meta-Chlorophenylpiperazine

meta-Chlorophenylpiperazine
Clinical data
Routes of
administration		Oral, intranasal, rectal
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
MetabolismLiver (CYP2D6)[2]
Elimination half-life4–14 hours[2][3]
ExcretionUrine
Identifiers
  • 1-(3-chlorophenyl)piperazine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.026.959 Edit this at Wikidata
Chemical and physical data
FormulaC10H13ClN2
Molar mass196.68 g·mol−1
3D model (JSmol)
  • Clc1cc(ccc1)N2CCNCC2
  • InChI=1S/C10H13ClN2/c11-9-2-1-3-10(8-9)13-6-4-12-5-7-13/h1-3,8,12H,4-7H2 checkY
  • Key:VHFVKMTVMIZMIK-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

meta-Chlorophenylpiperazine (mCPP) is a psychoactive drug of the phenylpiperazine class. It was initially developed in the late-1970s and used in scientific research before being sold as a designer drug in the mid-2000s.[4][5] It has been detected in pills touted as legal alternatives to illicit stimulants in New Zealand and pills sold as "ecstasy" in Europe and the United States.[6][7]

Despite its advertisement as a recreational substance, mCPP is actually generally considered to be an unpleasant experience and is not desired by drug users.[6] It lacks any reinforcing effects, but has "psychostimulant, anxiety-provoking, and hallucinogenic effects."[8][9][10][11] It is also known to produce dysphoric, depressive, and anxiogenic effects in rodents and humans,[12][13] and can induce panic attacks in individuals susceptible to them.[14][15][16][17] It also worsens obsessive–compulsive symptoms in people with the disorder.[18][19][20]

mCPP is known to induce headaches in humans and has been used for testing potential antimigraine medications.[21][22][23] It has potent anorectic effects and has encouraged the development of selective 5-HT2C receptor agonists for the treatment of obesity as well.[24][25][26][27]

Pharmacology

[edit]

Pharmacodynamics

[edit]
meta-Chlorophenylpiperazine[28]
Site Ki (nM) Species Refs
SERTTooltip Serotonin transporter 202–432 Human [29]
NETTooltip Norepinephrine transporter 1,940–4,360 Human [29]
DATTooltip Dopamine transporter ND ND ND
5-HT1A 44–400 Human [28][30]
5-HT1B 89–501 Human [28][31]
5-HT1D 210–1,300 Human [30][32]
5-HT1E ND ND ND
5-HT1F ND ND ND
5-HT2A 32–398 Human [28][11][30][33]
5-HT2B 3.2–63 Human [28][34][35]
5-HT2C 3.4–251 Human [28][11][33][36]
5-HT3 427 Human [28]
5-HT4 ND ND ND
5-HT5A  1,354 Human [28]
5-HT6 1,748 Human [28]
5-HT7 163 Human [28]
α1 97–2,900 Human [29][30]
  α1A 1,386 Human [28]
  α1B 915 Human [28]
  α1D ND ND ND
α2 112–570 Human [29][30]
  α2A 145 Human [28]
  α2B 106 Human [28]
  α2C 124 Human [28]
β 2,500 Human [30]
  β1 2,359 Human [28]
  β2 3,474 Human [28]
D1 7,000 Human [30]
D2 >10,000 Human [30]
D3 >10,000 Rat [28]
D4 ND ND ND
D5 >10,000 Human [28]
H1 326 Human [28]
mAChRs >10,000 Human [30]
nAChRsTooltip Nicotinic acetylcholine receptors >10,000 Human [28]
σ1 ND ND ND
σ2 8,350 Rat [28]
I1 759 Rat [28]
VDCCTooltip Voltage-dependent calcium channel 6,043 Rat [28]
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.

mCPP possesses significant affinity for the 5-HT1A, 5-HT1B, 5-HT1D, 5-HT2A, 5-HT2B, 5-HT2C, 5-HT3, and 5-HT7 receptors, as well as the SERT.[28] It also has some affinity for α1-adrenergic, α2-adrenergic, H1, I1, and NET.[28][37] It behaves as an agonist at most serotonin receptors.[38][39] mCPP has been shown to act not only as a serotonin reuptake inhibitor but as a serotonin releasing agent as well.[40]

mCPP's strongest actions are at the 5-HT2B and 5-HT2C receptors and its discriminative cue is mediated primarily by 5-HT2C.[28][41][42] Its negative effects such as anxiety, headaches, and appetite loss are likely mediated by its actions on the 5-HT2C receptor.[13][24][43] Other effects of mCPP include nausea, hypoactivity, and penile erection, the latter two the result of increased 5-HT2C activity and the former likely via 5-HT3 stimulation.[44][45][46]

