Alkaloids
Alkaloids are a group of naturally occurring chemical compounds, that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure are also attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
Alkaloids are produced by a large variety of organisms, including bacteria, fungi, plants, and animals, and are part of the group of natural products (also called secondary metabolites). Many alkaloids can be purified from crude extracts by acid-base extraction. Many alkaloids are toxic to other organisms. They often have pharmacological effects and are used as medications, as recreational drugs, or in entheogenic rituals. Examples are the local anesthetic and stimulant cocaine; the psychedelic psilocin; the stimulant caffeine; nicotine; the analgesic morphine; the antibacterial berberine; the anticancer compound vincristine; the antihypertension agent reserpine; the cholinomimeric galantamine; the spasmolysis agent atropine; the vasodilator vincamine; the anti-arhythmia compound quinidine; the anti-asthma therapeutic ephedrine; and the antimalarial drug quinine. Although alkaloids act on a diversity of metabolic systems in humans and other animals, they almost uniformly invoke a bitter taste.
The boundary between alkaloids and other nitrogen-containing natural compounds is not clear-cut. Compounds like amino acid peptides, proteins, nucleotides, nucleic acid, amines, and antibiotics are usually not called alkaloids. Natural compounds containing nitrogen in the exocyclic position (mescaline, serotonin, dopamine, etc.) are usually attributed to amines rather than alkaloids. Some authors, however, consider alkaloids a special case of amines.
Alkaloids are often divided into the following major groups:
"True alkaloids", which contain nitrogen in the heterocycle and originate from amino acids. Their characteristic examples are atropine, nicotine, and morphine. This group also includes some alkaloids that besides nitrogen heterocycle contain terpene (e.g., evonine ) or peptide fragments (e.g. ergotamine ). This group also includes piperidine alkaloids coniine and coniceine although they do not originate from amino acids.
"Protoalkaloids", which contain nitrogen and also originate from amino acids. Examples include mescaline, adrenaline and ephedrine.
Polyamine alkaloids – derivatives of putrescine, spermidine, and spermine.
Peptide and cyclopeptide alkaloids.
Pseudalkaloids – alkaloid-like compounds that do not originate from amino acids. This group includes, terpene-like and steroid-like alkaloids, as well as purine-like alkaloids such as caffeine, theobromine, theacrine and theophylline. Some authors classify as pseudoalkaloids such compounds such as ephedrine and cathinone. Those originate from the amino acid phenylalanine, but acquire their nitrogen atom not from the amino acid but through transamination.
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How does one define the difference between Cocoa, and Coca?
Cocoa is the common name for the bean of the cacao plant (note the different spelling) and the products that result from processing those beans after drying, roasting and grinding, not unlike the process for coffee. You are correct that cocoa is the primary ingredient in chocolate, in the form of cocoa powder, cocoa butter and cocoa solids.
The leaves of the coca plant (which is completely different from and in no way related to the cacao plant) contain a variety of naturally occurring chemical compounds called alkaloids, and one of the alkaloids found in the coca leaf is cocaine, a powerful and highly addictive stimulant. Coca leaves are used medicinally by the local peoples of western South America in teas and by chewing them, but of course it is most popularly used to produce cocaine.
The formula for Coca-cola originally contained an extract from the coca leaf, but not actual cocaine as we know it. Coca-cola was originally developed as a medicinal tonic, so the inclusion of coca extract and caffeine produced a stimulant effect, which made the drinker feel better, at least for a little while.
---------------
Cocaine
Cocaine (INN) (benzoylmethylecgonine, an ecgonine derivative) is a crystalline tropane alkaloid that is obtained from the leaves of the coca plant. The name comes from "coca" and the alkaloid suffix "-ine", forming "cocaine". It is a stimulant, an appetite suppressant, and a nonspecific voltage gated sodium channel blocker, which in turn causes it to produce anaesthesia at low doses. Biologically, cocaine acts as a serotonin–norepinephrine–dopamine reuptake inhibitor, also known as a triple reuptake inhibitor (TRI). It is addictive because of its effect on the mesolimbic reward pathway. It is markedly more dangerous than other CNS stimulants, including the entire amphetamine drug class, at high doses due to its effect on sodium channels, as blockade of Nav1.5 can cause sudden cardiac death.
