Etymemazine

Last updated
Etymemazine
Etymemazine.png
Clinical data
Other namesEthylisobutrazine
AHFS/Drugs.com International Drug Names
ATC code
  • none
Identifiers
  • 3-(2-ethylphenothiazin-10-yl)-N,N,2-trimethylpropan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C20H26N2S
Molar mass 326.50 g·mol−1
3D model (JSmol)
  • CCC(C=C3)=CC2=C3SC1=CC=CC=C1N2CC(C)CN(C)C
  • InChI=1S/C20H26N2S/c1-5-16-10-11-20-18(12-16)22(14-15(2)13-21(3)4)17-8-6-7-9-19(17)23-20/h6-12,15H,5,13-14H2,1-4H3
  • Key:USKHCLAXJXCWMO-UHFFFAOYSA-N
   (verify)

Etymemazine is an antipsychotic, antihistamine and anticholinergic drug of the phenothiazine chemical class, structurally related to cyamemazine and methotrimeprazine. [1]

Synthesis

Etymemazine can be synthesized by SN2 alkylation of 2-ethylphenothiazine (1) with 1-dimethylamino-2-methyl-3-chloropropane (2) using sodamide as a base. [2] [3]

Synthesis of etymemazine Etymemazine synthesis.svg
Synthesis of etymemazine

Related Research Articles

<span class="mw-page-title-main">Hoechst AG</span> German chemicals company

Hoechst AG was a German chemicals then life-sciences company that became Aventis Deutschland after its merger with France's Rhône-Poulenc S.A. in 1999. With the new company's 2004 merger with Sanofi-Synthélabo, it became a subsidiary of the resulting Sanofi-Aventis pharmaceuticals group.

<span class="mw-page-title-main">Henri Laborit</span> French surgeon, neurobiologist, writer and philosopher (1914-95)

Henri Laborit was a French surgeon, neurobiologist, writer and philosopher. In 1952, Laborit was instrumental in the development of the drug chlorpromazine, published his findings, and convinced three psychiatrists to test it on a patient, resulting in great success. Laborit was recognized for his work, but as a surgeon searching for an anesthetic, he came to be at odds with psychiatrists who made their own discoveries and competing claims.

<span class="mw-page-title-main">Roussel Uclaf</span> French pharmaceutical company

Roussel Uclaf S.A. was a French pharmaceutical company and one of several predecessor companies of today's Sanofi.

<span class="mw-page-title-main">Pagoclone</span> Chemical compound

Pagoclone is an anxiolytic agent from the cyclopyrrolone family, related to better-known drugs such as the sleeping medication zopiclone. It was synthesized by a French team working for Rhone-Poulenc & Rorer S.A. Pagoclone belongs to the class of nonbenzodiazepines, which have similar effects to the older benzodiazepine group, but with quite different chemical structures. It was never commercialised.

<span class="mw-page-title-main">Dalfopristin</span> Chemical compound

Dalfopristin is a semi-synthetic streptogramin antibiotic analogue of ostreogyrcin A. The combination quinupristin/dalfopristin was brought to the market by Rhone-Poulenc Rorer Pharmaceuticals in 1999. Synercid is used to treat infections by staphylococci and by vancomycin-resistant Enterococcus faecium.

Rhône-Poulenc was a French chemical and pharmaceutical company founded in 1928. In 1999, it merged with Hoechst AG to form Aventis. As of 2015, the pharmaceutical operations of Rhône-Poulenc are part of Sanofi and the chemicals divisions are part of Solvay group and Bayer Crop Science.

<span class="mw-page-title-main">Indalpine</span> Discontinued SSRI antidepressant drug

Indalpine is a selective serotonin reuptake inhibitor (SSRI) class drug that was briefly marketed. It was discovered in 1977 by the pharmacologists Le Fur and Uzan at Pharmuka, a small French pharmaceutical firm, who credit Baron Shopsin and his colleagues at NYU-Bellevue/NYU School of Medicine in New York with providing the basis for their work. They were particularly influenced by the series of "synthesis inhibitor studies" carried out by Shopsin's team during the early to mid 1970s, and in particular, the clinical report by Shopsin et al. (1976) relating to PCPA's rapid reversal of antidepressant response to tranylcypromine in depressed patients. This led to an understanding of the role of the monoamine neurotransmitter serotonin in the therapeutic effects of the available tricyclic and MAOI class antidepressants. The studies led to widespread recognition of a serotonin hypothesis of depression, contradicting theories that promoted the role of norepinephrine.

<span class="mw-page-title-main">Suproclone</span> Drug

Suproclone is a sedative and anxiolytic drug in the cyclopyrrolone family of drugs, developed by the French pharmaceutical company Rhône-Poulenc. Other cyclopyrrolone drugs include zopiclone, pagoclone and suriclone.

