Befiradol (free base)

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

MedKoo CAT#: 530114

CAS#: 208110-64-9

Description: Befiradol (free base) is a highly selective and potent 5-HT1A receptor agonist potentially for the treatment of drug-induced dyskinesia in patients with Parkinson's disease.


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Befiradol (free base) 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#: 530114
Name: Befiradol (free base)
CAS#: 208110-64-9
Chemical Formula: C20H22ClF2N3O
Exact Mass: 393.14
Molecular Weight: 393.86
Elemental Analysis: C, 60.99; H, 5.63; Cl, 9.00; F, 9.65; N, 10.67; O, 4.06


Synonym: F-13640; F13640; F 13640; NLX-112; NLX112; NLX 112

IUPAC/Chemical Name: (3-chloro-4-fluorophenyl)-[4-fluoro-4-[[(5-methylpyridin-2-yl)methylamino]methyl]piperidin-1-yl]methanone

InChi Key: HADZVNVXBKUQNB-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H22ClF2N3O/c1-14-3-6-18(24-12-14)25(2)13-20(23)7-9-26(10-8-20)19(27)15-4-5-17(22)16(21)11-15/h3-6,11-12H,7-10,13H2,1-2H3

SMILES Code: O=C(C1=CC=C(F)C(Cl)=C1)N2CCC(CN(C3=NC=C(C)C=C3)C)(F)CC2


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).

Harmonized System Code:
293490


Additional Information

Related CAS#
208110-64-9(Befiradol free base)
208110-65-0(Befiradol Fumarate)


References

1: McCreary AC, Varney MA, Newman-Tancredi A. The novel 5-HT1A receptor agonist, NLX-112 reduces l-DOPA-induced abnormal involuntary movements in rat: A chronic administration study with microdialysis measurements. Neuropharmacology. 2016 Jun;105:651-60. doi: 10.1016/j.neuropharm.2016.01.013. PubMed PMID: 26777281.

2: Iderberg H, McCreary AC, Varney MA, Kleven MS, Koek W, Bardin L, Depoortère R, Cenci MA, Newman-Tancredi A. NLX-112, a novel 5-HT1A receptor agonist for the treatment of L-DOPA-induced dyskinesia: Behavioral and neurochemical profile in rat. Exp Neurol. 2015 Sep;271:335-50. doi: 10.1016/j.expneurol.2015.05.021. PubMed PMID: 26037043.

3: Ren J, Ding X, Greer JJ. 5-HT1A receptor agonist Befiradol reduces fentanyl-induced respiratory depression, analgesia, and sedation in rats. Anesthesiology. 2015 Feb;122(2):424-34. doi: 10.1097/ALN.0000000000000490. PubMed PMID: 25313880.

4: Lladó-Pelfort L, Assié MB, Newman-Tancredi A, Artigas F, Celada P. In vivo electrophysiological and neurochemical effects of the selective 5-HT1A receptor agonist, F13640, at pre- and postsynaptic 5-HT1A receptors in the rat. Psychopharmacology (Berl). 2012 May;221(2):261-72. doi: 10.1007/s00213-011-2569-9. PubMed PMID: 22147258.

5: Bollinger S, Hübner H, Heinemann FW, Meyer K, Gmeiner P. Novel pyridylmethylamines as highly selective 5-HT(1A) superagonists. J Med Chem. 2010 Oct 14;53(19):7167-79. doi: 10.1021/jm100835q. PubMed PMID: 20860381.

6: Heusler P, Palmier C, Tardif S, Bernois S, Colpaert FC, Cussac D. [(3)H]-F13640, a novel, selective and high-efficacy serotonin 5-HT(1A) receptor agonist radioligand. Naunyn Schmiedebergs Arch Pharmacol. 2010 Oct;382(4):321-30. doi: 10.1007/s00210-010-0551-4. PubMed PMID: 20799027.

7: Brenchat A, Romero L, García M, Pujol M, Burgueño J, Torrens A, Hamon M, Baeyens JM, Buschmann H, Zamanillo D, Vela JM. 5-HT7 receptor activation inhibits mechanical hypersensitivity secondary to capsaicin sensitization in mice. Pain. 2009 Feb;141(3):239-47. doi: 10.1016/j.pain.2008.11.009. PubMed PMID: 19118950.

