3-MeO-PCE

Last updated
3-MeO-PCE
3-MeO-PCE.svg
Clinical data
Other names3-MeO-PCE; Methoxieticyclidine
Legal status
Legal status
  • CA: Schedule I
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class B
  • Illegal in Sweden and Switzerland
Identifiers
  • N-Ethyl-1-(3-methoxyphenyl)cyclohexan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C15H23NO
Molar mass 233.355 g·mol−1
3D model (JSmol)
  • CCNC1(CCCCC1)C2=CC(=CC=C2)OC
  • InChI=1S/C15H23NO/c1-3-16-15(10-5-4-6-11-15)13-8-7-9-14(12-13)17-2/h7-9,12,16H,3-6,10-11H2,1-2H3
  • Key:OFGOOZLOGUNDFS-UHFFFAOYSA-N

3-Methoxyeticyclidine (3-MeO-PCE), also known as methoxieticyclidine, [1] is a dissociative anesthetic that is qualitatively similar to PCE and PCP [1] and has been sold online as a designer drug. [2] [3] [4]

Contents

On October 18, 2012 the Advisory Council on the Misuse of Drugs in the United Kingdom released a report about methoxetamine, saying that the "harms of methoxetamine are commensurate with Class B of the Misuse of Drugs Act (1971)", despite the fact that the act does not classify drugs based on harm. The report went on to suggest that all analogues of methoxetamine should also become class B drugs and suggested a catch-all clause covering both existing and unresearched arylcyclohexamines, including 3-MeO-PCE. [5]

This report also described the receptor binding profile of methoxetamine and three additional dissociatives 3-MeO-PCP, 4-MeO-PCP, and 3-MeO-PCE, showing them to have significant affinity for the PCP site of the NMDA receptor (NMDAR) and was later published in more detail. [6]

3-MeO-PCE has Ki values of 61 nM for the NMDAR, 743 nM for the dopamine transporter, 2097 nM for the histamine H2 receptor, 964 nM for the alpha-2A adrenergic receptor, 115 nM for the serotonin transporter, 4519 nM for the σ1 receptor, and 525 nM for the σ2 receptor. [6]

3-MeO-PCE is banned in Sweden [7] [8] and Switzerland. [9]

As per Chile's Ley de drogas, aka Ley 20000, [10] all esters and ethers of PCE are illegal. As 3-MeO-PCE is an ether of PCE, it is thus illegal.

See also

Related Research Articles

<span class="mw-page-title-main">Phencyclidine</span> Dissociative hallucinogenic drug, mostly used recreationally

Phencyclidine or phenylcyclohexyl piperidine (PCP), also known as angel dust among other names, is a dissociative anesthetic mainly used recreationally for its significant mind-altering effects. PCP may cause hallucinations, distorted perceptions of sounds, and violent behavior. As a recreational drug, it is typically smoked, but may be taken by mouth, snorted, or injected. It may also be mixed with cannabis or tobacco.

<span class="mw-page-title-main">NMDA receptor antagonist</span> Class of anesthetics

NMDA receptor antagonists are a class of drugs that work to antagonize, or inhibit the action of, the N-Methyl-D-aspartate receptor (NMDAR). They are commonly used as anesthetics for animals and humans; the state of anesthesia they induce is referred to as dissociative anesthesia.

<span class="mw-page-title-main">Eticyclidine</span> Medication

Eticyclidine is a dissociative anesthetic drug with hallucinogenic effects. It is similar in effects to phencyclidine but is slightly more potent. PCE was developed by Parke-Davis in the 1970s and evaluated for anesthetic potential under the code name CI-400, but research into PCE was not continued after the development of ketamine, a similar drug with more favourable properties. PCE is slightly more potent than PCP and has similar effects, but its unpleasant taste and tendency to cause nausea made it less accepted by users. Due to its similarity in effects to PCP, PCE was placed into the Schedule 1 list of illegal drugs in the 1970s, although it was only briefly abused in the 1970s and 1980s and is now little known.

<span class="mw-page-title-main">Arylcyclohexylamine</span> Class of chemical compounds

Arylcyclohexylamines, also known as arylcyclohexamines or arylcyclohexanamines, are a chemical class of pharmaceutical, designer, and experimental drugs.

<span class="mw-page-title-main">3-MeO-PCP</span> Chemical compound

3-Methoxyphencyclidine (3-MeO-PCP) is a dissociative hallucinogen of the arylcyclohexylamine class related to phencyclidine (PCP) which has been sold online as a designer drug. It acts mainly as an NMDA receptor antagonist, though it has also been found to interact with the sigma σ1 receptor and the serotonin transporter. The drug does not possess any opioid activity nor does it act as a dopamine reuptake inhibitor.

