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MCPP

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Summary sheet: MCPP
MCPP
Chemical Nomenclature
Common names mCPP
Substitutive name meta-Chlorophenylpiperazine
Systematic name 1-(3-chlorophenyl)piperazine
Class Membership
Psychoactive class Stimulant
Chemical class Phenylpiperazine
Routes of Administration

WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.



⇣ Oral
Dosage
Threshold 15 mg
Light 20 - 50 mg
Common 50 - 120 mg
Strong 120 - 150 mg
Heavy 150 mg +
Duration
Onset 20 - 60 minutes
Come up 20 - 60 minutes
Peak 2 - 4 hours
Offset 3 - 8 hours









DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.

Interactions
Cocaine
MAOIs
Serotonin releasers
SSRIs
5-HTP


meta-Chlorophenylpiperazine (also known as mCPP) is a stimulant drug of the phenylpiperazine class. It was first synthesized as one in a series of potential novel antihistamines by Thomas H. Wicker Jr. in 1951 as part of his doctoral work at the University of Florida. [1] Unlike many other stimulants like amphetamine, mCPP is generally considered to be unpleasant. mCPP is notable for inducing anxiety[2], and causing migraines and severe headaches.[3] mCPP is occasionally encountered as an adulterant in street MDMA.[4]

Chemistry

This chemistry section is incomplete.

You can help by adding to it.

mCPP is a drug in the phenylpiperazine class. On the meta-position of the phenyl group, there is a chlorine atom.

Pharmacology

mCPP possesses significant affinity for the 5-HT1A, 5-HT1B, 5-HT1D, 5-HT2A, 5-HT2B, 5-HT2C, 5-HT3, and 5-HT7, as well as the SERT (serotonin transporter).[5] It also has some affinity for α1-adrenergic, α2-adrenergic, H1, I1 (Imidazoline receptor), and NET (norepinephrine transporter).[5][6] It behaves as an agonist at most serotonin receptors.[7][8] mCPP has been shown to act not only as a serotonin reuptake inhibitor but as a serotonin releasing agent as well.[9]

mCPP's strongest actions are at the 5-HT2B and 5-HT2C receptors and its discriminative cue is mediated primarily by 5-HT2C.[5][10][11] Its negative effects such as anxiety, headaches, and appetite loss are likely mediated by its actions on the 5-HT2C receptor.[12][13][14] 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.[15][16][17]

mCPP acts as a partial agonist of the human 5-HT2C receptor but as an antagonist of the human 5-HT2A and 5-HT2B receptors.[18][19] In accordance with its lack of agonism towards the human 5-HT2A receptor, there are no reports that mCPP produces hallucinogenic effects in humans.[18]

mCPP is an active metabolite of the antidepressant trazodone.[20]

Subjective effects

Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWiki contributors. As a result, they should be viewed with a healthy degree of skepticism.

It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.

Physical effects

Cognitive effects

Visual effects


Experience reports

There are currently no anecdotal reports which describe the effects of this compound within our experience index. Additional experience reports can be found here:

Toxicity and harm potential

This toxicity and harm potential section is a stub.

As a result, it may contain incomplete or even dangerously wrong information! You can help by expanding upon or correcting it.
Note: Always conduct independent research and use harm reduction practices if using this substance.

It is strongly recommended that one use harm reduction practices when using this drug.

Tolerance and addiction potential

mCPP is not known to be addictive, but there are not any studies exclusively on its addiction potential.

Dangerous interactions

mCPP is metabolized by cytochrome P450 2D6[21], and concurrently taking inhibitors of that enzyme results in increased serum levels of mCPP. Commonly encounter inhibitors of CYP2D6 include ciprofloxacin, bupropion (Wellbutrin), fluoxetine (Prozac) and grapefruit juice.[22]

Warning: Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).

Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.

