Tasimelteon
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MedKoo CAT#: 314205

CAS#: 609799-22-6

Description: Tasimelteon (trade name Hetlioz) is a drug approved by the FDA solely for the treatment of non-24-hour sleep–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

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Tasimelteon
CAS# 609799-22-6

Theoretical Analysis

MedKoo Cat#: 314205
Name: Tasimelteon
CAS#: 609799-22-6
Chemical Formula: C15H19NO2
Exact Mass: 245.14
Molecular Weight: 245.320
Elemental Analysis: C, 73.44; H, 7.81; N, 5.71; O, 13.04

Price and Availability

Size Price Availability Quantity
25mg USD 150 Ready to ship
50mg USD 250 Ready to ship
100mg USD 450 Ready to ship
200mg USD 750 Ready to ship
500mg USD 1450 Ready to ship
1g USD 2450 Ready to ship
2g USD 3950 2 Weeks
5g USD 5250 2 Weeks
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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:

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

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 37.3 152.17

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.

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
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: 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 vivo protocol: TBD

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 1: Tasimelteon (Hetlioz) for non-24-hour sleep-wake disorder. Med Lett Drugs Ther. 2014 Apr 28;56(1441):34-5. PubMed PMID: 24759294.

2: Dhillon S, Clarke M. Tasimelteon: first global approval. Drugs. 2014 Mar;74(4):505-11. doi: 10.1007/s40265-014-0200-1. PubMed PMID: 24610704.

3: Traynor K. Tasimelteon approved for circadian disorder in blind adults. Am J Health Syst Pharm. 2014 Mar 1;71(5):350. doi: 10.2146/news140017. PubMed PMID: 24534583.

4: Lankford DA. Tasimelteon for insomnia. Expert Opin Investig Drugs. 2011 Jul;20(7):987-93. doi: 10.1517/13543784.2011.583235. Epub 2011 May 9. Review. PubMed PMID: 21548834.

5: Hardeland R. Tasimelteon, a melatonin agonist for the treatment of insomnia and circadian rhythm sleep disorders. Curr Opin Investig Drugs. 2009 Jul;10(7):691-701. PubMed PMID: 19579175.

6: Rajaratnam SM, Polymeropoulos MH, Fisher DM, Roth T, Scott C, Birznieks G, Klerman EB. Melatonin agonist tasimelteon (VEC-162) for transient insomnia after sleep-time shift: two randomised controlled multicentre trials. Lancet. 2009 Feb 7;373(9662):482-91. doi: 10.1016/S0140-6736(08)61812-7. Epub 2008 Dec 4. Erratum in: Lancet. 2009 Apr 11;373(9671):1252. PubMed PMID: 19054552.