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间氯苯基哌嗪

维基百科，自由的百科全书
间氯苯基哌嗪
临床资料
给药途径口服给药、鼻内给药、直肠给药（英语：rectal administration）
ATC码
  • 未分配
法律规范状态
法律规范
药物动力学数据
药物代谢肝（CYP2D6）[1]
生物半衰期4至14小时[1][2]
排泄途径尿
识别信息
  • 1-(3-chlorophenyl)piperazine
CAS号6640-24-0  checkY
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard（英语：CompTox Chemicals Dashboard） (EPA)
ECHA InfoCard100.026.959 编辑维基数据链接
化学信息
化学式C10H13ClN2
摩尔质量196.68 g·mol−1
3D模型（JSmol（英语：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

间氯苯基哌嗪（英语缩写mCPP）是一种苯基哌嗪类精神活性药物。它最初于1970年代末开发并用于科学研究，然后在2000年代中期作为设计师药物出售。[4][5]该药物被发现存在于多种物质里，包括在新西兰被吹捧为非法兴奋剂的合法替代品药丸以及在欧洲和美国作为“摇头丸”出售的药丸。[6][7]

尽管间氯苯基哌嗪在广告中被宣传为一种娱乐物质，但实际上人们普遍认为吸食间氯苯基哌嗪是一种不愉快的体验，吸毒者并不想要这种体验。[6]它缺乏任何强化作用，但具有精神兴奋、引发焦虑和致幻作用。[8][9][10][11]它会对啮齿动物和人类产生烦躁、抑郁和焦虑作用，[12][13]并可能在易感个体中引起惊恐发作。[14][15][16][17]它还会加剧患有这种疾病的人的强迫症状。[18][19][20]

间氯苯基哌嗪已知会引起头痛，并已用于测试潜在的抗偏头痛药物（英语：Antimigraine drug）。[21][22][23]它具有有效的厌食作用（英语：Anorectic），并促进了选择性5-HT2C受体激动剂的开发，用于治疗肥胖症。[24][25][26][27]

