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4-HO-αMT

Chemical compound

Field	Value
verifiedrevid	413272685
image	4-HO-aMT Structure.svg
image_class	skin-invert-image
width	175px
image2	4-HO-αMT 3D.png
image_class2	bg-transparent
width2	200px
legal_status	Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar bills in other countries)
routes_of_administration	Oral
class	Serotonergic psychedelic; Hallucinogen
ATC_prefix	None
CAS_number	15066-09-8
CAS_supplemental	113997-84-5 (R isomer) 113997-85-6 (S isomer)
PubChem	14083213
ChemSpiderID_Ref
ChemSpiderID	23128298
UNII_Ref
UNII	3RP9EZV7GN
synonyms	4-HO-αMT; 4-HO-AMT; MP-14
IUPAC_name	3-(2-aminopropyl)-1H-indol-4-ol
C	11	H=14	N=2	O=1
SMILES	CC(N)CC1=CNC2=CC=CC(O)=C12
StdInChI_Ref
StdInChI	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
StdInChIKey_Ref
StdInChIKey	BYMNOLWNRCZVLJ-UHFFFAOYSA-N
melting_point	125
melting_high	126
melting_notes

| elimination_half-life =

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. 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. The drug is taken orally.

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4-HO-AMT was assessed in clinical studies and was reported by Murphree and Bircher, based on unpublished observations by these researchers, to be psychedelic at oral doses of 15 to 20mg and to have marked visual effects.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

Interactions

Pharmacology

Pharmacodynamics

4-HO-AMT has been found to produce electroencephalogram (EEG) changes in animals.

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.

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.

References

(1959). "Abwandlungsprodukte von Psilocybin und Psilocin. 2. Mitteilung über synthetische Indolverbindungen". Helvetica Chimica Acta.
(1972). "Psychotropic Drugs and Related Compounds". National Institute of Mental Health.
(1971). "Drill's Pharmacology in Medicine". McGraw-Hill.
(1983). "Research Advances in Alcohol and Drug Problems". Springer US.
"Erowid Online Books : "TIHKAL" - #48 a-MT".
(April 1980). "5-Methoxy-α-Methyltryptamine (α,O-Dimethylserotonin), A Hallucinogenic Homolog of Serotonin". Biol Psychiatry.
(1967). "Amines and Schizophrenia". Elsevier.
(August 2016). "Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens". European Neuropsychopharmacology.
(April 1963). "An electrographic study of psilocin and 4-methyl-α-methyl tryptamine (MP-809)". J Pharmacol Exp Ther.

Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

alpha-alkyltryptamines 4-hydroxytryptamines psychedelic-tryptamines

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