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	14083213
ChemSpider	23128298
ChEMBL	ChEMBL285823
Chemical and physical data
Formula	C11H14N2O
Molar mass	190.246 g·mol^−1
3D model (JSmol)	Interactive image
Melting point	125–126 °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 Key:BYMNOLWNRCZVLJ-UHFFFAOYSA-N
(verify)

See also

• α-Methyltryptamine
• 4-Methyl-αMT
• 5-Fluoro-αMT
• 5-Hydroxy-αMT
• 5-Methoxy-αMT
• 4-Hydroxy-DMT (Psilocin)

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".