4-HO-αMT

Chemical compound From Wikipedia, the free encyclopedia

4-HO-αMT (developmental code name MP-14), also known as 4-hydroxy-α-methyltryptamine, is a psychedelic drug of the tryptamine and α-alkyltryptamine families.^[1]^[2]^[5]^[6] 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.^[1]^[2]^[7] The drug is taken orally.^[1]^[2]^[3]

Other names4-HO-αMT; 4-HO-AMT; MP-14

Routes of
administrationOral^[1]^[2]^[3]

Drug classSerotonergic psychedelic; Hallucinogen

ATC code

None

Quick facts Clinical data, Other names ...

4-HO-αMT
Clinical data


Other names	4-HO-αMT; 4-HO-AMT; MP-14
Routes of administration	Oral^[1]^[2]^[3]
Drug class	Serotonergic psychedelic; Hallucinogen
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^Y
UNII	3RP9EZV7GN
CompTox Dashboard (EPA)	DTXSID501029399
Chemical and physical data
Formula	C₁₁H₁₄N₂O
Molar mass	190.246 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	125 to 126 °C (257 to 259 °F) ^[4]
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)

Use and effects

4-HO-AMT was assessed in clinical studies and was reported by Murphree and Bircher, based on unpublished observations by these researchers, to be psychedelic at oral doses of 15 to 20 mg and to have marked visual effects.^[1]^[2]^[7]^[3] Side effects have included abdominal pain, diarrhea, dizziness, headache, depressed feelings, dilated pupils, increased heart rate, increased blood pressure, urinary retention, and urinary hesitancy.^[1]^[2]^[7] It has been reported to have strongly increased effects on smooth muscle relative to AMT, which is implicated in the urinary difficulty.^[1]^[2]

Interactions

Pharmacology

Pharmacodynamics

4-HO-AMT has been found to produce electroencephalogram (EEG) changes in animals.^[6]^[8]

4-Hydroxylation of dimethyltryptamine (DMT) into the related compound psilocin (4-HO-DMT) has been found to abolish its serotonin release induction in human embryonic kidney 293 (HEK293) stably transfected with the serotonin transporter (SERT) in vitro.^[9]

Chemistry

Analogues

Analogues of 4-HO-AMT include α-methyltryptamine (AMT), 4-HO-AET, 5-MeO-AMT, 4-methyl-AMT, 5-fluoro-AMT, 6-fluoro-AMT, and α-methylserotonin (5-HO-AMT), among others.

History

4-HO-AMT was first described in the scientific literature by 1963.^[6]^[8]^[1]

References

[1]
Murphree HB, Bircher R (1971). "Psychotomimetic Drugs". In Drill VA, DiPalma JR (eds.). Drill's Pharmacology in Medicine. New York: McGraw-Hill. pp. 449–461. ISBN 9780070170063. OCLC 154387. OL 5318141M. 4-Hydroxy-α-methyltryptamine,98 in contrast, has markedly augmented visual effects. Doses of 15 to 20 mg cause abdominal pain and also commonly diarrhea. Tachycardia and increased blood pressures occur as well. Subjective effects include dizziness, headache, and depressed feelings. LSD-like effects including dilated pupils are not uncommon. One subject given 15 mg had urinary retention for 12 hr, followed by difficulty in urinating for another 12 hr. So altogether, this compound has strong effects on smooth muscle. [...] 98. Murphree, H. B., and R. Bircher: Unpublished Data.
[2]
Murphree H (1983). "The Pharmacology of Hallucinogens". Research Advances in Alcohol and Drug Problems. Boston, MA: Springer US. pp. 175–205. doi:10.1007/978-1-4613-3626-6_5. ISBN 978-1-4613-3628-0. Figure 4. Tryptamine and derivatives. [...] 4-Hydroxy-α-methyltryptamine [...] Addition of a hydroxyl group in the same position, carbon 4 of the ring of α-methyltryptamine (Fig. 4), caused a marked increase of effects on smooth muscle (Murphree and Bircher, personal observation). Oral doses of 15—20 mg caused abdominal pain and commonly diarrhea. Two subjects experienced difficulty urinating. Other effects were very much like those of lysergide: dizziness, headache, and depressed feelings, as well as dilated pupils and some increase in heart rate and blood pressure.
[3]
Kantor RE, Dudlettes SD, Shulgin AT (April 1980). "5-Methoxy-α-Methyltryptamine (α,O-Dimethylserotonin), A Hallucinogenic Homolog of Serotonin". Biol Psychiatry. 15 (2): 349–352. PMID 7417623. Table 1. Human Potency of the Hallucinogenic Tryptamines [...] Dosage (mg): 20^e. Route: Oral. Reference: Murphree and Bircher, 1971. [...] ^e An antidepressant rather than a hallucinogen in man. [...] Murphree, H. B. and Bircher, R. (1971). Psychotomimetic drugs, in Drill's Pharmacology in Medicine, McGraw Hill, New York, p. 449.
[4]
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.
[5]
Usdin E, Effron DH (1972). Psychotropic Drugs and Related Compounds. National Institute of Mental Health. p. 314.
[6]
Brodey JF, Steiner WG, Himwich HE (April 1963). "An electrographic study of psilocin and 4-methyl-α-methyl tryptamine (MP-809)". J Pharmacol Exp Ther. 140: 8–18. doi:10.1016/S0022-3565(25)26511-9. PMID 14015664. Archived from the original on 2025-04-07.
[7]
"Erowid Online Books : "TIHKAL" - #48 a-MT". 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.
[8]
Himwich HE (1967). "Comparative Neurophysiological Studies of Psychotomimetic N-Dimethylamines and N-Diethylamines and their Non-Psychotomimetic Congeners Devoid of the N-Dimethyl or N-Diethyl Configurations". Amines and Schizophrenia. Elsevier. pp. 137–149. doi:10.1016/b978-0-08-012039-3.50015-4. ISBN 978-0-08-012039-3. Retrieved 7 April 2025.
[9]
Rickli A, Moning OD, Hoener MC, Liechti ME (August 2016). "Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens" (PDF). European Neuropsychopharmacology. 26 (8): 1327–1337. doi:10.1016/j.euroneuro.2016.05.001. PMID 27216487. S2CID 6685927.