Tasimelteon
- CAS No.
- 609799-22-6
- Chemical Name:
- Tasimelteon
- Synonyms
- BMS 214778;Tasimalteon;(1R-trans)-N-[[2-(2,3-Dihydro-4-benzofuranyl)cyclopropyl]methyl]propanamide;Tasimelteon (1R-trans)-N-[[2-(2,3-Dihydro-4-benzofuranyl)cyclopropyl]methyl]propanamide;MA 1;VEC 162;asimelteon;tasimelteon;Hesimiqiong;Tasimelteon-d5
- CBNumber:
- CB41518537
- Molecular Formula:
- C15H19NO2
- Molecular Weight:
- 245.32
- MDL Number:
- MFCD09033789
- MOL File:
- 609799-22-6.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| Melting point | 78 °C |
|---|---|
| Boiling point | 442.6±24.0 °C(Predicted) |
| Density | 1.145 |
| storage temp. | 2-8°C |
| solubility | Chloroform (Slightly), Methanol (Slightly) |
| pka | 16.43±0.46(Predicted) |
| form | Solid |
| color | White to Off-White |
| InChI | 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 |
| InChIKey | PTOIAAWZLUQTIO-GXFFZTMASA-N |
| SMILES | C(NC[C@@H]1C[C@H]1C1=C2C(=CC=C1)OCC2)(=O)CC |
| FDA UNII | SHS4PU80D9 |
| ATC code | N05CH03 |
| UNSPSC Code | 12352200 |
| NACRES | NA.77 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS07,GHS08 |
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|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H336-H361 | |||||||||
| Precautionary statements | P201-P308+P313 | |||||||||
| target organs | Central nervous system | |||||||||
| WGK Germany | WGK 3 | |||||||||
| HS Code | 2937.90.9000 | |||||||||
| Storage Class | 11 - Combustible Solids | |||||||||
| Hazard Classifications | Repr. 2 STOT SE 3 |
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| NFPA 704 |
|
Tasimelteon price More Price(71)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | SML2030 | Tasimelteon ≥98% (HPLC) | 609799-22-6 | 10MG | $101 | 2026-04-30 | Buy |
| Sigma-Aldrich | SML2030 | Tasimelteon ≥98% (HPLC) | 609799-22-6 | 50MG | $380 | 2026-04-30 | Buy |
| TCI Chemical | T3813 | Tasimelteon | 609799-22-6 | 10MG | $64 | 2026-04-30 | Buy |
| TCI Chemical | T3813 | Tasimelteon | 609799-22-6 | 50MG | $224 | 2026-04-30 | Buy |
| Cayman Chemical | 23546 | Tasimelteon ≥98% | 609799-22-6 | 5mg | $37 | 2026-04-30 | Buy |
Tasimelteon Chemical Properties,Uses,Production
Description
Tasimelteon, which is marketed by Vanda Pharmaceuticals as Hetlioz and developed in partnership with Bristol-Myers Squibb, is a drug that was approved by the US FDA in January 2014 for the treatment of non-24-hour sleep–wake disorder (also called Non-24, N24 and N24HSWD). Tasimelteon is a melatonin MT1 and MT2 receptor agonist; because it exhibits a greater affinity to the MT2 receptor than MT1, is also known as Dual Melatonin Receptor Agonist.234 Two randomized controlled trials (phases II and III) demonstrated that tasimelteon improved sleep latency and maintenance of sleep with a shift in circadian rhythms, and therefore has the potential to treat patients with transient insomnia associated with circadian rhythm sleep disorders. Preclinical studies showed that the drug has similar phase-shifting properties to melatonin, but with less vasoconstrictive effects.
Uses
Tasimelteon is a novel drug, used in the treatment of non-24 hour sleep-wake disorder. It helps to correct the circadian rhythm disorder often seen in patients who are visually impaired.
Definition
ChEBI: A member of the class of 1-benzofurans that is propionamide in which one of the amide hydrogens is replaced by a [(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl group. A melatonin receptor agonist used for the treatment of non-24-hour sleep-wake disorder.
