Norsalsolinol Ethers
   HOME





Norsalsolinol Ethers
Norsalsolinol is a tetrahydroisoquinoline that is produced naturally in the body through the metabolism of dopamine. It has been shown to be a selective dopaminergic neurotoxin, and has been suggested as a possible cause of neurodegenerative conditions such as Parkinson's disease and the brain damage associated with alcoholism, although evidence for a causal relationship is unclear. The related compound (''R'')-salsolinol, which has been shown to be a product of ethanol metabolism, stereospecifically induces behavioral sensitization and leads to excessive alcohol intake in rats. See also * Substituted tetrahydroisoquinoline * 6-Hydroxydopamine * MPTP * Rotenone Rotenone is an odorless, colorless, crystalline isoflavone. It occurs naturally in the seeds and stems of several plants, such as the jicama vine, and in the roots of several other members of the Fabaceae. It was the first-described member of the ... References {{Phenethylamines Catechols Human pathological m ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Substituted Tetrahydroisoquinoline
A substituted tetrahydroisoquinoline is a tetrahydroisoquinoline with one or more chemical substituents. Many simple tetrahydroisoquinoline alkaloids related to mescaline are known and occur naturally in cactus species such as peyote (''Lophophora williamsii'') and ''Pachycereus pringlei'' among many others. Simple tetrahydroisoquinolines may be thought of as cyclized phenethylamines. As an example, anhalinine may be thought of as a cyclic compound, cyclized structural analog, analogue of mescaline. The simple tetrahydroisoquinolines are analogous in concept to the substituted β-carboline, β-carbolines and harmala alkaloids, which can be considered cyclized analogues of substituted tryptamine, tryptamines. Some of the simple tetrahydroisoquinolines, for instance pellotine, are known to be pharmacology, pharmacologically active, although none are known to have hallucinogenic activity. Known activities of simple tetrahydroisoquinolines include sedative and hypnotic effects, monoam ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Metabolism
Metabolism (, from ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the conversion of food to building blocks of proteins, lipids, nucleic acids, and some carbohydrates; and the elimination of metabolic wastes. These enzyme-catalyzed reactions allow organisms to grow and reproduce, maintain their Structures#Biological, structures, and respond to their environments. The word ''metabolism'' can also refer to the sum of all chemical reactions that occur in living organisms, including digestion and the transportation of substances into and between different cells, in which case the above described set of reactions within the cells is called intermediary (or intermediate) metabolism. Metabolic reactions may be categorized as ''catabolic''—the ''breaking down'' of compounds (for example, of glucose to pyruvate by c ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Dopamine
Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. It is an amine synthesized by removing a carboxyl group from a molecule of its precursor chemical, L-DOPA, which is synthesized in the brain and kidneys. Dopamine is also synthesized in plants and most animals. In the brain, dopamine functions as a neurotransmitter—a chemical released by neurons (nerve cells) to send signals to other nerve cells. The brain includes several distinct dopamine pathways, one of which plays a major role in the motivational component of reward-motivated behavior. The anticipation of most types of rewards increases the level of dopamine in the brain, and many addictive drugs increase dopamine release or block its reuptake into neurons following release. Other brain dopamine pathways are involved in motor control and in controllin ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Dopaminergic Neurotoxin
A monoamine neurotoxin, or monoaminergic neurotoxin, is a drug that selectively damages or destroys monoaminergic neurons. Monoaminergic neurons are neurons that signal via stimulation by monoamine neurotransmitters including serotonin, dopamine, and norepinephrine. Examples of monoamine neurotoxins include the serotonergic neurotoxins ''para''-chloroamphetamine (PCA), methylenedioxymethamphetamine (MDMA), and 5,7-dihydroxytryptamine (5,7-DHT); the dopaminergic neurotoxins oxidopamine (6-hydroxydopamine), MPTP, and methamphetamine; and the noradrenergic neurotoxins oxidopamine and DSP-4. In the case of serotonergic neurotoxins like MDMA, research suggests that simultaneous induction of serotonin and dopamine release, serotonin depletion, dopamine uptake and metabolism, hyperthermia, oxidative stress and antioxidant depletion, and/or drug metabolites may all be involved in the neurotoxicity. On the other hand, there is evidence that drug metabolites may not be involved. So ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Parkinson's Disease
Parkinson's disease (PD), or simply Parkinson's, is a neurodegenerative disease primarily of the central nervous system, affecting both motor system, motor and non-motor systems. Symptoms typically develop gradually and non-motor issues become more prevalent as the disease progresses. The motor symptoms are collectively called parkinsonism and include tremors, bradykinesia, spasticity, rigidity as well as postural instability (i.e., difficulty maintaining balance). Non-motor symptoms develop later in the disease and include behavior change (individual), behavioral changes or mental disorder, neuropsychiatric problems such as sleep abnormalities, psychosis, anosmia, and mood swings. Most Parkinson's disease cases are idiopathic disease, idiopathic, though contributing factors have been identified. Pathophysiology involves progressive nerve cell death, degeneration of nerve cells in the substantia nigra, a midbrain region that provides dopamine to the basal ganglia, a system invo ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Alcoholism
Alcoholism is the continued drinking of alcohol despite it causing problems. Some definitions require evidence of dependence and withdrawal. Problematic use of alcohol has been mentioned in the earliest historical records. The World Health Organization (WHO) estimated there were 283 million people with alcohol use disorders worldwide . The term ''alcoholism'' was first coined in 1852, but ''alcoholism'' and ''alcoholic'' are considered stigmatizing and likely to discourage seeking treatment, so diagnostic terms such as ''alcohol use disorder'' and ''alcohol dependence'' are often used instead in a clinical context. Alcohol is addictive, and heavy long-term alcohol use results in many negative health and social consequences. It can damage all the organ systems, but especially affects the brain, heart, liver, pancreas, and immune system. Heavy alcohol usage can result in trouble sleeping, and severe cognitive issues like dementia, brain damage, or Wernicke–Kors ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Salsolinol
Salsolinol is a substituted tetrahydroisoquinoline, tetrahydroisoquinoline derived from dopamine which plays a role in neurotransmission and is a dopaminergic neurotoxin. It has been linked to dopamine-related disorders including Parkinson's disease and alcohol use disorder. It is both synthesized in the human body and ingested in several common dietary sources. Chemistry and structure Salsolinol is a Catechol#Catechol_derivatives, catechol isoquinoline which is a yellow solid at room temperature. Salsolinol, as a chiral molecule, comes in two enantiomers: (''R'')-salsolinol and (''S'')-salsolinol. The two may have different biological effects. The racemate can be synthesized via a Pictet-Spengler reaction. A chemoenzymatic, enantioselective synthesis of the (''R'')-enantiomer has also been reported. Salsolinol has been used as a starting material to prepare some tetrahydroisoquinoline-based prospective drugs. Biochemistry Natural occurrence Salsolinol is found in several edi ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Substituted Tetrahydroisoquinoline
A substituted tetrahydroisoquinoline is a tetrahydroisoquinoline with one or more chemical substituents. Many simple tetrahydroisoquinoline alkaloids related to mescaline are known and occur naturally in cactus species such as peyote (''Lophophora williamsii'') and ''Pachycereus pringlei'' among many others. Simple tetrahydroisoquinolines may be thought of as cyclized phenethylamines. As an example, anhalinine may be thought of as a cyclic compound, cyclized structural analog, analogue of mescaline. The simple tetrahydroisoquinolines are analogous in concept to the substituted β-carboline, β-carbolines and harmala alkaloids, which can be considered cyclized analogues of substituted tryptamine, tryptamines. Some of the simple tetrahydroisoquinolines, for instance pellotine, are known to be pharmacology, pharmacologically active, although none are known to have hallucinogenic activity. Known activities of simple tetrahydroisoquinolines include sedative and hypnotic effects, monoam ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


