2,3,4,5-Tetramethoxyamphetamine

Tetramethoxyamphetamine, or 2,3,4,5-tetramethoxyamphetamine, is a lesser-known psychedelic drug and a substituted amphetamine. Tetramethoxyamphetamine was first synthesized by Alexander Shulgin. In his book PiHKAL (Phenethylamines i Have Known And Loved), the minimum dosage is listed as 50 mg, and the duration unknown. Tetramethoxyamphetamine produces a threshold, mydriasis, and a headache. Limited data exists about its pharmacological properties, metabolism, and toxicity.[1][2][3]

2,3,4,5-Tetramethoxyamphetamine
Legal status
Legal status
Identifiers
IUPAC name
  • 1-(2,3,4,5-tetramethoxyphenyl)propan-2-amine
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC13H19NO4
Molar mass253.298 g·mol−1
3D model (JSmol)
SMILES
  • CC(Cc1cc(c(c(c1OC)OC)OC)OC)N
InChI
  • 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 Y
  • Key:WVNJEHORYAZBRZ-UHFFFAOYSA-N Y
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References
  1. 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.
  2. 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.
  3. 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.
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