2-Methyl-iPALT

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2-Methyl-iPALT
Clinical data
Other names2-Me-iPALT; 2-Methyl-ALiPT; 2-Me-ALiPT; ASR-3002; ASR3002; 2-Methyl-N-isopropyl-N-allyltryptamine; 2-Methyl-N-allyl-N-isopropyltryptamine
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist
ATC code
  • None
Identifiers
  • N-[2-(2-methyl-1H-indol-3-yl)ethyl]-N-prop-2-enylpropan-2-amine
CAS Number
PubChem CID
Chemical and physical data
FormulaC17H24N2
Molar mass256.393 g·mol−1
3D model (JSmol)
  • CC1=C(C2=CC=CC=C2N1)CCN(CC=C)C(C)C
  • InChI=1S/C17H24N2/c1-5-11-19(13(2)3)12-10-15-14(4)18-17-9-7-6-8-16(15)17/h5-9,13,18H,1,10-12H2,2-4H3
  • Key:QXAIQMVRYZDEJS-UHFFFAOYSA-N

2-Methyl-iPALT, or 2-methyl-ALiPT, also known as 2-methyl-N-isopropyl-N-allyltryptamine or by its developmental code name ASR-3002, is a serotonin receptor modulator of the tryptamine family.[1] It is the 2-methyl derivative of iPALT.[1] The drug is very similar in structure to 2-methyl-DiPT, which Alexander Shulgin hypothesized would be a DiPT-like selective auditory hallucinogen but never synthesized nor tested.[1]

Pharmacology

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2-Methyl-iPALT is a non-selective serotonin receptor agonist, including of the serotonin 5-HT1B, 5-HT2A, 5-HT2B, and 5-HT6 receptors, but not of the serotonin 5-HT1A receptor.[1] However, it shows rather low, micromolar potency for most of these actions, with for example 264-fold lower potency as a serotonin 5-HT2A receptor agonist than the known psychedelic drug 5-MeO-iPALT (ASR-3001).[1] The drug is inactive as a monoamine reuptake inhibitor.[1]

Chemistry

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The chemical synthesis of 2-methyl-iPALT has been described.[1] Analogues of 2-methyl-iPALT include 5-MeO-iPALT (ASR-3001), 4-HO-iPALT, and 2-methyl-DiPT, among others.[1] 2-Methyl-iPALT was patented by the Alexander Shulgin Research Institute (ASRI) in 2024.[1]

See also

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References

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  1. ^ a b c d e f g h i US 20240277665A1, Daley PF, Cozzi NV, Callaway WB, "Asymmetric allyl tryptamines", issued 4 March 2024, assigned to Alexander Shulgin Research Institute Inc.