  • "[[DangerousInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] & "[[DangerousInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - 25x compounds are highly stimulating and physically straining. Combinations with MCPP should be strictly avoided due to the risk of excessive stimulation and heart strain. This can result in increased blood pressure, vasoconstriction, panic attacks, thought loops, seizures, and heart failure in extreme cases.
  • "[[UncertainInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Combining alcohol with stimulants can be dangerous due to the risk of accidental over-intoxication. Stimulants mask alcohol's depressant effects, which is what most people use to assess their degree of intoxication. Once the stimulant wears off, the depressant effects will be left unopposed, which can result in blackouts and severe respiratory depression. If mixing, the user should strictly limit themselves to only drinking a certain amount of alcohol per hour.
  • "[[UnsafeInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Combinations with DXM should be avoided due to its inhibiting effects on serotonin and norepinephrine reuptake. There is an increased risk of panic attacks and hypertensive crisis, or serotonin syndrome with serotonin releasers (MDMA, methylone, mephedrone, etc.). Monitor blood pressure carefully and avoid strenuous physical activity.
  • "[[UnsafeInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Any neurotoxic effects of MDMA are likely to be increased when other stimulants are present. There is also a risk of excessive blood pressure and heart strain (cardiotoxicity).
  • "[[UncertainInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Some reports suggest combinations with MXE may dangerously increase blood pressure and increase the risk of mania and psychosis.
  • "[[UncertainInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Both classes carry a risk of delusions, mania and psychosis, and these risk may be multiplied when combined.
  • "[[UnsafeInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - MCPP may be dangerous to combine with other stimulants like cocaine as they can increase one's heart rate and blood pressure to dangerous levels.
  • "[[DangerousInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Tramadol is known to lower the seizure threshold[23] and combinations with stimulants may further increase this risk.
  • "[[DangerousInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - This combination may increase the amount of neurotransmitters such as dopamine to dangerous or even fatal levels. Examples include syrian rue, banisteriopsis caapi, and some antidepressants.[24]
  • Cocaine - This combination may increase strain on the heart.

Serotonin syndrome risk

Combinations with the following substances can cause dangerously high serotonin levels. Serotonin syndrome requires immediate medical attention and can be fatal if left untreated.

This legality section is a stub.

As such, it may contain incomplete or wrong information. You can help by expanding it.

  • Austria: Since January 1, 2012, mCPP is illegal to possess, produce and sell under the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich).[citation needed]
  • Belgium: mCPP is a controlled substance as of October 22, 2006.[26]
  • Brazil: mCPP is a controlled substance (lista F2 da Portaria SVS/MS 344/98) since November 2008.[27]
  • China: As of October 2015, mCPP is a controlled substance in China.[28]
  • Denmark: mCPP is a controlled substance as of December 3, 2005.[29]
  • Finland: mCPP is a controlled substance.[citation needed]
  • Germany: mCPP is controlled under Anlage II BtMG (Narcotics Act, Schedule II)[30] as of March 1, 2007.[31] It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.[32]
  • Greece: mCPP is a controlled substance as of January 20, 2005.[29]
  • Hungary: mCPP is a controlled substance as of January 1, 2006.[29]
  • Japan: mCPP is a controlled substance since 2006.[citation needed]
  • Lithuania: mCPP is a controlled substance as of July 1, 2006.[29]
  • Norway: mCPP is a controlled substance.[citation needed]
  • Poland: mCPP is a controlled substance.[citation needed]
  • Russia: mCPP is a controlled substance.[citation needed]
  • Sweden: mCPP is a controlled substance.[citation needed]
  • Switzerland: mCPP is a controlled substance specifically named under Verzeichnis D.[33]
  • United Kingdom: mCPP is a Class C, Schedule 4 (Part 1) drug in the United Kingdom.[34]
  • United States: mCPP is unscheduled in the United States, but could be considered an analogue of benzylpiperazine if it is sold for human consumption.[citation needed]

