alpha-Methyltryptamine

Title: a-Methyltryptamine
CAS Registry Number: 299-26-3
CAS Name: a-Methyl-1H-indole-3-ethanamine
Additional Names: 3-(2-aminopropyl)indole; AMT; IT-290
Molecular Formula: C11H14N2
Molecular Weight: 174.24
Percent Composition: C 75.83%, H 8.10%, N 16.08%
Literature References: Synthetic hallucinogen; the (S)-(+)-form possesses more potent bioactivity. Prepn: H. R. Synder, L. Katz, J. Am. Chem. Soc. 69, 3140 (1947); A. S. F. Ash, W. R. Wragg, J. Chem. Soc. 1958, 3887; A. G. Terzian et al., Experientia 17, 493 (1961); D. H. Lloyd, D. E. Nichols, J. Org. Chem. 51, 4294 (1986). CNS effects in animals: J. R. Vane et al., Nature 191, 1068 (1961). Clinical pharmacology: H. B. Murphree et al., Clin. Pharmacol. Ther. 2, 722 (1961). Synthesis and activity of enantiomers: D. B. Repke, W. J. Ferguson, J. Heterocycl. Chem. 13, 775 (1976); R. A. Glennon et al., Biochem. Pharmacol. 32, 1267 (1983). Case report of intoxication: H. Long et al., Vet. Hum. Toxicol. 45, 149 (2003). GC-MS determn in blood and urine: T. Ishida et al., J. Chromatogr. B 823, 47 (2005).
Properties: White powder. Crystals from diethyl ether, mp 101-102° (Lloyd, Nichols). Also reported as mp 98-99° (Terzian).
Melting point: mp 101-102° (Lloyd, Nichols); mp 98-99°
Derivative Type: (S)-Form
CAS Registry Number: 7795-51-9
Properties: Crystals from ethyl acetate + hexane, mp 125-126°. [a]D25 +34.9° (c = 0.9 in methanol).
Melting point: mp 125-126°
Optical Rotation: [a]D25 +34.9° (c = 0.9 in methanol)
Derivative Type: (R)-Form
CAS Registry Number: 7795-52-0
Properties: mp 126-127°. [a]D25 -32.1° (c = 1.0 in methanol).
Melting point: mp 126-127°
Optical Rotation: [a]D25 -32.1° (c = 1.0 in methanol)
NOTE: This is a controlled substance (hallucinogen): 21 CFR, 1308.11.
alphaMNP alpha-Naphtholphthalein alpha-Peltatin alpha-Phellandrene alpha-Phenylacetamide

α-Methyltryptamine
AMT.svg
Alpha-Methyltryptamine-3d-sticks.png
Systematic (IUPAC) name
2-(1H-indol-3-yl)-1-methyl-ethylamine
Clinical data
Legal status Controlled (S8) (AU) Uncontrolled (CA) Legal (UK) Schedule I (US)
Routes Oral, Insufflation, Rectal, Smoked, IM, IV[1]
Identifiers
CAS number 299-26-3 YesY
ATC code None
PubChem CID 9287
DrugBank DB01446
ChemSpider 8930 YesY
ChEBI CHEBI:59020 YesY
ChEMBL CHEMBL30713 YesY
Synonyms Indopan; IT-290, IT-403, U-14,164E, 3-IT[1]
Chemical data
Formula C11H14N2 
Mol. mass 174.24 g/mol
 YesY (what is this?)  (verify)

α-Methyltryptamine (αMT, AMT, Indopan) is a psychedelic, stimulant, and entactogen drug of the tryptamine class.[2][3] It was originally developed as an antidepressant by workers at Upjohn in the 1960s.[4]