Reboxetine mesylate - CAS 71620-89-8

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Category
APIs
Product Name
Reboxetine mesylate
Catalog Number
71620-89-8
Synonyms
(2R)-2-[(R)-(2-ethoxyphenoxy)-phenylmethyl]morpholine; methanesulfonic acid; 2-((2-ethoxyphenoxy)benzyl)morpholine methanesulfonate; reboxetine; reboxetine mesylate; Vestra; 98769-84-7; Reboxetine mesilate; Reboxetine (mesylate); Edronax; PNU 155950E; FCE 20124; DSSTox_CID_25690; DSSTox_RID_81062; DSSTox_GSID_45690
CAS Number
71620-89-8
Description
Reboxetine mesylate is a potent and selective inhibitor of noradrenalin uptake (K i values are 1.1, 129 and > 10000 nM for rat NET, SERT and DAT respectively). Displays > 1000-fold selectivity over α -adrenoceptors, 5-HT, dopamine and muscarinic ACh receptors. Norepinephrine: IC50 = 8.2 nM; 5-HT: IC50 = 1.07 µM; H1: IC50 = 1.4 µM; α1 Adrenergic: IC50 = 10 µM NET: Ki= 1.1 nM (rat); Norepinephrine reuptake: Ki= 8.2 nM; [3H]-dopamine uptake to the human norepinephrine transporters: Ki= 11 nM (Madin–Darby canine kidney cells); SERT: Ki= 129 nM (rat); DAT: Ki>10 µM (rat)
Molecular Weight
409.50
Molecular Formula
C19H23NO3.CH3SO3H
Quantity
Grams-Kilos
Quality Standard
In-house standard
COA
Certificate of Analysis-Reboxetine mesylate 71620-89-8 B16H0114  
MSDS
Inquire
Canonical SMILES
CCOC1=CC=CC=C1OC(C2CNCCO2)C3=CC=CC=C3.CS(=O)(=O)O
InChI
1S/C19H23NO3.CH4O3S/c1-2-21-16-10-6-7-11-17(16)23-19(15-8-4-3-5-9-15)18-14-20-12-13-22-18;1-5(2,3)4/h3-11,18-20H,2,12-14H2,1H3;1H3,(H,2,3,4)/t18-,19-;/m1./s1
InChIKey
CGTZMJIMMUNLQD-STYNFMPRSA-N
Structure
CAS 71620-89-8 Reboxetine mesylate
Specification
Purity
≥ 98.0%
Melting Point
140-142ºC
Appearance
Off-white to white solid
Application
A potent and selective inhibitor of noradrenalin uptake (Norepinephrine: IC50 = 8.2 nM); Orally active antidepressant
Storage
Store in a dry and cool place.
Solubility
Soluble in water (82 mg/ml at 25° C), DMSO (82 mg/ml at 25° C), chloroform, methanol, and ethanol (<1 mg/ml at 25° C).
Reference Reading
1. Stereoselective synthesis of (2S,3R)- and (2R,3S)-iodoreboxetine; potential SPECT imaging agents for the noradrenaline transporter
Nicola K. Jobson, Rosemary Spike, Andrew R. Crawford, Andrew Sutherland*. Org. Biomol. Chem., 2008, 6, 2369–2376
A typical compound used in such studies is reboxetine, the well-known, selective noradrenaline re-uptake inhibitor. Reboxetine is commercially available under the names Edronax, Prolift,Vestra and Norebox for the treatment of depressive disorder and, while the drug ismarketed as a racemicmixture of (2R,3R)- and (2S,3S)-enantiomers, it is (2S,3S)-reboxetine that has the best affinity and selectivity for NAT. Using this information, the groups of Saji and Tamagnan have recently designed and synthesised a range of iodinated analogues of (2S,3S)-reboxetine for the SPECTimaging of NAT. Testing of these compounds showed one compound in particular, iodo-analogue to have excellent affinity (Ki 2.47 nM), good selectivity and significant potential as an imaging agent for NAT.
