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Ethocybin

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Ethocybin
Skeletal formula of ethocybin
Ball-and-stick model of the ethocybin molecule as a zwitterion
Clinical data
Other names4-Phosphoryloxy-N,N-diethyltryptamine; CEY-19; 4-phosphoryloxy-DET; 4-PO-DET
Routes of
administration		Oral[1]
Drug classSerotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Duration of action4–6 hours[1]
Identifiers
  • Phosphoric acid mono-[3-(2-diethylamino-ethyl)-1H-indol-4-yl] ester
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H21N2O4P
Molar mass312.306 g·mol−1
3D model (JSmol)
  • CCN(CC)CCC2=CNC1=CC=CC(OP(O)(O)=O)=C12
  • InChI=1S/C14H21N2O4P/c1-3-16(4-2)9-8-11-10-15-12-6-5-7-13(14(11)12)20-21(17,18)19/h5-7,10,15H,3-4,8-9H2,1-2H3,(H2,17,18,19) checkY
  • Key:AAVKQQUBPHSCML-UHFFFAOYSA-N checkY
  (verify)

Ethocybin (code name CEY-19), also known as 4-phosphoryloxy-N,N-diethyltryptamine (4-PO-DET), is a homologue of the mushroom alkaloid psilocybin, and a semi-synthetic psychedelic alkaloid of the tryptamine family.[1]

Pharmacology

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Ethocybin may be dephosphorylated in vivo to 4-HO-DET (ethocin), analogously to how psilocybin is metabolized to psilocin.[2] This chemical reaction takes place under strongly acidic conditions or enzymatically by phosphatases in the body. 4-HO-DET acts as a partial agonist at the 5-HT2A serotonin receptor.[3][4]

History

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Albert Hofmann was the first to produce ethocybin, soon after his discovery of psilocin and psilocybin.[5][6] It was first described by 1963.[5][6] The drug was known under the code name CEY-19.[6]

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United States

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Ethocybin is not controlled in the United States, but possession or sale may be considered illegal under the Federal Analog Act.

Research

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Ethocybin has been studied as a treatment for several disorders since the early 1960s, and numerous papers are devoted to this material.[citation needed] Its short-lived action was considered a virtue. A 2010 study found that ethocybin helped with bipolar affective disorder.[citation needed]

References

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  1. ^ a b c Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
  2. ^ "EMCDDA | Hallucinogenic mushrooms profile (chemistry, effects, other names (magic mushrooms, shrooms…), origin, mode of use, other names, medical use, control status)". www.emcdda.europa.eu. Retrieved 2020-01-22.
  3. ^ "EMCDDA | Hallucinogenic mushrooms profile (chemistry, effects, other names (magic mushrooms, shrooms…), origin, mode of use, other names, medical use, control status)". www.emcdda.europa.eu. Retrieved 2020-01-22.
  4. ^ Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, Olson RJ, Janowsky A, Abbas AI (April 2023). "Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter" (PDF). J Pharmacol Exp Ther. 385 (1): 62–75. doi:10.1124/jpet.122.001454. PMC 10029822. PMID 36669875.
  5. ^ a b US patent 3075992, Hofmann, Albert; Troxler, Franz., "Esters of indoles", issued 1963-1-29 
  6. ^ a b c Leuner H, Baer G (1965). "Two new short-acting hallucinogens of the psilocybin group". Neuropsychopharmacology. 4: 471–474.
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