See also

References

  1. ↑ Pollard, C. B., Wicker, T. H. (April 1954). "Derivatives of Piperazine. XXIV. Synthesis of 1-Arylpiperazines and Amino Alcohol Derivatives". Journal of the American Chemical Society. 76 (7): 1853–1855. doi:10.1021/ja01636a034. ISSN 0002-7863. 
  2. ↑ Kennett, G. A., Whitton, P., Shah, K., Curzon, G. (30 May 1989). "Anxiogenic-like effects of mCPP and TFMPP in animal models are opposed by 5-HT1C receptor antagonists". European Journal of Pharmacology. 164 (3): 445–454. doi:10.1016/0014-2999(89)90252-5. ISSN 0014-2999. 
  3. ↑ Leone, M., Attanasio, A., Croci, D., Filippini, G., D’Amico, D., Grazzi, L., Nespolo, A., Bussone, G. (12 July 2000). "The serotonergic agent m-chlorophenylpiperazine induces migraine attacks: A controlled study". Neurology. 55 (1): 136–139. doi:10.1212/wnl.55.1.136. ISSN 0028-3878. 
  4. ↑ Bossong, M., Brunt, T., Van Dijk, J., Rigter, S., Hoek, J., Goldschmidt, H., Niesink, R. (September 2010). "mCPP: an undesired addition to the ecstasy market". Journal of Psychopharmacology. 24 (9): 1395–1401. doi:10.1177/0269881109102541. ISSN 0269-8811. 
  5. ↑ 5.0 5.1 5.2 Roth, BL; Driscol, J. "PDSP Ki Database". Psychoactive Drug Screening Program (PDSP). University of North Carolina at Chapel Hill and the United States National Institute of Mental Health. Retrieved 14 August 2017. 
  6. ↑ Silverstone PH, Rue JE, Franklin M, et al. (September 1994). "The effects of administration of mCPP on psychological, cognitive, cardiovascular, hormonal and MHPG measurements in human volunteers". International Clinical Psychopharmacology. 9 (3): 173–8. doi:10.1097/00004850-199409000-00005. PMID 7814826. 
  7. ↑ Samanin R, Mennini T, Ferraris A, Bendotti C, Borsini F, Garattini S (August 1979). "Chlorophenylpiperazine: a central serotonin agonist causing powerful anorexia in rats". Naunyn-Schmiedeberg's Archives of Pharmacology. 308 (2): 159–63. doi:10.1007/BF00499059. PMID 503247. 
  8. ↑ Odagaki Y, Toyoshima R, Yamauchi T (May 2005). "Trazodone and its active metabolite m-chlorophenylpiperazine as partial agonists at 5-HT1A receptors assessed by [35S]GTPgammaS binding". Journal of Psychopharmacology (Oxford, England). 19 (3): 235–41. doi:10.1177/0269881105051526. PMID 15888508. 
  9. ↑ Pettibone DJ, Williams M (May 1984). "Serotonin-releasing effects of substituted piperazines in vitro". Biochemical Pharmacology. 33 (9): 1531–5. doi:10.1016/0006-2952(84)90424-6. PMID 6610423. 
  10. ↑ Callahan PM, Cunningham KA (May 1994). "Involvement of 5-HT2C receptors in mediating the discriminative stimulus properties of m-chlorophenylpiperazine (mCPP)". European Journal of Pharmacology. 257 (1–2): 27–38. doi:10.1016/0014-2999(94)90690-4. PMID 8082704. 
  11. ↑ Gommans J, Hijzen TH, Maes RA, Olivier B (June 1998). "Discriminative stimulus properties of mCPP: evidence for a 5-HT2C receptor mode of action". Psychopharmacology. 137 (3): 292–302. doi:10.1007/s002130050622. PMID 9683007. Archived from the original on 2002-01-12. 
  12. ↑ Kennett GA, Whitton P, Shah K, Curzon G (May 1989). "Anxiogenic-like effects of mCPP and TFMPP in animal models are opposed by 5-HT1C receptor antagonists". European Journal of Pharmacology. 164 (3): 445–54. doi:10.1016/0014-2999(89)90252-5. PMID 2767117. 
  13. ↑ Kennett GA, Curzon G (1988). "Evidence that hypophagia induced by mCPP and TFMPP requires 5-HT1C and 5-HT1B receptors; hypophagia induced by RU 24969 only requires 5-HT1B receptors". Psychopharmacology. 96 (1): 93–100. doi:10.1007/BF02431539. PMID 2906446. 
  14. ↑ Kennett GA, Curzon G (May 1988). "Evidence that mCPP may have behavioural effects mediated by central 5-HT1C receptors". British Journal of Pharmacology. 94 (1): 137–47. doi:10.1111/j.1476-5381.1988.tb11508.x. PMC 1853919 Freely accessible. PMID 3401632. 
