Tu banner alternativo

Substituted piperazine

In this article, we are going to explore Substituted piperazine and its impact in different contexts. From its origin to its current evolution, Substituted piperazine has been a topic of interest and debate in various areas. We will analyze its importance in contemporary society, its relevance in the academic field and its influence on technological development. Additionally, we will examine how Substituted piperazine has shaped people's opinions and attitudes over time and how it continues to be a reference point in today's world. Through this comprehensive analysis, we hope to shed light on Substituted piperazine and provide a more complete view of its impact on everyday life.

Tu banner alternativo

Substituted piperazines are a class of chemical compounds based on a piperazine core.[1] Some are used as recreational drugs and some are used in scientific research.[2]

List of substituted piperazines

Benzylpiperazines

See also: Benzylpiperazine § Chemical derivatives
Chemical structures of selected benzylpiperazines

Phenylpiperazines

See also: Phenylpiperazine

ortho-Substituted

Enpiprazole is known to produce oCPP as a metabolite. It was initially anticipated to produce oMeOPP as a metabolite, but this proved not to be the case.

meta-Substituted

Trazodone, nefazodone, etoperidone, mepiprazole, and others produce mCPP as a metabolite.[3]

para-Substituted

Multiple substitutions

Others

Other arylpiperazines

Many azapirones such as buspirone, gepirone, and tandospirone produce 1-PP as a metabolite.

By drug class

Antianginals

Antidepressants

Antihistamines

Antiserotonergics

Antipsychotics

Recreational Drugs

Urologicals

Others

Activities

Monoamine release (EC50Tooltip half-maximal effective concentration, nM) of arylpiperazines
Compound PAL # Serotonin Norepinephrine Dopamine Type Ref
1-Benzylpiperazine (BZP) ND 6050–>100000 62.2–68 175–600 NDRA [5][6][7][8][9][10]
1-Phenylpiperazine (PP) ND 880 186 2530 SNRA [11]
2-Me-PP (oMPP) PAL-169 175 39.1 296–542 SNDRA [11][12][10]
2-OMe-PP (oMeOPP) ND ND ND ND ND ND
2-TFM-PP (oTFMPP) ND 570 350 11200 SNRA [11]
2-SMe-PP (oMTPP) ND 270 >10000 >10000 SRA [11]
2-Et-PP (oEtPP) ND 290 830 >10000 SNRA [11]
2-Chloro-PP (oCPP) ND 310 26 >3000 NRA [11]
2-Bromo-PP (oBPP) ND 132 33 250 SNDRA [11]
2-Nitro-PP (oNPP) ND 1870 770 >10000 SNRA [11]
3-Chloro-PP (mCPP) ND 28–39 1400–>10000 >10000–63000 SRA [6][13][14][15]
3-Fluoro-PP (mFPP) ND 115 340 2400 SNRA [11]
3-Me-PP (mMPP) ND 110 >20000 >20000 SRA [11]
3-OMe-PP (mMeOPP) ND 650 >10000 >10000 SRA [11]
3-OH-PP (mOHPP) ND 230 174 2500 SNRA [11]
3-TFM-PP (TFMPP) ND 121 >10000 >10000 SRA [8][7][9]
4-Chloro-PP (pCPP) ND ND ND ND ND ND
4-Fluoro-PP (pFPP) ND 230 3200 >10000 SRA [11]
4-Me-PP (pMPP) PAL-233 220 >10000 >20000 SRA [11][10]
4-OMe-PP (pMeOPP) ND 3200 440–1500 6300–11000 SNDRA [11][6]
4-TFM-PP (pTFMPP) ND ND ND ND ND ND
4-Ac-PP (pAcPP) ND 50 150 3000 SNRA [11]
4-CN-PP (pCNPP) ND 36 6300 >10000 SRA [11]
4-Phenyl-PP (pPhPP) ND >10000 1520 5200 NDRA [11]
4-OH-PP (pOHPP) ND >10000 230 850 NDRA [11]
4-Nitro-PP (pNPP) PAL-175 19–43 >10000 >10000 SRA [11][4]
2,3-Dichloro-PP (2,3-DCPP) ND 10 36 108 SNDRA [11]
2,3-DiMe-PP (2,3-DMPP) PAL-218 24–26 13.7–56 1207–1320 SNRA [11][4][10]
2,4-Difluoro-PP (2,4-DFPP) ND 470 2300 >10000 SNRA [11]
3,4-Dichloro-PP (3,4-DCPP) ND ND ND ND ND ND
3,4-Difluoro-PP (3,4-DFPP) ND 76 9200 >10000 SRA [11]
3-TFM-4-Cl-PP (TFMCPP) PAL-179 33 >10000 >10000 SRA [4]
Notes: Assays were done using rat brain synaptosomes.

