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MedKoo Cat#: 319700 | Name: Piromelatine

Description:

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

Piromelatine, also known as NEU-P11, is a multimodal sleep drug under development by Neurim Pharmaceuticals. It is an agonist at melatonin MT1/MT2 and serotonin 5-HT1A/5-HT1D receptors. Pre-clinical studies showed antinociceptive, antihypertensive and cognitive benefits in rat disease models of pain, hypertension, and Alzheimer's disease.

Chemical Structure

Piromelatine
Piromelatine
CAS#946846-83-9

Theoretical Analysis

MedKoo Cat#: 319700

Name: Piromelatine

CAS#: 946846-83-9

Chemical Formula: C17H16N2O4

Exact Mass: 312.1110

Molecular Weight: 312.33

Elemental Analysis: C, 65.38; H, 5.16; N, 8.97; O, 20.49

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
NEU-P11; NEU-P 11; NEU-P-11; Piromelatine
IUPAC/Chemical Name
N-(2-(5-methoxy-1H-indol-3-yl)ethyl)-4-oxo-4H-pyran-2-carboxamide
InChi Key
PNTNBIHOAPJYDB-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H16N2O4/c1-22-13-2-3-15-14(9-13)11(10-19-15)4-6-18-17(21)16-8-12(20)5-7-23-16/h2-3,5,7-10,19H,4,6H2,1H3,(H,18,21)
SMILES Code
O=C(C1=CC(C=CO1)=O)NCCC2=CNC3=C2C=C(OC)C=C3
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, not in water
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

Preparing Stock Solutions

The following data is based on the product molecular weight 312.33 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
1: Zisapel N. Current Phase II investigational therapies for insomnia. Expert Opin Investig Drugs. 2015 Mar;24(3):401-11. doi: 10.1517/13543784.2015.987340. Epub 2014 Nov 25. Review. PubMed PMID: 25423562. 2: Hardeland R. Melatonin and Synthetic Melatoninergic Agonists in Psychiatric and Age-associated Disorders: Successful and Unsuccessful Approaches. Curr Pharm Des. 2015 Dec 14. [Epub ahead of print] PubMed PMID: 25248806. 3: Yu J, Wei J, Ji L, Hong X. Exploration on mechanism of a new type of melatonin receptor agonist Neu-p11 in hypoxia-reoxygenation injury of myocardial cells. Cell Biochem Biophys. 2014 Nov;70(2):999-1003. doi: 10.1007/s12013-014-0009-2. PubMed PMID: 24840226. 4: Liu YY, Yin D, Chen L, Qu WM, Chen CR, Laudon M, Cheng NN, Urade Y, Huang ZL. Piromelatine exerts antinociceptive effect via melatonin, opioid, and 5HT1A receptors and hypnotic effect via melatonin receptors in a mouse model of neuropathic pain. Psychopharmacology (Berl). 2014 Oct;231(20):3973-85. doi: 10.1007/s00213-014-3530-5. Epub 2014 Apr 4. PubMed PMID: 24700387. 5: Chen C, Fichna J, Laudon M, Storr M. Antinociceptive effects of novel melatonin receptor agonists in mouse models of abdominal pain. World J Gastroenterol. 2014 Feb 7;20(5):1298-304. doi: 10.3748/wjg.v20.i5.1298. PubMed PMID: 24574803; PubMed Central PMCID: PMC3921511. 6: She M, Hu X, Su Z, Zhang C, Yang S, Ding L, Laudon M, Yin W. Piromelatine, a novel melatonin receptor agonist, stabilizes metabolic profiles and ameliorates insulin resistance in chronic sleep restricted rats. Eur J Pharmacol. 2014 Mar 15;727:60-5. doi: 10.1016/j.ejphar.2014.01.037. Epub 2014 Jan 30. PubMed PMID: 24486392. 7: Huang L, Zhang C, Hou Y, Laudon M, She M, Yang S, Ding L, Wang H, Wang Z, He P, Yin W. Blood pressure reducing effects of piromelatine and melatonin in spontaneously hypertensive rats. Eur Rev Med Pharmacol Sci. 2013 Sep;17(18):2449-56. PubMed PMID: 24089222. 8: Li X, Cai S, Yin W, Hu X. Neu-p11 reduces clock/apelin expression in insulin-resistant mouse adipocyte model. Acta Biochim Biophys Sin (Shanghai). 2013 Sep;45(9):798-800. doi: 10.1093/abbs/gmt077. PubMed PMID: 23963596. 9: Wang PP, She MH, He PP, Chen WJ, Laudon M, Xu XX, Yin WD. Piromelatine decreases triglyceride accumulation in insulin resistant 3T3-L1 adipocytes: role of ATGL and HSL. Biochimie. 2013 Aug;95(8):1650-4. doi: 10.1016/j.biochi.2013.05.005. Epub 2013 May 23. PubMed PMID: 23707538. 10: He P, Ouyang X, Zhou S, Yin W, Tang C, Laudon M, Tian S. A novel melatonin agonist Neu-P11 facilitates memory performance and improves cognitive impairment in a rat model of Alzheimer' disease. Horm Behav. 2013 Jun;64(1):1-7. doi: 10.1016/j.yhbeh.2013.04.009. Epub 2013 May 4. PubMed PMID: 23651610. 11: Oertel R, Goltz L, Kirch W. Elucidation of Neu-P11 metabolism in urine of volunteers by liquid chromatography-tandem mass spectrometry. J Chromatogr A. 2013 Feb 22;1278:69-75. doi: 10.1016/j.chroma.2012.12.063. Epub 2013 Jan 8. PubMed PMID: 23336948. 12: Oertel R, Goltz L, Kirch W. Determination of the novel melatonin agonist Neu-P11 in plasma samples by liquid chromatography-tandem mass spectrometry. J Pharm Biomed Anal. 2013 Feb 23;74:66-70. doi: 10.1016/j.jpba.2012.09.020. Epub 2012 Oct 27. PubMed PMID: 23245235. 13: Paulis L, Simko F, Laudon M. Cardiovascular effects of melatonin receptor agonists. Expert Opin Investig Drugs. 2012 Nov;21(11):1661-78. doi: 10.1517/13543784.2012.714771. Epub 2012 Aug 23. Review. PubMed PMID: 22916799.