5-MeO-DBT

Last updated

5-MeO-DBT
5-MeO-DBT.svg
5-MeO-DBT 3D BS.png
Clinical data
Other names5-OMe-DBT; 5-Methoxy-DBT; 5-Methoxy-N,N-dibutyltryptamine; 5-MeO-BET; N,N-Bu-5-MeO-T
Drug class Non-selective serotonin receptor agonist; Serotonin 5-HT1A receptor agonist;
ATC code
  • None
Identifiers
  • N-butyl-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]butan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C19H30N2O
Molar mass 302.462 g·mol−1
3D model (JSmol)
  • CCCCN(CCCC)CCC1=CNC2=C1C=C(C=C2)OC
  • InChI=1S/C19H30N2O/c1-4-6-11-21(12-7-5-2)13-10-16-15-20-19-9-8-17(22-3)14-18(16)19/h8-9,14-15,20H,4-7,10-13H2,1-3H3
  • Key:WVGCRISHWANOTO-UHFFFAOYSA-N

5-MeO-DBT, also known as 5-methoxy-N,N-dibutyltryptamine, is a serotonin receptor modulator, and a rare substituted tryptamine derivative, which is thought to be a psychoactive substance. [1] [2]

Contents

Unlike many other related compounds it exhibits very low efficacy for the 5-HT2A receptor. [2]

5-MeO-DBT was first described in the literature by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved). [1] It was identified in a designer drug sample by a forensic laboratory in Slovenia in March 2021, [3] and assessed pharmachologically in 2023. [2] It is controlled under drug analogue legislation in a number of jurisdictions. [4]

Use and effects

In his book TiHKAL (Tryptamines I Have Known and Loved), Alexander Shulgin briefly mentioned 5-MeO-DBT and described it as a known compound with unknown activity. [1] Relatedly, the properties and effects of 5-MeO-DBT are unknown. [1] In any case, related drugs like dibutyltryptamine (DBT) and 4-HO-DPT have been reported to yield disappointing effects. [1] [5]

Interactions

Pharmacology

Pharmacodynamics

5-MeO-DBT activities
TargetAffinity (Ki, nM)
5-HT1A 337 (Ki)
267 (EC50 Tooltip half-maximal effective concentration)
106% (Emax Tooltip maximal efficacy)
5-HT2A 562 (Ki)
620a (EC50)
18%a (Emax)
5-HT2C 3,130 (Ki)
2,400a (EC50)
76%a (Emax)
SERT Tooltip Serotonin transporter1,180 (Ki)
2,120 ( 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: [2]

Based on limited evidence, 5-MeO-DBT acts as a non-selective serotonin receptor agonist with the highest potency and efficacy at the 5-HT1A receptor. [2] It has a similar potency to 5-MeO-MiPT for this target. [2] The substance, unlike many other substituted tryptamines, acts as a very weak and low efficacy partial agonist for the 5-HT2A receptor. [2] Among the group of related tryptamine analogues it also displayed the lowest efficacy for the 5-HT2C receptor. [2]

5-MeO-DBT decreased locomotor activity and failed to substitute for the discriminative stimulus effects of DOM in rodent drug discrimination tests. [5]

Chemistry

Analogues

Analogues of 5-MeO-DBT include dibutyltryptamine (DBT), 4-HO-DBT, 5-MeO-DMT, 5-MeO-DET, 5-MeO-DPT, 5-MeO-DiPT, and 5-MeO-DALT, among others. [1]

5-MeO-DsBT

5-MeO-DsBT is a notable skeletal isomer of 5-MeO-DBT. [1] It was very briefly mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved), but was described as an unknown compound. [1] Relatedly, its dose and duration were not described. [1]

History

5-MeO-DBT was first described in the literature by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved). [1]

Society and culture

United States

Alabama

5-MeO-DBT was made schedule I at the state level in Alabama on September 13, 2024. [4]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252. https://isomerdesign.com/pihkal/read/tk/36
  2. 1 2 3 4 5 6 7 8 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.
  3. ↑ "Analytical Report. 5-MeO-DBT" (PDF). Slovenia: Nacionalni Forenzični Laboratorij. 10 March 2021.
  4. 1 2 "Controlled Substances List" (PDF). www.alabamapublichealth.gov.
  5. 1 2 Hill RD, Shetty RA, Sumien N, Priddy J, Forster MJ, Gatch MB (September 2025). "Behavioral effects of three synthetic tryptamine derivatives in rodents". Journal of Psychopharmacology. 39 (9): 1007–1013. doi:10.1177/02698811251330737. ISSN   0269-8811. PMID   40183394.
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