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Methoxphenidine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Methoxphenidine
Clinical data
Routes of
administration
Oral, Rectal
Legal status
Legal status
Identifiers
  • (±)-1-[1-(2-methoxyphenyl)-2-phenylethyl]piperidine
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC20H25NO
Molar mass295.426 g·mol−1
3D model (JSmol)
  • COC1=C(C=CC=C1)C(CC2=CC=CC=C2)N3CCCCC3
  • InChI=1S/C20H25NO/c1-22-20-13-7-6-12-18(20)19(21-14-8-3-9-15-21)16-17-10-4-2-5-11-17/h2,4-7,10-13,19H,3,8-9,14-16H2,1H3
  • Key:QXXCUXIRBHSITD-UHFFFAOYSA-N

Methoxphenidine (methoxydiphenidine,2-MeO-Diphenidine,MXP) is adissociative of the diarylethylamine class that has been sold online as adesigner drug.[1][2] Methoxphenidine was first reported in a 1989 patent where it was tested as a treatment for neurotoxic injury.[3] Shortly after the 2013 UK ban on arylcyclohexylamines methoxphenidine and the related compounddiphenidine became available on the gray market, where it has been encountered as a powder and in tablet form.[4] Though diphenidine possesses higher affinity for the NMDA receptor, anecdotal reports suggest methoxphenidine has greater oral potency.[1] Of the three isomericanisyl-substituents methoxphenidine has affinity for theNMDA receptor that is higher than 4-MeO-diphenidine but lower than 3-MeO-diphenidine,[3][5] astructure–activity relationship shared by thearylcyclohexylamines.[6]

Side effects

[edit]

Acute methoxphenidine intoxication has been reported to produce confusion, hypertension, and tachycardia that was responsive to treatment with intravenouslorazepam,[7][8] methoxphenidine has also been associated with three published fatalities[9] and one case ofimpaired driving.[10]

Psychotic episodes have also been reported, including a murder in June 2014.[11]

Legal status

[edit]

As of October 2015 MXP is a controlled substance in China.[12]

MXP is also banned in Sweden.[13]

In Canada, MT-45 and its analogues were made Schedule I controlled substances, which includes DPD[clarification needed] in its structural group.[14] Possession without legal authority can result in maximum seven years imprisonment. Further,Health Canada amended theFood and Drug Regulations in May, 2016 to classify explicitly DPD as a restricted drug. Only those with a law enforcement agency, person with an exemption permit or institutions with Minister's authorization may possess the drug.

In Australia, theTherapeutic Goods Administration decided to include methoxphenidine as a Prohibited substance (Schedule 9) within theStandard for the Uniform Scheduling of Medicines and Poisons alongside four other phenidine analogs on 1 October 2024.[15]

See also

[edit]

References

[edit]
  1. ^abMorris 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):614–632.doi:10.1002/dta.1620.PMID 24678061.
  2. ^Van Hout MC, Hearne E (January–March 2015). ""Word of mouse": indigenous harm reduction and online consumerism of the synthetic compound methoxphenidine".Journal of Psychoactive Drugs.47 (1):30–41.doi:10.1080/02791072.2014.974002.PMID 25715070.S2CID 6204908.
  3. ^abEP 0346791, Gray NM, Cheng BK, "1,2-diarylethylamines for treatment of neurotoxic injury", issued 6 April 1994, assigned to GD Searle LLC 
  4. ^McLaughlin G, Morris N, Kavanagh PV, Power JD, O'Brien J, Talbot B, et al. (January 2016)."Test purchase, synthesis, and characterization of 2-methoxydiphenidine (MXP) and differentiation from its meta- and para-substituted isomers"(PDF).Drug Testing and Analysis.8 (1):98–109.doi:10.1002/dta.1800.PMID 25873326.S2CID 33626099.Archived(PDF) from the original on 2020-03-09. Retrieved2021-05-31.
  5. ^Sahai MA, Davidson C, Dutta N, Opacka-Juffry J (April 2018)."Mechanistic Insights into the Stimulant Properties of Novel Psychoactive Substances (NPS) and Their Discrimination by the Dopamine Transporter-In Silico and In Vitro Exploration of Dissociative Diarylethylamines".Brain Sciences.8 (4): 63.doi:10.3390/brainsci8040063.PMC 5924399.PMID 29642450.
  6. ^Wallach J, Kang H, Colestock T, Morris H, Bortolotto ZA, Collingridge GL, et al. (June 2016)."Pharmacological Investigations of the Dissociative 'Legal Highs' Diphenidine, Methoxphenidine and Analogues".PLOS ONE.11 (6) e0157021.Bibcode:2016PLoSO..1157021W.doi:10.1371/journal.pone.0157021.PMC 4912077.PMID 27314670.
  7. ^Hofer KE, Degrandi C, Müller DM, Zürrer-Härdi U, Wahl S, Rauber-Lüthy C, Ceschi A (December 2014)."Acute toxicity associated with the recreational use of the novel dissociative psychoactive substance methoxphenidine"(PDF).Clinical Toxicology.52 (10):1288–1291.doi:10.3109/15563650.2014.974264.PMID 25350467.S2CID 8513947.Archived(PDF) from the original on 2021-05-31. Retrieved2021-05-31.
  8. ^Helander A, Beck O, Bäckberg M (June 2015). "Intoxications by the dissociative new psychoactive substances diphenidine and methoxphenidine".Clinical Toxicology.53 (5):446–453.doi:10.3109/15563650.2015.1033630.PMID 25881797.S2CID 5962038.
  9. ^Elliott SP, Brandt SD, Wallach J, Morris H, Kavanagh PV (May 2015)."First reported fatalities associated with the 'research chemical' 2-methoxydiphenidine".Journal of Analytical Toxicology.39 (4):287–293.doi:10.1093/jat/bkv006.PMID 25698777.
  10. ^Stachel N, Jacobsen-Bauer A, Skopp G (March 2016). "A methoxydiphenidine-impaired driver".International Journal of Legal Medicine.130 (2):405–409.doi:10.1007/s00414-015-1280-5.PMID 26482953.S2CID 6483817.
  11. ^"Man who killed mother believing her to be a witch sentenced to minimum of five years in jail". BBC News. 17 June 2016.Archived from the original on 24 August 2020. Retrieved31 May 2021.
  12. ^"关于印发《非药用类麻醉药品和精神药品列管办法》的通知" [Notice on Issuing the Measures for the Listing and Control of Non-Medicinal Narcotic Drugs and Psychotropic Substances] (in Chinese). China Food and Drug Administration. 27 September 2015. Archived fromthe original on 1 October 2015. Retrieved1 October 2015.
  13. ^"Fler ämnen föreslås bli klassade som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 24 March 2015.Archived from the original on 24 September 2015. Retrieved21 October 2015.
  14. ^Arsenault D (1 June 2016)."Regulations Amending the Food and Drug Regulations (Parts G and J — Lefetamine, AH-7921, MT-45 and W-18)".Canada Gazette.150 (11).Archived from the original on 2017-12-02. Retrieved2016-11-17.
  15. ^"Notice of final decision to amend (or not amend) the current Poisons Standard - ACMS #44, ACCS #38, Joint ACMS-ACCS #36".Therapeutic Goods Administration. 27 September 2024. Retrieved5 October 2025.
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