5-HO-DET

5-HO-DET
Clinical data
Other names	5-OH-DET; 5-Hydroxy-DET; 5-Hydroxy-N,N-diethyltryptamine
Drug class	Serotonin receptor modulator
ATC code	None;
Identifiers
	IUPAC name 3-[2-(diethylamino)ethyl]-1H-indol-5-ol;
CAS Number	14009-42-8;
PubChem CID	26395;
ChemSpider	24590;
ChEMBL	ChEMBL142629;
CompTox Dashboard (EPA)	DTXSID80161229 ;
Chemical and physical data
Formula	C14H20N2O
Molar mass	232.327 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN(CC)CCC1=CNC2=C1C=C(C=C2)O;
	InChI InChI=1S/C14H20N2O/c1-3-16(4-2)8-7-11-10-15-14-6-5-12(17)9-13(11)14/h5-6,9-10,15,17H,3-4,7-8H2,1-2H3; Key:DLKZNHHXBDWTOP-UHFFFAOYSA-N;

5-HO-DET, or 5-hydroxy-DET, also known as 5-hydroxy-N,N-diethyltryptamine, is a serotonin receptor modulator of the tryptamine and 5-hydroxytryptamine families related to the psychedelic drug bufotenin (5-HO-DMT).^[1]^[2]^[3] It is the derivative of bufotenin in which the N,N-dimethyl groups have been replaced with N,N-diethyl groups.^[1]^[2] The drug is also the N,N-diethyl derivative of serotonin (5-hydroxytryptamine) and the 5-hydroxy derivative of diethyltryptamine (DET).^[1]^[2]

Pharmacology

5-HO-DET has been assessed and found to show high affinity for the serotonin 5-HT_1E and 5-HT_1F receptors.^[3] It was a potent serotonin receptor agonist in the rat stomach strip.^[4] The drug shows relatively low potency in terms of psychedelic-like behavioral effects in the conditioned avoidance response test in rodents.^[1]^[2] It has been suggested that this might be due to 5-HO-DET having poor lipophilicity and blood–brain barrier permeability analogously to bufotenin.^[1]^[2] However, 5-HO-DET has significantly greater lipophilicity than bufotenin owing to its ethyl instead of methyl groups (predicted log P = 1.9 and 1.2, respectively).^[5]^[6]

Analogues of 5-HO-DET include diethyltryptamine (DET), 4-HO-DET (ethocin), 4-AcO-DET (ethacetin), 4-PO-DET (ethocybin), 5-MeO-DET, bufotenin (5-HO-DMT), 5-HO-MET, 5-HO-DPT, 5-HO-DiPT, α-methylserotonin (5-HO-AMT), and N-methylserotonin (5-HO-NMT), among others.

5-HO-DET was first described in the scientific literature by Hunt and Brimblecombe by at least 1967.^[1]^[2]

1 2 3 4 5 6 Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. OL 4850660M. The weak activity at 5 mg./kg. (s.c.) of 5-hydroxy-N,N-diethyltryptamine in the open field test with rats may well be due to a similar lack of lipid solubility and consequent poor entry into the brain (Hunt and Brimblecombe, 1967).
1 2 3 4 5 6 Hunt RR, Brimblecombe RW (July 1967). "Synthesis and biological activity of some ring-substituted tryptamines". Journal of Medicinal Chemistry. 10 (4): 646–648. doi:10.1021/jm00316a027. PMID 4962512.
1 2 Klein MT, Dukat M, Glennon RA, Teitler M (June 2011). "Toward selective drug development for the human 5-hydroxytryptamine 1E receptor: a comparison of 5-hydroxytryptamine 1E and 1F receptor structure-affinity relationships". The Journal of Pharmacology and Experimental Therapeutics. 337 (3): 860–867. doi:10.1124/jpet.111.179606. PMC 3101003. PMID 21422162.
↑ Vane JR (March 1959). "The relative activities of some tryptamine analogues on the isolated rat stomach strip preparation". Br J Pharmacol Chemother. 14 (1): 87–98. doi:10.1111/j.1476-5381.1959.tb00933.x. PMC 1481817. PMID 13651584.
↑ "Indole, 3-(2-(diethylamino)ethyl)-5-hydroxy-". PubChem. U.S. National Library of Medicine. Retrieved 8 June 2025.
↑ "Bufotenin". PubChem. U.S. National Library of Medicine. Retrieved 8 June 2025.