4-HO-αMT

4-Hydroxy-α-methyltryptamine (4-HO-αMT) is a psychedelic drug of the tryptamine class. It is a close structural analogue of α-methyltryptamine (αMT) and produces similar effects to it, but with exacerbated side effects similarly to 5-MeO-αMT. Alexander Shulgin describes 4-HO-αMT briefly in his book TiHKAL:[2]

The 4-hydroxy analogue of αMT has been looked at in human subjects. It is reported to be markedly visual in its effects, with some subjects reporting dizziness and a depressed feeling. There were, however, several toxic signs at doses of 15 to 20 milligrams orally, including abdominal pain, tachycardia, increased blood pressure and, with several people, headache and diarrhea.

— Alexander Shulgin, (TiHKAL)
4-HO-αMT
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar bills in other countries)
Identifiers
IUPAC name
  • 3-(2-aminopropyl)-1H-indol-4-ol
CAS Number
  • 15066-09-8
    113997-84-5 (R isomer)
    113997-85-6 (S isomer)
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC11H14N2O
Molar mass190.246 g·mol−1
3D model (JSmol)
Melting point125–126 °C (257–259 °F) [1]
SMILES
  • CC(N)CC1=CNC2=CC=CC(O)=C12
InChI
  • InChI=1S/C11H14N2O/c1-7(12)5-8-6-13-9-3-2-4-10(14)11(8)9/h2-4,6-7,13-14H,5,12H2,1H3 Y
  • Key:BYMNOLWNRCZVLJ-UHFFFAOYSA-N Y
  (verify)

See also

References
  1. Troxler F, Seemann F, Hofmann A (1959). "Abwandlungsprodukte von Psilocybin und Psilocin. 2. Mitteilung über synthetische Indolverbindungen". Helvetica Chimica Acta (in German). 42 (6): 2073–2103. doi:10.1002/hlca.19590420638.
  2. "Erowid Online Books : "TIHKAL" - #48 a-MT".
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