参考资料

  1. ^ 1.0 1.1 Rotzinger S, Bourin M, Akimoto Y, Coutts RT, Baker GB. Metabolism of some "second"- and "fourth"-generation antidepressants: iprindole, viloxazine, bupropion, mianserin, maprotiline, trazodone, nefazodone, and venlafaxine. Cellular and Molecular Neurobiology. August 1999, 19 (4): 427–442. PMID 10379419. S2CID 19585113. doi:10.1023/a:1006953923305. 
  2. ^ Schatzberg AF, Nemeroff CB. The American Psychiatric Association Publishing Textbook of Psychopharmacology, Fifth Edition. American Psychiatric Pub. 2017: 460–. ISBN 978-1-58562-523-9. 
  3. ^ Anvisa. RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control]. Diário Oficial da União. 2023-07-24 (2023-07-25) [2023-08-27]. （原始内容存档于2023-08-27） （巴西葡萄牙语）. 
  4. ^ Bossong MG, Van Dijk JP, Niesink RJ. Methylone and mCPP, two new drugs of abuse?. Addiction Biology. December 2005, 10 (4): 321–323. PMID 16318952. S2CID 36169592. doi:10.1080/13556210500350794. （原始内容存档于2013-01-05）. 
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  6. ^ 6.0 6.1 Bossong MG, Brunt TM, Van Dijk JP, Rigter SM, Hoek J, Goldschmidt HM, Niesink RJ. mCPP: an undesired addition to the ecstasy market. Journal of Psychopharmacology. September 2010, 24 (9): 1395–1401. PMID 19304863. S2CID 11186375. doi:10.1177/0269881109102541. 
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  8. ^ World Health Organization. 1-(3-chlorophenyl) piperazine (mCPP) - Expert peer review on pre-review report (PDF). [2021-01-12]. （原始内容存档 (PDF)于2022-09-01）. 
  9. ^ Tancer ME, Johanson CE. The subjective effects of MDMA and mCPP in moderate MDMA users. Drug and Alcohol Dependence. December 2001, 65 (1): 97–101. PMID 11714594. doi:10.1016/s0376-8716(01)00146-6. 
  10. ^ Tancer M, Johanson CE. Reinforcing, subjective, and physiological effects of MDMA in humans: a comparison with d-amphetamine and mCPP. Drug and Alcohol Dependence. October 2003, 72 (1): 33–44. PMID 14563541. doi:10.1016/S0376-8716(03)00172-8. 
  11. ^ Nelson DL, Lucaites VL, Wainscott DB, Glennon RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, -HT(2B) and 5-HT2C receptors. Naunyn-Schmiedeberg's Archives of Pharmacology. January 1999, 359 (1): 1–6. PMID 9933142. S2CID 20150858. doi:10.1007/pl00005315. 
  12. ^ Rajkumar R, Pandey DK, Mahesh R, Radha R. 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. April 2009, 608 (1–3): 32–41. PMID 19269287. doi:10.1016/j.ejphar.2009.02.041. 
  13. ^ Kennett GA, Whitton P, Shah K, Curzon G. Anxiogenic-like effects of mCPP and TFMPP in animal models are opposed by 5-HT1C receptor antagonists. European Journal of Pharmacology. May 1989, 164 (3): 445–454. PMID 2767117. doi:10.1016/0014-2999(89)90252-5. 
  14. ^ Klein E, Zohar J, Geraci MF, Murphy DL, Uhde TW. Anxiogenic effects of m-CPP in patients with panic disorder: comparison to caffeine's anxiogenic effects. Biological Psychiatry. November 1991, 30 (10): 973–984 [2024-04-11]. PMID 1756202. S2CID 43010184. doi:10.1016/0006-3223(91)90119-7. （原始内容存档于2020-09-15）. 
  15. ^ Charney DS, Woods SW, Goodman WK, Heninger GR. Serotonin function in anxiety. II. Effects of the serotonin agonist MCPP in panic disorder patients and healthy subjects. Psychopharmacology. 1987, 92 (1): 14–24. PMID 3110824. S2CID 43079787. doi:10.1007/bf00215473. 
  16. ^ Van Veen JF, Van der Wee NJ, Fiselier J, Van Vliet IM, Westenberg HG. 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. October 2007, 17 (10): 637–642. PMID 17481859. S2CID 41601926. doi:10.1016/j.euroneuro.2007.03.005. 
  17. ^ van der Wee NJ, Fiselier J, van Megen HJ, Westenberg HG. Behavioural effects of rapid intravenous administration of meta-chlorophenylpiperazine in patients with panic disorder and controls. European Neuropsychopharmacology. October 2004, 14 (5): 413–417. PMID 15336303. S2CID 28987431. doi:10.1016/j.euroneuro.2004.01.001. 
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  19. ^ Broocks A, Pigott TA, Hill JL, Canter S, Grady TA, L'Heureux F, Murphy DL. 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. June 1998, 79 (1): 11–20 [2024-04-11]. PMID 9676822. S2CID 30339598. doi:10.1016/S0165-1781(98)00029-8. （原始内容存档于2020-09-15）. 
  20. ^ Pigott TA, Zohar J, Hill JL, Bernstein SE, Grover GN, Zohar-Kadouch RC, Murphy DL. Metergoline blocks the behavioral and neuroendocrine effects of orally administered m-chlorophenylpiperazine in patients with obsessive-compulsive disorder. Biological Psychiatry. March 1991, 29 (5): 418–426. PMID 2018816. S2CID 37648659. doi:10.1016/0006-3223(91)90264-M. 
  21. ^ Leone M, Attanasio A, Croci D, Filippini G, D'Amico D, Grazzi L, et al. The serotonergic agent m-chlorophenylpiperazine induces migraine attacks: A controlled study. Neurology. July 2000, 55 (1): 136–139. PMID 10891925. S2CID 27617431. doi:10.1212/wnl.55.1.136. 
  22. ^ 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. February 2001, 21 (1): 46–52. PMID 11298663. S2CID 8471836. doi:10.1046/j.1468-2982.2001.00157.x 可免费查阅. 
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  24. ^ Kennett GA, Curzon G. 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. 1988, 96 (1): 93–100. PMID 2906446. S2CID 21417374. doi:10.1007/BF02431539. 
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外部链接

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