MedKoo Cat#: 581248 | Name: Piperazine Citrate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Piperazine Citrate is an organic compound that consists of a six-membered ring, containting two nitrogen atoms at opposite positions in the ring. Piperazine is a white crystal powder with a melting point of 190 Celcius. Piperazine Citrate was first introduced in 1953 as an Anthelmintic. Piperazine Citrate in generally used for the paralisation of parasites, which allow the body to easily remove or expel the invading organism. The Piperazine Citrate is being used as an anthelmintic for humans and animals against roundworms and pinworm infections. The Piperazine Citrate is also used in the manufacture of plastics, resins, pesticides and other materials. The Piperazine Citrate blocks the response of the worm muscle to acetylcholine, presumably by causing hyperpolarisation of nerve endings which causes an flaccid paralysation of the worm. An overdoses of Piperazine Citrate can cause coughing, colic, spams, sweating and vomiting.

Chemical Structure

Piperazine Citrate
Piperazine Citrate
CAS#144-29-6 (citrate)

Theoretical Analysis

MedKoo Cat#: 581248

Name: Piperazine Citrate

CAS#: 144-29-6 (citrate)

Chemical Formula: C24H46N6O14

Exact Mass: 642.3072

Molecular Weight: 642.66

Elemental Analysis: C, 44.85; H, 7.22; N, 13.08; O, 34.85

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 Weeks
25g USD 450.00 2 Weeks
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Synonym
Piperazine Citrate; AI3-27243; DAK 63; Exopin; Oxyzin; Pipizan; Vermago;
IUPAC/Chemical Name
Piperazine, 2-hydroxy-1,2,3-propanetricarboxylate (3:2)
InChi Key
JDDHUROHDHPVIO-UHFFFAOYSA-N
InChi Code
InChI=1S/2C6H8O7.3C4H10N2/c2*7-3(8)1-6(13,5(11)12)2-4(9)10;3*1-2-6-4-3-5-1/h2*13H,1-2H2,(H,7,8)(H,9,10)(H,11,12);3*5-6H,1-4H2
SMILES Code
O=C(CC(C(O)=O)(O)CC(O)=O)O.O=C(CC(C(O)=O)(O)CC(O)=O)O.N1CCNCC1.N2CCNCC2.N3CCNCC3
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Biological target:
Piperazine (1,4-Diazacyclohexane) citrate is a gamma-aminobutyric acid (GABA) agonist.
In vitro activity:
This work presents a library of 34 piperazine-derived small molecules as potential Flaviviridae NS3 protease inhibitors. The library was developed through a privileged structures-based design and then biologically screened using a live virus phenotypic assay to determine the half-maximal inhibitor concentration (IC50) of each compound against ZIKV and DENV. Two lead compounds, 42 and 44, with promising broad-spectrum activity against ZIKV (IC50 6.6 µM and 1.9 µM respectively) and DENV (IC50 6.7 µM and 1.4 µM respectively) and a good security profile were identified. Reference: Bioorg Chem. 2023 Apr;133:106408. https://pubmed.ncbi.nlm.nih.gov/36801791/
In vivo activity:
LPD (ligustrazine piperazine derivative) treatment dose-dependently reduced Aβ40 and Aβ42 levels in PC12 cells stably transfected with APP695swe and PSEN1dE9. Intragastric administration of LPD for 3 months dose-dependently reversed cognitive deficits in APP/PS1 mice. LPD treatment substantially decreased hippocampal Aβ plaques in APP/PS1 mice and decreased the levels of Aβ40 and Aβ42 in vivo and in vitro. Moreover, LPD treatment induced mitophagy in vivo and in vitro and increased brain 18F-FDG uptake in APP/PS1 mice. Reference: Alzheimers Res Ther. 2022 Oct 11;14(1):150. https://pubmed.ncbi.nlm.nih.gov/36217155/
Solvent mg/mL mM
Solubility
DMSO 2.2 3.38
