7-Methyl-α-ethyltryptamine

7-Methyl-α-ethyltryptamine (7-Me-αET) is a tryptamine derivative related to α-ethyltryptamine (αET). It was discovered by a team at Upjohn in the early 1960s.[1] It has similar pharmacological effects to αET, but is both 3-4 times more potent as a serotonin releasing agent, and 10 times more potent as a monoamine oxidase inhibitor,[2][3] making it potentially hazardous as this pharmacological profile is shared with drugs such as PMA and 4-MTA, which are known to be dangerous in humans when used at high doses.

7-Methyl-α-ethyltryptamine
Identifiers
IUPAC name
  • 1-(7-methyl-1H-indol-3-yl)butan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H18N2
Molar mass202.301 g·mol−1
3D model (JSmol)
SMILES
  • CCC(N)CC1=CNC2=C(C)C=CC=C21
InChI
  • InChI=1S/C13H18N2/c1-3-11(14)7-10-8-15-13-9(2)5-4-6-12(10)13/h4-6,8,11,15H,3,7,14H2,1-2H3
  • Key:NBLFITFQOPGXLS-UHFFFAOYSA-N

See also

References
  1. U.S. Patent 3,296,072
  2. Hester JB, Greig ME, Anthony WC, Heinzelman RV, Szmuszkovicz J (May 1964). "Enzyme Inhibitory Activity of 3-(2-Aminobutyl)indole Derivatives". Journal of Medicinal Chemistry. 7 (3): 274–9. doi:10.1021/jm00333a006. PMID 14204959.
  3. Burningham RA, Arimura GK, Yunis AA (July 1966). "Effect of Monase and related compounds on uptake of 5-hydroxytryptamine by platelets". Proceedings of the Society for Experimental Biology and Medicine. 122 (3): 711–4. doi:10.3181/00379727-122-31233. PMID 5918937. S2CID 24949288.


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