4-MeO-DiPT

4-MeO-DiPT
Clinical data
Other names4-OMe-DiPT; 4-Methoxy-N,N-diisopropyltryptamine; D-4200; N,N-Diisopropyl-4-methoxytryptamine
Drug classNon-selective serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonin reuptake inhibitor
ATC code
  • None
Identifiers
  • N-Isopropyl-N-[2-(4-methoxy-1H-indol-3-yl)ethyl]-2-propanamine
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H26N2O
Molar mass274.408 g·mol−1
3D model (JSmol)
  • CC(C)N(CCC1=CNC2=C1C(=CC=C2)OC)C(C)C
  • InChI=1S/C17H26N2O/c1-12(2)19(13(3)4)10-9-14-11-18-15-7-6-8-16(20-5)17(14)15/h6-8,11-13,18H,9-10H2,1-5H3
  • Key:WIVWUNUDMXNQJD-UHFFFAOYSA-N

4-MeO-DiPT, also known as 4-methoxy-N,N-diisopropyltryptamine, is a novel serotonin receptor modulator of the tryptamine family related to known psychedelic tryptamines like psilocin (4-HO-DMT) and 5-MeO-DMT.[1][2] It is the 4-methoxy analog of DiPT and the O-methyl ether of 4-HO-DiPT.[1] Very little data exists about the human use, metabolism, and toxicity of 4-MeO-DiPT.[1][2]

Use and effects

4-MeO-DiPT is not known to have been assessed in humans.[2] It is unknown whether the drug produces psychedelic effects in humans.[2]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

4-MeO-DiPT activities
Target Affinity (Ki, nM)
5-HT1A 2,830 (Ki)
1,930 (EC50Tooltip half-maximal effective concentration)
113% (EmaxTooltip maximal efficacy)
5-HT2A 500 (Ki)
870a (EC50)
92%a (Emax)
5-HT2C 833 (Ki)
179a (EC50)
85%a (Emax)
SERT 12 (Ki)
11 (IC50)
Notes: The smaller the value, the more avidly the drug interacts with the site. Footnotes: a = Stimulation of IP1Tooltip inositol phosphate formation. Sources: [1]

4-MeO-DiPT acts as a serotonin reuptake inhibitor and non-selective serotonin receptor agonist, including of the serotonin 5-HT2A, and 5-HT2C receptors.[1] It shows the highest potency as a serotonin reuptake inhibitor with 40- to 50-fold selectivity for the serotonin transporter (SERT) over the 5-HT2A receptor, moderate potency as an agonist of the 5-HT2C receptor, and low potency with high efficacy as an agonist of the 5-HT1A receptor.[1] Affinities towards receptors outside of the serotonin receptor family have not yet been assessed.[1]

Increased extracellular concentrations of serotonin, resulting from SERT blockade, similarly to 4-MeO-MiPT may compete at 5-HT2A, altering or blunting effects mediated by this receptor.[1] This profile makes 4-MeO-DiPT a potential candidate for elucidating the role of SERT blockade in the mechanisms underlying serotonergic psychedelic action.[1]

Chemistry

4-MeO-DiPT is a synthetic derivative of the substituted tryptamine and 4-methoxytryptamine families.[1][2] It is the 4-methoxy analogue of N,N-diisopropyltryptamine (DiPT) and the O-methyl ether of 4-HO-DiPT.[1][2][3]

Analogues

Analogues of 4-MeO-DiPT include N,N-diisopropyltryptamine (DiPT), 4-methoxytryptamine (4-MeO-T), 4-MeO-MiPT, 4-MeO-DMT, 4-HO-DiPT, 4-AcO-DiPT, 5-MeO-DiPT, 5-MeO-DMT, and psilocin (4-HO-DMT), among others.[1][2][3]

History

4-MeO-DiPT was briefly mentioned by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known Loved).[2] Subsequently, it was described and studied further in the early 2020s.[3][1]

Society and culture

United States

4-MeO-DiPT is not an explicitly controlled substance in the United States, but may be considered a Schedule I controlled substance in this country as it is a positional isomer of 5-MeO-DiPT.[4][5]

See also

References

  1. ^ a b c d e f g h i j k l m Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, et al. (April 2023). "Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter". The Journal of Pharmacology and Experimental Therapeutics. 385 (1): 62–75. doi:10.1124/jpet.122.001454. PMC 10029822. PMID 36669875.
  2. ^ a b c d e f g h Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. "The 5-MeO-DMT has already been mentioned, and the remaining two would be 4-MeO-DMT and 4-MeO-DIPT. The former is a known compound but has not been measured in man. The latter is not a known compound."
  3. ^ a b c Lee HZ, Ng JY, Ong MC, Lim JL, Yap TW (November 2020). "Technical note: Unequivocal identification of 5-methoxy-DiPT with NOESY NMR and GC-IRD". Forensic Science International. 316 (110537) 110537. doi:10.1016/j.forsciint.2020.110537. PMID 33099269.
  4. ^ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
  5. ^ Drug Enforcement Administration (3 December 2007). "Definition of "Positional Isomer" as It Pertains to the Control of Schedule I Controlled Substances". Federal Register.
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