Fisons plc was a British multinational pharmaceutical, scientific instruments and horticultural chemicals company headquartered in Ipswich, United Kingdom. It was listed on the London Stock Exchange and was once a constituent of the FTSE 100 Index. It was acquired by Rhone-Poulenc in 1995.

<span class="mw-page-title-main">Levophacetoperane</span> Stimulant drug

Levophacetoperane is a psychostimulant developed by Rhône-Poulenc in the 1950s. The drug has been used as an antidepressant and anorectic. It is the reverse ester of methylphenidate.

<span class="mw-page-title-main">Cyamemazine</span> Antipsychotic medication

Cyamemazine (Tercian), also known as cyamepromazine, is a typical antipsychotic drug of the phenothiazine class which was introduced by Theraplix in France in 1972 and later in Portugal as well.

<span class="mw-page-title-main">Periciazine</span> Typical antipsychotic medication

Periciazine (INN), also known as pericyazine (BAN) or propericiazine, is a drug that belongs to the phenothiazine class of typical antipsychotics.

<span class="mw-page-title-main">Dimetotiazine</span> Chemical compound

Dimetotiazine (INN) is a phenothiazine drug used for the treatment of migraine. It is a serotonin antagonist and histamine antagonist.

<span class="mw-page-title-main">Perazine</span> Typical antipsychotic medication

Perazine (Taxilan) is a moderate-potency typical antipsychotic of the phenothiazine class. It is quite similar to chlorpromazine, and acts as a dopamine antagonist. A 2014 systematic review compared it with other antipsychotic drugs:

<span class="mw-page-title-main">Chlorproethazine</span> Chemical compound

Chlorproethazine, sold under the brand name Neuriplege, is a drug of the phenothiazine group described as a muscle relaxant or tranquilizer which is or has been marketed in Europe as a topical cream for the treatment of muscle pain. It has been associated with photoallergic contact dermatitis.

<span class="mw-page-title-main">Thioproperazine</span> Typical antipsychotic medication

Thioproperazine, sold under the brand name Majeptil, is a typical antipsychotic of the phenothiazine group which is used as a tranquilizer, antiemetic, sedative, and in the treatment of schizophrenia and manic phase of bipolar disorder. Majeptil is available in 10 mg tablets.

<span class="mw-page-title-main">Prothipendyl</span> Chemical compound

Prothipendyl, 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 agitation in psychotic syndromes. It differs from promazine only by the replacement of one carbon atom with a nitrogen atom in the tricyclic ring system. Prothipendyl is said to not possess antipsychotic effects, and in accordance, appears to be a weaker dopamine receptor antagonist than other phenothiazines.

<span class="mw-page-title-main">Metapramine</span> Chemical compound

Metapramine is a tricyclic antidepressant (TCA) developed by Rhone Poulenc that was introduced for the treatment of depression in France in 1984. In addition to its efficacy against affective disorders, it also has analgesic properties, and may be useful in the treatment of pain.

<span class="mw-page-title-main">Piperoxan</span> Chemical compound

Piperoxan, also known as benodaine, was the first antihistamine to be discovered. This compound, derived from benzodioxan, was prepared in the early 1930s by Daniel Bovet and Ernest Fourneau at the Pasteur Institute in France. Formerly investigated by Fourneau as an α-adrenergic-blocking agent, they demonstrated that it also antagonized histamine-induced bronchospasm in guinea pigs, and published their findings in 1933. Bovet went on to win the 1957 Nobel Prize in Physiology or Medicine for his contribution. One of Bovet and Fourneau's students, Anne-Marie Staub, published the first structure–activity relationship (SAR) study of antihistamines in 1939. Piperoxan and analogues themselves were not clinically useful due to the production of toxic effects in humans and were followed by phenbenzamine (Antergan) in the early 1940s, which was the first antihistamine to be marketed for medical use.

<span class="mw-page-title-main">Poulenc Frères</span>

Poulenc Frères was a French chemical, pharmaceutical and photographic supplies company that had its origins in a Paris pharmacy founded in 1827. From 1852 it began to manufacture photographic chemicals. It took the name Poulenc Frères in 1881, and by 1900 had a range of high-quality products. That year it went public as the Établissements Poulenc Frères. It began production of synthetic medicines, and continued to grow during World War I (1914–18). In 1928 it merged with the Société des usines chimiques du Rhône to form Rhône-Poulenc.

References

  1. Milne GW (2002). "Etymemazine". Drugs: Synonyms and Properties (2nd ed.). Aldershot, Hampshire, England: Ashgate. p. 3945. ISBN   978-0-566-08491-1.
  2. GB 789703 (1958 to Rhone Poulenc Sa).
  3. Robert Michel Jacob, et al. U.S. Patent 2,837,518 (1956 to Rhone Poulenc Sa)