Explore mCPP | PiHKAL · info

Exploring mCPP. To explore a different substance…

Names

mCPP
meta-Chlorophenylpiperazine
3-ClPP

IUPAC name

1-(3-Chlorophenyl)piperazine

ID 806 · Formula C₁₀H₁₃ClN₂ · Molecular weight 196.677

InChI InChI=1S/C10H13ClN2/c11-9-2-1-3-10(8-9)13-6-4-12-5-7-13/h1-3,8,12H,4-7H2

InChI Key VHFVKMTVMIZMIK-UHFFFAOYSA-N This stereoisomer Any stereoisomer

SMILES Clc1cccc(c1)N1CCNCC1

ChemSpider 1314
PubChem 1355
Wikidata Q286112
Erowid mCPP
Wikipedia meta-Chlorophenylpiperazine
PsychonautWiki MCPP
Project Response mCPP (962-10A)

Shulgin Index #24 oCPP · Table 8Page 357Row 6

Phenethylamine: Von der Strucktur zur Funktion mCPP: 3.12 (87) 249

Baumann, MH; Clark, RD; Budzynski, AG; Partilla, JS; Blough, BE; Rothman, RB. N-Substituted piperazines abused by humans mimic the molecular mechanism of 3,4-methylenedioxymethamphetamine (MDMA, or ‘Ecstasy’). Neuropsychopharmacol., 1 Mar 2005, 30 (3), 550–560. 184 kB. https://doi.org/10.1038/sj.npp.1300585

Acuña-Castillo, C; Villalobos, C; Moya, PR; Sáez, P; Cassels, BK; Huidobro-Toro, JP. Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT_2A and 5-HT_2C receptors. Br. J. Pharmacol., 1 Jun 2002, 136 (4), 510–519. 232 kB. https://doi.org/10.1038/sj.bjp.0704747

Marona-Lewicka, D; Nichols, DE. Further evidence that the delayed temporal dopaminergic effects of LSD are mediated by a mechanism different than the first temporal phase of action. Pharmacol. Biochem. Behav., 1 Jan 2007, 87 (4), 453–461. 266 kB. https://doi.org/10.1016/j.pbb.2007.06.001

Staack, RF; Maurer, HH. Metabolism of designer drugs of abuse. Curr. Drug Metab., 1 Jun 2005, 6 (3), 259–274. 104 kB. https://doi.org/10.2174/1389200054021825 #mCPP

Bossong, MG; van Dijk, JP; Niesink, RJM. Methylone and mCPP, two new drugs of abuse? Addict. Biol., 1 Dec 2005, 10 (4), 321–323. 69 kB. https://doi.org/10.1080/13556210500350794

Partilla, JS; Dempsey, AG; Nagpal, AS; Blough, BE; Baumann, MH; Rothman, RB. Interaction of amphetamines and related compounds at the vesicular monoamine transporter. J. Pharmacol. Exp. Ther., 1 Oct 2006, 319 (1), 237–246. 367 kB. https://doi.org/10.1124/jpet.106.103622

Byrska, B; Zuba, D; Stanaszek, R. Determination of piperazine derivatives in “legal highs”. Probl. Forensic Sci., , 81, 101–113. 852 kB. #mCPP GC,LC,MS,UV

Maurer, HH. Mass spectra of select benzyl- and phenyl- piperazine designer drugs. Microgram J., 1 Jan 2004, 2 (1–4), 22–26. 326 kB. MS

Zuba, D; Byrska, B. Prevalence and co-existence of active components of ‘legal highs’. Drug Test. Anal., 1 Jun 2013, 5 (6), 420–429. 1.3 MB. https://doi.org/10.1002/dta.1365

Chang-Fong, J; Addo, J; Dukat, M; Smith, C; Mitchell, NA; Herrick-Davis, K; Teitler, M; Glennon, RA. Evaluation of isotryptamine derivatives at 5-HT₂ serotonin receptors. Bioorg. Med. Chem. Lett., 21 Jan 2002, 12 (2), 155–158. 118 kB. https://doi.org/10.1016/S0960-894X(01)00713-2 #mCPP

EMCDDA. New drugs in Europe, 2011, European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 Apr 2012. 401 kB.

