meta-hlorofenilpiperazin

*meta*-Hlorofenilpiperazin
(IUPAC) ime
	1-(3-hlorofenil)piperazin
Klinički podaci
Identifikatori
CAS broj	6640-24-0
ATC kod	nije dodeljen
PubChem	1355
ChemSpider	1314
ChEBI	CHEBI:10588
ChEMBL	CHEMBL478
Hemijski podaci
Formula	C10H13ClN2
Mol. masa	196,676 g/mol
SMILES	eMolekuli & PubHem
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 ; Key: VHFVKMTVMIZMIK-UHFFFAOYSA-N
Farmakokinetički podaci
Metabolizam	Hepatic
Poluvreme eliminacije	2-6 sata
Izlučivanje	Renalno
Farmakoinformacioni podaci
Trudnoća	?
Pravni status
Način primene	Oralno, nazalno, rektalno

meta-Hlorofenilpiperazin (mCPP) je psihoaktivni lek iz fenilpiperazinske klase. On je razvijen krajem 1970-tih i korišten je u naučnim istraživanjima, pre nego što je postao dezijnirana droga sredinom 2000-tih.^[5]^[6] mCPP je detektovan u pilulama koje su reklamirane kao legalne alternative za nedopuštne stimulanse u Novom Zelandu i u pilulama koje su prodavane kao "ekstazi" u Evropi i Sjedinjenim Državama.^[7]^[8]

Uprkos pokušaja da se uvede u upotrebu kao rekreaciona supstanca, mCPP se zapravo generalno smatra nepoželjnim jer proizvodi neprijatna iskustva.^[7] Njemu nedostaju potkrepljujući efekti,^[9] proizvodi depresivne i anksiogene efekte kod glodara i ljudi,^[10]^[11] i može da indukuje panične napade kod osoba koje su im podložne.^[12]^[13]^[14]^[15] On takođe pogoršava opsesivno-kompulzivne simptome kod ljudi sa tim poremećajem.^[16]^[17]^[18]

Povezano

1-Benzilpiperazin (BZP)
1-Metil-4-benzilpiperazin (MBZP)
1,4-Dibenzilpiperazin (DBZP)
3-Trifluorometilfenilpiperazin (TFMPP)
3,4-Metilendioksi-1-benzilpiperazin (MDBZP)
4-Bromo-2,5-dimetoksi-1-benzilpiperazin (2C-B-BZP)
4-Fluorofenilpiperazin (pFPP)
4-Metoksifenilpiperazin (MeOPP)
Etoperidon, Nefazodon, Trazodon - Metaboliziju se u mCPP.
Hipazin - Srodni piperazinski serotoninski agonist.
Org 12,962

