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Chemical compound
Ethocybin
Other names 4-Phosphoryloxy-N ,N -diethyltryptamine; CEY-39; 4-phosphoryloxy-DET; 4-PO-DET
ATC code
Legal status
Phosphoric acid mono-[3-(2-diethylamino-ethyl)-1H-indol-4-yl] ester
CAS Number
ChemSpider
UNII
CompTox Dashboard (
EPA )
Formula C 14 H 21 N 2 O 4 P
Molar mass 312.306 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)
Y Key:AAVKQQUBPHSCML-UHFFFAOYSA-N
Y
(verify)
Ethocybin (CEY-19 ; 4-phosphoryloxy-DET; 4-PO-DET) is a
homologue of the mushroom
alkaloid
psilocybin , and a
semi-synthetic
psychedelic
alkaloid of the
tryptamine family. 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 .
[1]
[2]
Chemistry
As with psilocybin, miprocybin and metocybin, ethocybin is a
prodrug that is converted into the
pharmacologically active compound
ethocin in the body by
dephosphorylation .
[3] This
chemical reaction takes place under strongly
acidic conditions or
enzymatically by
phosphatases in the body.
Albert Hofmann was the first to produce this chemical, soon after his discovery of
psilocin and
psilocybin .
[4] It was sold under the code name CEY-39.
Pharmacology
As with psilocybin, ethocybin is rapidly dephosphorylated in the body to
4-HO-DET which then acts as a
partial agonist at the
5-HT2A
serotonin receptor in the brain where it mimics the effects of
serotonin (5-HT).
[5]
Medicine
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 showed that Ethocybin helped with
bipolar affective disorder .
Effects
Ethocybin is absorbed through the lining of the mouth and stomach. Effects begin 20–45 minutes after ingestion, and last from 2–4 hours depending on dose, species, and individual metabolism.[
citation needed ] The effects are somewhat shorter compared to psilocybin.
Pharmacology
Ethocybin is probably metabolized mostly in the
liver where it becomes ethocin, but is also broken down by the enzyme
monoamine oxidase .[
citation needed ]
Mental and physical tolerance to psilocybin builds and dissipates quickly. Taking ethocybin more than three or four times in a week (especially two days in a row) can result in diminished effects. Tolerance dissipates after a few days, so frequent users often keep doses spaced five to seven days apart to avoid the effect.
Legality
Ethocybin is not controlled in the US, but possession or sale may be considered illegal under the
Federal Analog Act .
References
^
"NCATS Inxight: Drugs — 4-PHOSPHORYLOXY N,N-DIETHYLTRYPTAMINE" . drugs.ncats.io . Retrieved 2020-01-22 .
^ Gartz J (1989). "Biotransformation of tryptamine derivatives in mycelial cultures of Psilocybe". Journal of Basic Microbiology . 29 (6): 347–52.
doi :
10.1002/jobm.3620290608 .
PMID
2614674 .
S2CID
43308695 .
^
"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 .
^
US patent 3075992 , Hofmann, Albert; Troxler, Franz., "Esters of indoles", issued 1963-1-29
^
"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 .
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E-6801
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