meta-Chlorophenylpiperazine

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meta-Chlorophenylpiperazine
MCPP.svg
MCPP3d.png
Systematic (IUPAC) name
1-(3-chlorophenyl)piperazine
Clinical data
Legal status
Routes of
administration		 Oral, Nasal, Rectal
Pharmacokinetic data
Metabolism Hepatic
Biological half-life 2-6 hours
Excretion Renal
Identifiers
CAS Number 6640-24-0 N
ATC code none
PubChem CID: 1355
IUPHAR/BPS 142
ChemSpider 1314 YesY
UNII REY0CNO998 N
ChEBI CHEBI:10588 YesY
ChEMBL CHEMBL478 YesY
Chemical data
Formula C10H13ClN2
Molecular mass 196.676 g/mol
  • 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 YesY
  • Key:VHFVKMTVMIZMIK-UHFFFAOYSA-N YesY
 NYesY (what is this?)  (verify)
Tablets containing mCPP confiscated by the DEA in Vernon Hills, Illinois

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.[1][2] 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.[3][4]

Despite its advertisement as a recreational substance, mCPP is actually generally considered to be an unpleasant experience and is not desired by drug users.[3] It lacks any reinforcing effects,[5] produces depressive and anxiogenic effects in rodents and humans,[6][7] and can induce panic attacks in individuals susceptible to them.[8][9][10][11] It also worsens obsessive-compulsive symptoms in people with the disorder.[12][13][14]

mCPP is known to induce headaches in humans and has been used for testing potential antimigraine medications.[15][16][17] It has potent anorectic effects and has encouraged the development of selective 5-HT2C receptor agonists for the treatment of obesity as well.[18][19][20][21]

Meta-chlorophenylpiperazine is a major metabolite of the psychotropic drugs trazodone and nefazodone, and may be responsible for some of their side-effects, such as headaches and migraines induced many hours after initial consumption.

Pharmacology

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.[22] It also has some affinity for α1-adrenergic, α2-adrenergic, H1, I1, and NET.[22][23] It behaves as an agonist at most or all serotonin receptors.[22][24][25] mCPP has been shown to act not only as a reuptake inhibitor of serotonin but as a releasing agent as well.[26]

mCPP's strongest actions are at the 5-HT2B and 5-HT2C receptors and its discriminative cue is mediated primarily by 5-HT2C.[22][27][28] Its negative effects such as anxiety, headaches, and appetite loss are likely mediated by its actions on the 5-HT2C receptor,[7][18][29] whereas its psychedelic effects at high doses are caused by 5-HT2A activation. 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.[30][31][32]

Binding affinity (Ki [nM]) towards cloned human receptors where data is available

Protein Ki (nM)[33]
SERT 265.1
NET 3150
5-HT1A 43.9
5-HT1B 251.9
5-HT1D 285.5
5-HT2A 54.5
5-HT2B 30.3
5-HT2C 13.04
5-HT3 427
5-HT5A 1354
5-HT6 1748
5-HT7 162.5
α1A 1386
α1B 914.6
α2A 145.1
α2B 105.8
α2C 123.5
β1 2359
β2 3474
D1 7000 (HB)
D2 >10000 (HB)
D3 >10000 (RC)
D5 >10000
BDZ receptor >10000 (HB)
I1 758.9 (RPC12)
σ2 8350 (RPC12)
H1 326.3
mAChRs >10000 (HB)

Legend:
RC - Cloned rat receptor
HB - Human brain receptor
RPC12 - Rat PC12 receptor
Bold text indicates non-cloned human receptor binding affinities.

Pharmacokinetics

mCPP is metabolized via the CYP2D6 isoenzyme by hydroxylation to p-hydroxy-mCPP (OH-mCPP).[34] Caution should be exercised in coprescribing inhibitors or substrates of CYP2D6 with drugs such as trazodone and nefazodone that have mCPP as a metabolite.[34]

Legal status

Belgium

mCPP is illegal in Belgium.[35]

Brazil

mCPP is illegal in Brazil.[36]

China

As of October 2015 mCPP is a controlled substance in China.[37]

Czech Republic

mCPP is legal in the Czech Republic.[38]

Denmark

mCPP is illegal in Denmark.[39]

Finland

mCPP is illegal in Finland.

Germany

mCPP is illegal in Germany.

Hungary

mCPP is illegal in Hungary since 2012.04.02.

Japan

mCPP is illegal in Japan since 2006.10.13

Netherlands

mCPP is not illegal in the Netherlands. [40]

New Zealand

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.[41] However, it is important to note that mCPP is legally used for scientific research.

Norway

mCPP is illegal in Norway.

Russia

mCPP is illegal in Russia.

Sweden

mCPP is illegal in Sweden.

Poland

mCPP is illegal in Poland.

United States

mCPP is not scheduled at the federal level in the United States,[42] 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.

Florida

"Chlorophenylpiperazine" is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[43]

See also

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ 3.0 3.1 Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ 7.0 7.1 Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  16. ↑ Martin RS & Martin GR. Investigations into migraine pathogenesis: time course for effects of m-CPP, BW723C86 or glyceryl trinitrate on appearance of Fos-like immunoreactivity in rat trigeminal nucleus caudalis (TNC). Cephalalgia 2001; 21:46–52. London. ISSN 0333-10245
  17. ↑ Petkov VD, Belcheva S, Konstantinova E. Anxiolytic effects of dotarizine, a possible antimigraine drug. Methods Find Exp Clin Pharmacol. 1995 Dec;17(10):659-68.
  18. ↑ 18.0 18.1 Lua error in package.lua at line 80: module 'strict' not found.
  19. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  20. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  21. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  22. ↑ 22.0 22.1 22.2 22.3 Lua error in package.lua at line 80: module 'strict' not found.
  23. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  24. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  25. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  26. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  27. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  28. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  29. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  30. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  31. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  32. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  33. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  34. ↑ 34.0 34.1 Lua error in package.lua at line 80: module 'strict' not found.
  35. ↑ EMCDDA
  36. ↑ ANVISA resolution - Portaria SVS/MS 344/98
  37. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  38. ↑ [1]
  39. ↑ Erowid.org
  40. ↑ http://wetten.nl/BWBR0001941/geldigheidsdatum_05-08-2015
  41. ↑ Misuse of Drugs (Classification of BZP) Amendment Bill 2008
  42. ↑ 21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.
  43. ↑ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL
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