References

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ Bossong MG, Van Dijk JP, Niesink RJ (December 2005). „Methylone and mCPP, two new drugs of abuse?”. Addiction Biology 10 (4): 321–3. DOI:10.1080/13556210500350794. PMID 16318952. Arhivirano iz originala na datum 2013-01-05. Pristupljeno 2014-04-05.
↑ Lecompte Y, Evrard I, Arditti J (2006). „[Metachlorophenylpiperazine (mCPP): a new designer drug]” (French). Thérapie 61 (6): 523–30. PMID 17348609.
↑ ^7,0 ^7,1 Bossong M, Brunt T, Van Dijk J, et al. (March 2009). „mCPP: an undesired addition to the ecstasy market”. Journal of Psychopharmacology (Oxford, England) 24 (9): 1395–401. DOI:10.1177/0269881109102541. PMID 19304863. ^{[mrtav link]}
↑ Vogels N, Brunt TM, Rigter S, van Dijk P, Vervaeke H, Niesink RJ (December 2009). „Content of ecstasy in the Netherlands: 1993-2008”. Addiction (Abingdon, England) 104 (12): 2057–66. DOI:10.1111/j.1360-0443.2009.02707.x. PMID 19804461. Arhivirano iz originala na datum 2013-01-05. Pristupljeno 2014-04-05.
↑ Tancer M, Johanson CE (October 2003). „Reinforcing, subjective, and physiological effects of MDMA in humans: a comparison with d-amphetamine and mCPP”. Drug and Alcohol Dependence 72 (1): 33–44. DOI:10.1016/S0376-8716(03)00172-8. PMID 14563541.
↑ Rajkumar R, Pandey DK, Mahesh R, Radha R (April 2009). „1-(m-Chlorophenyl)piperazine induces depressogenic-like behaviour in rodents by stimulating the neuronal 5-HT(2A) receptors: proposal of a modified rodent antidepressant assay”. European Journal of Pharmacology 608 (1-3): 32–41. DOI:10.1016/j.ejphar.2009.02.041. PMID 19269287.
↑ 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.
↑ Klein E, Zohar J, Geraci MF, Murphy DL, Uhde TW (November 1991). „Anxiogenic effects of m-CPP in patients with panic disorder: comparison to caffeine's anxiogenic effects”. Biological Psychiatry 30 (10): 973–84. DOI:10.1016/0006-3223(91)90119-7. PMID 1756202.
↑ Charney DS, Woods SW, Goodman WK, Heninger GR (1987). „Serotonin function in anxiety. II. Effects of the serotonin agonist MCPP in panic disorder patients and healthy subjects”. Psychopharmacology 92 (1): 14–24. PMID 3110824.
↑ Van Veen JF, Van der Wee NJ, Fiselier J, Van Vliet IM, Westenberg HG (October 2007). „Behavioural effects of rapid intravenous administration of meta-chlorophenylpiperazine (m-CPP) in patients with generalized social anxiety disorder, panic disorder and healthy controls”. European Neuropsychopharmacology : the Journal of the European College of Neuropsychopharmacology 17 (10): 637–42. DOI:10.1016/j.euroneuro.2007.03.005. PMID 17481859.
↑ van der Wee NJ, Fiselier J, van Megen HJ, Westenberg HG (October 2004). „Behavioural effects of rapid intravenous administration of meta-chlorophenylpiperazine in patients with panic disorder and controls”. European Neuropsychopharmacology : the Journal of the European College of Neuropsychopharmacology 14 (5): 413–7. DOI:10.1016/j.euroneuro.2004.01.001. PMID 15336303.
↑ Hollander E, DeCaria CM, Nitescu A, et al. (January 1992). „Serotonergic function in obsessive-compulsive disorder. Behavioral and neuroendocrine responses to oral m-chlorophenylpiperazine and fenfluramine in patients and healthy volunteers”. Archives of General Psychiatry 49 (1): 21–8. PMID 1728249. ^{[mrtav link]}
↑ Broocks A, Pigott TA, Hill JL, et al. (June 1998). „Acute intravenous administration of ondansetron and m-CPP, alone and in combination, in patients with obsessive-compulsive disorder (OCD): behavioral and biological results”. Psychiatry Research 79 (1): 11–20. DOI:10.1016/S0165-1781(98)00029-8. PMID 9676822.
↑ Pigott TA, Zohar J, Hill JL, et al. (March 1991). „Metergoline blocks the behavioral and neuroendocrine effects of orally administered m-chlorophenylpiperazine in patients with obsessive-compulsive disorder”. Biological Psychiatry 29 (5): 418–26. DOI:10.1016/0006-3223(91)90264-M. PMID 2018816.

Spoljašnje veze

	Portal Medicina
	Portal Hemija

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[pmid16318952-5] Bossong MG, Van Dijk JP, Niesink RJ (December 2005). „Methylone and mCPP, two new drugs of abuse?”. Addiction Biology 10 (4): 321–3. DOI:10.1080/13556210500350794. PMID 16318952. Arhivirano iz originala na datum 2013-01-05. Pristupljeno 2014-04-05.

[pmid17348609-6] Lecompte Y, Evrard I, Arditti J (2006). „[Metachlorophenylpiperazine (mCPP): a new designer drug]” (French). Thérapie 61 (6): 523–30. PMID 17348609.