Clark, CR; DeRuiter, J. Analytical and synthetic studies on designer drugs of the piperazine class, US DOJ, 1 Dec 2014. 15.6 MB. #3-ClPP

Arbo, MD; Bastos, ML; Carmo, HF. Piperazine compounds as drugs of abuse. Drug Alcohol Depend., 1 May 2012, 122 (3), 174-185. 523 kB. https://doi.org/10.1016/j.drugalcdep.2011.10.007

Helm, K. Synthese und funktionelle In-vitro-Pharmakologie neuer Liganden des 5-HT_2A-Rezeptors aus der Klasse. Ph. D. Thesis, Universität Regensburg, Dresden, 1 Jan 2014. 3.2 MB. #36 LC,MS,NMR,IR

Cheng, J; Kozikowski, AP. We need 2C but not 2B: Developing serotonin 2C (5-HT_2C) receptor agonists for the treatment of CNS disorders. ChemMedChem, 1 Dec 2015, 10 (12), 1963–1967. 1.1 MB. https://doi.org/10.1002/cmdc.201500437 #4

Cheng, J; Giguère, PM; Onajole, OK; Lv, W; Gaisin, A; Gunosewoyo, H; Schmerberg, CM; Pogorelov, VM; Rodriguiz, RM; Vistoli, G; Wetsel, WC; Roth, BL; Kozikowski, AP. Optimization of 2-phenylcyclopropylmethylamines as selective serotonin 2C receptor agonists and their evaluation as potential antipsychotic agents. J. Med. Chem., 26 Feb 2015, 58 (4), 1992–2002. 1.9 MB. https://doi.org/10.1021/jm5019274 #5

Martins, D. Analysis of new psychoactive substances: A contribution to forensic chemistry. M. Sc. Thesis, Universidade do Porto, 1 Jan 2014. 2.5 MB. #12 MS,NMR,other

Adamowicz, P; Zuba, D. Discrimination among designer drug isomers by chromatographic and spectrometric methods. In Chromatographic Techniques in the Forensic Analysis of Designer Drugs; Kowalska, T; Sajewicz, M; Sherma, J, Eds., CRC Press, Taylor & Francis Group, 1 Jan 2018; pp 211–232. 1.1 MB.

Nagai, F; Nonaka, R; Kamimura, KSH. The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain. Eur. J. Pharmacol., 22 Mar 2007, 559 (2), 132–137. 399 kB. https://doi.org/10.1016/j.ejphar.2006.11.075 #3CPP

Takahashi, M; Nagashima, M; Suzuki, J; Seto, T; Yasuda, I; Yoshida, T. Creation and application of psychoactive designer drugs data library using liquid chromatography with photodiode array spectrophotometry detector and gas chromatography–mass spectrometry. Talanta, 15 Feb 2009, 77 (4), 1245–1272. 1.2 MB. https://doi.org/10.1016/j.talanta.2008.07.062 #3CPP

Seto, T; Takahashi, M; Nagashima, M; Suzuki, J; Yasuda, I. The identifications and the aspects of the commercially available uncontrolled drugs purchased between Apr. 2003 and Mar. 2004. Ann. Rep. Tokyo Metr. Inst. P. H., 1 Jan 2005, 56 75–80. 1.2 MB. #3CPP MS,NMR,UV

Machiko, N; Takako, S; Misako, T; Suzuki, H; Yasuda, I. Analytical methods and spectrum data of 4 Governor-designated drugs. Ann. Rep. Tokyo Metr. Inst. P. H., 1 Jan 2005, 56 59–64. 1.9 MB. #3CPP LC,MS,NMR,IR,UV,TLC

EMCDDA. New drugs in Europe, 2005, European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 May 2006. 1.2 MB. #mCPP

Suzuki, J; Seto, T; Nagashima, M; Takahashi, M; Okumoto, C; Yasuda, I. Measurement of purity of Governor-designated drugs and estimated structural formula of the impurities. Ann. Rep. Tokyo Metr. Inst. P. H., 1 Jan 2005, 56 69–74. 1.0 MB. #3CPP LC,MS,UV,TLC,other

Bishop, SC; McCord, BR; Gratz, SR; Loeliger, JR; Witkowski, MR. Simultaneous separation of different types of amphetamine and piperazine designer drugs by capillary electrophoresis with a chiral selector. J. Forensic Sci., 1 Mar 2005, 50 (2), 1–10. 597 kB. https://doi.org/10.1520/JFS2004239 #mCPP LC,MS,UV,other

