α-Methyltryptamine

α-Methyltryptamine
Clinical data
Trade namesIndopan; Indopane
Other namesalpha-Methyltryptamine; αMT; α-ET; AMT; IT-290; IT-403 ((+)-αMT); NSC-97069; PAL-17;[1] Ro 3-0926; U-14,164E; U-14,164-E; 3-(2-Aminopropyl)indole; 3-API; 3-IT; α-Methyl-3-indoleethanamine; Metryptamine; Amtryptamine
Routes of
administration		Oral, insufflation, rectal, smoked, IM, IV[2]
Drug classEntactogen; Stimulant; Psychedelic; Hallucinogen; Monoamine releasing agent; Serotonin receptor agonist; Monoamine oxidase inhibitor
ATC code
  • None
Legal status
Legal status
  • AU: S8 (Controlled drug)
  • BR: Class F2 (Prohibited psychotropics)[3]
  • CA: Unscheduled
  • DE: Anlage I (Authorized scientific use only)
  • UK: Class A
  • US: Schedule I
Pharmacokinetic data
Onset of action3–4 hours[4]
Duration of action12–24 hours[4]
Identifiers
IUPAC name
  • 1-(1H-Indol-3-yl)propan-2-amine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.522
Chemical and physical data
FormulaC11H14N2
Molar mass174.247 g·mol−1
3D model (JSmol)
SMILES
  • NC(CC1=CNC2=C1C=CC=C2)C
InChI
  • InChI=1S/C11H14N2/c1-8(12)6-9-7-13-11-5-3-2-4-10(9)11/h2-5,7-8,13H,6,12H2,1H3 Y
  • Key:QSQQQURBVYWZKJ-UHFFFAOYSA-N Y
  (verify)

α-Methyltryptamine (αMT, AMT) is a psychedelic, stimulant, and entactogen drug of the substituted tryptamine family.[5][6] It was originally developed as an antidepressant at Upjohn in the 1960s, and was used briefly as an antidepressant in the Soviet Union under the brand name Indopan or Indopane before being discontinued.[4][7][8]

Side effects of αMT include agitation, restlessness, confusion, lethargy, pupil dilation, jaw clenching, and rapid heart rate, among others.[4][9] αMT acts as a releasing agent of serotonin, norepinephrine, and dopamine, as a serotonin receptor agonist, and as a weak monoamine oxidase inhibitor.[1] αMT is a substituted tryptamine and is closely related to α-ethyltryptamine (αET) and other α-alkylated tryptamines.[1][5]

αMT appears to have first been described by at least 1929.[10][11] It started being more studied in the late 1950s and was briefly used as an antidepressant in the Soviet Union in the 1960s.[4][12][9][13][14] The drug started being used recreationally in the 1960s, with use increasing in the 1990s, and cases of death have been reported.[4][13][9][12] αMT is a controlled substance in various countries, including the United States.[13][4]

  1. ^ a b c Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, et al. (October 2014). "Alpha-ethyltryptamines as dual dopamine-serotonin releasers". Bioorganic & Medicinal Chemistry Letters. 24 (19): 4754–4758. doi:10.1016/j.bmcl.2014.07.062. PMC 4211607. PMID 25193229.
  2. ^ Cite error: The named reference urlErowid AMT Vault : FAQ by Dialtonez was invoked but never defined (see the help page).
  3. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  4. ^ a b c d e f g Barceloux DG (20 March 2012). Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants. John Wiley & Sons. pp. 196–199. ISBN 978-0-471-72760-6.
  5. ^ a b "#48 a-MT". Erowid Online Books: TIHKAL.
  6. ^ "AMT (alpha-methyltryptamine)". Erowid Vault.
  7. ^ Iversen L (11 November 2013). Handbook of Psychopharmacology: Volume 14 Affective Disorders: Drug Actions in Animals and Man. Springer Science & Business Media. pp. 132–. ISBN 978-1-4613-4045-4.
  8. ^ Halberstadt AL, Geyer MA (17 May 2013). "Neuropharmacology of lysergic acid diethylamide (LSD) and other hallucinogens.". In Miller PM, Ball SA, Bates ME, Blume AW, Kampman KM, Kavanagh DJ, Larimer ME, Petry NM, De Witte P (eds.). Biological Research on Addiction: Comprehensive Addictive Behaviors and Disorders. Vol. 2. Academic Press. pp. 625–635 (632). doi:10.1016/B978-0-12-398335-0.00061-3. ISBN 978-0-12-398360-2.
  9. ^ a b c Cite error: The named reference BolandAndolloHime2005 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference GaddumHameed1954 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference Seki1929 was invoked but never defined (see the help page).
  12. ^ a b Cite error: The named reference ElliottBrandtFreeman2013 was invoked but never defined (see the help page).
  13. ^ a b c Cite error: The named reference AraújoCarvalhoBastos2015 was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference TittarelliMannocchiPantano2015 was invoked but never defined (see the help page).
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