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Ecogonine
Ecgonine (tropane derivative) is a tropane alkaloid found naturally in coca leaves. It has a close structural relation to cocaine: it is both a metabolite and a precursor, and as such, it is a controlled substance in many jurisdictions, as are some substances which can be used as precursors to ecgonine itself. Structurally, ecgonine is a cycloheptane derivative with a nitrogen bridge. It is obtained by hydrolysis of cocaine with acids or alkalis, and crystallizes with one molecule of water, the crystals melting at 198–199 °C. It is levorotary, and on warming with alkalis gives iso-ecgonine, which is dextrorotary. It is a tertiary base, and has the properties of an acid and an alcohol. It is the carboxylic acid corresponding to tropine, for it yields the same products on oxidation, and by treatment with phosphorus pentachloride is converted into anhydroecgonine, C9H13NO2, which, when heated to 280 °C with hydrochloric acid, eliminates carbon dioxide and yields trop ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tropane
Tropane is a nitrogenous Bicyclic molecule, bicyclic organic compound. It is mainly known for the other alkaloids derived from it, which include atropine and cocaine, among others. Tropane alkaloids occur in plants of the families Erythroxylaceae (including coca) and Solanaceae (including Mandragora officinarum, mandrake, henbane, deadly nightshade, datura, potato, tomato). Structurally, tropane is cycloheptane with a nitrogen bridge between carbons 1 and 5 and an additional methyl group attached to the nitrogen. While carbons 1 and 5 are asymmetric carbons, tropane itself is optically inactive due to mirror symmetry. 8-Azabicyclo[3.2.1]octane (tropane without the ''N''-methyl group) is known as nortropane or nor-tropane. See also * Phenyltropane * Tropane alkaloid * Tropine References {{Reflist Tropanes, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phosphorus Pentachloride
Phosphorus pentachloride is the chemical compound with the formula PCl5. It is one of the most important phosphorus chlorides, others being PCl3 and POCl3. PCl5 finds use as a chlorinating reagent. It is a colourless, water-sensitive and moisture-sensitive solid, although commercial samples can be yellowish and contaminated with hydrogen chloride. Structure The structures for the phosphorus chlorides are invariably consistent with VSEPR theory. The structure of PCl5 depends on its environment. Gaseous and molten PCl5 is a neutral molecule with trigonal bipyramidal geometry and (''D''3h) symmetry. The hypervalent nature of this species (as well as of , see below) can be explained with the inclusion of non-bonding molecular orbitals (molecular orbital theory) or resonance (valence bond theory). This trigonal bipyramidal structure persists in nonpolar solvents, such as CS2 and CCl4. In the solid state PCl5 is an ionic compound, formulated . In solutions of polar solvents, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tropane Alkaloids Found In Erythroxylum Coca
Tropane is a nitrogenous bicyclic organic compound. It is mainly known for the other alkaloids derived from it, which include atropine and cocaine, among others. Tropane alkaloids occur in plants of the families Erythroxylaceae (including coca) and Solanaceae (including mandrake, henbane, deadly nightshade, datura, potato, tomato). Structurally, tropane is cycloheptane with a nitrogen bridge between carbons 1 and 5 and an additional methyl group attached to the nitrogen. While carbons 1 and 5 are asymmetric carbons, tropane itself is optically inactive due to mirror symmetry. 8-Azabicyclo .2.1ctane (tropane without the ''N''-methyl group) is known as nortropane or nor-tropane. See also * Phenyltropane * Tropane alkaloid * Tropine Tropine is a derivative of tropane containing a hydroxyl group at the third carbon. It is also called 3-tropanol. Tropine is a central building block of many chemicals active in the nervous system, including tropane alkaloids. Some of these comp . ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Troparil
Troparil (also known as (–)-2β-Carbomethoxy-3β-phenyltropane, WIN 35,065-2, or β-CPT) is a stimulant drug used in scientific research. Troparil is a phenyltropane-based dopamine reuptake inhibitor (DRI) that is derived from methylecgonidine. Troparil is a few times more potent than cocaine as a dopamine reuptake inhibitor, but is less potent as a serotonin reuptake inhibitor, and has a duration spanning a few times longer, since the phenyl ring is directly connected to the tropane ring through a non-hydrolyzable carbon-carbon bond. The lack of an ester linkage removes the local anesthetic action from the drug, so troparil is a pure stimulant. This change in activity also makes troparil slightly less cardiotoxic than cocaine. The most commonly used form of troparil is the tartrate salt, but the hydrochloride and naphthalenedisulfonate salts are also available, as well as the free base. Background The first known published synthesis of troparil and the related compound WIN 354 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tropinone
Tropinone is an alkaloid, famously synthesised in 1917 by Robert Robinson as a synthetic precursor to atropine, a scarce commodity during World War I. Tropinone and the alkaloids cocaine and atropine all share the same tropane core structure. Its corresponding conjugate acid at pH 7.3 major species is known as tropiniumone. Synthesis The first synthesis of tropinone was by Richard Willstätter in 1901. It started from the seemingly related cycloheptanone, but required many steps to introduce the nitrogen bridge; the overall yield for the synthesis path is only 0.75%. Willstätter had previously synthesized cocaine from tropinone, in what was the first synthesis and elucidation of the structure of cocaine. Robinson's "double Mannich" reaction The 1917 synthesis by Robinson is considered a classic in total synthesis due to its simplicity and biomimetic approach. Tropinone is a bicyclic molecule, but the reactants used in its preparation are fairly simple: succinaldehyde, met ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Salicylmethylecgonine
