Methoxypiperamide

Methoxypiperamide
Legal status
Legal status	AU: S9 (Prohibited substance); EU: List I (Hungary);
Identifiers
	IUPAC name (4-Methoxyphenyl)(4-methylpiperazin-1-yl)methanone;
CAS Number	67023-02-3;
PubChem CID	805654;
ChemSpider	704980;
UNII	QD2GQ3VGF4;
CompTox Dashboard (EPA)	DTXSID501032899 ;
Chemical and physical data
Formula	C13H18N2O2
Molar mass	234.299 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=CC=C(C=C1)C(=O)N2CCN(CC2)C;
	InChI InChI=1S/C13H18N2O2/c1-14-7-9-15(10-8-14)13(16)11-3-5-12(17-2)6-4-11/h3-6H,7-10H2,1-2H3; Key:DWPVVZZGGGCRRM-UHFFFAOYSA-N;

Methoxypiperamide (also known as MeOP and MEXP) is a psychoactive drug of the piperazine class that has been sold online as a designer drug.^[1]^[2] It is the 4-methoxy-α-keto analog of methylbenzylpiperazine.

Very little data exists about the pharmacology and toxicity of methoxypiperamide; however, the US state of Vermont classifies it as a hallucinogen.

Legal status

Methoxypiperamide is a controlled substance in Vermont as of January 2016,^[3] and also in Hungary.^[4]

References

^ Power JD, Scott KR, Gardner EA, Curran McAteer BM, O'Brien JE, Brehon M, et al. (January 2014). "The syntheses, characterization and in vitro metabolism of nitracaine, methoxypiperamide and mephtetramine". Drug Testing and Analysis. 6 (7–8): 668–675. doi:10.1002/dta.1616. PMID 24574100.
^ Meyer MR, Holderbaum A, Kavanagh P, Maurer HH (October 2015). "Low resolution and high resolution MS for studies on the metabolism and toxicological detection of the new psychoactive substance methoxypiperamide (MeOP)". Journal of Mass Spectrometry. 50 (10): 1163–1174. Bibcode:2015JMSp...50.1163M. doi:10.1002/jms.3635. PMID 26456786.
^ "Regulated Drugs Rule" (PDF). Vermont Department of Health. Archived from the original (PDF) on 5 June 2016. Retrieved 14 October 2015.
^ "A Magyarországon megjelent, a Kábítószer és Kábítószer-függőség Európai Megfigyelő Központjának Korai Jelzőrendszerébe (EMCDDA EWS) 2005 óta bejelentett ellenőrzött anyagok büntetőjogi vonatkozású besorolása" [Criminal law classification of controlled substances published in Hungary and reported to the Early Warning System of the European Monitoring Center for Drugs and Drug Addiction (EMCDDA EWS) since 2005] (PDF). Daath (Hungarian Psychedelic Society) (in Hungarian). 3 September 2015.

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[Power_2014-1] Power JD, Scott KR, Gardner EA, Curran McAteer BM, O'Brien JE, Brehon M, et al. (January 2014). "The syntheses, characterization and in vitro metabolism of nitracaine, methoxypiperamide and mephtetramine". Drug Testing and Analysis. 6 (7–8): 668–675. doi:10.1002/dta.1616. PMID 24574100.

[2] Meyer MR, Holderbaum A, Kavanagh P, Maurer HH (October 2015). "Low resolution and high resolution MS for studies on the metabolism and toxicological detection of the new psychoactive substance methoxypiperamide (MeOP)". Journal of Mass Spectrometry. 50 (10): 1163–1174. Bibcode:2015JMSp...50.1163M. doi:10.1002/jms.3635. PMID 26456786.

[3] "Regulated Drugs Rule" (PDF). Vermont Department of Health. Archived from the original (PDF) on 5 June 2016. Retrieved 14 October 2015.