See also

References

  1. ^ Laras, Y.; Garino, C.; Dessolin, J.; Weck, C.; Moret, V.; Rolland, A.; Kraus, J.-L. (2009-02-01). "New N4-substituted piperazine naphthamide derivatives as BACE-1 inhibitors". Journal of Enzyme Inhibition and Medicinal Chemistry. 24 (1): 181–187. doi:10.1080/14756360802048939. ISSN 1475-6366. PMID 18770069. S2CID 85385527.
  2. ^ Alghamdi, Saad; Alshehri, Mohammed M.; Asif, Mohammad (2022). "The Neuropharmacological Potential of Piperazine Derivatives: A Mini- Review". Mini-Reviews in Organic Chemistry. 19 (7): 798–810. doi:10.2174/1570193x19666220119120211.
  3. ^ Costa Alegre MD, Barbosa DJ, Dinis-Oliveira RJ (February 2025). "Metabolism of m-CPP, trazodone, nefazodone, and etoperidone: clinical and forensic aspects". Drug Metab Rev. 57 (2): 115–146. doi:10.1080/03602532.2025.2465482. PMID 39945551.
  4. ^ a b c d e Rothman RB, Partilla JS, Baumann MH, Lightfoot-Siordia C, Blough BE (April 2012). "Studies of the biogenic amine transporters. 14. Identification of low-efficacy "partial" substrates for the biogenic amine transporters". J Pharmacol Exp Ther. 341 (1): 251–262. doi:10.1124/jpet.111.188946. PMC 3364510. PMID 22271821.
  5. ^ Rothman RB, Baumann MH (2006). "Therapeutic potential of monoamine transporter substrates". Curr Top Med Chem. 6 (17): 1845–1859. doi:10.2174/156802606778249766. PMID 17017961.
  6. ^ a b c Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". Eur J Pharmacol. 559 (2–3): 132–137. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101.
  7. ^ a b Baumann MH, Clark RD, Budzynski AG, Partilla JS, Blough BE, Rothman RB (October 2004). "Effects of "Legal X" piperazine analogs on dopamine and serotonin release in rat brain". Ann N Y Acad Sci. 1025: 189–197. Bibcode:2004NYASA1025..189B. doi:10.1196/annals.1316.024. PMID 15542717.
  8. ^ a b Baumann MH, Clark RD, Budzynski AG, Partilla JS, Blough BE, Rothman RB (March 2005). "N-substituted piperazines abused by humans mimic the molecular mechanism of 3,4-methylenedioxymethamphetamine (MDMA, or 'Ecstasy')". Neuropsychopharmacology. 30 (3): 550–560. doi:10.1038/sj.npp.1300585. PMID 15496938.
  9. ^ a b Blough B (July 2008). "Dopamine-releasing agents" (PDF). In Trudell ML, Izenwasser S (eds.). Dopamine Transporters: Chemistry, Biology and Pharmacology. Hoboken : Wiley. pp. 305–320. ISBN 978-0-470-11790-3. OCLC 181862653. OL 18589888W.
  10. ^ a b c d Reith ME, Blough BE, Hong WC, Jones KT, Schmitt KC, Baumann MH, Partilla JS, Rothman RB, Katz JL (February 2015). "Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter". Drug Alcohol Depend. 147: 1–19. doi:10.1016/j.drugalcdep.2014.12.005. PMC 4297708. PMID 25548026.
  11. ^ a b c d e f g h i j k l m n o p q r s t u v w x Severinsen K, Kraft JF, Koldsø H, Vinberg KA, Rothman RB, Partilla JS, Wiborg O, Blough B, Schiøtt B, Sinning S (September 2012). "Binding of the amphetamine-like 1-phenyl-piperazine to monoamine transporters". ACS Chem Neurosci. 3 (9): 693–705. doi:10.1021/cn300040f. PMC 3447394. PMID 23019496.
  12. ^ Kohut SJ, Jacobs DS, Rothman RB, Partilla JS, Bergman J, Blough BE (December 2017). "Cocaine-like discriminative stimulus effects of "norepinephrine-preferring" monoamine releasers: time course and interaction studies in rhesus monkeys". Psychopharmacology (Berl). 234 (23–24): 3455–3465. doi:10.1007/s00213-017-4731-5. PMC 5747253. PMID 28889212.
  13. ^ Rothman RB, Baumann MH (July 2002). "Therapeutic and adverse actions of serotonin transporter substrates". Pharmacol Ther. 95 (1): 73–88. doi:10.1016/s0163-7258(02)00234-6. PMID 12163129.
  14. ^ Rothman RB, Baumann MH (April 2002). "Serotonin releasing agents. Neurochemical, therapeutic and adverse effects". Pharmacol Biochem Behav. 71 (4): 825–836. doi:10.1016/s0091-3057(01)00669-4. PMID 11888573.
  15. ^ Rothman RB, Baumann MH, Blough BE, Jacobson AE, Rice KC, Partilla JS (November 2010). "Evidence for noncompetitive modulation of substrate-induced serotonin release". Synapse. 64 (11): 862–869. doi:10.1002/syn.20804. PMC 2941209. PMID 20842720.
Wikious
Boobota
Sagapedia