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5-MeO-DBT

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5-MeO-DBT
Clinical data
Other names5-OMe-DBT; 5-Methoxy-DBT; 5-Methoxy-N,N-dibutyltryptamine; 5-MeO-BET; N,N-Bu-5-MeO-T
Drug classNon-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
FormulaC19H30N2O
Molar mass302.462 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]

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

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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

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

Pharmacology

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Pharmacodynamics

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5-MeO-DBT activities
Target Affinity (Ki, nM)
5-HT1A 337 (Ki)
267 (EC50Tooltip half-maximal effective concentration)
106% (EmaxTooltip maximal efficacy)
5-HT2A 562 (Ki)
620a (EC50)
18%a (Emax)
5-HT2C 3,130 (Ki)
2,400a (EC50)
76%a (Emax)
SERTTooltip Serotonin transporter 1,180 (Ki)
2,120 (IC50)
Notes: The smaller the value, the more avidly the drug interacts with the site. Footnotes: a = Stimulation of IP1Tooltip 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

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Analogues

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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

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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

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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

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United States

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

See also

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References

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  1. ^ a b c d e f g h i j 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. ^ a b c d e f g h 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. ^ a b "Controlled Substances List" (PDF). www.alabamapublichealth.gov.
  5. ^ a b 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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