Chemistry:5-MeO-DBT

From HandWiki

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]

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 encountered as a novel designer drug by 2019[3][4] and was assessed pharmacologically in 2023.[2] The drug is controlled under drug analogue legislation in a number of jurisdictions.[5]

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][6]

Interactions

Pharmacology

Pharmacodynamics

5-MeO-DBT activities
Target Affinity (Ki, nM)
5-HT1A 337 (Ki)
267 (EC50)
106% (Emax)
5-HT2A 562 (Ki)
620a (EC50)
18%a (Emax)
5-HT2C 3,130 (Ki)
2,400a (EC50)
76%a (Emax)
SERT 1,180 (Ki)
2,120 (IC50)

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.[6]

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, 5-MeO-DALT, and 5-MeO-DsBT, among others.[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] It was encountered as a novel designer drug by 2019.[3][4]

Society and culture

United States

Alabama

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

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. http://www.erowid.org/library/books_online/tihkal/tihkal.shtml.  https://isomerdesign.com/pihkal/read/tk/36
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 Cite error: Invalid <ref> tag; no text was provided for refs named Kozell_2023b
  3. ↑ 3.0 3.1 "N,N-Bu-5-MeO-T (5-MeO-DBT)" (in ru). https://aipsin.com/newsubstance/527/. 
  4. ↑ 4.0 4.1 "Analytical Report. 5-MeO-DBT". Slovenia: Nacionalni Forenzični Laboratorij. 10 March 2021. https://www.policija.si/apps/nfl_response_web/0_Analytical_Reports_final/5-MeO-DBT-ID-2212-20_report.pdf. 
  5. ↑ 5.0 5.1 "Controlled Substances List". https://www.alabamapublichealth.gov/blog/assets/controlledsubstanceslist.pdf. 
  6. ↑ 6.0 6.1 "Behavioral effects of three synthetic tryptamine derivatives in rodents" (in en). Journal of Psychopharmacology 39 (9): 1007–1013. September 2025. doi:10.1177/02698811251330737. ISSN 0269-8811. PMID 40183394. https://journals.sagepub.com/doi/10.1177/02698811251330737. 



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