Nitroparacetamol

Orders received during 11/25~11/29 will be shipped in 11/30/2020 due to Thanksgiving holiday.

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

MedKoo CAT#: 529324

CAS#: 326850-30-0

Description: Nitroparacetamol is a nitric oxide (NO) donor potentially for the treatment of pain.


Price and Availability

Size Price Shipping out time Quantity
Inquire bulk and customized quantity

Pricing updated 2020-11-25. Prices are subject to change without notice.

Nitroparacetamol is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 529324
Name: Nitroparacetamol
CAS#: 326850-30-0
Chemical Formula: C12H14N2O6
Exact Mass: 282.0852
Molecular Weight: 282.25
Elemental Analysis: C, 51.07; H, 5.00; N, 9.93; O, 34.01


Synonym: NCX-701; NCX701; NCX 701

IUPAC/Chemical Name: 4-acetamidophenyl 4-(nitrooxy)butanoate

InChi Key: XTMOQAKCOFLCRZ-UHFFFAOYSA-N

InChi Code: InChI=1S/C12H14N2O6/c1-9(15)13-10-4-6-11(7-5-10)20-12(16)3-2-8-19-14(17)18/h4-7H,2-3,8H2,1H3,(H,13,15)

SMILES Code: O=C(OC1=CC=C(NC(C)=O)C=C1)CCCO[N+]([O-])=O


Technical Data

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


References

1: Molina C, Herrero JF. Subeffective doses of nitroparacetamol (NCX-701) enhance the antinociceptive activity of the α₂-adrenoceptor agonist medetomidine. Pharmacol Biochem Behav. 2011 Sep;99(3):385-90. doi: 10.1016/j.pbb.2011.05.022. PubMed PMID: 21640748.

2: Romero-Sandoval EA, Curros-Criado MM, Gaitan G, Molina C, Herrero JF. Nitroparacetamol (NCX-701) and pain: first in a series of novel analgesics. CNS Drug Rev. 2007 Fall;13(3):279-95. Review. PubMed PMID: 17894645.

3: Alfonso Romero-Sandoval E, Molina C, Herrero JF. Enhancement of the analgesic activity of paracetamol and nitroparacetamol by the oral administration of all-trans retinoic acid. Neuropharmacology. 2006 Sep;51(4):858-65. PubMed PMID: 16870215.

4: Gaitán G, Ahuir FJ, Herrero JF. Enhancement of fentanyl antinociception by subeffective doses of nitroparacetamol (NCX-701) in acute nociception and in carrageenan-induced monoarthritis. Life Sci. 2005 May 20;77(1):85-95. PubMed PMID: 15848221.

5: Zhu YZ, Chong CL, Chuah SC, Huang SH, Nai HS, Tong HT, Whiteman M, Moore PK. Cardioprotective effects of nitroparacetamol and paracetamol in acute phase of myocardial infarction in experimental rats. Am J Physiol Heart Circ Physiol. 2006 Feb;290(2):H517-24. PubMed PMID: 16172162.

6: Gaitán G, Del Soldato P, Herrero JF. Low doses of nitroparacetamol or dexketoprofen trometamol enhance fentanyl antinociceptive activity. Eur J Pharmacol. 2003 Nov 28;481(2-3):181-8. PubMed PMID: 14642784.

7: Marshall M, Keeble J, Moore PK. Effect of a nitric oxide releasing derivative of paracetamol in a rat model of endotoxaemia. Br J Pharmacol. 2006 Nov;149(5):516-22. PubMed PMID: 16940991; PubMed Central PMCID: PMC2014676.

8: al-Swayeh OA, Futter LE, Clifford RH, Moore PK. Nitroparacetamol exhibits anti-inflammatory and anti-nociceptive activity. Br J Pharmacol. 2000 Aug;130(7):1453-6. PubMed PMID: 10928944; PubMed Central PMCID: PMC1572245.

9: Futter LE, al-Swayeh OA, Moore PK. A comparison of the effect of nitroparacetamol and paracetamol on liver injury. Br J Pharmacol. 2001 Jan;132(1):10-2. PubMed PMID: 11156555; PubMed Central PMCID: PMC1572565.

10: Alfonso Romero-Sandoval E, Del Soldato P, Herrero JF. The effects of sham and full spinalization on the antinociceptive effects of NCX-701 (nitroparacetamol) in monoarthritic rats. Neuropharmacology. 2003 Sep;45(3):412-9. PubMed PMID: 12871658.

11: Romero-Sandoval EA, Mazario J, Howat D, Herrero JF. NCX-701 (nitroparacetamol) is an effective antinociceptive agent in rat withdrawal reflexes and wind-up. Br J Pharmacol. 2002 Mar;135(6):1556-62. PubMed PMID: 11906970; PubMed Central PMCID: PMC1573254.

12: Marshall M, Moore PK. Effect of nitric oxide releasing paracetamol and flurbiprofen on cytokine production in human blood. Eur J Pharmacol. 2004 Jan 12;483(2-3):317-22. PubMed PMID: 14729123.

13: Salahifar E, Nematollahi D, Bayat M, Mahyari A, Amiri Rudbari H. Regioselective Green Electrochemical Approach to the Synthesis of Nitroacetaminophen Derivatives. Org Lett. 2015 Oct 2;17(19):4666-9. doi: 10.1021/acs.orglett.5b01837. PubMed PMID: 26381590.

14: Curros-Criado MM, Herrero JF. Antinociceptive effects of NCX-701 (nitro-paracetamol) in neuropathic rats: enhancement of antinociception by co-administration with gabapentin. Br J Pharmacol. 2009 Sep;158(2):601-9. doi: 10.1111/j.1476-5381.2009.00343.x. PubMed PMID: 19645711; PubMed Central PMCID: PMC2757700.

15: Mamuk S, Melli M. Effect of aspirin, paracetamol and their nitric oxide donating derivatives on exudate cytokine and PGE2 production in zymosan-induced air pouch inflammation in rats. Eur J Pharmacol. 2007 Apr 30;561(1-3):220-5. PubMed PMID: 17320862.

16: Zhang YH, Ji H, Peng SX. [A novel class of anti-inflammatory and analgesic drugs--NO-donating NSAIDs]. Yao Xue Xue Bao. 2007 Apr;42(4):352-7. Review. Chinese. PubMed PMID: 17633199.

17: Cirino G, Distrutti E, Wallace JL. Nitric oxide and inflammation. Inflamm Allergy Drug Targets. 2006 Apr;5(2):115-9. Review. PubMed PMID: 16613570.

18: Joshi GP. NCX-701. NicOx. Curr Opin Investig Drugs. 2004 Jul;5(7):755-9. PubMed PMID: 15298073.

19: Evans CE, Butcher C. The influence on human osteoblasts in vitro of non-steroidal anti-inflammatory drugs which act on different cyclooxygenase enzymes. J Bone Joint Surg Br. 2004 Apr;86(3):444-9. PubMed PMID: 15125136.

20: Ilag VL. Future Pain Drugs - Europe 2003. 15-16 September 2003, London, UK. IDrugs. 2003 Nov;6(11):1024-6. PubMed PMID: 15270029.