Tasimelteon | CAS#609799-22-6 | Melatonin Receptor Agonist

MedKoo Cat#: 314205 | Name: Tasimelteon

Description:

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

Tasimelteon (trade name Hetlioz) is a drug approved by the FDA solely for the treatment of non-24-hour sleepÂ–wake disorder (often designated as N24HSWD) in totally blind adults. It is a selective agonist for the melatonin receptors MT1 and MT2 in the suprachiasmatic nucleus of the brain, similar to other members of the melatonin receptor agonist class of which ramelteon (2005) and agomelatine (2009) were the first approved.

Chemical Structure

Tasimelteon

CAS#609799-22-6

Theoretical Analysis

MedKoo Cat#: 314205

Name: Tasimelteon

CAS#: 609799-22-6

Chemical Formula: C15H19NO2

Exact Mass: 245.1416

Molecular Weight: 245.32

Elemental Analysis: C, 73.44; H, 7.81; N, 5.71; O, 13.04

Price and Availability

Size	Price	Availability
25mg	USD 150.00	Ready to ship
50mg	USD 250.00	Ready to ship
100mg	USD 450.00	Ready to ship
200mg	USD 750.00	Ready to ship
500mg	USD 1,450.00	Ready to ship
1g	USD 2,450.00	Ready to ship
2g	USD 3,950.00	2 Weeks
5g	USD 5,250.00	2 Weeks

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Related CAS #

No Data

Synonym

BMS214778, BMS-214778, BMS 214778, VEC162, VEC-162, VEC 162, Tasimelteon, Hetlioz

IUPAC/Chemical Name

N-(((1R,2R)-2-(2,3-dihydrobenzofuran-4-yl)cyclopropyl)methyl)propionamide

InChi Key

PTOIAAWZLUQTIO-GXFFZTMASA-N

InChi Code

InChI=1S/C15H19NO2/c1-2-15(17)16-9-10-8-13(10)11-4-3-5-14-12(11)6-7-18-14/h3-5,10,13H,2,6-9H2,1H3,(H,16,17)/t10-,13+/m0/s1

SMILES Code

CCC(NC[C@H]1[C@H](C2=C3CCOC3=CC=C2)C1)=O

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

Certificate of Analysis

View CoA: current batch, Lot#XPR70316

QC Data

View QC data: current batch, Lot#XPR70316

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Tasimelteon (BMS-214778) is an orally active and selective dual melatonin receptor agonist (DMRA).

In vitro activity:

Tasimelteon had no significant interaction with any other commonly screened receptors or enzyme binding sites tested, including a wide array of receptors of neurotransmitter systems such as dopamine, norepinephrine, serotonin, GABA, acetylcholine, opioid, N-methyl-d-aspartate (NMDA), hypocretin (orexin), and cannabinoid; this finding supports the observation that tasimelteon did not produce signs or symptoms indicative of abuse potential in animal or clinical studies and did not produce withdrawal symptoms after discontinuation of chronic administration. Tasimelteon's receptor binding profile is distinct from that of two other molecules known to bind both melatonin receptors, ramelteon and agomelatine; ramelteon has 8 times lower affinity for the MT2 receptor than for the MT1 receptor, and agomelatine, a non-specific melatonin agonist, has a 4.4 times lower affinity for the MT2 receptor than for the MT1 receptor and binds also to several serotonin 5-HT2 receptors. Reference: Neuropharmacology. 2015 Apr;91:142-7. https://pubmed.ncbi.nlm.nih.gov/25534555/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	37.3	152.17

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 245.32 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. Lavedan C, Forsberg M, Gentile AJ. Tasimelteon: a selective and unique receptor binding profile. Neuropharmacology. 2015 Apr;91:142-7. doi: 10.1016/j.neuropharm.2014.12.004. Epub 2014 Dec 19. PMID: 25534555.

In vitro protocol:

In vivo protocol:

