4-HO-MBT

4-HO-MBT

Clinical data
Other names	4-OH-MBT; 4-Hydroxy-N-methyl-N-butyltryptamine
ATC code	None
Identifiers
IUPAC name 3-[2-[butyl(methyl)amino]ethyl]-1H-indol-4-ol
PubChem CID	21786587
ChemSpider	10513077
Chemical and physical data
Formula	C15H22N2O
Molar mass	246.354 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCCN(C)CCC1=CNC2=C1C(=CC=C2)O
InChI InChI=1S/C15H22N2O/c1-3-4-9-17(2)10-8-12-11-16-13-6-5-7-14(18)15(12)13/h5-7,11,16,18H,3-4,8-10H2,1-2H3 Key:CVGNGEGPBYQCMP-UHFFFAOYSA-N

4-HO-MBT, also known as 4-hydroxy-N-methyl-N-butyltryptamine, is a chemical compound of the tryptamine and 4-hydroxytryptamine families related to the psychedelic drug psilocin (4-HO-DMT). ^{[1] [2]} It was briefly described by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved), but was not tested by him and its properties and effects are unknown. ^[1] 4-HO-MBT was first described in the scientific literature by David Repke and colleagues in 1981. ^[2]

Chemistry

Isomers

There are four possible isomers of 4-HO-MBT, with the others including 4-HO-MiBT, 4-HO-MsBT, and 4-HO-MtBT. ^[1] Of these, only 4-HO-MtBT has been tested as a possible psychedelic drug. ^[1] According to Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved), a dose of 15 mg 4-HO-MtBT orally produced virtually no effects. ^[1] Higher doses were not explored. ^[1]

Analogues

Analogues of 4-HO-MBT include methylbutyltryptamine (MBT), 4-HO-MET (metocin), 4-HO-MPT (meprocin), psilocin (4-HO-DMT), and 4-HO-DBT, among others. ^[1]

See also

• Substituted tryptamine

References

1. Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252. https://isomerdesign.com/pihkal/read/tk/23#5133 "How far can this argument be pushed? What about one of the N-alkyl groups [of 4-HO-MPT] having four carbons? Keeping the other N-alkyl group as the smallest and most simple methyl group, all four isomeric compounds are known. There is the n-butyl isomer (4-HO-MBT, an oil), the isobutyl isomer (4-HO-MIBT, mp 142–145 °C), the secondary butyl isomer (4-HO-MSBT, mp 138–140 °C) and the tertiary butyl isomer (4-HO-MTBT, mp 225–226 °C). Of these four materials only 4-HO-MTBT has been looked at as a possible psychedelic. Some 15 milligrams produced virtually no effects, maybe a hint of something in a few minutes and then nothing. Probably pure placebo."
2. Repke, David B.; Ferguson, Wilfred J.; Bates, Dallas K. (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 3 November 2025.

External links

• 4-HO-MBT - Isomer Design