2,3,5,6-Tetramethoxyamphetamine

2,3,5,6-Tetramethoxyamphetamine
Clinical data
Other names	2,3,5,6-TeMA; TeMA-3
Identifiers
	IUPAC name 1-(2,3,5,6-tetramethoxyphenyl)propan-2-amine;
CAS Number	23693-28-9;
Chemical and physical data
Formula	C13H21NO4
Molar mass	255.314 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COc1cc(OC)c(c(c1OC)CC(N)C)OC;
	InChI InChI=1S/C13H21NO4/c1-8(14)6-9-12(17-4)10(15-2)7-11(16-3)13(9)18-5/h7-8H,6,14H2,1-5H3; Key:UMWIVVHAMHPTBF-UHFFFAOYSA-N;

2,3,5,6-Tetramethoxyamphetamine (2,3,5,6-TeMA), also known as TeMA-3, is a chemical compound of the phenethylamine and amphetamine families related to the psychedelic drug mescaline (3,4,5-trimethoxyphenethylamine).^[1]^[2]^[3] 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] The fluorescence of TeMA-3 has been studied.^[4] Very little appears to be known about TeMA-3.^[1]

References

^ ^a ^b ^c 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.
^ 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. pp. 930–931. ISBN 978-3-03788-700-4. OCLC 858805226.
^ ^a ^b 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.
^ 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.