TBD

1: Noguchi Y, Masuda R, Aizawa H, Yoshimura T. Relationship Between Melatonin Receptor Agonists and Parkinson's Disease. J Pineal Res. 2024 Aug;76(5):e13002. doi: 10.1111/jpi.13002. PMID: 39119925. 2: Gopinathan A, Sankhe R, Rathi E, Kodi T, Upadhya R, Pai KSR, Kishore A. An in silico drug repurposing approach to identify HDAC1 inhibitors against glioblastoma. J Biomol Struct Dyn. 2024 Apr 30:1-14. doi: 10.1080/07391102.2024.2335293. Epub ahead of print. PMID: 38686917. 3: Connolly PJ, Quigg M, Davis EM. Improvement in non-24-h sleep-wake rhythm disorder in a sighted individual treated with a melatonin receptor agonist. Sleep Med. 2024 Apr;116:41-42. doi: 10.1016/j.sleep.2023.10.041. Epub 2024 Feb 20. PMID: 38422783. 4: Smieszek SP, Kaden AR, Johnson CE, Brzezynski JL, Xiao C, Polymeropoulos CM, Birznieks G, Emsellem HA, Polymeropoulos MH. Corrigendum: Case report: A patient with Delayed Sleep-Wake Phase Disorder and Optic Nerve Hypoplasia treated with tasimelteon: a case study. Front Neurosci. 2024 Jan 8;17:1344915. doi: 10.3389/fnins.2023.1344915. Erratum for: Front Neurosci. 2023 Nov 14;17:1287514. doi: 10.3389/fnins.2023.1287514. PMID: 38260023; PMCID: PMC10800617. 5: Smieszek SP, Kaden AR, Johnson CE, Brzezynski JL, Xiao C, Polymeropoulos CM, Birznieks G, Emsellem HA, Polymeropoulos MH. Case report: A patient with Delayed Sleep-Wake Phase Disorder and Optic Nerve Hypoplasia treated with tasimelteon: a case study. Front Neurosci. 2023 Nov 14;17:1287514. doi: 10.3389/fnins.2023.1287514. Erratum in: Front Neurosci. 2024 Jan 08;17:1344915. doi: 10.3389/fnins.2023.1344915. PMID: 38033548; PMCID: PMC10682171. 6: Atan YS, Subaşı M, Güzel Özdemir P, Batur M. The Effect of Blindness on Biological Rhythms and the Consequences of Circadian Rhythm Disorder. Turk J Ophthalmol. 2023 Apr 20;53(2):111-119. doi: 10.4274/tjo.galenos.2022.59296. PMID: 37089032; PMCID: PMC10127541. 7: Petrini A, Ievoli G, Migliorini F, Taddei M, Siciliano S. A Self-Immolative Linker for the pH-Responsive Release of Amides. Molecules. 2023 Mar 7;28(6):2445. doi: 10.3390/molecules28062445. PMID: 36985417; PMCID: PMC10060004. 8: Kim HK, Yang KI. Melatonin and melatonergic drugs in sleep disorders. Transl Clin Pharmacol. 2022 Dec;30(4):163-171. doi: 10.12793/tcp.2022.30.e21. Epub 2022 Dec 23. PMID: 36632077; PMCID: PMC9810491. 9: Polymeropoulos CM, Polymeropoulos VM, Czeisler EL, Fisher MA, Smieszek SP, Xiao C, Birznieks G, Polymeropoulos MH. Once-daily tasimelteon (VEC-162) for jet lag following transmeridian travel: A multicenter, randomized, double-blind, placebo-controlled trial. Front Neurol. 2022 Sep 15;13:901467. doi: 10.3389/fneur.2022.901467. PMID: 36188367; PMCID: PMC9521676. 10: Erland LAE, Dumigan CR, Forsyth JA, Frolova L, Yasunaga AB, Pun W, Li ITS, Deyholos MK, Murch SJ. Mammalian Melatonin Agonist Pharmaceuticals Stimulate Rhomboid Proteins in Plants. Biomolecules. 2022 Jun 24;12(7):882. doi: 10.3390/biom12070882. PMID: 35883439; PMCID: PMC9313243. 11: Ravikumar M, Mohan S, Velpandian C. The Involvement of Melatonin and Tasimelteon against Alzheimer's Disease. Curr Drug Saf. 2023;18(3):284-296. doi: 10.2174/1574886317666220517125644. PMID: 35585820. 12: Leelaviwat N, Mekraksakit P, Cross KM, Landis DM, McLain M, Sehgal L, Payne JD. Melatonin: Translation of Ongoing Studies Into Possible Therapeutic Applications Outside Sleep Disorders. Clin Ther. 2022 May;44(5):783-812. doi: 10.1016/j.clinthera.2022.03.008. Epub 2022 Apr 8. PMID: 35400533. 13: Wang YQ, Jiang YJ, Zou MS, Liu J, Zhao HQ, Wang YH. Antidepressant actions of melatonin and melatonin receptor agonist: Focus on pathophysiology and treatment. Behav Brain Res. 2022 Feb 26;420:113724. doi: 10.1016/j.bbr.2021.113724. Epub 2021 Dec 18. PMID: 34929236. 14: Prodhan AHMSU, Cavestro C, Kamal MA, Islam MA. Melatonin and Sleep Disturbances in Alzheimer's Disease. CNS Neurol Disord Drug Targets. 2021;20(8):736-754. doi: 10.2174/1871527320666210804155617. PMID: 34348635. 15: Polymeropoulos CM, Brooks J, Czeisler EL, Fisher MA, Gibson MM, Kite K, Smieszek SP, Xiao C, Elsea SH, Birznieks G, Polymeropoulos MH. Tasimelteon safely and effectively improves sleep in Smith-Magenis syndrome: a double-blind randomized trial followed by an open-label extension. Genet Med. 2021 Dec;23(12):2426-2432. doi: 10.1038/s41436-021-01282-y. Epub 2021 Jul 27. PMID: 34316024; PMCID: PMC8629754. 16: Oishi A, Gbahou F, Jockers R. Melatonin receptors, brain functions, and therapies. Handb Clin Neurol. 2021;179:345-356. doi: 10.1016/B978-0-12-819975-6.00022-4. PMID: 34225974. 17: Torres R, Fisher M, Birznieks G, Polymeropoulos C, Kay GG, Xiao C, Polymeropoulos MH. Simulated driving performance in healthy adults after night- time administration of 20 mg tasimelteon. J Sleep Res. 2022 Feb;31(1):e13430. doi: 10.1111/jsr.13430. Epub 2021 Jun 21. PMID: 34152055; PMCID: PMC9285441. 18: Steele TA, St Louis EK, Videnovic A, Auger RR. Circadian Rhythm Sleep-Wake Disorders: a Contemporary Review of Neurobiology, Treatment, and Dysregulation in Neurodegenerative Disease. Neurotherapeutics. 2021 Jan;18(1):53-74. doi: 10.1007/s13311-021-01031-8. Epub 2021 Apr 12. PMID: 33844152; PMCID: PMC8116400. 19: Nishimon S, Nishino N, Nishino S. Advances in the pharmacological management of non-24-h sleep-wake disorder. Expert Opin Pharmacother. 2021 Jun;22(8):1039-1049. doi: 10.1080/14656566.2021.1876665. Epub 2021 Feb 23. PMID: 33618599. 20: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Tasimelteon. 2020 Dec 21. PMID: 33355733.