4-HO-DSBT

4-HO-DSBT
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 (4-hydroxy-N,N-di-sec-butyltryptamine) is a tryptamine derivative which acts as a serotonin receptor agonist. It was first made by Alexander Shulgin and is mentioned in his book TiHKAL, but was never tested by him.^[1] However it has subsequently 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]

References

^ 4-HO-DBT TiHKAL entry
^ McKenna DJ, Repke DB, Lo L, Peroutka SJ (March 1990). "Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes". Neuropharmacology. 29 (3): 193–8. doi:10.1016/0028-3908(90)90001-8. PMID 2139186. S2CID 24188017.

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[1] 4-HO-DBT TiHKAL entry

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

[1]

[2]

Identifiers

IUPAC name 3-[2-[di(butan-2-yl)amino]ethyl]-1H-indol-4-ol
CAS Number	127507-01-1^N 4-HO-DBT: 63065-89-4^Y
PubChem CID	21786580
ChemSpider	10513070
UNII	E943EL34UU 4-HO-DBT: R3EY4G4BLQ^Y
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

See also

References