[pmid19304863-7] 7,0 ^7,1 Bossong M, Brunt T, Van Dijk J, et al. (March 2009). „mCPP: an undesired addition to the ecstasy market”. Journal of Psychopharmacology (Oxford, England) 24 (9): 1395–401. DOI:10.1177/0269881109102541. PMID 19304863. ^{[mrtav link]}

[pmid19804461-8] Vogels N, Brunt TM, Rigter S, van Dijk P, Vervaeke H, Niesink RJ (December 2009). „Content of ecstasy in the Netherlands: 1993-2008”. Addiction (Abingdon, England) 104 (12): 2057–66. DOI:10.1111/j.1360-0443.2009.02707.x. PMID 19804461. Arhivirano iz originala na datum 2013-01-05. Pristupljeno 2014-04-05.

[pmid14563541-9] Tancer M, Johanson CE (October 2003). „Reinforcing, subjective, and physiological effects of MDMA in humans: a comparison with d-amphetamine and mCPP”. Drug and Alcohol Dependence 72 (1): 33–44. DOI:10.1016/S0376-8716(03)00172-8. PMID 14563541.

[pmid19269287-10] Rajkumar R, Pandey DK, Mahesh R, Radha R (April 2009). „1-(m-Chlorophenyl)piperazine induces depressogenic-like behaviour in rodents by stimulating the neuronal 5-HT(2A) receptors: proposal of a modified rodent antidepressant assay”. European Journal of Pharmacology 608 (1-3): 32–41. DOI:10.1016/j.ejphar.2009.02.041. PMID 19269287.

[pmid2767117-11] 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.

[pmid1756202-12] Klein E, Zohar J, Geraci MF, Murphy DL, Uhde TW (November 1991). „Anxiogenic effects of m-CPP in patients with panic disorder: comparison to caffeine's anxiogenic effects”. Biological Psychiatry 30 (10): 973–84. DOI:10.1016/0006-3223(91)90119-7. PMID 1756202.

[pmid3110824-13] Charney DS, Woods SW, Goodman WK, Heninger GR (1987). „Serotonin function in anxiety. II. Effects of the serotonin agonist MCPP in panic disorder patients and healthy subjects”. Psychopharmacology 92 (1): 14–24. PMID 3110824.

[pmid17481859-14] Van Veen JF, Van der Wee NJ, Fiselier J, Van Vliet IM, Westenberg HG (October 2007). „Behavioural effects of rapid intravenous administration of meta-chlorophenylpiperazine (m-CPP) in patients with generalized social anxiety disorder, panic disorder and healthy controls”. European Neuropsychopharmacology : the Journal of the European College of Neuropsychopharmacology 17 (10): 637–42. DOI:10.1016/j.euroneuro.2007.03.005. PMID 17481859.

[pmid15336303-15] van der Wee NJ, Fiselier J, van Megen HJ, Westenberg HG (October 2004). „Behavioural effects of rapid intravenous administration of meta-chlorophenylpiperazine in patients with panic disorder and controls”. European Neuropsychopharmacology : the Journal of the European College of Neuropsychopharmacology 14 (5): 413–7. DOI:10.1016/j.euroneuro.2004.01.001. PMID 15336303.

[pmid1728249-16] Hollander E, DeCaria CM, Nitescu A, et al. (January 1992). „Serotonergic function in obsessive-compulsive disorder. Behavioral and neuroendocrine responses to oral m-chlorophenylpiperazine and fenfluramine in patients and healthy volunteers”. Archives of General Psychiatry 49 (1): 21–8. PMID 1728249. ^{[mrtav link]}

[pmid9676822-17] Broocks A, Pigott TA, Hill JL, et al. (June 1998). „Acute intravenous administration of ondansetron and m-CPP, alone and in combination, in patients with obsessive-compulsive disorder (OCD): behavioral and biological results”. Psychiatry Research 79 (1): 11–20. DOI:10.1016/S0165-1781(98)00029-8. PMID 9676822.

[pmid2018816-18] Pigott TA, Zohar J, Hill JL, et al. (March 1991). „Metergoline blocks the behavioral and neuroendocrine effects of orally administered m-chlorophenylpiperazine in patients with obsessive-compulsive disorder”. Biological Psychiatry 29 (5): 418–26. DOI:10.1016/0006-3223(91)90264-M. PMID 2018816.

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