Phenylpropanolamine ppa is a sympathomimetic agent which is used as a decongestant and appetite suppressant. Ephedrine is a naturally occurring alkaloid in different species of ephedra. Know about technical details of ephedrine sulfate like. These considerations, as we have stated elsewhere,1 led us into an. The mutagenicity of nnitrosomethamphetamine and nnitrosoephedrine synthesized from methamphetamine and ephedrine in our laboratory was proved to be significant by the modified method of the ames assay using salmonella typhimurium ta100 and ta98 and e. The biosynthesis of ephedrine canadian journal of chemistry. Ephedrinetype alkaloid content of nutritional supplements.
It is used as a drug and has structure and activity similar to those of adrenaline, which raises blood pressure, heart. In the case of pseudoephedrine, the nuclear magnetic resonance data of the crude reaction mixture indicate the presence of three isomeric compounds 5, 6, and 7, which were separated by fractional crystallization, while ephedrine afforded the. Phase equilibriums, chemical equilibriums, and solutions. Ephedrine is an alkaloid that is present in various forms of the ephedrine family, and which is still extracted from ephedra sinica and ephedra equisetina. The chemistry of these methods will be discussed, referenced and precursors highlighted. Among the various syntheses of the ephedrine alkaloids, the following are worthy of mention. Enantioselective synthesis of 1s,2spseudoephedrine. What is the difference between threoerythro ephedrine. Figure 3 the chemical structures of important catecholamines. Catalyzed decarboxylative asymmetric protonation dap. It has a role as a neurotoxin, a psychotropic drug, a central nervous system stimulant, a xenobiotic and an environmental contaminant.
Application ephedrine hydrochloride was used in the control of the inflammatory response. These metrics are regularly updated to reflect usage leading up to the last few days. Uncle festers drug chemistry books free in pdf format. The medicinal chemistry course adme adsorption, distribution, metabolism and excretion of drugs drugreceptor interactions development of drugs screening techniques combinatorial chemistry d. The spectrum exhibits several distinct features in this range that are characteristic of the crystal form of the compound. In the ussr kazakhstan, kirghizia, and other republics the total alkaloid contents of various ephedra species are 1. In saquinavir synthesis, the halfacid is resolved as its salt with l ephedrine.
Ephedrine sulfate increases the flow of coronary, cerebral and muscle blood. Conformational equilibria of ephedrine and pseudoephedrine. The exact mechanism by which ephedrine sulfate affects skeletal muscle contractions is unknown. Supercritical extraction of pseudoephedrine from pills pdf biotransformations for ephedrine production pdf lphenylacetylcarbinol lpac from benzaldehyde pdf phenylpropanolamine by reductive amination of lpac, made by fermentation of benzaldehyde. The secondary amine having the molecular structure shown below. I extract ephedrine pills from the gas station and pseudoephedrine pills from the grocery store to. Onset with intravenous use is fast, while injection into a muscle can take 20. Isolation, analysis, and synthesis of ephedrine and its derivatives. An organic chemistry laboratory experiment illustrating stereoisomerism. Debunking the myth of ephedrinemethamphetamine in chicken feed.
Ephedrine and norephedrine, the nasal decongestants, have been use illegally as the starting materials for amphetamine and methamphetamine synthesis 68. Ephedrine is a sympathomimetic amine commonly used as a stimulant, concentration aid, decongestant, appetite suppressant, and to treat hypotension associated with anaesthesia. Learn more about these metrics article views are the countercompliant sum of full text article downloads since november 2008 both pdf and html across all institutions and individuals. Clinically, dephedrine is used to a large extent as an antiasthmatic and, formerly, as a presser amine to restore low blood pressure as a result of trauma. Proton nmr spectra suggest that the conformation with trans vicinal hydrogens is favored for ephedrine as the free base in deuterium oxide, although in non. Not to be confused with pseudoephedrine or epinephrine. Methamphetamine is a member of the class of amphetamines in which the amino group of samphetamine carries a methyl substituent. Canadian journal of chemistry canadian science publishing. Ephedrine exhibits optical isomerism and has two chiral centres, giving rise to four stereo isomers. Why you need alevel chemistry to study pharmacy feature. Ephedrine and pseudoephedrine, their isolation, constitution. This is a document from a chemistry laboratory that. This molecule is selected based on the selfaggregating behavior through.
The optimal separation for methamphetamine was achieved by a trefoil amy1 150 x 2. The effects of varying stationary phases, alcohol modifiers, and amine additives were assessed. Ephedrine c10h15no cid 9294 structure, chemical names, physical and. Pdf chemical composition of various ephedra species. Ephedrine is a medication used to prevent low blood pressure during spinal anesthesia. Since ephedrine contains two chiral carbon atoms, four compounds are possible. From 1969, this boy my brother was able to attend school more regularly and even play sport and we had no more middle of the night trips to hospital. It was commonly used in prescription and overthecounter cough and cold preparations. Department of chemistry, mcmaster university, hamilton, ont. This is a historical archive the forum is readonly. The formation of heterobicycles by condensation of 1r, 2r. The following year, approximately 9,000 prescriptions of methamphetamine were dispensed and sold to individuals in 2018.
The total alkaloid contents of various ephedra species containing ephedrine vary from 0. How can you deduce from the structure that probenecid is. Ephedrine is a centrally acting respiratory stimulant and can increase motor activity. The reaction yields dlephedrine with a small admixture of dlpseudo ephedrine.
