5-MeO-DBT

5-MeO-DBT

File:5-MeO-DBT.svg
File:5-MeO-DBT 3D BS.png
Clinical data
Other names	5-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
IUPAC name N-butyl-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]butan-1-amine
CAS Number	73785-42-9
PubChem CID	53485365
ChemSpider	30798625
UNII	Q454YC4LIK
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C19H30N2O
Molar mass	302.462 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCCN(CCCC)CCC1=CNC2=C1C=C(C=C2)OC
InChI 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.

Unlike many other related compounds it exhibits very low efficacy for the 5-HT_2A receptor.

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

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. Relatedly, the properties and effects of 5-MeO-DBT are unknown. In any case, related drugs like dibutyltryptamine (DBT) and 4-HO-DPT have been reported to yield disappointing effects.

Interactions

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

Pharmacology

Pharmacodynamics

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:

Based on limited evidence, 5-MeO-DBT acts as a non-selective serotonin receptor agonist with the highest potency and efficacy at the 5-HT_1A receptor. It has a similar potency to 5-MeO-MiPT for this target. The substance, unlike many other substituted tryptamines, acts as a very weak and low efficacy partial agonist for the 5-HT_2A receptor. Among the group of related tryptamine analogues it also displayed the lowest efficacy for the 5-HT_2C receptor.

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

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.

5-MeO-DsBT

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

History

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

Society and culture

Legal status

United States

Alabama

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

See also

• Substituted tryptamine

External links

• 5-MeO-DBT - Isomer Design