N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate
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N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate
''N'',''O''-Dimethyl-4β-(2-naphthyl)piperidine-3β-carboxylate (DMNPC) is a piperidine based stimulant drug which is synthesised from arecoline. It is similar to nocaine in chemical structure, and has two and a half times more activity than cocaine as a dopamine reuptake inhibitor. However it is also a potent serotonin reuptake inhibitor, with similar affinity to fluoxetine. Clearly it is not just the SS enantiomer of the title compound that is an active MAT inhibitor. Effect of ''N''-demethylation For the SR enantiomer, increased DAT affinity is seen upon demethylation. This is the same choice of isomer used in the production of Paxil. Simplification A substantially simpler method that ablates the carbomethoxy ester substituent can be found by D. Koch in Ex2: See also * 1-Methyl-3-propyl-4-(p-chlorophenyl)piperidine * Naphthylamphetamine * Naphyrone * List of cocaine analogues This is a list of cocaine analogues. A cocaine analogue is an (usually) artificial c ...
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1-Methyl-3-propyl-4-(p-chlorophenyl)piperidine
1-Methyl-3-propyl-4-(''p''-chlorophenyl)piperidine is a drug developed by a team led by Alan Kozikowski, which acts as a potent dopamine reuptake inhibitor, and was developed as a potential therapeutic agent for the treatment of cocaine addiction. As with related compounds such as nocaine, it is a structurally simplified derivative of related phenyltropane compounds. Its activity at the serotonin and noradrenaline transporters has not been published, though most related 4-phenylpiperidine derivatives are relatively selective for inhibiting dopamine reuptake over the other monoamine neurotransmitters. While several of its isomers are active, the (3''S'',4''S'')- enantiomer is by far the most potent. The rearranged structural isomer 2- -(4-chlorophenyl)butyliperidine is also a potent inhibitor of dopamine reuptake. See also * 4-Fluoropethidine * Allylprodine * JZ-IV-10 * N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate * WY-46824 WY-46824 is a norepinephrine-dopamine r ...
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Nocaine
(+)-CPCA (nocaine, 3α-carbomethoxy-4β-(4-chlorophenyl)-''N''-methylpiperidine aka CTDP 31,446 ) is a stimulant drug similar in structure to pethidine (an opioid that possesses NDRI actions) and to RTI-31, but nocaine is lacking the two-carbon bridge of RTI-31's tropane skeleton. This compound was first developed as a substitute agent for cocaine. Since this time many substituted phenylpiperidine derivatives have been discovered, hybridizing the basic nocaine structure with that of other similar molecules such as methylphenidate, meperidine and modafinil to create a large family of derivatives with a range of activity profiles and potential applications. This is a significant field of research with much work ongoing, and dozens of novel compounds have been developed although none have yet come to market. The nocaine family includes a diverse assortment of piperidine based cocaine mimics. The parent compound nocaine was developed in an attempt to develop a substitute drug fo ...
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Naphyrone
Naphyrone, also known as O-2482 and naphthylpyrovalerone, is a substituted cathinone drug derived from pyrovalerone that acts as a triple reuptake inhibitor, producing stimulant effects and has been reported as a novel designer drug. No safety or toxicity data is available on the drug. The drug has been marketed under the name NRG-1, although only a minority of samples of substances sold under this name have been found to actually contain naphyrone, and even samples that proved to contain genuine β-naphyrone were in some cases also found to contain the 1-naphthyl isomer α-naphyrone in varying proportions, further confusing the reported effects profile. Use in the United Kingdom Naphyrone emerged as a new legal high in the United Kingdom only months after the ban of similar drug mephedrone (which was also a cathinone derivative). Until July 2010 the substance was not controlled by the Misuse of Drugs Act 1971 and was therefore not illegal for someone to possess. The Medi ...