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 642.66 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Del Rosario García-Lozano M, Dragoni F, Gallego P, Mazzotta S, López-Gómez A, Boccuto A, Martínez-Cortés C, Rodríguez-Martínez A, Pérez-Sánchez H, Manuel Vega-Pérez J, Antonio Del Campo J, Vicenti I, Vega-Holm M, Iglesias-Guerra F. Piperazine-derived small molecules as potential Flaviviridae NS3 protease inhibitors. In vitro antiviral activity evaluation against Zika and Dengue viruses. Bioorg Chem. 2023 Apr;133:106408. doi: 10.1016/j.bioorg.2023.106408. Epub 2023 Feb 4. PMID: 36801791. 2. Liang T, Xie Z, Dang B, Wang J, Zhang T, Luan X, Lu T, Cao C, Chen X. Discovery of indole-piperazine derivatives as selective histone deacetylase 6 inhibitors with neurite outgrowth-promoting activities and neuroprotective activities. Bioorg Med Chem Lett. 2023 Feb 1;81:129148. doi: 10.1016/j.bmcl.2023.129148. Epub 2023 Jan 21. PMID: 36690041. 3. Li Z, Meng X, Ma G, Liu W, Li W, Cai Q, Wang S, Huang G, Zhang Y. Increasing brain glucose metabolism by ligustrazine piperazine ameliorates cognitive deficits through PPARγ-dependent enhancement of mitophagy in APP/PS1 mice. Alzheimers Res Ther. 2022 Oct 11;14(1):150. doi: 10.1186/s13195-022-01092-7. PMID: 36217155; PMCID: PMC9552451. 4. Ni H, Hatit MZC, Zhao K, Loughrey D, Lokugamage MP, Peck HE, Cid AD, Muralidharan A, Kim Y, Santangelo PJ, Dahlman JE. Piperazine-derived lipid nanoparticles deliver mRNA to immune cells in vivo. Nat Commun. 2022 Aug 15;13(1):4766. doi: 10.1038/s41467-022-32281-5. PMID: 35970837; PMCID: PMC9376583.
In vitro protocol:
1. Del Rosario García-Lozano M, Dragoni F, Gallego P, Mazzotta S, López-Gómez A, Boccuto A, Martínez-Cortés C, Rodríguez-Martínez A, Pérez-Sánchez H, Manuel Vega-Pérez J, Antonio Del Campo J, Vicenti I, Vega-Holm M, Iglesias-Guerra F. Piperazine-derived small molecules as potential Flaviviridae NS3 protease inhibitors. In vitro antiviral activity evaluation against Zika and Dengue viruses. Bioorg Chem. 2023 Apr;133:106408. doi: 10.1016/j.bioorg.2023.106408. Epub 2023 Feb 4. PMID: 36801791. 2. Liang T, Xie Z, Dang B, Wang J, Zhang T, Luan X, Lu T, Cao C, Chen X. Discovery of indole-piperazine derivatives as selective histone deacetylase 6 inhibitors with neurite outgrowth-promoting activities and neuroprotective activities. Bioorg Med Chem Lett. 2023 Feb 1;81:129148. doi: 10.1016/j.bmcl.2023.129148. Epub 2023 Jan 21. PMID: 36690041.
In vivo protocol:
1. Li Z, Meng X, Ma G, Liu W, Li W, Cai Q, Wang S, Huang G, Zhang Y. Increasing brain glucose metabolism by ligustrazine piperazine ameliorates cognitive deficits through PPARγ-dependent enhancement of mitophagy in APP/PS1 mice. Alzheimers Res Ther. 2022 Oct 11;14(1):150. doi: 10.1186/s13195-022-01092-7. PMID: 36217155; PMCID: PMC9552451. 2. Ni H, Hatit MZC, Zhao K, Loughrey D, Lokugamage MP, Peck HE, Cid AD, Muralidharan A, Kim Y, Santangelo PJ, Dahlman JE. Piperazine-derived lipid nanoparticles deliver mRNA to immune cells in vivo. Nat Commun. 2022 Aug 15;13(1):4766. doi: 10.1038/s41467-022-32281-5. PMID: 35970837; PMCID: PMC9376583.
