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SML2030

Sigma-Aldrich

Tasimelteon

≥98% (HPLC)

Sinônimo(s):

(1R, 2R)-N-[2- (2,3-Dihydrobenzofuran-4-yl)cyclopropylmethyl]propanamide, BMS-214778, Hetlioz, MA 1, N-[[(1R,2R)-2-(2,3-Dihydro-4-benzofuranyl)cyclopropyl]methyl]propanamide, VEC-162

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About This Item

Fórmula empírica (Notação de Hill):
C15H19NO2
Número CAS:
609799-22-6
Peso molecular:
245.32
Número MDL:
MFCD09033789
Código UNSPSC:
12352200

Ensaio

≥98% (HPLC)

forma

powder

cor

white to beige

solubilidade

DMSO: 2 mg/mL, clear

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

O=C(CC)NC[C@@H]1C[C@H]1C2=C3C(OCC3)=CC=C2

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

chave InChI

PTOIAAWZLUQTIO-GXFFZTMASA-N

Ações bioquímicas/fisiológicas

Tasimelteon is a Dual Melatonin Receptor Agonist (DMRA) recently approved (Hetlioz) for the treatment of Non-24-hour sleep–wake disorder, a disorder primarily found in the totally blind, where a lack of normal synchronization between the 24-hour light–dark cycle and the endogenous circadian rhythm causes it to drift out of alignment with conventional sleep–wake schedules. The endogenous rhythm of the circadian pacemaker in the suprachiasmatic nuclei (SCN) is typically slightly longer than 24 h and therefore must be synchronized to the 24-hour day, normally by light, but exogenous melatonin can also phase-shift circadian rhythms. Tasimelteon is a selective agonist for the SCN melatonin receptors MT1 and MT2 with greater affinity for the MT2 receptor thought to be more important in mediating circadian rhythm phase-shifting. EC50 values are 0.75 nM for MT1 and 0.1 nM for MT2 measured by inhibition of forskolin-stimulated cAMP accumulation in NIH-3T3 cells expressing human MT1 and MT2.

Pictogramas

Exclamation markHealth hazard
GHS07,GHS08

Palavra indicadora

Warning

Frases de perigo

H336 - H361

Classificações de perigo

Repr. 2 - STOT SE 3

Órgãos-alvo

Central nervous system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Certificados de análise (COA)

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Wilbur P Trey Williams et al.
Pharmacotherapy, 36(9), 1028-1041 (2016-08-09)
Circadian rhythm sleep-wake disorders (CRSWDs) are characterized by persistent or recurrent patterns of sleep disturbance related primarily to alterations of the circadian rhythm system or the misalignment between the endogenous circadian rhythm and exogenous factors that affect the timing or
Christian Lavedan et al.
Neuropharmacology, 91, 142-147 (2014-12-24)
Hetlioz(®) (tasimelteon) is the first approved treatment in the United States for Non-24-Hour Sleep-Wake Disorder (Non-24). We present here data on the in vitro binding affinity of tasimelteon for both human melatonin receptors MT1 and MT2, as well as the

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