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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] |
2′-Acetoxycocaine
2′-Acetoxycocaine (''ortho''-acetoxy-cocaine) is a cocaine analog, with a quicker effect onset than cocaine. The acetoxy branch renders the molecule a QSAR of a 4-fold increase over cocaine in its binding potency for the dopamine transporter & a 35-fold enhanced affinity for the norepinephrine transporter. It also has a reduced selectivity for the serotonin transporter (though only due to its greater increase at NET & DAT binding being of such an order of magnitude more by comparison). In overall binding affinity (not uptake inhibition) it displaces ligands better across the board than cocaine in all monoamine categories. Salicylmethylecgonine would be an intermediate metabolite ''in vivo'' in humans (therefore affecting the overall effect profile of the administered 2′-acetoxy analog via its metabolic route; giving it nearly three times the affinity for DAT, after onset, and greaten the affinity that is would have for NET by a halve more than on upon initial exposure, after r ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ecgonine
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 Carbo ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
RTI-160
RTI-160 (benzoylecgonine dimethylamide) is a tropane derivative drug with stimulant effects, having similar potency as a dopamine reuptake inhibitor to cocaine. It is synthesized by an amide condensation reaction between benzoylecgonine and dimethylamine. See also * 3-(p-Fluorobenzoyloxy)tropane * 4′-Fluorococaine * Cocaethylene * Cocaine reverse ester * RTI-229 * 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 t ... References {{stimulants Tropanes Dopamine reuptake inhibitors Stimulants Local anesthetics Benzoate esters Dimethylamino compounds ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
List Of Cocaine Analogues
This is a list of cocaine analogues. A cocaine analogue is an (usually) artificial construct of a novel chemical compound from (often the starting point of natural) cocaine's molecular structure, with the result product sufficiently similar to cocaine to display similarity in, but alteration to, its chemical function. Within the scope of analogous compounds created from the structure of cocaine, so named "cocaine analogues" retain 3''β''-benzoyloxy or similar functionality (the term specifically used usually distinguishes from phenyltropanes, but in the broad sense generally, as a category, includes them) on a tropane skeleton, as compared to other stimulants of the kind. Many of the semi-synthetic cocaine analogues ''proper'' which have been made & studied have consisted of among the nine following classes of compounds: * stereoisomers of cocaine * 3''β''-phenyl ring substituted analogues * 2''β''-substituted analogues * ''N''-modified analogues of cocaine * 3''β''-carbamoyl ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Methylecgonine Cinnamate
Methylecgonine cinnamate is a natural tropane alkaloid found within the coca plant. Its more common name, cinnamoylcocaine, reflects its close structural similarity to cocaine. It is pharmacologically inactive,Merck Chemical Index, 1985 but some studies funded by anti-drug agencies imply that it is active when smoked. Furthermore, the discovery of differing impurity products yielding methylecgonine cinnamate in confiscated cocaine have led enforcing agencies to postulate that illicit manufacturers have changed their oxidation procedures when refining cocaine from a crude form. Methylecgonine cinnamate can dimerize to the truxillic acid derivative truxilline. Methylecgonine cinnamate is mentioned in patents of active cocaine analogue structures. See also * Coca alkaloids * 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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cocaine Reverse Ester
Cocaine reverse ester, (also known as Reverse ester cocaine or REC) is a tropane derivative drug which is a reverse ester of cocaine, with the 2-COOCH3 methoxycarbonyl group swapped to an isomeric OCOCH3 acetoxy group. It was synthesised because of the observation that the reverse ester pairs of several structurally related substances show similar activity to each other (see e.g. methylphenidate vs phacetoperane, pethidine vs desmethylprodine). Cocaine reverse ester however did not produce cocaine-like stimulant effects in animal studies, and is also illegal in many jurisdictions as a structural isomer of cocaine; nevertheless it has attracted attention from vendors of quasi-legal designer drugs as a potential alternative to cocaine. See also * 3-(p-Fluorobenzoyloxy)tropane * 4′-Fluorococaine * Benzoylecgonine * Methylecgonine cinnamate * RTI-160 * Salicylmethylecgonine Salicylmethylecgonine, (2′-Hydroxycocaine) is a tropane derivative drug which is both a synthetic ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tropane
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 In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated a ...) is known as nortropane or nor-tropane. See also * Phenyltropane * Tropane alkaloid ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Salicylate Esters