<span class="mw-page-title-main">4-MeO-PCP</span> Chemical compound

4-Methoxyphencyclidine is a dissociative anesthetic drug that has been sold online as a research chemical. The synthesis of 4-MeO-PCP was first reported in 1965 by the Parke-Davis medicinal chemist Victor Maddox. A 1999 review published by a chemist using the pseudonym John Q. Beagle suggested the potency of 4-MeO-PCP in man was reduced relative to PCP, two years later Beagle published a detailed description of the synthesis and qualitative effects of 4-MeO-PCP, which he said possessed 70% the potency of PCP. 4-MeO-PCP was the first arylcyclohexylamine research chemical to be sold online, it was introduced in late 2008 by a company trading under the name CBAY and was followed by several related compounds such as 3-MeO-PCP and methoxetamine. 4-MeO-PCP has lower affinity for the NMDA receptor than PCP, but higher affinity than ketamine, it is orally active in a dosage range similar to ketamine, with some users requiring doses in excess of 100 mg for desired effects. Users have reported substantial differences in active dose, these discrepancies can be partially explained by the presence of unreacted PCC and other impurities in samples sold on the grey market. 4-MeO-PCP has Ki values of 404 nM for the NMDA receptor, 713 nM for the norepinephrine transporter, 844 nM for the serotonin transporter, 296 nM for the σ1 receptor and 143 nM for the σ2 receptor.

<span class="mw-page-title-main">Methoxetamine</span> Dissociative drug

Methoxetamine, abbreviated as MXE, is a dissociative hallucinogen that has been sold as a designer drug. It differs from many dissociatives such as ketamine and phencyclidine (PCP) that were developed as pharmaceutical drugs for use as general anesthetics in that it was designed specifically for recreational use. It is a rare example of a drug being so widely controlled without having an existing medical use.

<i>N</i>-Ethylnorketamine Chemical compound

N-Ethylnorketamine is a designer drug which is presumed to have similar properties to ketamine, a dissociative anesthetic drug with hallucinogenic and sedative effects. It has been sold over the internet since around September 2012, and identified in seized drug samples by analytical laboratories in the UK and other European countries.

<span class="mw-page-title-main">Diphenidine</span> Chemical compound

Diphenidine is a dissociative anesthetic that has been sold as a designer drug. The synthesis of diphenidine was first reported in 1924, and employed a Bruylants reaction analogous to the one that would later be used to discover phencyclidine in 1956. Shortly after the 2013 UK ban on arylcyclohexylamines, diphenidine and the related compound methoxphenidine became available on the grey market. Anecdotal reports describe high doses of diphenidine producing "bizarre somatosensory phenomena and transient anterograde amnesia." Diphenidine and related diarylethylamines have been studied in vitro as treatments for neurotoxic injury and are antagonists of the NMDA receptor. In dogs diphenidine exhibits greater antitussive potency than codeine phosphate.

<span class="mw-page-title-main">Methoxphenidine</span> Chemical compound

Methoxphenidine is a dissociative of the diarylethylamine class that has been sold online as a designer drug. Methoxphenidine was first reported in a 1989 patent where it was tested as a treatment for neurotoxic injury. Shortly after the 2013 UK ban on arylcyclohexylamines methoxphenidine and the related compound diphenidine became available on the gray market, where it has been encountered as a powder and in tablet form. Though diphenidine possesses higher affinity for the NMDA receptor, anecdotal reports suggest methoxphenidine has greater oral potency. Of the three isomeric anisyl-substituents methoxphenidine has affinity for the NMDA receptor that is higher than 4-MeO-Diphenidine but lower than 3-MeO-Diphenidine, a structure–activity relationship shared by the arylcyclohexylamines.

<span class="mw-page-title-main">Ephenidine</span> Chemical compound

Ephenidine is a dissociative anesthetic that has been sold online as a designer drug. It is illegal in some countries as a structural isomer of the banned opioid drug lefetamine, but has been sold in countries where it is not yet banned.

<span class="mw-page-title-main">3-MeO-PCMo</span> Chemical compound

3-MeO-PCMo is a dissociative anesthetic drug which is similar in structure to phencyclidine and been sold online as a designer drug. The inhibitory effect of 3-MeO-PCMo on the reduction in the density of the drebrin clusters by NMDAR stimulation with glutamic acid is lower than that of PCP or 3-MeO-PCP, with half maximal inhibitory concentration (IC50) values of 26.67 μM (3-MeO-PCMo), 2.02 μM (PCP) and 1.51 μM (3-MeO-PCP).

<span class="mw-page-title-main">3-HO-PCP</span> Chemical compound

3-Hydroxyphencyclidine (3-HO-PCP) is a dissociative of the arylcyclohexylamine class related to phencyclidine (PCP) that has been sold online as a designer drug.