Luethi, D; Liechti, ME. Monoamine transporter and receptor interaction profiles in vitro predict reported human doses of novel psychoactive stimulants and psychedelics. Int. J. Neuropsychoph., 1 Oct 2018, 21 (10), 926–931. 254 kB. https://doi.org/10.1093/ijnp/pyy047 #S1 Piperazines m-CPP

Okamoto, K; Akimoto, S; Ando, T; Ikeda, Y; Kurashima, N. Differentiation of regioisomeric analogs of controlled substances using GC-IR. JCCL, 1 Oct 2016, (56), 49–70. 4.5 MB. #3CPP Japanese, English abstract GC,MS,IR

Glennon, RA; Slusher, RM; Lyon, RA; Titeler, M; McKenney, JD. 5-HT₁ and 5-HT₂: Binding characteristics of some quipazine analogs. J. Med. Chem., 1 Nov 1986, 29 (11), 2375–2380. 819 kB. https://doi.org/10.1021/jm00161a038 #1b other

Simmler, LD; Rickli, A; Schramm, Y; Hoener, MC; Liechti, ME. Pharmacological profiles of aminoindanes, piperazines, and pipradrol derivatives. Biochem. Pharmacol., 15 Mar 2014, 88 (2), 237–244. 504 kB. https://doi.org/10.1016/j.bcp.2014.01.024 #m-CPP

Nakagawasai, O; Arai, Y; Satoh, S; Satoh, N; Neda, M; Hozumi, M; Oka, R; Hiraga, H; Tadano, T. Monoamine oxidase and head-twitch response in mice: Mechanisms of α-methylated substrate derivatives. Neurotoxicology, 1 Jan 2004, 25 (1), 223–232. 169 kB. https://doi.org/10.1016/S0161-813X(03)00101-3 #m-CPP

Martins, D; Garrido, EMPJ; Borges, F; Garrido, JMPJ. Voltammetric profiling of new psychoactive substances: Piperazine derivatives. J. Electroanal. Chem., 1 Feb 2021, 883 (115054). 1.2 MB. https://doi.org/10.1016/j.jelechem.2021.115054 #mCPP other

Doi, K; Miyazawa, M; Fujii, H; Kojima, T. The analysis of the chemical drugs among structural isomer. Yakugaku Zasshi, 1 Sep 2006, 126 (9), 815–823. 371 kB. https://doi.org/10.1248/yakushi.126.815 #3CPP GC,LC,MS,NMR,IR,TLC

Philp, M; Shimmon, R; Stojanovska, N; Tahtouh, M; Fu, S. Development and validation of a presumptive colour spot test method for the detection of piperazine analogues in seized illicit materials. Anal. Methods, 1 Jan 2013, 5 (20), 5402. 783 kB. https://doi.org/10.1039/c3ay40511g #1-(3-Chlorophenyl)piperazine (mC MS,NMR,IR,spot

Canal, CE; Booth, RG; Morgan, D. Support for 5-HT_2C receptor functional selectivity in vivo utilizing structurally diverse, selective 5-HT_2C receptor ligands and the 2,5-dimethoxy-4-iodoamphetamine elicited head-twitch response model. Neuropharmacology, 1 Jul 2013, 70, 112–121. 1.1 MB. https://doi.org/10.1016/j.neuropharm.2013.01.007 #mCPP

Schoenwald, RD; Gadiraju, RR; Barfknecht, CF. Serotonin antagonists for use as antiglaucoma agents and their ocular penetration. Eur. J. Pharm. Biopharm., 1 Jun 1997, 43 (3), 273–281. 688 kB. https://doi.org/10.1016/S0939-6411(97)00055-6 #2

Maurer, HH; Kraemer, T; Springer, D; Staack, RF. Chemistry, pharmacology, toxicology, and hepatic metabolism of designer drugs of the amphetamine (Ecstasy), piperazine, and pyrrolidinophenone types. A synopsis. Ther. Drug Monit., 1 Apr 2004, 26 (2), 127–131. 121 kB.

2-ClPP · oCPP

4-ClPP · pCPP

7 Dec 2019 · · Isomer Design