Unlike most molecules, cocaine has pockets with both high hydrophilic and lipophilic efficiency, violating the rule of hydrophilic-lipophilic balance. This causes it to cross the blood–brain barrier far better than other psychoactive chemicals and may even induce blood-brain barrier breakdown.
It is controlled internationally by the Single Convention on Narcotic Drugs (Schedule I, preparation in Schedule III).
----------------
Atropine
Atropine is a naturally occurring tropane alkaloid extracted from deadly nightshade (Atropa belladonna), Jimson weed (Datura stramonium), mandrake (Mandragora officinarum) and other plants of the family Solanaceae. It is a secondary metabolite of these plants and serves as a drug with a wide variety of effects.
In general, atropine counters the "rest and digest" activity of glands regulated by the parasympathetic nervous system. This occurs because atropine is a competitive antagonist of the muscarinic acetylcholine receptors (acetylcholine being the main neurotransmitter used by the parasympathetic nervous system). Atropine dilates the pupils, increases heart rate, and reduces salivation and other secretions.
Atropine is a core medicine in the World Health Organization's "Essential Drugs List", which is a list of minimum medical needs for a basic health care system.
------------------
Nicotine
Nicotine is a potent parasympathomimetic alkaloid found in the nightshade family of plants (Solanaceae) and a stimulant drug. It is a nicotinic acetylcholine receptor agonist. It is made in the roots and accumulates in the leaves of the plants. It constitutes approximately 0.6–3.0% of the dry weight of tobacco and is present in the range of 2–7 µg/kg of various edible plants. It functions as an antiherbivore chemical; consequently, nicotine was widely used as an insecticide in the past and nicotine analogs such as imidacloprid are currently widely used.
In smaller doses (an average cigarette yields about 1 mg of absorbed nicotine), the substance acts as a stimulant in mammals, while high amounts (500–1000 mg) can be harmful. This stimulant effect is likely a major contributing factor to the dependence-forming properties of tobacco smoking. According to the American Heart Association, nicotine addiction has historically been one of the hardest addictions to break, while the pharmacological and behavioral characteristics that determine tobacco addiction are similar to those determining addiction to heroin and cocaine. The nicotine content of popular American-brand cigarettes has slowly increased over the years, and one study found that there was an average increase of 1.78% per year between the years of 1998 and 2005. This was found for all major market categories of cigarettes.
Research in 2011 found that nicotine inhibits chromatin-modifying enzymes (class I and II histone deacetylases); this inhibition has been shown to increase the ability of cocaine to cause an addiction.
-----------------
Morphine
Morphine (INN) (/ˈmɔrfiːn/; MS Contin, MSIR, Avinza, Kadian, Oramorph, Roxanol, Kapanol) is a potent opiate analgesic drug that is used to relieve severe pain. It was first isolated in 1804 by Friedrich Sertürner, which is generally believed to be the first ever isolation of a natural plant alkaloid in history. It was first distributed by him in 1817; and first commercially sold by Merck in 1827, which at the time was a single small chemists' shop. It was more widely used after the invention of the hypodermic needle in 1857. Sertürner originally named the substance morphium after the Greek god of dreams Morpheus (Greek: Μορφεύς) for its tendency to cause sleep.
After it was isolated from opium by Sertürner, the traditional way to obtain morphine had been by chemical processing of opium. In India, opium harvested by licensed poppy farmers is dehydrated to uniform levels of hydration at government processing centers, and then sold to pharmaceutical companies, which extract morphine from the opium. However in Turkey and Tasmania morphine is obtained by harvesting and processing the fully mature dry seed pods, with attached stalks, called poppy straw. By not harvesting opium at all, and by obtaining morphine only from the dry poppy straw, and not from opium, and by using a large scale industrial process to do so, at factories located near the poppy farms, opportunities for illicitly diverting opium from the crop, and for illicit production of morphine, and heroin from the opium, are reduced. In Turkey, a water extraction process is used. In Tasmania, a solvent extraction process is used.
