4-MeO-DiPT

Last updated

4-MeO-DiPT
4-MeO-DiPT.svg
4-MeO-DiPT-3d-sticks.png
Clinical data
Other names4-OMe-DiPT; 4-Methoxy-N,N-diisopropyltryptamine; D-4200; N,N-Diisopropyl-4-methoxytryptamine
Drug class Non-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
Formula C17H26N2O
Molar mass 274.408 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]

Contents

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

Pharmacology

Pharmacodynamics

4-MeO-DiPT activities
TargetAffinity (Ki, nM)
5-HT1A 2,830 (Ki)
1,930 (EC50 Tooltip half-maximal effective concentration)
113% (Emax Tooltip 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 IP1 Tooltip 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]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 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. 1 2 3 4 5 6 7 8 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. 1 2 3 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.
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