8: Deseure K, Bréand S, Colpaert FC. Curative-like analgesia in a neuropathic pain model: parametric analysis of the dose and the duration of treatment with a high-efficacy 5-HT(1A) receptor agonist. Eur J Pharmacol. 2007 Jul 30;568(1-3):134-41. PubMed PMID: 17512927.

9: Colpaert FC. 5-HT(1A) receptor activation: new molecular and neuroadaptive mechanisms of pain relief. Curr Opin Investig Drugs. 2006 Jan;7(1):40-7. Review. PubMed PMID: 16425670.

10: Colpaert FC, Deseure K, Stinus L, Adriaensen H. High-efficacy 5-hydroxytryptamine 1A receptor activation counteracts opioid hyperallodynia and affective conditioning. J Pharmacol Exp Ther. 2006 Feb;316(2):892-9. PubMed PMID: 16254131.

11: Kiss I, Degryse AD, Bardin L, Gomez de Segura IA, Colpaert FC. The novel analgesic, F 13640, produces intra- and postoperative analgesia in a rat model of surgical pain. Eur J Pharmacol. 2005 Oct 31;523(1-3):29-39. PubMed PMID: 16226246.

12: Buritova J, Larrue S, Aliaga M, Besson JM, Colpaert F. Effects of the high-efficacy 5-HT1A receptor agonist, F 13640 in the formalin pain model: a c-Fos study. Eur J Pharmacol. 2005 May 9;514(2-3):121-30. PubMed PMID: 15910798.

13: You HJ, Colpaert FC, Arendt-Nielsen L. The novel analgesic and high-efficacy 5-HT1A receptor agonist F 13640 inhibits nociceptive responses, wind-up, and after-discharges in spinal neurons and withdrawal reflexes. Exp Neurol. 2005 Jan;191(1):174-83. PubMed PMID: 15589524.

14: Deseure KR, Adriaensen HF, Colpaert FC. Effects of the combined continuous administration of morphine and the high-efficacy 5-HT1A agonist, F 13640 in a rat model of trigeminal neuropathic pain. Eur J Pain. 2004 Dec;8(6):547-54. PubMed PMID: 15531223.

15: Bardin L, Assié MB, Pélissou M, Royer-Urios I, Newman-Tancredi A, Ribet JP, Sautel F, Koek W, Colpaert FC. Dual, hyperalgesic, and analgesic effects of the high-efficacy 5-hydroxytryptamine 1A (5-HT1A) agonist F 13640 [(3-chloro-4-fluoro-phenyl)-[4-fluoro-4-{[(5-methyl-pyridin-2-ylmethyl)-amino]-me thyl}piperidin-1-yl]methanone, fumaric acid salt]: relationship with 5-HT1A receptor occupancy and kinetic parameters. J Pharmacol Exp Ther. 2005 Mar;312(3):1034-42. PubMed PMID: 15528450.

16: Colpaert FC, Wu WP, Hao JX, Royer I, Sautel F, Wiesenfeld-Hallin Z, Xu XJ. High-efficacy 5-HT1A receptor activation causes a curative-like action on allodynia in rats with spinal cord injury. Eur J Pharmacol. 2004 Aug 16;497(1):29-33. PubMed PMID: 15321732.

17: De Laat AP. Pain in Europe. IV. Fourth Congress of the European Federation of IASP Chapters (EFIC). J Orofac Pain. 2004 Winter;18(1):69-70. PubMed PMID: 15022537.

18: Wu WP, Hao JX, Xu XJ, Wiesenfeld-Hallin Z, Koek W, Colpaert FC. The very-high-efficacy 5-HT1A receptor agonist, F 13640, preempts the development of allodynia-like behaviors in rats with spinal cord injury. Eur J Pharmacol. 2003 Oct 8;478(2-3):131-7. PubMed PMID: 14575797.

19: Pauwels PJ, Colpaert FC. Ca2+ responses in Chinese hamster ovary-K1 cells demonstrate an atypical pattern of ligand-induced 5-HT1A receptor activation. J Pharmacol Exp Ther. 2003 Nov;307(2):608-14. PubMed PMID: 12970382.

20: Buritova J, Tarayre JP, Besson JM, Colpaert F. The novel analgesic and high-efficacy 5-HT1A receptor agonist, F 13640 induces c-Fos protein expression in spinal cord dorsal horn neurons. Brain Res. 2003 Jun 6;974(1-2):212-21. PubMed PMID: 12742639.