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Eucaine
Eucaine, also known as β-eucaine or Betacaine, is a drug that was previously used as a local anesthetic. It was designed as an Functional analog (chemistry), analog of cocaine and was one of the first synthetic chemical compounds to find general use as an anesthetic. It is a white, crystalline solid. Prior to World War I, Britain imported eucaine from Germany. During the war, a team including Jocelyn Field Thorpe and Martha Annie Whiteley developed a synthesis in Britain. The brand name Betacaine can sometimes refer to a preparation containing lidocaine, not eucaine. Synthesis Condensation of diacetonamine [625-04-7] (1) with acetaldehyde (paraldehyde) rather than acetone gives the piperidone containing one less methyl group, i.e. 2,2,6-trimethylpiperidin-4-one [3311-23-7] (2). Reduction of the ketone with sodium amalgam gives the alcohol as a mixture of isomers, 2,2,6-trimethylpiperidin-4-ol (3). Benzoylation then affords beta-eucaine (4). See also * α-Eucaine, a related ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Eucaine (beta) Synthesis
Eucaine, also known as β-eucaine or Betacaine, is a drug that was previously used as a local anesthetic. It was designed as an analog of cocaine and was one of the first synthetic chemical compounds to find general use as an anesthetic. It is a white, crystalline solid. Prior to World War I, Britain imported eucaine from Germany. During the war, a team including Jocelyn Field Thorpe and Martha Annie Whiteley developed a synthesis in Britain. The brand name Betacaine can sometimes refer to a preparation containing lidocaine, not eucaine. Synthesis Condensation of diacetonamine 25-04-7(1) with acetaldehyde Acetaldehyde (IUPAC systematic name ethanal) is an organic chemical compound with the formula CH3 CHO, sometimes abbreviated by chemists as MeCHO (Me = methyl). It is a colorless liquid or gas, boiling near room temperature. It is one of the mos ... (paraldehyde) rather than acetone gives the piperidone containing one less methyl group, i.e. 2,2,6-trimethylpiperidin-4 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
α-Eucaine
α-Eucaine (''alpha''-eucaine) is a drug that was previously used as a local anesthetic. It was designed as an Functional analog (chemistry), analog of cocaine and was one of the first synthetic chemical compounds to find general use as an anesthetic. Synthesis The Aldol condensation between two equivalents of acetone gives Mesityl oxide [141-79-7] (1) (isophorone is a side-product of this reaction). Ammonolysis of mesityl oxide formed diacetonamine [625-04-7] (2). The reaction of this product with acetone then gives 2,2,6,6-tetramethyl-4-piperidone [826-36-8] (3). ''N''-methylation of the secondary amine gives 1,2,2,6,6-pentamethylpiperidin-4-one [5554-54-1] (4). Cyanohydrin formation giveCID:434556(5). Esterification of the tertiary alcohol with benzoyl chloride gives (6). Pinner reaction of the nitrile with EtOH/H+ affords alpha-eucaine (7). See also * Eucaine, or β-eucaine, a related local anesthetic References Local anesthetics Piperidines Benzoate esters Methyl ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Local Anesthetic
A local anesthetic (LA) is a medication that causes absence of pain sensation. In the context of surgery, a local anesthetic creates an absence of pain in a specific location of the body without a loss of consciousness, as opposed to a general anesthetic. When it is used on specific nerve pathways (local anesthetic nerve block), paralysis (loss of muscle power) also can be achieved. Examples Short Duration & Low Potency Procaine Chloroprocaine Medium Duration & Potency Lidocaine Prilocaine High Duration & Potency Tetracaine Bupivacaine Cinchocaine Ropivacaine Clinical LAs belong to one of two classes: aminoamide and aminoester local anesthetics. Synthetic LAs are structurally related to cocaine. They differ from cocaine mainly in that they have a very low abuse potential and do not produce hypertension or (with few exceptions) vasoconstriction. They are used in various techniques of local anesthesia such as: * Topical anesthesia (surface) * Topical administration ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Functional Analog (chemistry)
In chemistry and pharmacology, functional analogs are chemical compounds that have similar physical, chemical, biochemical, or pharmacological properties. Functional analogs are not necessarily structural analogs with a similar chemical structure. An example of pharmacological functional analogs are morphine, heroin and fentanyl, which have the same mechanism of action, but fentanyl is structurally quite different from the other two with significant variance in dosage. File:Morphin - Morphine.svg, Morphine File:Heroin - Heroine.svg, Heroin File:Fentanyl2DCSD.svg, Fentanyl See also *Federal Analogue Act The Federal Analogue Act, , is a section of the United States Controlled Substances Act passed in 1986 which allows any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were listed in ... References Chemical nomenclature Pharmacology {{pharma-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cocaine
Cocaine (from , from , ultimately from Quechuan languages, Quechua: ''kúka'') is a central nervous system (CNS) stimulant mainly recreational drug use, used recreationally for its euphoria, euphoric effects. It is primarily obtained from the leaves of two Coca species native to South America, ''Erythroxylum coca'' and ''Erythroxylum novogranatense''. After extraction from coca leaves and further processing into cocaine hydrochloride (powdered cocaine), the drug is often Insufflation (medicine), snorted, applied topical administration, topically to the mouth, or dissolved and injection (medicine), injected into a vein. It can also then be turned into free base form (crack cocaine), in which it can be heated until sublimated and then the vapours can be smoking, inhaled. Cocaine stimulates the mesolimbic pathway, reward pathway in the brain. Mental effects may include an euphoria, intense feeling of happiness, sexual arousal, psychosis, loss of contact with reality, or psychomo ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