Synthesis
Activation of commercial bis-ethanol 250 with 2.5 equivalents of the Vilsmeier salt 251 followed by treatment with base resulted an intramolecular cyclization reaction with the proximal phenol and concomitant elimination of the remaining imidate to deliver the vinylated dihydrobenzofuran 252 in 76% yield. Interestingly, this reaction could be performed on multi-kilogram scale, required no chromatographic purification, and generated environmentallyfriendly DMF and HCl as byproducts. Sharpless asymmetric dihydroxylation of olefin 252 delivered diol 253 in 86% yield and impressive enantioselectivity (>99% ee). This diol was then activated with trimethylsilyl chloride and then treated with base to generate epoxide 254. Next, a modified Horner¨CWadsworth¨C Emmons reaction involving triethylphosphonoacetate (TEPA, 255) was employed to convert epoxide 254 to cyclopropane 256. The reaction presumably proceeds through removal of the acidic TEPA proton followed by nucleophilic attack at the terminal epoxide carbon. The resulting alkoxide undergoes an intramolecular phosphoryl transfer reaction resulting in an enolate, which then attacked the newly formed phosphonate ester in an SN2 fashion resulting in the trans-cyclopropane ester, which was ultimately saponified and re-acidified to furnish cyclopropane acid 256. Conversion of this acid to the corresponding primary amide preceded carbonyl reduction with sodium borohydride. The resulting amine was acylated with propionyl chloride to furnish tasimelteon (XXXI) as the final product in 86% yield across the four-step sequence.
storage
Store at -20°C
Tasimelteon Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Hefei HomeSunshine Pharmaceutical Technology Co., Ltd. | 0551-65523315 17705606359 | errol@homesunshinepharma.com | China | 64 | 58 |
| Hubei Hicks Biochemical Co., Ltd | 17362916295; 17362916295 | w17362916295@163.com | China | 3985 | 58 |
| Shanghai Boyle Chemical Co., Ltd. | sales@boylechem.com | China | 2915 | 55 | |
| ZHIWE CHEMTECH CO LTD | 021-20221225 13917446399 | zwchem@163.com | China | 529 | 61 |
| Nanjing Chemlin Chemical Co., Ltd | 025-83697070 13770331960 | info@chemlin.com.cn | China | 16305 | 64 |
| Shanghai Hanhong Scientific Co.,Ltd. | 021-54306202 13764082696 | info@hanhongsci.com | China | 42917 | 64 |
| Daicel Chiral Technologies (China)CO.,LTD | 021-50460086-9 15921403865 | han_yajun@dctc.daicel.com | China | 7909 | 65 |
| China Langchem Inc. | 0086-21-58956006 | China | 7798 | 57 | |
| Hunan Hui Bai Shi Biotechnology Co., Ltd. | 0731-85526065 13308475853 | ivy@hnhbsj.com | China | 7236 | 62 |
| S.Z. PhyStandard Bio-Tech. Co., Ltd. | 0755-83725681-603 | China | 4484 | 50 |
View Lastest Price from Tasimelteon manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2026-09-11 | Tasimelteon
609799-22-6
|
1g | More Than 99% | 100kg/Month | BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD. | ||
 |
2026-09-11 | Tasimelteon
609799-22-6
|
1KG | 99%min | 100kg | WUHAN FORTUNA CHEMICAL CO., LTD | ||
 |
2026-07-27 | Tasimelteon
609799-22-6
|
$38.00-113.00 | 98.93% | 10g | TargetMol Chemicals Inc. |
-
- Tasimelteon
609799-22-6
- $0.00
- More Than 99%
- BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
-
- Tasimelteon
609799-22-6
- $0.00
- 99%min
- WUHAN FORTUNA CHEMICAL CO., LTD
-
- Tasimelteon
609799-22-6
- $38.00-113.00
- 98.93%
- TargetMol Chemicals Inc.