  15. ↑ Kłodzińska A, Jaros T, Chojnacka-Wójcik E, Maj J (1989). "Exploratory hypoactivity induced by m-trifluoromethylphenylpiperazine (TFMPP) and m-chlorophenylpiperazine (m-CPP)". Journal of Neural Transmission. Parkinson's Disease and Dementia Section. 1 (3): 207–18. doi:10.1007/BF02248670. PMID 2775468. 
  16. ↑ Walsh AE, Smith KA, Oldman AD, Williams C, Goodall EM, Cowen PJ (September 1994). "m-Chlorophenylpiperazine decreases food intake in a test meal". Psychopharmacology. 116 (1): 120–2. doi:10.1007/BF02244883. PMID 7862925. 
  17. ↑ Stancampiano R, Melis MR, Argiolas A (August 1994). "Penile erection and yawning induced by 5-HT1C receptor agonists in male rats: relationship with dopaminergic and oxytocinergic transmission". European Journal of Pharmacology. 261 (1–2): 149–55. doi:10.1016/0014-2999(94)90313-1. PMID 8001637. 
  18. ↑ 18.0 18.1 Nelson DL, Lucaites VL, Wainscott DB, Glennon RA (1999). "Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors". Naunyn Schmiedebergs Arch. Pharmacol. 359 (1): 1–6. doi:10.1007/pl00005315. PMID 9933142. 
  19. ↑ Thomas DR, Gager TL, Holland V, Brown AM, Wood MD (1996). "m-Chlorophenylpiperazine (mCPP) is an antagonist at the cloned human 5-HT2B receptor". NeuroReport. 7 (9): 1457–60. doi:10.1097/00001756-199606170-00002. PMID 8856697. 
  20. ↑ Fong, M. H., Garattini, S., Caccia, S. (12 April 2011). "1- m -Chlorophenylpiperazine is an active metabolite common to the psychotropic drugs trazodone, etoperidone and mepiprazole". Journal of Pharmacy and Pharmacology. 34 (10): 674–675. doi:10.1111/j.2042-7158.1982.tb04701.x. ISSN 2042-7158. 
  21. ↑ Rotzinger, S., Fang, J., Coutts, R. T., Baker, G. B. (1 December 1998). "Human CYP2D6 and metabolism of m-chlorophenylpiperazine". Biological Psychiatry. 44 (11): 1185–1191. doi:10.1016/S0006-3223(97)00483-6. ISSN 0006-3223. 
  22. ↑ P450 Drug Interaction Table | http://medicine.iupui.edu/CLINPHARM/ddis/main-table
  23. ↑ Talaie, H.; Panahandeh, R.; Fayaznouri, M. R.; Asadi, Z.; Abdollahi, M. (2009). "Dose-independent occurrence of seizure with tramadol". Journal of Medical Toxicology. 5 (2): 63–67. doi:10.1007/BF03161089. eISSN 1937-6995. ISSN 1556-9039. OCLC 163567183. 
  24. ↑ Gillman, P. K. (2005). "Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity". British Journal of Anaesthesia. 95 (4): 434–441. doi:10.1093/bja/aei210 Freely accessible. eISSN 1471-6771. ISSN 0007-0912. OCLC 01537271. PMID 16051647. 
  25. ↑ Gillman, P. K. (2005). "Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity". British Journal of Anaesthesia. 95 (4): 434–441. doi:10.1093/bja/aei210 Freely accessible. eISSN 1471-6771. ISSN 0007-0912. OCLC 01537271. PMID 16051647. 
  26. ↑ "BELGIUM: New substances controlled include mCPP and khat". European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). Retrieved December 28, 2019. 
  27. ↑ "MCPP é incluída na lista de substâncias psicotrópicas" (in português). Agência Nacional de Vigilância Sanitária. Archived from the original on July 19, 2011. Retrieved December 28, 2019. 
  28. ↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015. 
  29. ↑ 29.0 29.1 29.2 29.3 "Europol–EMCDDA Active Monitoring Report on a new psychoactive substance: 1-(3-chlorophenyl)piperazine (mCPP)" (PDF). European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). December 2005. Retrieved April 19, 2020. 
  30. ↑ "Anlage II BtMG" (in Deutsch). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 25, 2019. 
  31. ↑ "Zwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften" (PDF) (in Deutsch). Bundesanzeiger Verlag. Retrieved December 28, 2019. 
  32. ↑ "§ 29 BtMG" (in Deutsch). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 25, 2019. 
  33. ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in Deutsch). Bundeskanzlei [Federal Chancellery of Switzerland]. Retrieved January 1, 2020. 
  34. ↑ List of most commonly encountered drugs currently controlled under the misuse of drugs legislation 
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