4-HO-DsBT

4-HO-DsBT
Clinical data
Other names	4-HO-DSBT; 4-Hydroxy-N,N-di-sec-butyltryptamine
Identifiers
	IUPAC name 3-[2-[di(butan-2-yl)amino]ethyl]-1H-indol-4-ol;
CAS Number	127507-01-1 ; 4-HO-DBT: 63065-89-4 ;
PubChem CID	21786580;
ChemSpider	10513070;
UNII	E943EL34UU; 4-HO-DBT: R3EY4G4BLQ ;
CompTox Dashboard (EPA)	DTXSID001045425 ;
Chemical and physical data
Formula	C18H28N2O
Molar mass	288.435 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC(C)N(CCc1c[nH]c2cccc(O)c12)C(C)CC;
	InChI InChI=1S/C18H28N2O/c1-5-13(3)20(14(4)6-2)11-10-15-12-19-16-8-7-9-17(21)18(15)16/h7-9,12-14,19,21H,5-6,10-11H2,1-4H3; Key:SMKFHUHBZWMALV-UHFFFAOYSA-N;

4-HO-DsBT, also known as 4-hydroxy-N,N-di-sec-butyltryptamine, is a tryptamine derivative which acts as a serotonin receptor agonist.^[1]^[2]

Use and effects

4-HO-DsBT was first made by Alexander Shulgin and is mentioned in his book TiHKAL (Tryptamines I Have Known and Loved), but was never tested by him.^[1]

Interactions

Pharmacology

Pharmacodynamics

It has been tested in vitro and unlike the n-butyl and isobutyl isomers which are much weaker, the s-butyl derivative retains reasonable potency, with a similar 5-HT_2A receptor affinity to MiPT but better selectivity over the 5-HT_1A and 5-HT_2B subtypes.^[2]

Chemistry

Analogues

Analogues of 4-HO-DsBT include 4-HO-DBT, 4-HO-DiBT, 4-HO-DtBT, 4-HO-DiPT, 4-HO-McPeT, 4-HO-PiPT, 5-MeO-DBT, dibutyltryptamine (DBT), and N-tert-butyltryptamine (NtBT), among others.

History

4-HO-DsBT was first described in the scientific literature by David Repke and colleagues by 1981.^[3]

References

1 2 4-HO-DBT TiHKAL entry "Back to the rational world. Two n-butyl groups gives the compound 4-HO-DBT, the theme of this recipe. It is not active at 20 milligrams, but I suspect that it will be so at a somewhat higher dose. There is the secondary-isomer, 4-hydroxy-N,N-di-sec-butyltryptamine (4-HO-DSBT, an oil that never crystallized) which should be an isomer of increased activity, but it has not been assayed. The iso-isomer (4-HO-DIBT, mp 152–154 °C) should be yet less active as the steric mess around that important nitrogen atom is much larger, and indeed it is not active at the same 20 milligram level. The tertiary isomer (4-HO-DTBT) has yet to be made and, as it is extremely crowded around that innocent nitrogen atom, it may be unmakable. The activity is unknown, as the compound itself is unknown. The four methyl butyl possibilities are all known, and are mentioned in the recipe for 4-HO-MPT."
1 2 McKenna DJ, Repke DB, Lo L, Peroutka SJ (March 1990). "Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes". Neuropharmacology. 29 (3): 193–198. doi:10.1016/0028-3908(90)90001-8. PMID 2139186. S2CID 24188017.
↑ Repke DB, Ferguson WJ, Bates DK (1981). "Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-,3-[2-( N-methyl-N-alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols". Journal of Heterocyclic Chemistry. 18 (1): 175–179. doi:10.1002/jhet.5570180131. ISSN 0022-152X. Retrieved 1 November 2025.

External links

4-HO-DSBT - Isomer Design

[TiHKAL-1] 1 2 4-HO-DBT TiHKAL entry "Back to the rational world. Two n-butyl groups gives the compound 4-HO-DBT, the theme of this recipe. It is not active at 20 milligrams, but I suspect that it will be so at a somewhat higher dose. There is the secondary-isomer, 4-hydroxy-N,N-di-sec-butyltryptamine (4-HO-DSBT, an oil that never crystallized) which should be an isomer of increased activity, but it has not been assayed. The iso-isomer (4-HO-DIBT, mp 152–154 °C) should be yet less active as the steric mess around that important nitrogen atom is much larger, and indeed it is not active at the same 20 milligram level. The tertiary isomer (4-HO-DTBT) has yet to be made and, as it is extremely crowded around that innocent nitrogen atom, it may be unmakable. The activity is unknown, as the compound itself is unknown. The four methyl butyl possibilities are all known, and are mentioned in the recipe for 4-HO-MPT."

[McKenna_1990-2] 1 2 McKenna DJ, Repke DB, Lo L, Peroutka SJ (March 1990). "Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes". Neuropharmacology. 29 (3): 193–198. doi:10.1016/0028-3908(90)90001-8. PMID 2139186. S2CID 24188017.

[Repke_1981-3] Repke DB, Ferguson WJ, Bates DK (1981). "Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-,3-[2-( N-methyl-N-alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols". Journal of Heterocyclic Chemistry. 18 (1): 175–179. doi:10.1002/jhet.5570180131. ISSN 0022-152X. Retrieved 1 November 2025.

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