Introduction：Basic information about Clemastine fumarate CAS 14976-57-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Clemastine fumarate Basic information
| Product Name: | Clemastine fumarate |
| Synonyms: | CLEMASTINE FUMARATE;CLEMASTINE FUMARATE SALT;(+)-2-(2-((p-chloro-alpha-methyl-alpha-phenylbenzyl)oxy)ethyl)-1-methylpyrro;(+)-2-(2-((p-chloro-alpha-methyl-alpha-phenylbenzyl)oxy)ethyl)-1-methylpyrroli;(+)-lfumarate(1:1);1-methyl-2-(2-(methyl-p-chlorodiphenylmethyloxy)ethyl)pyrrolidine;(2R)-2-[2-[(1R)-1-(4-CHLOROPHENYLETHOXY)]ETHYL]-1-METHYL-2-PYRROLIDINE FUMARATE;2-(2-(1-(4-chlorophenyl)-1-phenylethoxy)ethyl)-1-methylpyrrolidine |
| CAS: | 14976-57-9 |
| MF: | C25H30ClNO5 |
| MW: | 459.96 |
| EINECS: | 239-055-2 |
| Product Categories: | antianaphylaxis;TAVIST;Histaminergics;Antagonists;Neurotransmitters;Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals |
| Mol File: | 14976-57-9.mol |
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Clemastine fumarate Chemical Properties
| Melting point | 158-162°C |
| alpha | D21 +16.9° (methanol) |
| Boiling point | 154°C (rough estimate) |
| density | 1.0247 (rough estimate) |
| refractive index | 1.5790 (estimate) |
| storage temp. | 2-8°C |
| solubility | DMSO: soluble5mg/mL (clear solution; warmed) |
| form | powder |
| color | white to beige |
| Optical Rotation | [α]/D +15 to +25°, c = 1 in methanol |
| InChIKey | PMGQWSIVQFOFOQ-YKVZVUFRSA-N |
| SMILES | [C@@](C)(OCC[C@H]1CCCN1C)(C1C=CC=CC=1)C1=CC=C(Cl)C=C1.C(/C(=O)O)=C\C(=O)O |&1:0,5,r| |
| CAS DataBase Reference | 14976-57-9(CAS DataBase Reference) |
Safety Information
| WGK Germany | 3 |
| RTECS | UY0704600 |
| HS Code | 2933992600 |
| Storage Class | 11 - Combustible Solids |
| Hazardous Substances Data | 14976-57-9(Hazardous Substances Data) |
| Toxicity | LD50 in mice, rats (mg/kg): 730, 3550 orally; 43, 82 i.v. (Weimann) |
Clemastine fumarate Usage And Synthesis
| Chemical Properties | White Solid |
| Originator | Tavegyl,Sandoz,France,1967 |
| Uses | H1 Histamine receptor antagonist. Antihistaminic. |
| Uses | anti-inflammatory |
| Uses | Clemastine fumarate is a selective histamine H1 receptor antagonist (Ki = 0.26 nM) that also displays high affinity for muscarinic receptors (Ki = 16 nM). It has also recently been identified as a positive allosteric modulator of P2X7 receptor signaling. Clemastine fumarate has long been used to inhibit histamine-induced bronchoconstriction in asthma and airway hyperresponsive studies. |
| Definition | ChEBI: The fumaric acid salt of clemastine. An antihistamine with antimuscarinic and moderate sedative properties, it is used for the symptomatic relief of allergic conditions such as rhinitis, urticaria, conjunctivitis and in pruritic (severe itching) skin condiions. |
| Manufacturing Process | 9.9 g of α-methyl-p-chlorobenzhydrol are added to a suspension of 2.3 g ofpowdered sodamide in 30 cc of benzene. Subsequently 7.4 g of Nmethylpyrrolidyl-(2)-ethyl chloride are added and the solution is heated to theboil at reflux for 20 hours. Then shaking is first effected with water and then 4times each time with 25 cc of 2 N hydrochloric acid. The acid extracts aremade alkaline with potassium hydroxide solution while cooling strongly, andthe precipitated oil is extracted with ether. After drying of the ethereal solutionover potassium carbonate, the solvent is evaporated and the residue isfractionally distilled in a high vacuum, whereby N-methyl-2-[2'-(α-methyl-pchlorobenzhydryloxy)-ethyl]-pyrrolidine boils over at 154°C/0.02 mm Hg. Thebase is converted to the fumarate by reaction with fumaric acid. |
| Brand name | Tavist (Novartis). |
| Therapeutic Function | Antihistaminic |
| General Description | Dextrorotatory clemastine, R,R-2[2[1-(4-chlorophenyl)-1-phenylethoxy]ethyl]-1- methylpyrrolidine hydrogen furnarate (1:1) (Tavist), has two chiral centers, each of which has the (R) absolute configuration. A comparison of the activities of the enantiomers indicates that the asymmetric center close to the terminal side chain nitrogen is of lesser importance to antihistaminic activity.
? This member of the ethanolamine series is characterized by a long duration of action, with an activity that reaches a maximum in 5 to 7 hours and persists for 10 to 12 hours. It is well absorbed when administered orally, and it is excreted primarily in the urine. The side effects are those usually encountered with this series of antihistamines. Clemastine is closely related to chlorphenoxamine, which is used for its central cholinergic-blocking activity. Therefore, it is not surprising that clemastine has significant antimuscarinic activity. |
| Biological Activity | H 1 -receptor antagonist. Clinically-used antihistamine. |
| Biochem/physiol Actions | Clemastine fumarate is an antihistamine H1-antagonist and anticholinergic that also has antipruritic activity. |
| Veterinary Drugs and Treatments | Clemastine may be used for symptomatic relief of histamine1-relatedallergic conditions. |
| storage | Store at RT |
Clemastine fumarate Preparation Products And Raw materials
| Raw materials | Sodium amide-->Fumaric acid |
