen. It was first synthesized by Alexander Shulgin, who named it after the first letter of the Hebrew alphabet. In his book PiHKAL, Shulgin lists the dosage range as 5–10 mg, with effects typically lasting for 6 to 8 hours.

<span class="mw-page-title-main">2C-T-17</span> Chemical compound

2C-T-17 or 2,5-dimethoxy-4-(β-secbutylthio)phenethylamine is a psychedelic phenethylamine of the 2C family. It was presumably first synthesized by Alexander Shulgin and reported in his book PiHKAL .

<span class="mw-page-title-main">Ariadne (drug)</span> Psychoactive phenethylamine drug

Ariadne, also known chemically as 4C-D or 4C-DOM, by its developmental code name BL-3912, and by its former tentative brand name Dimoxamine, is a little-known psychoactive drug of the phenethylamine, amphetamine, and phenylisobutylamine families. It is a homologue of the psychedelics 2C-D and DOM.

Dimethoxyamphetamine (DMA) is a series of six lesser-known psychedelic drugs similar in structure to the three isomers of methoxyamphetamine and six isomers of trimethoxyamphetamine. The isomers are 2,3-DMA, 2,4-DMA, 2,5-DMA, 2,6-DMA, 3,4-DMA, and 3,5-DMA. Three of the isomers were characterized by Alexander Shulgin in his book PiHKAL. Little is known about their dangers or toxicity.

Trimethoxyphenethylamines (TMPEA) are a group of positional isomers of the psychedelic cactus alkaloid mescaline. Some of them are described in the book PiHKAL by Alexander Shulgin and Ann Shulgin.

<span class="mw-page-title-main">3-Methoxyamphetamine</span> Stimulant drug of the amphetamine class

3-Methoxyamphetamine (3-MA), also known as meta-methoxyamphetamine (MMA), is a monoamine releasing agent (MRA) of the amphetamine family. It is a positional isomer of para-methoxyamphetamine.

<span class="mw-page-title-main">2,5-Dimethoxyamphetamine</span> Pharmaceutical compound

2,5-Dimethoxyamphetamine (2,5-DMA), also known as DMA-4 or as DOH, is a drug of the phenethylamine and amphetamine families. It is one of the dimethoxyamphetamine (DMA) series of positional isomers. The drug is notable in being the parent compound of the DOx (4-substituted-2,5-dimethoxyamphetamine) series of drugs.

<span class="mw-page-title-main">2,5-Dimethoxy-4-fluoroamphetamine</span> Chemical compound

2,5-Dimethoxy-4-fluoroamphetamine (DOF) is a psychedelic drug of the phenethylamine and amphetamine classes. Alexander Shulgin briefly describes DOF in his book PiHKAL:

Animal studies that have compared DOF to the highly potent DOI and DOB imply that the human activity will be some four to six times less than these two heavier halide analogues.

DO<i>x</i> Class of chemical compounds

4-Substituted-2,5-dimethoxyamphetamines (DOx) is a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- position of the phenyl ring. They are 4-substituted derivatives of 2,5-dimethoxyamphetamine.

<span class="mw-page-title-main">3,4-Dimethoxyamphetamine</span> Pharmaceutical compound

3,4-Dimethoxyamphetamine (3,4-DMA), or simply dimethoxyamphetamine (DMA), is a psychedelic drug of the phenethylamine and amphetamine families. It is one of the dimethoxyamphetamine (DMA) series of positional isomers.

<span class="mw-page-title-main">2,4-Dimethoxyamphetamine</span> Pharmaceutical compound

2,4-Dimethoxyamphetamine (2,4-DMA), also known as DMA-3, is a drug of the phenethylamine and amphetamine families. It is one of the dimethoxyamphetamine (DMA) series of positional isomers.

References

  1. 1 2 3 4 Shulgin AT, Shulgin A (1991). "#158 TMA-2 2,4,5-TRIMETHOXYAMPHETAMINE". PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. ISBN   9780963009609. OCLC   25627628.
  2. 1 2 3 Shulgin A, Manning T, Daley PF (2011). "#118. TMA-2". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . Vol. 1. Berkeley: Transform Press. ISBN   978-0-9630096-3-0.
  3. Shulgin AT, Shulgin A (1991). "#157 TMA 3,4,5-TRIMETHOXYAMPHETAMINE". PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. ISBN   9780963009609. OCLC   25627628.
  4. Nichols, David E. (2012). "Structure–activity relationships of serotonin 5-HT 2A agonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling. 1 (5): 559–579. doi: 10.1002/wmts.42 . ISSN   2190-460X.
  5. 1 2 3 4 5 Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME (2019). "Receptor Interaction Profiles of 4-Alkoxy-Substituted 2,5-Dimethoxyphenethylamines and Related Amphetamines". Front Pharmacol. 10: 1423. doi: 10.3389/fphar.2019.01423 . PMC   6893898 . PMID   31849671.