2,3,4,6-Tetramethoxyamphetamine

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2,3,4,6-Tetramethoxyamphetamine
2,3,4,6-Tetramethoxyamphetamine.svg
Clinical data
Other names2,3,4,6-TeMA; TeMA-2
Identifiers
  • 1-(2,3,4,6-tetramethoxyphenyl)propan-2-amine
CAS Number
Chemical and physical data
Formula C13H21NO4
Molar mass 255.314 g·mol−1
3D model (JSmol)
  • COc1cc(OC)c(c(c1CC(N)C)OC)OC
  • InChI=1S/C13H21NO4/c1-8(14)6-9-10(15-2)7-11(16-3)13(18-5)12(9)17-4/h7-8H,6,14H2,1-5H3
  • Key:DJUKQNSUJQBHFW-UHFFFAOYSA-N

2,3,4,6-Tetramethoxyamphetamine (2,3,4,6-TeMA), also known as TeMA-2, is a chemical compound of the phenethylamine and amphetamine families related to the psychedelic drug mescaline (3,4,5-trimethoxyphenethylamine). [1] [2] [3] [4] It was first described in the scientific literature by Alexander Shulgin and colleagues in 1969, but had not been synthesized or assessed by them at that time. [1] [3] As such, the potential hallucinogenic activity of TeMA-2 is unknown. [2] [4] The fluorescence of TeMA-2 has been studied. [1] [2] [4] TeMA-2 is said to be a virtually unexplored substance. [2]

Contents

See also

References

  1. 1 2 3 Shulgin A, Manning T, Daley P (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . Vol. 1. Berkeley: Transform Press. pp. xix, 282. ISBN   978-0-9630096-3-0.
  2. 1 2 3 4 Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. p. 923. ISBN   978-3-03788-700-4. OCLC   858805226. Das Derivat 2,3,4,6-Tetramethoxyphenethylamin (11) wurde im Jahre 1955 von Benington, Morin und Clark hergestellt [6] und später auf die Wechselwirkung mit der Aminoxidase geprüft [7, 8] (siehe auch Tabelle 1 in Kapitel 8.6). Interessanterweise schienen alle Phenethylamine mit mehr als drei MCO-Gruppen nicht signifikant deaminiert zu werden. Das analoge 2,3,4,6-Tetramethoxyamphetamin (12) wurde nur einmal in der Literatur erwähnt (Bestimmung der nativen Fluoreszenz, zur Evaluierung der Struktur-Aktivitäts-Beziehung im Vergleich zu anderen Phenylalkylaminen) [9] und ist somit eine nahezu unerforschte Substanz.
  3. 1 2 Shulgin AT, Sargent T, Naranjo C (February 1969). "Structure--activity relationships of one-ring psychotomimetics". Nature. 221 (5180): 537–541. Bibcode:1969Natur.221..537S. doi:10.1038/221537a0. PMID   5789297.
  4. 1 2 3 Antun F, Smythies JR, Benington F, Morin RD, Barfknecht CF, Nichols DE (January 1971). "Native fluorescence and hallucinogenic potency of some amphetamines". Experientia. 27 (1): 62–63. doi:10.1007/BF02137743. PMID   5549244.



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