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| Guaifenesin Chemical Properties |
| Melting point |
77-81 °C |
| Boiling point |
215 °C (19 mmHg) |
| density |
1.1825 (rough estimate) |
| refractive index |
1.5550 (estimate) |
| Fp |
215°C/19mm |
| storage temp. |
Refrigerator |
| solubility |
50g/l (experimental) |
| form |
neat |
| pka |
13.53±0.20(Predicted) |
| Water Solubility |
5 g/100 mL (25 ºC) |
| Merck |
14,4555 |
| BRN |
2049375 |
| InChIKey |
HSRJKNPTNIJEKV-UHFFFAOYSA-N |
| CAS DataBase Reference |
93-14-1(CAS DataBase Reference) |
| NIST Chemistry Reference |
3-(O-phenoxy)-1,2-propanediol(93-14-1) |
| EPA Substance Registry System |
Guaifenesin (93-14-1) |
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| Guaifenesin Usage And Synthesis |
| Description |
Guaifenesin is an oral expectorant drug. The expectorant action of guaifenesin is mediated by stimulation of the gastrointestinal tract. It is a common ingredient in prescription and over-the-counter medications used to treat cough due to colds and minor upper respiratory infections. |
| References |
[1] Peter V. Dicpinigaitis and Yvonne E. Gayle, Effect of Guaifenesin on Cough Reflex Sensitivity, 2003, vol. 124, 2178-2181
[2] Leonid Kagan, Eran Lavy and Ammon Hoffmann, Effect of mode of administration on guaifenesin pharmacokinetics and expectorant action in the rat model, Pulmonary Pharmacology & Therapeutics, 2009, vol. 22, 260-265 |
| Chemical Properties |
White Solid |
| Originator |
GG Cen,Central,US,1975 |
| Uses |
Centrally acting muscle relaxant with expectorant properties |
| Uses |
Used to assist the expectoration of phlegm from the airways in acute respiratory tract infections. |
| Manufacturing Process |
A mixture of o-phenol (57 g), glycidol (32 g) and pyridine (1 g) is warmed to 95°C at which temperature a vigorous reaction takes place. The reaction mixture is cooled to prevent the temperature rising above 110°C. When the exothermic reaction has subsided the reactants are heated at 95°C for one hour longer and then distilled under low pressure. The main fraction boils in the range 176°C to 180°C/0.5 mm. It crystallizes on cooling. Recrystallization from benzene gives the pure product, MP 78.5°C to 79.0°C. |
| Brand name |
Mucinex (Adams). |
| Therapeutic Function |
Expectorant |
| Mechanism of action |
Guaiphenesin facilitates secretion from bronchial mucous membranes, thus relieving a cough in colds, bronchitis, and bronchial asthma. |
| Chemical Synthesis |
Guaiphenesin, 3-(o-phenoxy)-1,2-propandiol (23.2.3), is synthesized by reacting guiacol with 3-chloropropan-1,2-diol or with glycidol.
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| Veterinary Drugs and Treatments |
In veterinary medicine, guaifenesin is used to induce muscle relaxation and restraint as an adjunct to anesthesia for short procedures (30 – 60 minutes) in large and small animal species. There are combination oral products containing guaifenesin for treating respiratory conditions in horses.
In human medicine, guaifenesin has long been touted as an oral expectorant, but definitive proof of its efficacy is lacking. |
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| Guaifenesin Preparation Products And Raw materials |
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