6-Hydroxydopamine
Oxidopamine, also known as 6-hydroxydopamine (6-OHDA) or 2,4,5-trihydroxyphenethylamine, is a synthetic monoaminergic neurotoxin used by researchers to selectively destroy dopaminergic and noradrenergic neurons in the brain. The main use for oxidopamine in scientific research is to induce Parkinsonism in laboratory animals by lesioning the dopaminergic neurons of the substantia nigra pars compacta, in order to develop and test new medicines and treatments for Parkinson's disease. History The neurotoxin oxidopamine has first been described in 1959. Years later, in 1968 the first model exploiting oxidopamine neurotoxicity was developed by Ungerstedt, obtaining an animal model of akinesia with a very high mortality rate. Ever since, oxidopamine has become an abundantly used neurotoxin for making animal models with Parkinson's disease. Usage The toxin oxidopamine is an antagonist of the neurotransmitter dopamine, and is commonly used for making experimental animal models in Pa ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


MPTP
MPTP (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine) is an organic compound. It is classified as a tetrahydropyridine. It is of interest as a precursor to the monoaminergic neurotoxin MPP+, which causes permanent symptoms of Parkinson's disease by destroying dopaminergic neurons in the substantia nigra of the brain. It has been used to study disease models in various animals. While MPTP itself has no psychoactive effects, the compound may be accidentally produced during the manufacture of MPPP, a synthetic opioid drug with effects similar to those of morphine and pethidine (meperidine). The Parkinson-inducing effects of MPTP were first discovered following accidental injection as a result of contaminated MPPP. Toxicity Injection of MPTP causes rapid onset of Parkinsonism, hence users of MPPP contaminated with MPTP will develop these symptoms. MPTP itself is not toxic, but it is a lipophilic compound and can therefore cross the blood–brain barrier. Once inside the brai ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


Rotenone
Rotenone is an odorless, colorless, crystalline isoflavone. It occurs naturally in the seeds and stems of several plants, such as the jicama vine, and in the roots of several other members of the Fabaceae. It was the first-described member of the family of chemical compounds known as rotenoids. Rotenone is approved for use as a piscicide to remove alien fish species, see ''Uses.'' It has also been used as a broad-spectrum insecticide, but its use as an insecticide has been banned in many countries. Discovery The earliest written record of the now-known rotenone-containing plants used for killing leaf-eating caterpillars was in 1848; for centuries, these same plants had been used to poison fish. The active chemical component was first isolated in 1895 by a French botanist, Emmanuel Geoffroy, who called it ''nicouline'', from a specimen of ''Robinia nicou'', now called '' Deguelia utilis'', while traveling in French Guiana. He wrote about this research in his thesis, publishe ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  




Catechols
Catechol ( or ), also known as pyrocatechol or 1,2-dihydroxybenzene, is an organic compound with the molecular formula . It is the ''ortho'' isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amounts. It was first discovered by destructive distillation of the plant extract catechin. About 20,000 tonnes of catechol are now synthetically produced annually as a commodity organic chemical, mainly as a precursor to pesticides, flavors, and fragrances. Small amounts of catechol occur in fruits and vegetables. Isolation and synthesis Catechol was first isolated in 1839 by Edgar Hugo Emil Reinsch (1809–1884) by distilling it from the solid tannic preparation catechin, which is the residuum of catechu, the boiled or concentrated juice of ''Mimosa catechu'' ('' Acacia catechu''). Upon heating catechin above its decomposition point, a substance that Reinsch first named ''Brenz-Katechusäure'' (burned catechu acid) sublimated as a white efflore ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]