5-HO-DET

Category:Articles with short descriptionCategory:Short description is different from Wikidata
5-HO-DET
Clinical data
Other names5-OH-DET; 5-Hydroxy-DET; 5-Hydroxy-N,N-diethyltryptamine
Drug classSerotonin receptor modulator
ATC code
Identifiers
  • 3-[2-(diethylamino)ethyl]-1H-indol-5-ol
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H20N2O
Molar mass232.327 g·mol−1
3D model (JSmol)
  • CCN(CC)CCC1=CNC2=C1C=C(C=C2)O
  • 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
Category:Chemical pages without DrugBank identifier#*Category:Articles without KEGG source#*Category:Articles without UNII source#*Category:Drugs with no legal statusCategory:Articles containing unverified chemical infoboxes#*

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]

It 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).[4][5] 5-HO-DET has been assessed and found to show high affinity for the serotonin 5-HT1E and 5-HT1F receptors.[3]

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

See also

References

  1. 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).
  2. 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.
  3. 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.
  4. ↑ "Indole, 3-(2-(diethylamino)ethyl)-5-hydroxy-". PubChem. U.S. National Library of Medicine. Retrieved 8 June 2025.
  5. ↑ "Bufotenin". PubChem. U.S. National Library of Medicine. Retrieved 8 June 2025.


Category:5-Hydroxytryptamines Category:N,N-Dialkyltryptamines Category:Serotonin receptor modulators Category:Diethylamino compounds


Category:5-Hydroxytryptamines Category:All stub articles Category:Articles containing unverified chemical infoboxes Category:Articles with short description Category:Articles without KEGG source Category:Articles without UNII source Category:Chemical pages without DrugBank identifier Category:Diethylamino compounds Category:Drugs not assigned an ATC code Category:Drugs with no legal status Category:Hallucinogen stubs Category:N,N-Dialkyltryptamines Category:Serotonin receptor modulators Category:Short description is different from Wikidata