2. Co(III)(salen)-catalyzed HKR of two stereocentered alkoxy- and azido epoxides: a concise enantioselective synthesis of (S,S)-reboxetine and (+)-epi-cytoxazone
R. Santhosh Reddy, Pandurang V. Chouthaiwale, Gurunath Suryavanshi, Vilas B. Chavan, Arumugam Sudalai*. Chem. Commun., 2010, 46, 5012–5014
A wide range of synthetic applications of this HKR procedure is readily envisaged and is amply illustrated in the short synthesis of (S,S)-reboxetine, a selective norepinephrine reuptake inhibitor (NRI), and (+)-epi-cytoxazone, a cytokine modulator. For (S,S)-reboxetine, chiral epoxide was chosen as the starting material. Regiospecific opening of epoxide 4a with 30%NH4OH gave amino alcohol 16 in 83% yield, which was condensed with chloroacetyl chloride under basic conditions to afford imide in 72% yield. Alcohol was obtained in 88% yield by a standard sequence of reactions. The transformation of alcohol to (S,S)-reboxetine was achieved in 98% ee.
3. The use of environmental metrics to evaluate green chemistry improvements to the synthesis of (S,S)-reboxetine succinate
Georges Assaf, Graham Checksfield, Doug Critcher, Peter J. Dunn, Laurence J. Harris*. Green Chem., 2012, 14, 123–129
(±)-Reboxetine mesylate is a selective norepinephrine uptake (NRI) inhibitor which is marketed as the racemate, under the trade name EdronaxTM, for the treatment of depression, in more than 60 countries. The (S,S)-enantiomer is significantly more active than the racemate in a number of studies and has undergone clinical evaluation as the succinate salt 2 for a number of indications in the pain therapeutic area. The chemical development program for (S,S)-reboxetine succinate was very much influenced by the unusual history of the compound. Pharmacia had manufactured 15000 kg of (±)-reboxetine mesylate or late stage intermediates, such as 3 in readiness for a US approval of EdronaxTM. When this approval did not occur it was clear that only a small proportion of the stock would be required to support the other markets and the remainder was“written off” and made available to the research organisation. Not surprisingly the large stock pile ofmaterialwas initially used as a starting point for the synthesis of (S,S)-reboxetine succinate, the single enantiomer which was being developed for new indications in the pain area. The development work was being carried out at a time when the discipline ofGreen Chemistry was becoming more established in the pharmaceutical industry. As such, in this article we focus on the environmental (and cost) improvements that were achieved through process development and synthetic route design coupled with rigorous measurement and analysis of Green Chemistry metrics.
4. Synthesis of morpholine or piperazine derivatives through gold-catalyzed cyclization reactions of alkynylamines or alkynylalcohols
Liang-Feng Yao, Yuan Wang, Kuo-Wei Huang*. Org.Chem. Front., 2015, 2, 721-725
Morpholine and piperazine derivatives have attracted considerable attention owing to their occurrence in biologically active natural products and pharmaceuticals, such as antivertigo/ antiemetic agent Buclizine, antibacterial agent Grepafloxacin hydrochloride, gyrase and topoisomerase IV inhibitor Gatifloxacin, and antidepressant drug Reboxetine. They also serve as versatile building blocks in organic synthesis. While various methodologies have been established on the synthesis of morpholine and piperazine derivatives, there are still several challenges to overcome, including the limitation of starting materials, harsh reaction conditions, low efficiency, poor selectivity, etc. Only very few literature reports exist to provide a mild and highly regioselective access to functiona-lized-morpholine and piperazine derivatives. Alkynylamines and alkynylalcohols can be used to assemble various heterocyclic compounds and can serve as precursors for morpholine and piperazine derivatives. They typically undergo two different pathways to afford endo-or exo-cyclization products
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