Piperazine adipate | CAS#142-88-1

MedKoo Cat#: 591174 | Name: Piperazine adipate

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Description:

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

Piperazine is biochemical, which may be an alternative treatment for ascariasis caused by Ascaris lumbricoides (roundworm) and enterobiasis (oxyuriasis) caused by Enterobius vermicularis (pinworm). Piperazine is especially useful in the treatment of partial intestinal obstruction caused by Ascaris worms, which is a condition primarily seen in children. Piperazine blocks the response of the worm muscle (best studied in Ascaris ) to acetylcholine, presumably by causing hyperpolarization of nerve endings, resulting in flaccid paralysis of the worm. While the worm is paralyzed, it is dislodged from the intestinal lumen and expelled live from the body by normal intestinal peristalsis.

Chemical Structure

Piperazine adipate

CAS#142-88-1 (adipate)

Theoretical Analysis

MedKoo Cat#: 591174

Name: Piperazine adipate

CAS#: 142-88-1 (adipate)

Chemical Formula: C10H20N2O4

Exact Mass: 232.1423

Molecular Weight: 232.28

Elemental Analysis: C, 51.71; H, 8.68; N, 12.06; O, 27.55

Price and Availability

Size	Price	Availability	Quantity
5g	USD 250.00	2 Weeks
25g	USD 350.00	2 weeks

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Related CAS #

110-85-0 (free base) 142-88-1 (adipate) 144-29-6 (citrate) 7140-78-5 (citrate hydrate) 142-63-2 (hydrate) 18534-18-4 (phosphate) 7433-23-0 (sebacate)

Synonym

Piperazine adipate; NSC 74383; NSC-74383; NSC74383;

IUPAC/Chemical Name

Hexanedioic acid, compd. with piperazine (1:1)

InChi Key

BVEGEKOBSPXUJS-UHFFFAOYSA-N

InChi Code

InChI=1S/C6H10O4.C4H10N2/c7-5(8)3-1-2-4-6(9)10;1-2-6-4-3-5-1/h1-4H2,(H,7,8)(H,9,10);5-6H,1-4H2

SMILES Code

O=C(O)CCCCC(O)=O.N1CCNCC1

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

Product Data

Instruction

View handling instruction

Biological target:

Piperazine adipate is a potent broad spectrum anthelmintic against many common worm infections in mammals.

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
	Water	28.7	123.32

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 232.28 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.

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:

