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4-HO-αMT

From Wikipedia, the free encyclopedia
(Redirected from4-HO-AMT)
Chemical compound

Pharmaceutical compound
4-HO-αMT
Clinical data
Other names4-HO-αMT; 4-HO-AMT; MP-14
Routes of
administration
Oral[1][2][3][3]
Drug classSerotonergic psychedelic;Hallucinogen
ATC code
  • None
Legal status
Legal status
Identifiers
  • 3-(2-aminopropyl)-1H-indol-4-ol
CAS Number
  • 15066-09-8
    113997-84-5 (R isomer)
    113997-85-6 (S isomer)
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC11H14N2O
Molar mass190.246 g·mol−1
3D model (JSmol)
Melting point125 to 126 °C (257 to 259 °F)[4]
  • CC(N)CC1=CNC2=CC=CC(O)=C12
  • 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 checkY
  • Key:BYMNOLWNRCZVLJ-UHFFFAOYSA-N checkY
  (verify)

4-HO-αMT (developmental code nameMP-14), also known as4-hydroxy-α-methyltryptamine, is apsychedelic drug of thetryptamine andα-alkyltryptamine families.[1][2][5][6] It is a closestructural analogue ofα-methyltryptamine (αMT) and produces similar effects to it, but with exacerbatedside effects similarly to5-MeO-αMT.[1][2][7] The drug is takenorally.[1][2][3][3]

Use and effects

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4-HO-AMT was assessed inclinical studies and was reported by Murphree and Bircher, based on unpublished observations by these researchers, to bepsychedelic atoral doses of 15 to 20 mg and to have markedvisual effects.[1][2][7][3]Side effects have includedabdominal pain,diarrhea,dizziness,headache,depressed feelings,dilated pupils,increased heart rate,increased blood pressure,urinary retention, andurinary hesitancy.[1][2][7] It has been reported to have strongly increased effects onsmooth muscle relative to AMT, which is implicated in the urinary difficulty.[1][2]

Interactions

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See also:Psychedelic drug § Interactions, andTrip killer § Serotonergic psychedelic antidotes

Pharmacology

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Pharmacodynamics

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

4-Hydroxylation ofdimethyltryptamine (DMT) into the related compoundpsilocin (4-HO-DMT) has been found to abolish itsserotonin release induction inhuman embryonic kidney 293 (HEK293) stablytransfected with theserotonin transporter (SERT)in vitro.[9]

History

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

See also

[edit]

References

[edit]
  1. ^abcdefghMurphree 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. ^abcdefgMurphree H (1983). "The Pharmacology of Hallucinogens".Research Advances in Alcohol and Drug Problems. Boston, MA: Springer US. p. 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. ^abcdeKantor 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): 20e. 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. ^abcBrodey 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.
  7. ^abc"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. ^abHimwich 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. p. 137–149.doi:10.1016/b978-0-08-012039-3.50015-4.ISBN 978-0-08-012039-3. Retrieved7 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.

External links

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