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Piperidine
Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic compound, heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless liquid with an odor described as objectionable, and typical of amines. The name comes from the genus name ''Piper (genus), Piper'', which is the Latin word for Black pepper, pepper. Although piperidine is a common organic compound, it is best known as a representative structure element within many pharmaceuticals and alkaloids, such as natural-occurring Solenopsin, solenopsins. Production Piperidine was first reported in 1850 by the Scottish chemist Thomas Anderson (chemist), Thomas Anderson and again, independently, in 1852 by the French chemist Auguste André Thomas Cahours, Auguste Cahours, who named it. Both of them obtained piperidine by reacting piperine with nitric acid. Industrially, piperidine is produced by the hydrogenation o ...
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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 a ...
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Naphthylamphetamine
Naphthylaminopropane (PAL-287) is an experimental drug under investigation as of 2007 for the treatment of alcohol and stimulant addiction. Naphthylisopropylamine acts as a non-neurotoxic releasing agent of serotonin, norepinephrine, and dopamine, with EC50 values of 3.4 nM, 11.1 nM, and 12.6 nM, respectively. It also has affinity for the 5-HT2A, 5-HT2B, and 5-HT2C receptors (EC50 values = 466 nM, 40 nM, and 2.3 nM, respectively), and acts as a full agonist at 5-HT2B and as a partial agonist at 5-HT2C, while its affinity for 5-HT2A is probably too low to be significant. In animal studies, naphthylisopropylamine was shown to reduce cocaine self-administration, yet produced relatively weak stimulant effects when administered alone, being a (much) lesser stimulant than d-amphetamine for comparison. Further research is now being conducted in primates to see if it will be a useful substitute for treating drug addiction in humans as well. An important observation is that in ...
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Paxil
Paroxetine, sold under the brand names Paxil and Seroxat among others, is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. It is used to treat major depressive disorder, obsessive-compulsive disorder, panic disorder, social anxiety disorder, posttraumatic stress disorder, generalized anxiety disorder and premenstrual dysphoric disorder. It has also been used in the treatment of premature ejaculation and hot flashes due to menopause. It is taken by mouth. Common side effects include drowsiness, dry mouth, loss of appetite, sweating, trouble sleeping, and sexual dysfunction. Serious side effects may include suicidal thoughts in those under the age of 25, serotonin syndrome, and mania. While the rate of side effects appears similar compared to other SSRIs and SNRIs, antidepressant discontinuation syndromes may occur more often. Use in pregnancy is not recommended, while use during breastfeeding is relatively safe. It is believed to work by blocking t ...
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Stimulant
Stimulants (also often referred to as psychostimulants or colloquially as uppers) is an overarching term that covers many drugs including those that increase activity of the central nervous system and the body, drugs that are pleasurable and invigorating, or drugs that have Sympathomimetic drug, sympathomimetic effects. Stimulants are widely used throughout the world as prescription medicines as well as without a prescription (either legally or Prohibition (drugs), illicitly) as performance-enhancing substance, performance-enhancing or recreational drug use, recreational drugs. Among narcotics, stimulants produce a noticeable crash or ''Comedown (drugs), comedown'' at the end of their effects. The most frequently prescribed stimulants as of 2013 were lisdexamfetamine (Vyvanse), methylphenidate (Ritalin), and amphetamine (Adderall). It was estimated in 2015 that the percentage of the world population that had used cocaine during a year was 0.4%. For the category "amphetamines and p ...
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Fluoxetine
Fluoxetine, sold under the brand names Prozac and Sarafem, among others, is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. It is used for the treatment of major depressive disorder, obsessive–compulsive disorder (OCD), bulimia nervosa, panic disorder, and premenstrual dysphoric disorder. It is also approved for treatment of major depressive disorder in adolescents and children 8 years of age and over. It has also been used to treat premature ejaculation. Fluoxetine is taken by mouth. Common side effects include indigestion, trouble sleeping, sexual dysfunction, loss of appetite, dry mouth, and rash. Serious side effects include serotonin syndrome, mania, seizures, an increased risk of suicidal behavior in people under 25 years old, and an increased risk of bleeding. Antidepressant discontinuation syndrome is less likely to occur with fluoxetine than with other antidepressants, but it still happens in many cases. Fluoxetine taken during pregnan ...
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