In comparison studies, mCPP has approximately 10-fold selectivity for the human 5-HT2C receptor over the human 5-HT2A and 5-HT2B receptors (Ki = 3.4 nM vs. 32.1 and 28.8 nM).[11] It acts as a partial agonist of the human 5-HT2A[47] and 5-HT2C[48] receptors but as an antagonist of the human 5-HT2B receptors.[49]

Despite acting as a serotonin 5-HT2A receptor agonist, mCPP has been described as non-hallucinogenic.[50] However, hallucinations have occasionally been reported when large doses of mCPP are taken.[50]

Pharmacokinetics

[edit]

mCPP is metabolized via the CYP2D6 isoenzyme by hydroxylation to para-hydroxy-mCPP (p-OH-mCPP) and this plays a major role in its metabolism.[2][51][52] The elimination half-life of mCPP is 4 to 14 hours.[2]

mCPP is a metabolite of a variety of other piperazine drugs including trazodone, nefazodone, etoperidone, enpiprazole, mepiprazole, cloperidone, peraclopone, and BRL-15,572.[52][additional citation(s) needed] It is formed by dealkylation via CYP3A4.[52] Caution should be exercised in concomitant administration of CYP2D6 inhibitors such as bupropion, fluoxetine, paroxetine, and thioridazine with drugs that produce mCPP as a metabolite as these drugs are known to increase concentrations of the parent molecule (e.g., trazodone) and of mCPP.[51][2]

Chemistry

[edit]

Analogues

[edit]

Analogues of mCPP include:

Some additional analogues include quipazine, ORG-12962, and 3C-PEP.

Society and culture

[edit]
Tablets containing mCPP confiscated by the DEA in Vernon Hills, Illinois.
Tablets containing mCPP confiscated by the Kriminalpolizei in Europe at the end of 2008.
[edit]

Belgium

[edit]

mCPP is illegal in Belgium.[53]

Brazil

[edit]

mCPP is illegal in Brazil.[54]

Canada

[edit]

mCPP is not a controlled drug in Canada.

China

[edit]

As of October 2015 mCPP is a controlled substance in China.[55]

Czech Republic

[edit]

mCPP is legal in the Czech Republic.[56]

Denmark

[edit]

mCPP is illegal in Denmark.[57][unreliable source?]

Finland

[edit]

mCPP is illegal in Finland.

Germany

[edit]

mCPP is illegal in Germany.

Hungary

[edit]

mCPP is illegal in Hungary since 2012.

Japan

[edit]

mCPP is illegal in Japan since 2006.

Netherlands

[edit]

mCPP is legal in the Netherlands.[58]

New Zealand

[edit]

Based on the recommendation of the EACD, the New Zealand government has passed legislation which placed BZP, along with the other piperazine derivatives TFMPP, mCPP, pFPP, MeOPP and MBZP, into Class C of the New Zealand Misuse of Drugs Act 1975. A ban was intended to come into effect in New Zealand on December 18, 2007, but the law change did not go through until the following year, and the sale of BZP and the other listed piperazines became illegal in New Zealand as of 1 April 2008. An amnesty for possession and usage of these drugs remained until October 2008, at which point they became completely illegal.[59] However, mCPP is legally used for scientific research.

Norway

[edit]

mCPP is illegal in Norway.

Russia

[edit]

mCPP is illegal in Russia.

Sweden

[edit]

mCPP is illegal in Sweden.

Poland

[edit]

mCPP is illegal in Poland.

United States

[edit]

mCPP is not scheduled at the federal level in the United States,[60] but it is possible that it could be considered a controlled substance analog of BZP, in which case purchase, sale, or possession could be prosecuted under the Federal Analog Act.

However, "chlorophenylpiperazine" is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in this state.[61]

Turkey

[edit]

mCPP is illegal in Turkey since 20/05/2009.[62]

See also

[edit]

References

[edit]
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