| Methylecgonidine | |
|---|---|
 | |
| IUPAC name | Methyl (1S,5R)-8-methyl-8-azabicyclo[3. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general 2. 1]oct-3-ene-4-carboxylate |
| Other names | Anhydromethylecgonine Anhydroecgonine methyl ester |
| Identifiers | |
| CAS number | [43021-26-7] |
| PubChem | |
| SMILES | CN1[C@H]2CC[C@@H]1C(=CC2)C(=O)OC |
| Properties | |
| Molecular formula | C10H15NO2 |
| Molar mass | 181. CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 232 g/mol |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
Methylecgonidine (anhydromethylecgonine; anhydroecgonine methyl ester) is a chemical intermediate derived from ecgonine or cocaine. In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly Ecgonine is an Organic chemical and Tropane alkaloid found naturally in Coca leaves Cocaine ( benzoylmethyl ecgonine) is a Crystalline Tropane Alkaloid that is obtained from the leaves of the Coca plant
Methylecgonidine is a pyrolysis product formed when crack cocaine is smoked, making this substance a useful biomarker to specifically test for use of crack cocaine, as opposed to powder cocaine which does not form methylecgonidine as a metabolite. Pyrolysis is the Chemical decomposition of organic materials by heating in the absence of Oxygen or any other reagents except possibly Steam Crack cocaine or crack is a solid smokable form of Cocaine. It is a freebase form of cocaine that can be made using baking soda ( Sodium bicarbonate Metabolomics is the "systematic study of the unique chemical fingerprints that specific cellular processes leave behind" - specifically the study of their small-molecule metabolite [1] Methylecgonidine has a relatively short half-life of 18-21 minutes, after which it is metabolised to ecgonidine, meaning that the relative concentrations of the two compounds can be used to estimate how recently crack cocaine has been smoked. Ecgonidine (anhydroecgonine is an Alkaloid related to Ecgonine and Cocaine. Methylecgonidine has been shown to be specifically more harmful to the body than other byproducts of cocaine; for example to the heart,[2] lungs[3] & liver. [4]
It is also used in scientific research for the manufacture of phenyltropane analogues such as Troparil, Dichloropane, Iometopane and CFT. Phenyltropanes ( PTs) are a class of Cocaine -like Psychoactive Stimulants Phenyl[[tropane]] compounds comprise a large family of For other uses see Analog (disambiguation. In Chemistry, analogs or analogues are compounds in which one or Methylecgonidine could also theoretically be used to produce cocaine and so may be a controlled substance in some countries. Cocaine ( benzoylmethyl ecgonine) is a Crystalline Tropane Alkaloid that is obtained from the leaves of the Coca plant A controlled substance is generally a drug or chemical whose manufacture possession and use are regulated by a government
When methylecgonidine is made synthetically for research purposes, it is usually produced by reacting cocaine or ecgonine with hydrochloric acid, yielding ecgonidine (anhydroecgonine), followed by methylation to yield methylecgonidine. Hydrochloric acid is the Solution of Hydrogen chloride ( H[[Chlorine Cl]] in water Ecgonidine (anhydroecgonine is an Alkaloid related to Ecgonine and Cocaine. [5] Alternatively it can be made in a two step reaction by reacting 2,4,6-cycloheptatriene-7-carboxylic acid with first a mixture of methylamine and sodium hydroxide, followed by reaction with a mixture of methanol and sulfuric acid. Methylamine is the Chemical compound with a formula of CH3NH2 Sodium hydroxide ( Na[[hydroxide OH]]) also known as Lye, caustic soda and (incorrectly according to IUPAC nomenclature Methanol, also known as methyl alcohol, carbinol, wood alcohol, wood naphtha or wood spirits, is a Chemical compound Sulfuric (or sulphuric acid, H 2 S[[oxygen O]]4 is a strong Mineral acid. [6]
References
- ^ Scheidweiler KB, Plessinger MA, Shojaie J, Wood RW, Kwong TC. Pharmacokinetics and pharmacodynamics of methylecgonidine, a crack cocaine pyrolyzate. Journal of Pharmacology and Experimental Therapeutics. 2003 Dec;307(3):1179-87.
- ^ Pharmacokinetics and Pharmacodynamics of Methylecgonidine, a Crack Cocaine Pyrolyzate - Scheidweiler et al. 307 (3): 1179 Figure IG6 - Journal of Pharmacology And Experimental Therapeutics
- ^ British Journal of Pharmacology - Abstract of article: Evidence for cocaine and methylecgonidine stimulation of M2 muscarinic receptors in cultured human embryonic lung cells
- ^ Studies on Hydrolytic and Oxidative Metabolic Pathways of Anhydroecgonine Methyl Ester (Methylecgonidine) Using Microsomal Preparations from Rat Organs (Chemical Research in Toxicology/ACS Publications)
- ^ Satendra Singh. Chemistry, Design, and Structure-Activity Relationship of Cocaine Antagonists. Chemistry Reviews (2000); (100):925-1024
- ^ Kline RH, Wright J, Fox KM, Eldefrawi ME. Journal of Medicinal Chemistry. (1990); (33):2024
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