ethocybin
{{Short description|Psychedelic drug}}
{{Drugbox
| verifiedrevid = 447614829
| image = Ethocybin.png
| width = 200
| alt = Skeletal formula of ethocybin
| image2 = Ethocybin zwitterion 3D ball.png
| alt2 = Ball-and-stick model of the ethocybin molecule as a zwitterion
| width2 = 220
| tradename =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| routes_of_administration = Oral
| class = Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
| legal_AU =
| legal_CA =
| legal_UK = Class A
| legal_US =
| legal_DE = Anlage I
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| duration_of_action = 4–6 hours
| excretion =
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 60480-02-6
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Z47K2YT973
| ATC_prefix = None
| ATC_suffix =
| PubChem = 53633102
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21106438
| synonyms = 4-Phosphoryloxy-N,N-diethyltryptamine; CEY-19; 4-phosphoryloxy-DET; 4-PO-DET
| IUPAC_name = Phosphoric acid mono-[3-(2-diethylamino-ethyl)-1H-indol-4-yl] ester
| C=14 | H=21 | N=2 | O=4 | P=1
| SMILES = CCN(CC)CCC2=CNC1=CC=CC(OP(O)(O)=O)=C12
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = AAVKQQUBPHSCML-UHFFFAOYSA-N
}}
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.{{CiteTiHKAL}} Effects of ethocybin are comparable to those of a shorter LSD or psilocybin trip, although intensity and duration vary depending on dosage, individual physiology, and set and setting.{{Cite web|url=https://drugs.ncats.io/drug/Z47K2YT973|title=NCATS Inxight: Drugs — 4-PHOSPHORYLOXY N,N-DIETHYLTRYPTAMINE|website=drugs.ncats.io|language=en|access-date=2020-01-22}}{{cite journal | vauthors = Gartz J | title = Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe | journal = Journal of Basic Microbiology | volume = 29 | issue = 6 | pages = 347–52 | date = 1989 | pmid = 2614674 | doi = 10.1002/jobm.3620290608 | s2cid = 43308695 }}
Effects
Effects begin 20 to 45{{nbsp}}minutes after ingestion, and last from 2 to 4{{nbsp}}hours depending on dose, species, and individual metabolism.{{Citation needed|date=March 2009}} The effects are somewhat shorter compared to psilocybin.{{Citation needed|date=April 2025}}
Mental and physical tolerance to psilocybin builds and dissipates quickly.{{Citation needed|date=April 2025}} Taking ethocybin more than three or four times in a week (especially two days in a row) can result in diminished effects.{{Citation needed|date=April 2025}} Tolerance dissipates after a few days, so frequent users often keep doses spaced five to seven days apart to avoid the effect.{{Citation needed|date=April 2025}}
Pharmacology
As with psilocybin, ethocybin is rapidly dephosphorylated in the body to 4-HO-DET (ethocin).{{Cite web|url=http://www.emcdda.europa.eu/publications/drug-profiles/mushrooms|title=EMCDDA {{!}} Hallucinogenic mushrooms profile (chemistry, effects, other names (magic mushrooms, shrooms…), origin, mode of use, other names, medical use, control status)|website=www.emcdda.europa.eu|access-date=2020-01-22}} This chemical reaction takes place under strongly acidic conditions or enzymatically by phosphatases in the body. Then, 4-HO-DET acts as a partial agonist at the 5-HT2A serotonin receptor in the brain where it mimics the effects of serotonin (5-HT).{{Cite web|url=http://www.emcdda.europa.eu/publications/drug-profiles/mushrooms|title=EMCDDA {{!}} Hallucinogenic mushrooms profile (chemistry, effects, other names (magic mushrooms, shrooms…), origin, mode of use, other names, medical use, control status)|website=www.emcdda.europa.eu|access-date=2020-01-22}}{{cite journal | vauthors = Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, Olson RJ, Janowsky A, Abbas AI | title = Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter | journal = J Pharmacol Exp Ther | volume = 385 | issue = 1 | pages = 62–75 | date = April 2023 | pmid = 36669875 | pmc = 10029822 | doi = 10.1124/jpet.122.001454 | url = https://pmc.ncbi.nlm.nih.gov/articles/PMC10029822/pdf/jpet.122.001454.pdf}}
History
Albert Hofmann was the first to produce ethocybin, soon after his discovery of psilocin and psilocybin.{{US patent reference | number = 3075992 | y = 1963 | m = 1 | d = 29 | inventor = Hofmann, Albert; Troxler, Franz. | title = Esters of indoles }}{{cite journal | vauthors = Leuner H, Baer G | title = Two new short-acting hallucinogens of the psilocybin group | date = 1965 | journal = Neuropsychopharmacology | volume = 4 | issue = | pages = 471-474 | url = https://web.archive.org/web/20250422014123/https://bibliography.maps.org/resources/download/19910}} It was first described by 1963. The drug was known under the code name CEY-19.
Legal status
=United States=
Ethocybin is not controlled in the United States, but possession or sale may be considered illegal under the Federal Analog Act.
Research
Ethocybin has been studied as a treatment for several disorders since the early 1960s, and numerous papers are devoted to this material.{{Citation needed|date=March 2009}} Its short-lived action was considered a virtue. A 2010 study found that ethocybin helped with bipolar affective disorder.{{Citation needed|date=April 2025}}
References
{{Reflist}}
External links
- [https://isomerdesign.com/pihkal/explore/5057 4-PO-DET (Ethocybin) - Isomer Design]
- [https://isomerdesign.com/pihkal/read/tk/16 4-HO-DET and 4-H2PO4-DET - TiHKAL - Isomer Design]
- [https://www.erowid.org/library/books_online/tihkal/tihkal16.shtml 4-HO-DET and 4-H2PO4-DET - TiHKAL - Erowid]
- [https://bitnest.netfirms.com/external/SST/91 - CEY 19 - Trout's Notes]
{{Psychedelics}}
{{Serotonin receptor modulators}}
{{Tryptamines}}
Category:N,N-Dialkyltryptamines
Category:Diethylamino compounds