Salicylmethylecgonine, (2′-Hydroxycocaine) is a tropane derivative drug which is both a synthetic analogue and a possible active metabolite of cocaine. Its potency ''in vitro'' is around 10x that of cocaine, although it is only around three times more potent than cocaine when administered to mice (likely owing to it having a higher LogP: 2.89 than that of cocaine: 2.62) Note however that the compound 2′-Acetoxycocaine would act as a prodrug to Salicylmethylecgonine in humans, and has a more efficient partition coefficient which would act as a delivery system and would circumvent this reason for a drop in potency. Salicylmethylecgonine also shows increased behavioral stimulation compared to cocaine similar to the phenyltropanes. The hydroxy branch renders the molecule a QSAR of a 10-fold increase over cocaine in its binding potency for the dopamine transporter & a 52-fold enhanced affinity for the norepinephrine transporter. It also has a reduced selectivity for the seroton ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Methylecgonidine
Methylecgonidine (anhydromethylecgonine; anhydroecgonine methyl ester; AEME) is a chemical intermediate derived from ecgonine or cocaine. 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. 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. Methylecgonidine has been shown to be specifically more harmful to the body than other byproducts of cocaine; for example to the heart, lungs & liver. The toxicity is due to a partial agonist effect at M1 and M3 muscarinic receptors, leading to DNA fragmentation and neuronal death by apoptosis. AEME is also used in scientific research for the manufacture of p ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Dihydrocuscohygrine
Dihydrocuscohygrine is an alkaloid that has been isolated from coca leaves. See also * Cuscohygrine * Pseudotropine Pseudotropine (3β-tropanol, ψ-tropine, 3-pseudotropanol, or PTO) is a derivative of tropane and an isomer of tropine. Pseudotropine can be found in the ''Coca'' plant along with several other alkaloids See also * Pseudotropine acyltransfe ... References {{alkaloid-stub Alkaloids found in Erythroxylum coca ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cocaethylene
Cocaethylene (ethylbenzoylecgonine) is the ethyl ester of benzoylecgonine. It is structurally similar to cocaine, which is the methyl ester of benzoylecgonine. Cocaethylene is formed by the liver when cocaine and ethanol coexist in the blood. In 1885, cocaethylene was first synthesized (according to edition 13 of the ''Merck Index''), and in 1979, cocaethylene's side effects were discovered. Metabolic production from cocaine Cocaethylene is the byproduct of concurrent consumption of alcohol and cocaine as metabolized by the liver. Normally, metabolism of cocaine produces two primarily biologically inactive metabolites—benzoylecgonine and ecgonine methyl ester. The hepatic enzyme carboxylesterase is an important part of cocaine's metabolism because it acts as a catalyst for the hydrolysis of cocaine in the liver, which produces these inactive metabolites. If ethanol is present during the metabolism of cocaine, a portion of the cocaine undergoes transesterification with ethanol, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Anhydroecgonine
Ecgonidine (anhydroecgonine) is an alkaloid related to ecgonine and cocaine. It has a structure with a cycloheptene ring, with a nitrogen bridge, and a carboxylic acid side chain. Methylecgonidine is produced by pyrolysis in the process of smoking crack cocaine, and then subsequently metabolised to ecgonidine, and so these two compounds can be tested for as a specific biomarker for crack cocaine use. Ecgonidine is formed as a metabolite of methylecgonidine, and so the relative concentrations of the two compounds can be used to gauge how recently crack cocaine was smoked. If levels of methylecgonidine are higher, then the drug was smoked recently; however after a longer time period mainly ecgonidine will be present. Ecgonidine has a half-life in the body of around 94–137 minutes, and so can be used to detect use of crack cocaine up to 8–10 hours after the drug is consumed. See also * Coca alkaloids * Ecgonine * Tropacocaine Tropacocaine (tropacaine, benzoylpseudotropine, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Coca Alkaloid
Coca alkaloids are the alkaloids found in the coca plant, ''Erythroxylum coca''.Variation of Alkaloid Content in Erythroxylum coca Leaves from Leaf Bud to Leaf Drop. Emanuel L. Johnson and Stephen D. Emche, Ann. Bot., 1994, volume 73, issue 6, pages 645-650, They are predominantly of either the pyrrolidine or the tropane types. __NOTOC__ Tropane-type alkaloids * Benzoylecgonine * Cocaine * Ecgonidine * Ecgonine * Hydroxytropacocaine * Methylecgonine cinnamate * Tropacocaine * Truxilline Pyrrolidine-type alkaloids * Cuscohygrine * Dihydrocuscohygrine * Hygrine * Nicotine See also * Cocaine metabolites (Human) * Coca wine, an alcoholic beverage combining wine with extracted coca alkaloids * Methylecgonidine * Troparil Troparil (also known as (–)-2β-Carbomethoxy-3β-phenyltropane, WIN 35,065-2, or β-CPT) is a stimulant drug used in scientific research. Troparil is a phenyltropane-based dopamine reuptake inhibitor (DRI) that is derived from methylecgonidine ... R ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