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: Fisher MA, Jacobs DE, Hutchinson MJ, Dick IG. Studies on the control of Toxocara canis in breeding kennels. Vet Parasitol. 1994 Oct;55(1-2):87-92. PubMed PMID: 7886923. 2: Javed I, Akhtar MS, Rahman ZU, Khaliq T, Ahmad M. Comparative anthelminthic efficacy and safety of Caesalpinia crista seed and piperazine adipate in chickens with artificially induced Ascaridia galli infection. Acta Vet Hung. 1994;42(1):103-9. PubMed PMID: 7810393. 3: Gupta S, Sanyal SN, Duggal CL. Study of the acetylcholinesterase activity of Ascaridia galli: kinetic properties and the effect of anthelmintics. Acta Vet Hung. 1991;39(3-4):165-74. PubMed PMID: 1785436. 4: Kozin IuI, Cherniavskii VI. [Immunomodulation in patients with cavernous kidney tuberculosis using piperazine adipinate and amniocene]. Probl Tuberk. 1991;(6):29-32. Russian. PubMed PMID: 1780305. 5: Pomazan VA, Korzun VG, Pankov NV, Beloshitskaia IG. [Experience with the prevention of enterobiasis in children from preschool institutions of the Zhitomir district]. Pediatriia. 1990;(7):82-3. Russian. PubMed PMID: 2251064. 6: Meyer HH, Brenner P. [Cleft hand and cleft foot abnormalities as a possible teratogenic side effect of the anthelmintic piperazine?]. Internist (Berl). 1988 Mar;29(3):217-9. German. PubMed PMID: 3288576. 7: Sharma RK, Singh K, Saxena KK. The effect of piperazine adipate and parbendazole on the carbohydrate metabolism of Ascaridia galli and Heterakis gallinae. Angew Parasitol. 1987 Dec;28(4):207-10. PubMed PMID: 3445963. 8: Sharma RK, Singh K, Saxena KK. Effect of parbendazole and piperazine adipate on the activity of some enzymes of Ascaridia galli and Heterakis gallinae. Vet Parasitol. 1987 May;24(3-4):211-20. PubMed PMID: 3617427. 9: Hennig UG, Galindo-Prince OC, Cortinas de Nava C, Savage EA, von Borstel RC. A comparison of the genetic activity of pyrvinium pamoate with that of several other anthelmintic drugs in Saccharomyces cerevisiae. Mutat Res. 1987 Feb;187(2):79-89. PubMed PMID: 3543669. 10: Grzywacz M. Integumentomuscular sac of Ascaris lumbricoides suis L: a biomembrane for studies on the transport of chemical substances. Pol J Pharmacol Pharm. 1986 Jul-Aug;38(4):335-41. PubMed PMID: 2430266. 11: Savitskaia LN, Fedorovskaia RF. [Effectiveness and influence of piperazine adipinate on the immunological indices of furunculosis patients]. Vestn Dermatol Venerol. 1985 Sep;(9):9-12. Russian. PubMed PMID: 3879066. 12: Glinka R, Grzywacz M, Kotełko B, Majchrzak M, Malinowski H, Mikołajewska H, Mikiciukolasik E, Szkukliński J. Investigations of anthelminthic activity and synthesis of new derivatives of perhydroazepine, perhydro-1,4-diazepine, perhydro-1,4-oxazepine and perhydro-1,5-oxazocine. Pol J Pharmacol Pharm. 1980 Sep-Oct;32(5):773-7. PubMed PMID: 7196575. 13: Kadłubowski R, Rebizak L. [Study of compounds with potential antiparasitic effect. V. Antihistaminics]. Wiad Parazytol. 1980;26(1):59-64. Polish. PubMed PMID: 6106984. 14: Berger JR, Globus M, Melamed E. Acute transitory cerebellar dysfunction associated with piperazine adipate. Arch Neurol. 1979 Mar;36(3):180-1. PubMed PMID: 435142. 15: Grzywacz M. Application of the isotope technique in pharmacodynamic analysis of penetration of drugs into parasites. Mater Med Pol. 1975 Oct-Dec;7(4):311-3. PubMed PMID: 1214519. 16: Rim HJ, Ha JH, Lee JS, Hyun I, Uh KB. Pyrantel embonate in mass treatment of ascariasis and comparison with piperazine adipate and santonin-kainic acid complex. Kisaengchunghak Chapchi. 1974 Dec;12(2):141-146. PubMed PMID: 12913476. 17: Jarnicka-Stanios H. [Usefulness of idalbin and piperazine adipate in the treatment of enterobiasis in children]. Wiad Lek. 1973 Feb 15;26(4):373-7. Polish. PubMed PMID: 4688826. 18: Vaidya AB, Ambani LM, Karandikar PV, Sheth UK. Piperazine adipate in tropical eosinophilia--a preliminary study. Indian J Med Sci. 1971 Oct;25(10):684-9. PubMed PMID: 4943620. 19: Kühn W, Buchwalder R, Gräfner G, Hiepe T. [Drug control of eelworm in the domestic chicken, using piperazine adipate, with special reference to laying performance]. Monatsh Veterinarmed. 1971 Jul 15;26(14):540-2. German. PubMed PMID: 5131926. 20: Kühn W, Buchwalder R, Gräfner G, Hiepe T. [Control of ascriasis in the domestic fowl by use of piperazine adipate--with special reference to laying performance]. Monatsh Veterinarmed. 1971 Jul;26(14):540-2. German. PubMed PMID: 5113708.