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meta-Chlorophenylpiperazine

From Wikipedia, the free encyclopedia
Stimulant
Pharmaceutical compound
meta-Chlorophenylpiperazine
Clinical data
Routes of
administration		Oral,intranasal,rectal
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismLiver (CYP2D6)[2]
Eliminationhalf-life4–14 hours[2][3]
ExcretionUrine
Identifiers
  • 1-(3-chlorophenyl)piperazine
CAS Number
PubChemCID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.026.959Edit 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 apsychoactive drug of thephenylpiperazine class. It was initially developed in the late-1970s and used inscientific research before being sold as adesigner drug in the mid-2000s.[4][5] It has been detected in pills touted as legal alternatives to illicitstimulants inNew Zealand and pills sold as "ecstasy" inEurope and theUnited States.[6][7]

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

mCPP is known to induceheadaches in humans and has been used for testing potentialantimigraine medications.[21][22][23] It has potentanorectic effects and has encouraged the development of selective5-HT2C receptoragonists for the treatment ofobesity as well.[24][25][26][27]

Pharmacology

[edit]

Pharmacodynamics

[edit]
meta-Chlorophenylpiperazine[28]
SiteKi (nM)SpeciesRefs
SERTTooltip Serotonin transporter202–432Human[29]
NETTooltip Norepinephrine transporter1,940–4,360Human[29]
DATTooltip Dopamine transporterNDNDND
5-HT1A44–400Human[28][30]
5-HT1B89–501Human[28][31]
5-HT1D210–1,300Human[30][32]
5-HT1ENDNDND
5-HT1FNDNDND
5-HT2A32–398Human[28][11][30][33]
5-HT2B3.2–63Human[28][34][35]
5-HT2C3.4–251Human[28][11][33][36]
5-HT3427Human[28]
5-HT4NDNDND
5-HT5A 1,354Human[28]
5-HT61,748Human[28]
5-HT7163Human[28]
α197–2,900Human[29][30]
  α1A1,386Human[28]
  α1B915Human[28]
  α1DNDNDND
α2112–570Human[29][30]
  α2A145Human[28]
  α2B106Human[28]
  α2C124Human[28]
β2,500Human[30]
  β12,359Human[28]
  β23,474Human[28]
D17,000Human[30]
D2>10,000Human[30]
D3>10,000Rat[28]
D4NDNDND
D5>10,000Human[28]
H1326Human[28]
mAChRs>10,000Human[30]
nAChRsTooltip Nicotinic acetylcholine receptors>10,000Human[28]
σ1NDNDND
σ28,350Rat[28]
I1759Rat[28]
VDCCTooltip Voltage-dependent calcium channel6,043Rat[28]
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.

mCPP possesses significantaffinity for the5-HT1A,5-HT1B,5-HT1D,5-HT2A,5-HT2B,5-HT2C,5-HT3, and5-HT7 receptors, as well as theSERT.[28][37] It also has some affinity forα1-adrenergic,α2-adrenergic,H1,I1, andNET.[28][38] It behaves as anagonist at most serotonin receptors.[39][40] mCPP has been shown to act not only as aserotonin reuptake inhibitor but as aserotonin releasing agent as well.[41]

mCPP's strongest actions are at the 5-HT2B and 5-HT2C receptors and its discriminative cue is mediated primarily by 5-HT2C.[28][42][43] Its negative effects such asanxiety,headaches, andappetite loss are likely mediated by its actions on the 5-HT2C receptor.[13][24][44] Other effects of mCPP includenausea,hypoactivity, andpenile erection, the latter two the result of increased 5-HT2C activity and the former likely via 5-HT3 stimulation.[45][46][47] mCPP is known to induce migraines and this may be mediated by serotonin 5-HT2B receptor agonism.[48]

In comparison studies, mCPP has approximately 10-foldselectivity 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 apartial agonist of the human 5-HT2A[49] and 5-HT2C[50] receptors but as anantagonist of the human 5-HT2B receptors.[51]

mCPP produces thehead-twitch response, a behavioral proxy ofpsychedelic effects, in rodents, and hence may behallucinogenic in humans.[52] Despite this however, mCPP has been described as non-hallucinogenic in humans.[53] In any case,hallucinations have occasionally been reported when large doses of mCPP are taken.[53]

Pharmacokinetics

[edit]

mCPP ismetabolized via theCYP2D6isoenzyme byhydroxylation topara-hydroxy-mCPP (p-OH-mCPP) and this plays a major role in its metabolism.[2][54][55] Theelimination half-life of mCPP is 4 to 14 hours.[2]

mCPP is ametabolite of a variety of other piperazine drugs includingtrazodone,nefazodone,etoperidone,mepiprazole,cloperidone,peraclopone, andBRL-15,572.[55][additional citation(s) needed] It is formed bydealkylation viaCYP3A4.[55] Caution should be exercised in concomitant administration ofCYP2D6inhibitors such asbupropion,fluoxetine,paroxetine, andthioridazine 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.[54][2]

Chemistry

[edit]

Analogues

[edit]

Analogues of mCPP include:

Some additional analogues includequipazine,ORG-12962, and3C-PEP.

Society and culture

[edit]
Tablets containing mCPP confiscated by theDEA inVernon Hills, Illinois.
Tablets containing mCPP confiscated by theKriminalpolizei inEurope at the end of 2008.

Legal status

[edit]

Belgium

[edit]

mCPP is illegal in Belgium.[56]

Brazil

[edit]

mCPP is illegal inBrazil.[57]

Canada

[edit]

mCPP is not a controlled drug in Canada.

China

[edit]

As of October 2015 mCPP is a controlled substance in China.[58]

Czech Republic

[edit]

mCPP is legal in the Czech Republic.[59]

Denmark

[edit]

mCPP is illegal in Denmark.[60][unreliable source?]

Finland

[edit]

mCPP is illegal inFinland.

Germany

[edit]

mCPP is illegal inGermany.

Hungary

[edit]

mCPP is illegal inHungary since 2012.

Japan

[edit]

mCPP is illegal inJapan since 2006.

Netherlands

[edit]

mCPP is legal inthe Netherlands.[61]

New Zealand

[edit]

Based on the recommendation of theEACD, 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.[62] However, mCPP is legally used for scientific research.

Norway

[edit]

mCPP is illegal inNorway.

Russia

[edit]

mCPP is illegal inRussia.

Sweden

[edit]

mCPP is illegal inSweden.

Poland

[edit]

mCPP is illegal inPoland.

United States

[edit]

mCPP is not scheduled at the federal level in theUnited States,[63] but it is possible that it could be considered a controlled substance analog ofBZP, in which case purchase, sale, or possession could be prosecuted under theFederal Analog Act.

However, "chlorophenylpiperazine" is a Schedule Icontrolled substance in the state ofFlorida making it illegal to buy, sell, or possess in this state.[64]

United Arab Emirates

mCPP is illegal in the UAE, the country has strict drug laws, and many psychoactive substances are classified as controlled or prohibited.[65]

Turkey

[edit]

mCPP is illegal inTurkey since 20/05/2009.[66]

See also

[edit]

References

[edit]
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