Ethocybin

  1. Home
  2. Wiki
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 action2–6 hours[1][2][3][4][5]
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 also known as 4-phosphoryloxy-N,N-diethyltryptamine (4-PO-DET) or as CEY-19, is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to the psilocybin-containing mushroom alkaloid psilocybin.[1] It is assumed to act as a prodrug of 4-HO-DET (CZ-74) analogously to how psilocybin (4-PO-DMT) acts as a prodrug of psilocin (4-HO-DMT).[1][6] The drug was first described in the literature by Albert Hofmann and colleagues at Sandoz by 1963.[7][8]

Use and effects

[edit]
See also: 4-HO-DET § Use and effects

Interactions

[edit]
See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

[edit]
See also: 4-HO-DET § Pharmacology

Ethocybin may be dephosphorylated in vivo to 4-HO-DET (ethocin), analogously to how psilocybin (4-PO-DMT) is metabolized to psilocin (4-HO-DMT).[9] This chemical reaction takes place under strongly acidic conditions or enzymatically by phosphatases in the body. 4-HO-DET acts as a partial agonist of the serotonin 5-HT2A receptor.[10][11]

History

[edit]

Albert Hofmann and colleagues working at Sandoz were the first to synthesize and describe ethocybin (CEY-19) along with 4-HO-DET (CZ-74), which shortly followed his discovery of psilocin and psilocybin.[7][8] They first described the drug in a patent by 1963.[7][8] Along with 4-HO-DET, ethocybin was one of the earliest structurally modified or synthetic psychedelic tryptamines to be developed.[2][5]

Society and culture

[edit]
[edit]

United States

[edit]

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

Research

[edit]

Ethocybin, under the code name CEY-19 and along with 4-HO-DET (CZ-74), has been studied in psychedelic-assisted psychotherapy.[4][1][8]

See also

[edit]

References

[edit]
  1. ^ a b c d e Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
  2. ^ a b Nichols DE (2018). Chemistry and Structure-Activity Relationships of Psychedelics. Current Topics in Behavioral Neurosciences. Vol. 36. pp. 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. PMID 28401524. One of the earliest modifications of the tryptamines to be studied for psychoactive effects was the N,N-diethyl analogue of psilocin (CZ-74, 16). Both CZ-74 and its O-phosphoryl derivative CEY 19 (17) were studied in humans. Qualitatively, these compounds were very similar to psilocin and psilocybin, respectively, but had somewhat reduced durations of action (Leuner and Baer 1965).
  3. ^ Shulgin AT (1976). "Psychotomimetic Agents". In Gordon M (ed.). Psychopharmacological Agents: Use, Misuse and Abuse. Medicinal Chemistry: A Series of Monographs. Vol. 4. Academic Press. pp. 59–146. doi:10.1016/b978-0-12-290559-9.50011-9. ISBN 978-0-12-290559-9. Although the N-dealkylated homologs are as yet untested clinically, the N,N-diethyl homologs of psilocybin and of psilocin have been studied in man (Leunder and Baer, 1965). These compounds [CEY-19, (XXXIII); CZ-74, (XXXIV)] in dosages of from 5 to 20 mg appear to resemble psilocybin in the qualitative nature of their action but to be of shorter duration. Maximum effects are obtained in an hour, and 2 hours later the subject is for the most part recovered, thus providing a valuable time course for psychiatric therapy.
  4. ^ a b Passie, Torsten (7 November 2022). "History of the Use of Hallucinogens in Psychiatric Treatment". In Grob, Charles S.; Grigsby, Jim (eds.). Handbook of Medical Hallucinogens. Guilford Publications. pp. 95–118. ISBN 978-1-4625-5189-7. Psycholytic therapy underwent a number of modifications during its active years. Some European therapists experimented with shorter-acting psilocybin derivatives such as CZ-74 (4-hydroxy-N,N-diethyltryptamine, also known as 4-HO-DET; Baer, 1967; Shulgin & Shulgin, 2014), which has a duration of 4—6 hours and is phenomenologically similar to LSD; CEY-19 (phosphoryloxy-N,N-diethyltryptamine, also known as 4-PO-DET or ethocybin), which has a duration of 2—4 hours and is also similar to LSD, and the mescaline derivative 2-CD (2,5-dimethoxy-4-methylphenethylamine; Schlichting, 1989). Therapists in the United States experimented with the short-acting dipropyltrytamine (DP T) in psycholytic therapy (Soskin, 1975; Soskin, Grof, & Richards, 1973), as well as in psychedelic therapy (Richards, Rhead, DiLeo, Yensen, & Kurland, 1977).
  5. ^ a b Ross S, Franco S, Reiff C, Agin-Liebes G (9 March 2021). "Psilocybin". In Grob CS, Grigsby J (eds.). Handbook of Medical Hallucinogens. Guilford Publications. pp. 181–214. ISBN 978-1-4625-4544-5. Sandoz began manufacturing and distributing pure synthetic psilocybin pills (under the name Indocybin) to curious physicians and researchers around the world and would do so until recalling the drug in 1965 due to a growing political backlash in the United States (Hofmann, 2005). Sandoz also produced two synthetic drugs derived from mushroom-extracted psilocybin, CZ-74 (4-hydroxy-N,N-diethyltryptamine) and CEY-19 (4-phosphoryloxy-N,N-diethyltryptamine), both of which are shorter (approximately 3 hours in duration) acting than psilocybin (Baer, 1967). [...]
  6. ^ Klein AK, Chatha M, Laskowski LJ, Anderson EI, Brandt SD, Chapman SJ, McCorvy JD, Halberstadt AL (April 2021). "Investigation of the Structure-Activity Relationships of Psilocybin Analogues". ACS Pharmacol Transl Sci. 4 (2): 533–542. doi:10.1021/acsptsci.0c00176. PMC 8033608. PMID 33860183.
  7. ^ a b c US patent 3075992, Hofmann, Albert; Troxler, Franz., "Esters of indoles", issued 1963-1-29 
  8. ^ a b c d Leuner H, Baer G (1965). "Two new short-acting hallucinogens of the psilocybin group". Neuropsychopharmacology. 4: 471–474. Archived from the original on 2025-04-22.
  9. ^ "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.
  10. ^ "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.
  11. ^ 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". J Pharmacol Exp Ther. 385 (1): 62–75. doi:10.1124/jpet.122.001454. PMC 10029822. PMID 36669875.
[edit]