Chemistry:5-HO-DET

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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

Pharmacodynamics

5-HO-DET 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]

History

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

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. 1975. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. https://bitnest.netfirms.com/external/Books/978-0-85608-011-1. "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. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 "Synthesis and biological activity of some ring-substituted tryptamines". Journal of Medicinal Chemistry 10 (4): 646–648. July 1967. doi:10.1021/jm00316a027. PMID 4962512. 
  3. ↑ 3.0 3.1 "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. June 2011. doi:10.1124/jpet.111.179606. PMID 21422162. 
  4. ↑ "Indole, 3-(2-(diethylamino)ethyl)-5-hydroxy-". PubChem. U.S. National Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/compound/26395. 
  5. ↑ "Bufotenin". PubChem. U.S. National Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/compound/10257. 




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