Salicylic acid is an organic compound with the formula HOC6H4COOH. A colorless (or white), bitter-tasting solid, it is a precursor to and a metabolite of acetylsalicylic acid (aspirin). It is a plant hormone, and has been listed by the EPA Toxic Substances Control Act (TSCA) Chemical Substance Inventory as an experimental teratogen. The name is from Latin for willow tree, from which it was initially identified and derived. It is an ingredient in some anti-acne products. Salts and esters of salicylic acid are known as salicylates. Uses Medicine Salicylic acid as a medication is commonly used to remove the outermost layer of the skin. As such, it is used to treat warts, psoriasis, acne vulgaris, ringworm, dandruff, and ichthyosis. Similar to other hydroxy acids, salicylic acid is an ingredient in many skincare products for the treatment of seborrhoeic dermatitis, acne, psoriasis, calluses, corns, keratosis pilaris, acanthosis nigricans, ichthyosis, and warts. Uses in ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Local Anesthetics
A local anesthetic (LA) is a medication that causes absence of all sense, sensation (including pain) in a specific body part without loss of consciousness, providing local anesthesia, as opposed to a general anesthetic, which eliminates all sensation in the entire body and causes unconsciousness. Local anesthetics are most commonly used to eliminate pain during or after surgery. When it is used on specific nerve pathways (local anesthetic nerve block), paralysis (loss of muscle function) also can be induced. Classification LAs are of 2 types: *Clinical LAs: **amino amide LAs **amino ester LAs *Synthetic LAs **Cocaine derivatives Synthetic cocaine-derived LAs differ from cocaine because they have a much lower abuse potential and do not cause hypertension vasoconstriction (with few exceptions). The suffix "-caine" at the ends of these medication names is derived from the word "cocaine", because cocaine was formerly used as a local anesthetic. Examples Short Duration of Actio ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Stimulants
Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition, mood, and physical performance. Some stimulants occur naturally, while others are exclusively synthetic. Common stimulants include caffeine, nicotine, amphetamines, cocaine, methylphenidate, and modafinil. Stimulants may be subject to varying forms of regulation, or outright prohibition, depending on jurisdiction. Stimulants increase activity in the sympathetic nervous system, either directly or indirectly. Prototypical stimulants increase synaptic concentrations of excitatory neurotransmitters, particularly norepinephrine and dopamine (e.g., methylphenidate). Other stimulants work by binding to the receptors of excitatory neurotransmitters (e.g., nicotine) or by blocking the activity of endogenous agents that promote sleep ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Dopamine Reuptake Inhibitors
A dopamine reuptake inhibitor (DRI) is a class of drug which acts as a reuptake inhibitor of the monoamine neurotransmitter dopamine by blocking the action of the dopamine transporter (DAT). Reuptake inhibition is achieved when extracellular dopamine not absorbed by the postsynaptic neuron is blocked from re-entering the presynaptic neuron. This results in increased extracellular concentrations of dopamine and increase in dopaminergic neurotransmission. DRIs are used in the treatment of attention-deficit hyperactivity disorder (ADHD) and narcolepsy for their psychostimulant effects, and in the treatment of obesity and binge eating disorder for their appetite suppressant effects. They are sometimes used as antidepressants in the treatment of mood disorders, but their use as antidepressants is limited given that strong DRIs have a high abuse potential and legal restrictions on their use. Lack of dopamine reuptake and the increase in extracellular levels of dopamine have been ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tropanes
Tropane alkaloids are a class of bicyclic .2.1alkaloids and secondary metabolites that contain a tropane ring in their chemical structure. Tropane alkaloids occur naturally in many members of the plant family Solanaceae. Certain tropane alkaloids such as cocaine and scopolamine are notorious for their psychoactive effects, related usage and cultural associations. Particular tropane alkaloids such as these have pharmacological properties and can act as anticholinergics or stimulants. Classification Anticholinergics Anticholinergic drugs and deliriants: * Atropine, racemic hyoscyamine, from the deadly nightshade ('' Atropa belladonna'') * Hyoscyamine, the ''levo''-isomer of atropine, from henbane ('' Hyoscyamus niger''), mandrake ('' Mandragora officinarum'') and the sorcerers' tree ('' Latua pubiflora''). * Scopolamine, from henbane and ''Datura'' species (Jimson weed) All three acetylcholine-inhibiting chemicals can also be found in the leaves, stems, and flowers ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
