2,3,4,5-Tetramethoxyamphetamine

2,3,4,5-Tetramethoxyamphetamine
Clinical data
Other namesTeMA; TA; 2,3,4,5-TeMA; 2,3,4,5-Tetramethoxyamphetamine; 2,3,4,5-Tetramethoxyphenylisopropylamine; 2-Methoxy-TMA; 2-Methoxy-3,4,5-TMA; 3-Methoxy-TMA-2; 3-Methoxy-2,4,5-TMA
ATC code
  • None
Legal status
Legal status
Identifiers
  • 1-(2,3,4,5-tetramethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H21NO4
Molar mass255.314 g·mol−1
3D model (JSmol)
  • CC(Cc1cc(c(c(c1OC)OC)OC)OC)N
  • InChI=1S/C13H21NO4/c1-8(14)6-9-7-10(15-2)12(17-4)13(18-5)11(9)16-3/h7-8H,6,14H2,1-5H3 checkY
  • Key:WVNJEHORYAZBRZ-UHFFFAOYSA-N checkY
  (verify)

Tetramethoxyamphetamine (TeMA), or 2,3,4,5-tetramethoxyamphetamine (2,3,4,5-TeMA), also known as 2-methoxy-TMA or 3-methoxy-TMA-2, is a drug of the phenethylamine and amphetamine families related to mescaline (3,4,5-trimethoxyphenethylamine).[1][2]

In his book PiHKAL (Phenethylamines I Have Known And Loved), Alexander Shulgin lists TeMA's "probably above 50 mg" orally and its duration as unknown.[1][2] In an earlier publication, it was said to produce threshold effects at a dose of 30 mg orally and long-lived effects at a dose of 50 mg orally.[2] The effects of TeMA have been reported to include disinhibition, intoxication, pupil dilation, and headache.[1][2] It is said to be roughly 6 times as potent as mescaline.[3]

TeMA has been said to be the only amphetamine with more than three methoxy groups known to be hallucinogenic.[2] However, subsequently, the psychedelic properties of TeMA were questioned.[4] Limited data exists about its pharmacological properties, metabolism, and toxicity.[5][6][7] It was first described in the scientific literature by at least 1975.[3][2] Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.[1] The drug is a controlled substance in Canada under phenethylamine blanket-ban language.[8]

See also

References

  1. ^ a b c d Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. https://www.erowid.org/library/books_online/pihkal/pihkal145.shtml
  2. ^ a b c d e f Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6. 3.1.11. 2,3,4,5-Tetramethoxyphenylisopropylamine: Only one substituted phenylisopropylamine with more than three methoxyl groups has been established as being psychotomimetic. This is 2,3,4,5-tetramethoxyphenylisopropylamine (44, 2,3,4,5-tetramethoxyamphetamine). A threshold level of central activity is evident at a 30 mg dose orally, and a relatively long-lived disinhibited intoxication is produced by a 50-mg dosage. Compound (44) has been recorded as having six times the potency of mescaline (Shulgin et ai., 1969), but additional studies will be needed to establish the qualitative nature of its action.
  3. ^ a b Brimblecombe RW, Pinder RM (1975). "Phenylalkylamines and Their Derivatives". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 55–97.
  4. ^ Nichols DE (1994). "Medicinal Chemistry and Structure–Activity Relationships". In Cho AK, Segal DS (eds.). Amphetamine and Its Analogs: Psychopharmacology, Toxicology, and Abuse. Academic Press. pp. 3–41. ISBN 978-0-12-173375-9. Finally, 2,3,4,5-tetramethoxyamphetamine was reported earlier to be active in humans (Shulgin, 1978). However, the more recent description of its effects leaves some doubt about this conclusion (Shulgin and Shulgin, 1991).
  5. ^ Kier LB, Hall LH (December 1977). "Structure-activity studies on hallucinogenic amphetamines using molecular connectivity". Journal of Medicinal Chemistry. 20 (12): 1631–6. doi:10.1021/jm00222a019. PMID 592329.
  6. ^ Clare BW (February 1990). "Structure-activity correlations for psychotomimetics. 1. Phenylalkylamines: electronic, volume, and hydrophobicity parameters". Journal of Medicinal Chemistry. 33 (2): 687–702. doi:10.1021/jm00164a036. PMID 2299636.
  7. ^ Clare BW (September 1998). "The frontier orbital phase angles: novel QSAR descriptors for benzene derivatives, applied to phenylalkylamine hallucinogens". Journal of Medicinal Chemistry. 41 (20): 3845–56. doi:10.1021/jm980144c. PMID 9748359.
  8. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
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