[4] "A Magyarországon megjelent, a Kábítószer és Kábítószer-függőség Európai Megfigyelő Központjának Korai Jelzőrendszerébe (EMCDDA EWS) 2005 óta bejelentett ellenőrzött anyagok büntetőjogi vonatkozású besorolása" [Criminal law classification of controlled substances published in Hungary and reported to the Early Warning System of the European Monitoring Center for Drugs and Drug Addiction (EMCDDA EWS) since 2005] (PDF). Daath (Hungarian Psychedelic Society) (in Hungarian). 3 September 2015.

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v t e Piperazines
Simple piperazines (no additional rings)	Aminoethylpiperazine Diethylcarbamazine HEPPS Midafotel Piperazine PIPES
Phenylpiperazines	2C-B-PP 3,4-CFP Acaprazine Antrafenine Aripiprazole Batoprazine Bifeprunox BRL-15,572 Ciprofloxacin CSP-2503 Dapiprazole DCPP DMPP Diphenylpiperazine Dropropizine EGIS-12,233 Elopiprazole Eltoprazine Enpiprazole Ensaculin Etoperidone Flesinoxan Fluanisone Flibanserin Fluprazine Itraconazole Ketoconazole Levodropropizine Lorpiprazole mCPP Mefway MeOPP Mepiprazole Naftopidil Naluzotan Naphthylpiperazine Nefazodone Niaprazine Oxypertine Pardoprunox pCPP pFPP Posaconazole S-14,506 S-14,671 S-15,535 SB-258,585 SB-271,046 SB-357,134 SB-399,885 Sonepiprazole TFMPP Tolpiprazole Trazodone Urapidil Vesnarinone Vilazodone Vortioxetine WAY-100,135 WAY-100,635
Benzylpiperazines	2C-B-BZP 3-Methylbenzylpiperazine Befuraline Bifeprunox Buclizine BZP Chlorbenzoxamine DBZP Fipexide Imatinib MBZP MDBZP Meclozine Methoxypiperamide NSI-189 Piberaline Piribedil RN-1747 Sunifiram Trimetazidine Vesnarinone
Diphenylalkylpiperazines (benzhydrylalkylpiperazines)	AD-1211 Almitrine Amperozide BRL-15,572 Buclizine BW373U86 Cetirizine Chlorbenzoxamine Chlorcyclizine Cinnarizine Clocinizine Cyclizine DBL-583 Diphenpipenol Diphenylmethylpiperazine Dotarizine DPI-221 DPI-287 DPI-3290 GBR-12,783 GBR-12,935 GBR-13,069 GBR-13,098 GBR-13,119 Hydroxyzine JJC8-088 Lidoflazine Manidipine Meclozine MT-45 Oxatomide SNC-80 Vanoxerine
Pyrimidinylpiperazines	Buspirone Dasatinib Eptapirone Gepirone Ipsapirone Piribedil Pyrimidinylpiperazine Revospirone Tandospirone Tirilazad Trimazosin Umespirone Zalospirone
Pyridinylpiperazines	Atevirdine Azaperone Delavirdine Mirtazapine ORG-12962 Pyridinylpiperazine
Benzo(iso)thiazolyl piperazines	Lurasidone Perospirone Revospirone Tiospirone Ziprasidone
Tricyclics (piperazine attached via side chain)	Amoxapine Clopenthixol Clorotepine Clozapine Cyanothepin Doclothepin Docloxythepin Flupentixol Fluphenazine Isofloxythepin Loxapine Meperathiepin Metitepine Octomethothepin Olanzapine Opipramol Oxyclothepin Oxyprothepin Peradithiepin Perathiepin Perazine Perphenazine Pirenzepine Prochlorperazine Thiethylperazine Thiothixene Trifluoperazine Trifluthepin Zuclopenthixol
Others/Uncategorized	6-Nitroquipazine AP-238 Azimilide Bucinnazine Cinepazet Cinepazic acid Cinepazide CPD-1 Cyclohexylpiperazine EGIS-7625 Hexocyclium Indinavir JNJ-7777120 Lodenafil MK-212 Mirodenafil PB-28 Quipazine Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VUF-6002 WY-46824 Zipeprol

Legal status

See also

References