<span class="mw-page-title-main">2-Fluorodeschloroketamine</span> Chemical compound

2-Fluorodeschloroketamine is a dissociative anesthetic related to ketamine. Its sale and use as a designer drug has been reported in various countries. It is an analogue of ketamine where the chlorine group has been replaced by fluorine. Due to its recent emergence, the pharmacological specifics of the compound are mostly unclear, but effects are reported to be similar to its parent compound, ketamine.

<span class="mw-page-title-main">3-Methyl-PCPy</span> Chemical compound

3-Methyl-PCPy (3-Me-PCPy) is an arylcyclohexylamine derivative with an unusual spectrum of pharmacological effects, acting as both a potent NMDA antagonist and also a triple reuptake inhibitor which inhibits reuptake of all three monoamine neurotransmitters serotonin, dopamine and noradrenaline. It also acts as a high affinity sigma receptor ligand, selective for the σ2 subtype. It produces both stimulant and dissociative effects in animal behavioural studies.

<span class="mw-page-title-main">2-Oxo-PCE</span> Chemical compound

2-Oxo-PCE is a dissociative anesthetic of the arylcyclohexylamine class that is closely related to deschloroketamine and eticyclidine, and has been sold online as a designer drug.

<span class="mw-page-title-main">Methoxisopropamine</span> Chemical compound

MXiPr is a recreational designer drug with dissociative effects. It is an arylcyclohexylamine derivative, related to drugs such as ketamine and methoxetamine. It was first identified in Slovenia in December 2020, and was made illegal in Hungary in April 2021.

<span class="mw-page-title-main">3-Methyl-PCP</span> Chemical compound

3-Methyl-PCP is a recreational designer drug with dissociative effects. It is an arylcyclohexylamine derivative, related to drugs such as 3'-MeO-PCP and 3'-Me-PCPy. It was first synthesised in the 1960s, but was only identified on the illicit market in Hungary in September 2020, and was made illegal in Hungary in April 2021.

<span class="mw-page-title-main">Fluorexetamine</span> Chemical compound

Fluorexetamine is a recreational designer drug from the arylcyclohexylamine family, with dissociative effects. Effects are slightly more stimulating than regular ketamine. Still produces analgesic effects with stimulating dissociative effects. Has reportedly been sold over the internet since around 2017, though has remained relatively uncommon.

<span class="mw-page-title-main">Hydroxetamine</span> Chemical compound

Hydroxetamine is a recreational designer drug from the arylcyclohexylamine family, with dissociative effects. It is known as an active metabolite of the dissociative designer drug methoxetamine, but has also been sold in its own right since late 2019.

References

  1. 1 2 Morris H, Wallach J (July–August 2014). "From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs". Drug Testing and Analysis. 6 (7–8): 614–32. doi:10.1002/dta.1620. PMID   24678061.
  2. De Paoli G, Brandt SD, Wallach J, Archer RP, Pounder DJ (June 2013). "From the street to the laboratory: analytical profiles of methoxetamine, 3-methoxyeticyclidine and 3-methoxyphencyclidine and their determination in three biological matrices". Journal of Analytical Toxicology. 37 (5): 277–83. doi: 10.1093/jat/bkt023 . PMID   23552616.
  3. Wallach J, Colestock T, Cicali B, Elliott SP, Kavanagh PV, Adejare A, et al. (August 2016). "Syntheses and analytical characterizations of N-alkyl-arylcyclohexylamines" (PDF). Drug Testing and Analysis. 8 (8): 801–15. doi:10.1002/dta.1861. PMID   26360516. S2CID   1599386.
  4. "3-MeO-PCE". New Synthetic Drugs Database. Archived from the original on 2016-07-29. Retrieved 2016-08-27.
  5. "Advisory Council on the Misuse of Drugs (ACMD) Methoxetamine report, 2012". UK Home Office. 18 October 2012.
  6. 1 2 Roth BL, Gibbons S, Arunotayanun W, Huang XP, Setola V, Treble R, Iversen L (March 2013). "The ketamine analogue methoxetamine and 3- and 4-methoxy analogues of phencyclidine are high affinity and selective ligands for the glutamate NMDA receptor". PLOS ONE. 8 (3): e59334. Bibcode:2013PLoSO...859334R. doi: 10.1371/journal.pone.0059334 . PMC   3602154 . PMID   23527166.
  7. "Elva nya ämnen klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 28 June 2018.
  8. Riksdagsförvaltningen. "Förordning (1992:1554) om kontroll av narkotika". riksdagen.se (in Swedish).
  9. "Verordnung des EDI vom 30. Mai 2011 über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien (Betäubungsmittelverzeichnisverordnung, BetmVV-EDI)" (in German). Der Bundesrat.
  10. "SUSTITUYE LA LEY Nº 19.366, QUE SANCIONA EL TRAFICO ILICITO DE ESTUPEFACIENTES Y SUSTANCIAS SICOTROPICAS" (in Spanish). Bibloteca Del Congreso Nacional. 22 October 2015. Retrieved 6 February 2018.