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IUPAC name [1-(Dimethylamino)-2-methylbutan-2-yl] benzoate | |
Other names Stovaine; Benzoic acid [1-(dimethylaminomethyl)-1-methylpropyl] ester | |
Identifiers | |
3D model (JSmol) | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.010.375 |
EC Number |
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KEGG | |
PubChem CID | |
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CompTox Dashboard (EPA) | |
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Properties | |
C14H21NO2 | |
Molar mass | 235.327 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Amylocaine was the first synthetic local anesthetic. It was synthesized and patented under the name Stovaine by Ernest Fourneau at the Pasteur Institute in 1903. [1] It was used mostly in spinal anesthesia. [2]
Amylocaine can be synthesized beginning with chloroacetone (1). [3] [4] [5] [6] [7] Grignard reaction of chloroacetone with magnesium ethyl bromide gives 1-chloro-2-methyl-butan-2-ol (2). Heating with dimethylamine gives 1-(dimethylamino)-2-methylbutan-2-ol (3). These two steps can also be treated as interchangeable. Esterification with benzoyl chloride completed the synthesis of amylocaine (4). [3] [4]
Halothane, sold under the brand name Fluothane among others, is a general anaesthetic. It can be used to induce or maintain anaesthesia. One of its benefits is that it does not increase the production of saliva, which can be particularly useful in those who are difficult to intubate. It is given by inhalation.
The year 1901 in science and technology involved some significant events, listed below.
The year 1935 in science and technology involved some significant events, listed below.
Epibatidine is a chlorinated alkaloid that is secreted by the Ecuadoran frog Epipedobates anthonyi and poison dart frogs from the Ameerega genus. It was discovered by John W. Daly in 1974, but its structure was not fully elucidated until 1992. Whether epibatidine is the first observed example of a chlorinated alkaloid remains controversial, due to challenges in conclusively identifying the compound from the limited samples collected by Daly. By the time that high-resolution spectrometry was used in 1991, there remained less than one milligram of extract from Daly's samples, raising concerns about possible contamination. Samples from other batches of the same species of frog failed to yield epibatidine.
Prontosil is an antibacterial drug of the sulfonamide group. It has a relatively broad effect against gram-positive cocci but not against enterobacteria. One of the earliest antimicrobial drugs, it was widely used in the mid-20th century but is little used today because better options now exist. The discovery and development of this first sulfonamide drug opened a new era in medicine, because it greatly widened the success of antimicrobial chemotherapy in an era when many physicians doubted its still largely untapped potential. At the time, disinfectant cleaners and topical antiseptic wound care were widely used but there were very few antimicrobial drugs to use safely inside living bodies. Antibiotic drugs derived from microbes, which we rely on heavily today, did not yet exist. Prontosil was discovered in 1932 by a research team at the Bayer Laboratories of the IG Farben conglomerate in Germany led by Gerhard Domagk. Domagk received the 1939 Nobel Prize in Physiology or Medicine for that discovery.
Sulfanilamide is a sulfonamide antibacterial drug. Chemically, it is an organic compound consisting of an aniline derivatized with a sulfonamide group. Powdered sulfanilamide was used by the Allies in World War II to reduce infection rates and contributed to a dramatic reduction in mortality rates compared to previous wars. Sulfanilamide is rarely if ever used systemically due to toxicity and because more effective sulfonamides are available for this purpose. Modern antibiotics have supplanted sulfanilamide on the battlefield; however, sulfanilamide remains in use today in the form of topical preparations, primarily for treatment of vaginal yeast infections such as vulvovaginitis caused by Candida albicans.
Zomepirac is an orally effective nonsteroidal anti-inflammatory drug (NSAID) that has antipyretic actions. It was developed by McNeil Pharmaceutical, approved by the FDA in 1980, and sold as the sodium salt zomepirac sodium, under the brand name Zomax. Due to its clinical effectiveness, it was preferred by doctors in many situations and obtained a large share of the analgesics market; however, it was subsequently withdrawn in March 1983 due to its tendency to cause serious anaphylaxis in a small, but unpredictable, subset of the patient population.
Methylecgonidine is a chemical intermediate derived from ecgonine or cocaine.
Chlorobutanol (trichloro-2-methyl-2-propanol) is an organic compound with the formula CCl3C(OH)(CH3)2. The compound is an example of a chlorohydrin. The compound is a preservative, sedative, hypnotic and weak local anesthetic similar in nature to chloral hydrate. It has antibacterial and antifungal properties. Chlorobutanol is typically used at a concentration of 0.5% where it lends long term stability to multi-ingredient formulations. However, it retains antimicrobial activity at 0.05% in water. Chlorobutanol has been used in anesthesia and euthanasia of invertebrates and fishes. It is a white, volatile solid with a camphor-like odor.
Mephentermine is a cardiac stimulant.
Lucien Bull was a pioneer in chronophotography. Chronophotography is defined as "a set of photographs of a moving object, taken for the purpose of recording and exhibiting successive phases of motion."
Diclofensine (Ro 8-4650) was developed by Hoffmann-La Roche in the 1970s in the search for a new antidepressant. It was found that the (S)-isomer was responsible for activity. Diclofensine is a stimulant drug which acts as a triple monoamine reuptake inhibitor, primarily inhibiting the reuptake of dopamine and norepinephrine, with affinities (Ki) of 16.8 nM, 15.7 nM, and 51 nM for DAT, NET, and SERT (dopamine, norepinephrine and serotonin transporters), respectively. It was found to be an effective antidepressant in human trials, with relatively few side effects, but was ultimately dropped from clinical development, possibly due to concerns about its abuse potential.
Acedapsone (INN) is an antimicrobial drug, which also has antimalarial activity.
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.
Ernest Fourneau was a French pharmacist who graduated in 1898 for the Paris university specialist in medicinal chemistry and pharmacology. He played a major role in the discovery of synthetic local anesthetics such as amylocaine, as well as in the synthesis of suramin. He authored more than two hundred scholarly works, and has been described as having "helped to establish the fundamental laws of chemotherapy that have saved so many human lives".
Ketocaine (INN) is an amino ether local anesthetic of the butyrophenone family used topically for pain relief. It is marketed in Italy.
Jacques Tréfouël was a French medical chemist. He collaborated closely with his wife, Thérèse Tréfouël, including on the discovery of sulfanilamide.
Alain Fuchs is a Swiss-born French Doctor of Science and chemistry Professor, specialized in molecular simulation. He served as the president of Chimie ParisTech - PSL from 2006 to 2010. He has served as the president of the French National Centre for Scientific Research from 2010 to 2017.' He became an Officer of the Legion of Honour in 2014.
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.
Germaine Benoit was a French chemical engineer, pharmacologist and biologist, best known for her contributions to the study of sympathomimetic drugs.