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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