Illustrated glossary of organic chemistry ephedrine. Radiation chemistry, photochemistry, and photographic and other reprographic processes. In veterinary medicine, it is used to control urinary incontinence in dogs ppa is also known as. The chemical structure of ephedrine, and its isomer oh. Chemical constituents of the stems of ephedra sinica. Download download structure elucidation of ephedrine pdf read online read online structure elucidation of ephedrine pdf structural elucidation of reserpine structure elucidation of camphor ppt structure elucidation of quercetin ppt nicotine structure elucidation structural elucidation of papaverine structure elucidation of terpenoids structure elucidation of. Mullen grsc mici dublin city university september 1991 under the direction and supervision of paraic james bsc phd. The stimulants such as amphetamine, methamphetamine, ephedrine, and norephedrine are common drugs of abuse.
Ephedrine is a synthetic noncatecholamine agonist at. It is shown by c nuclear magnetic resonance spectroscopy. Ephedrinetype alkaloid content of nutritional supplements containing ephedra sinica mahuang as determined by high performance liquid chromatography b. Before 1969, adrenaline or ephedrine were used to treat asthma, and asthmatics suffered from serious side effects. In these laboratories large amounts of ephedrine have been prepared and it. It has also been used for asthma, narcolepsy, and obesity but is not the preferred treatment. It is shown by c nuclear magnetic resonance spectroscopy that the labelled c 2 fragment of 2,3 c 2pyruvic acid is transferred intact into the cmethyl group and the adjacent carbon atom of the ephedra alkaloids, norephedrine, ephedrine, norpseudoephedrine, and pseudoephedrine, in growing plants of ephedragerardiana.
The ephedrine pseudoephedrine route requires a source of the ephedrine or pseudoephedrine. A serotonin syndrome has been reported in a patient taking paroxetine and an over the counter cold medicine containing ephedrine. The altmetric attention score is a quantitative measure of the attention that a research article has received online. Methamphetamine is chemically and pharmacologically similar to amphetamine although it has more potent effec ts on.
Hive stimulants the hive discussing the chemistry of. Conformational behavior of norephedrine, ephedrine, and. Ephedrine is given as an intravenous bolus of 5 to 10 mg. On the other hand, the modern chemistry is interested in the development of new synthetic meth ods to. The success of ephedrine in the treatment of asthma and allied conditions has created a demand for the drug which encourages the search for a more easily available source or, failing this, a cheaper but effective substitute.
In patients with myasthenia gravis, administration of ephedrine sulfate injection, usp produces a real but modest increase in motor power. A pharmacological study of the ephedrine isomers pdf. It is often used to prevent low blood pressure during. The terahertz thz spectrum of the pharmaceutical 1r,2s. Two primary routes for synthesis of meth used by clandestine laboratories in the usa. Pdf synthesis, structure and biological activity of ephedra. A disadvantage of this method, noted by temnikova 9 who verified it, is the cumbersome preparation of the starting material we used propionic acid as the starting material for synthesis of ephedrine, as this acid is a byproduct in the manufacture of acetoacetic ester and can be easily obtained. Ephedrine is a sympathomimetic amine and substituted amphetamine. There is also a similarity in their chemical structure. By convention, the pair of enantiomers with the stereochemistry 1r,2s and 1s,2r is designated ephedrine, while the pair of enantiomers with the stereochemistry 1r,2r and 1s,2s is called pseudoephedrine. Chemistry stack exchange is a question and answer site for scientists, academics, teachers, and students in the field of chemistry. Synthesis of ephedrine and methcathinone from propionic acid. It is effective in the same dose range when administered intramuscularly, albeit.
The synthesis and pharmacology of ephedrine analogues a thesis submitted for the degree of master of science in chemistry by aidan j. Comprehensive reference work on the extraction and synthesis of pseudo ephedrine. A conclusive identification of the different conformers of the neurotransmitters ephedrine, norephedrine, and pseudoephedrine has been carried out in the gasphase by molecular beam fourier transform microwave mbftmw spectroscopy. As a phenethylamine, ephedrine has a similar chemical structure to amphetamines. The synthesis and pharmacology of ephedrine analogues.
Precursor is sudafed from the drug store and involves the use of reducing agents like hydrogen or hydrogen iodide and red phosphorus. Because of the presence of two asymmetric atoms, there are four isomeric forms. Ephedrine is used as a new structuredirecting agent for the synthesis of nanoporous aluminophosphates. Ephedrine sulfate drug information, uses, side effects. This finding serves to identify pyruvate as the elusive. Additionally, this molecule possesses two chiral centers, which could enhance a potential. It is in teresting to note that while ephedrine was prepared in its pure state sixteen years before epinephrine. It has also been reported to be effective in treating daytime urinary incontinence in children. A thesis submitted for the degree of master of science in chemistry. Pdf pharmacological effects of ephedrine researchgate. Pdf the medicinal significance of ephedra is based on the sympathomimetic properties of ephedrine e alkaloids. It is similar in molecular structure to phenylpropanolamine, methamphetamine, and epinephrine adrenaline. Persons with disabilities having problems accessing the pdf files below may call 301 7963634 for assistance.
417 1156 847 98 657 840 1447 346 513 955 920 319 406 1537 631 100 1485 145 1001 965 1561 234 383 485 1418 1622 868 66 99 501 367 1028 1088 678 166 91 151 1118 250 163 243 254 1401 495 1366 1153 337 1115 934 1168