1: Abiramalatha T, Mehndiratta S, Rajeshwari K, Dubey AP. Piperazine citrate induced myoclonus in a child. Indian J Pharmacol. 2013 Nov-Dec;45(6):640. doi: 10.4103/0253-7613.121391. PubMed PMID: 24347782; PubMed Central PMCID: PMC3847264. 2: Ghasi S, Ogbonna A, Mbah A. Impact of subchronic administration of piperazine citrate on the electrocardiogram of the rat. Am J Ther. 2012 Mar;19(2):81-7. doi: 10.1097/MJT.0b013e3181bbf6d4. PubMed PMID: 20215962. 3: Onuaguluchi G, Ghasi S. Electrocardiographic profile of oral piperazine citrate in healthy volunteers. Am J Ther. 2006 Jan-Feb;13(1):43-7. PubMed PMID: 16428921. 4: Ghasi S, Onuaguluchi G. Time course of effect of piperazine citrate on the electrocardiogram of the rat. Am J Ther. 2007 Nov-Dec;14(6):524-32. PubMed PMID: 18090878. 5: Quirce S, Pelta R, Sastre J. Occupational asthma due to piperazine citrate. J Investig Allergol Clin Immunol. 2006;16(2):138-9. PubMed PMID: 16689189. 6: Onuaguluchi G, Mezue WC. Some effects of piperazine citrate on skeletal muscle and central nervous system. Arch Int Pharmacodyn Ther. 1987 Nov;290(1):104-16. PubMed PMID: 3446036. 7: Das Gupta V. Quantitative determination of piperazine citrate in piperazine citrate syrup USP. Am J Hosp Pharm. 1976 Mar;33(3):283-4. PubMed PMID: 3967. 8: Rettig T. Hypocalcemic tetany induced by piperazine citrate in a mountain lion. Vet Med Small Anim Clin. 1981 Nov;76(11):1632-4. PubMed PMID: 6916544. 9: Kale OO. Controlled comparative study of the efficacy of pyrantel pamoate and a combined regimen of piperazine citrate and bephenium hydroxynaphthoate in the treatment of intestinal nemathelminthiases. Afr J Med Med Sci. 1981 Mar-Jun;10(1-2):63-7. PubMed PMID: 6287829. 10: BROWN HW, STERMAN MM. Treatment of Ascaris lumbricoides infections with piperazine citrate. Am J Trop Med Hyg. 1954 Jul;3(4):750-4. PubMed PMID: 13180836. 11: Tricker AR, Kumar R, Siddiqi M, Khuroo MS, Preussmann R. Endogenous formation of N-nitrosamines from piperazine and their urinary excretion following antihelmintic treatment with piperazine citrate. Carcinogenesis. 1991 Sep;12(9):1595-9. PubMed PMID: 1893519. 12: Onuaguluchi G, Igbo IN. Comparative antiarrhythmic and local anaesthetic effects of piperazine citrate and lignocaine hydrochloride. Arch Int Pharmacodyn Ther. 1985 Apr;274(2):253-66. PubMed PMID: 4026459. 13: DiPietro JA, Todd KS Jr, Lock TF, Reuter-Dallman V. Evaluation of febantel used concurrently with piperazine citrate in horses. J Am Vet Med Assoc. 1985 Feb 1;186(3):262-4. PubMed PMID: 3972687. 14: SWARTZWELDER C, MILLER JH, SAPPENFIELD RW. The treatment of cases of ascariasis with piperazine citrate with observations of the effect of the drug on other helminthiases. Am J Trop Med Hyg. 1955 Mar;4(2):326-31. PubMed PMID: 14361913. 15: URELES AL. Two case histories of serum sickness-like reaction following piperazine citrate (antepar). Antibiotic Med Clin Ther (New York). 1958 Sep;5(9):585-6. PubMed PMID: 13571965. 16: MANN PH, HARFENIST M, DE BEER EJ. The effectiveness of piperazine citrate against intestinal helminths of the cat and dog. J Parasitol. 1955 Dec;41(6):575-8. PubMed PMID: 13272109. 17: BURGSTEDT HJ. [Anthelmintic effect of piperazine citrate on oxyria and ascarides]. Munch Med Wochenschr. 1955 Apr 22;97(16):531-4. German. PubMed PMID: 13253515. 18: RATSCHOW M. [Piperazine citrate in the management of ascariasis]. Medizinische. 1956 Dec 15;10(50):1790-1. German. PubMed PMID: 13399700. 19: ETTELDORF JN, CRAWFORD LV. Treatment of ascariasis in children; use of 1-diethylcarbamyl-4-methyl piperazine dihydrogen citrate (hetrazan). J Am Med Assoc. 1950 Jul 1;143(9):797-8. PubMed PMID: 15421820. 20: SAIF M. On the single-dose treatment of ascariasis with piperazine citrate. J Egypt Med Assoc. 1957;40(8):557-60. PubMed PMID: 13525528.