Pipazetate () (brand names Dipect, Lenopect, Selvigon, Theratuss, Toraxan), or pipazethate (), is a 1-aza

phenothiazine Phenothiazine, abbreviated PTZ, is an organic compound that has the formula S(C6H4)2NH and is related to the thiazine-class of heterocyclic compounds. Derivatives of phenothiazine are highly bioactive and have widespread use and rich history. ...

drug that was briefly marketed as a

cough suppressant Cold medicines are a group of medicinal, medications taken individually or in Combination drug, combination as a Symptomatic treatment, treatment for the symptoms of the common cold and similar conditions of the upper respiratory tract. The ter ...

. It binds to the

sigma-1 receptor The sigma-1 receptor (σ1R), one of two sigma receptor subtypes, is a Chaperone (protein), chaperone protein at the endoplasmic reticulum (ER) that modulates calcium signaling through the IP3 receptor. In humans, the σ1 receptor is encoded by ...

with an IC₅₀ value of 190 nM. It also has local anesthetic action, and in large doses can produce seizures. As the brand name Theratuss, it was approved by the FDA in 1962, on evidence of safety only. It was withdrawn from the US market in 1972 when the manufacturer,

Bristol Myers Squibb The Bristol-Myers Squibb Company, Trade name, doing business as Bristol Myers Squibb (BMS), is an American multinational pharmaceutical company. Headquartered in Princeton, New Jersey, BMS is one of the world's largest pharmaceutical companies ...

, failed to produce evidence of efficacy. Clinical studies showed that it did not decrease cough frequency at recommended dosages. Infrequent side effects include nausea, vomiting, drowsiness, fatigue, rash,

tachycardia Tachycardia, also called tachyarrhythmia, is a heart rate that exceeds the normal resting rate. In general, a resting heart rate over 100 beats per minute is accepted as tachycardia in adults. Heart rates above the resting rate may be normal ...

and seizures.

Synthesis

Note: 1-azaphenothiazine is also used for making

Prothipendyl Prothipendyl (brand names Dominal, Timovan, Tolnate), also known as azapromazine or phrenotropin, is an anxiolytic, antiemetic, and antihistamine of the azaphenothiazine group which is marketed in Europe and is used to treat anxiety and agitatio ...

Isothipendyl Isothipendyl is a 1st generation H1 antagonist (antihistamine) and anticholinergic used as an antipruritic. In the 2020s, at least, it is rarely used in the first line relief of allergies due to the anticholinergic side effect of somnolence bu ...

The reaction of 1-azaphenothiazine 61-96-1(1) with phosgene gives 1-azaphenothiazine-10-carbonyl chloride 4231-78-4(2). The reaction of this reactive intermediate with 2- -(piperidyl)ethoxythanol 603-43-8(3) gives the ester, thus completing the synthesis of ''Pipazethate'' (4).

References

{{Tricyclics Antitussives Sigma receptor modulators Pyridobenzthiazines 1-Piperidinyl compounds Carbamates Ethers Withdrawn drugs Ethanolamines