Morphine is the most abundant opiate found in opium, the dried latex extracted by shallowly slicing the unripe seedpods of the Papaver somniferum poppy. Morphine was the first active principle purified from a plant source and is one of at least 50 alkaloids of several different types present in opium, poppy straw concentrate, and other poppy derivatives. Morphine is generally 8 to 14 percent of the dry weight of opium, although specially bred cultivars reach 26 percent or produce little morphine at all (under 1 percent, perhaps down to 0.04 percent). The latter varieties, including the 'Przemko' and 'Norman' cultivars of the opium poppy, are used to produce two other alkaloids, thebaine and oripavine, which are used in the manufacture of semi-synthetic and synthetic opioids like oxycodone and etorphine and some other types of drugs. P. bracteatum does not contain morphine or codeine, or other narcotic phenanthrene-type, alkaloids. This species is rather a source of thebaine. Occurrence of morphine in other Papaverales and Papaveraceae, as well as in some species of hops and mulberry trees has not been confirmed. Morphine is produced most predominantly early in the life cycle of the plant. Past the optimum point for extraction, various processes in the plant produce codeine, thebaine, and in some cases negligible amounts of hydromorphone, dihydromorphine, dihydrocodeine, tetrahydro-thebaine, and hydrocodone (these compounds are rather synthesized from thebaine and oripavine). The human body produces endorphins, which are endogenous opioid peptides that function as neurotransmitters and have similar effects.
In clinical medicine, morphine is regarded as the gold standard, or benchmark, of opioid analgesics used to relieve severe or agonizing pain and suffering. Like other opioids, such as oxycodone, hydromorphone, and diacetylmorphine (heroin), morphine acts directly on the central nervous system (CNS) to relieve pain.
Morphine has a high potential for addiction; tolerance and psychological dependence develop rapidly, although physiological dependence may take several months to develop.
Tolerance to respiratory depression and euphoria develops more rapidly than tolerance to analgesia, and many chronic pain patients are being maintained on a stable dose, for many years.
--------------
Caffeine
Caffeine is a bitter, white crystalline xanthine alkaloid and a stimulant drug. Caffeine is found in varying quantities in the seeds, leaves, and fruit of some plants, where it acts as a natural pesticide that paralyzes and kills certain insects feeding on the plants, as well as enhancing the reward memory of pollinators. It is most commonly consumed by humans in infusions extracted from the seed of the coffee plant and the leaves of the tea bush, as well as from various foods and drinks containing products derived from the kola nut. Other sources include yerba maté, guarana berries, guayusa, and the yaupon holly.
In humans, caffeine acts as a central nervous system stimulant, temporarily warding off drowsiness and restoring alertness. Studies have shown that caffeine potentially induces chromosomal aberrations, and shows both teratogenic and mutagenic properties. It is the world's most widely consumed psychoactive drug, but unlike many other psychoactive substances, it is legal and unregulated in nearly all parts of the world. Beverages containing caffeine, such as coffee, tea, soft drinks, and energy drinks, enjoy great popularity. In North America, 90% of adults consume caffeine daily.
Part of the reason caffeine is classified by the Food and Drug Administration as GRAS (generally recognized as safe) is that toxic doses (over 10 grams for an average adult) are much higher than typically used doses (less than 500 milligrams). Ordinary consumption can have low health risks, even when carried on for years – there may be a modest protective effect against some diseases, including Parkinson's disease, and certain types of cancer. Some people experience sleep disruption if they consume caffeine, especially during the evening hours, but others show little disturbance and the effect of caffeine on sleep is highly variable.
Evidence of a risk to pregnancy is equivocal, but some authorities have concluded that prudent advice is for pregnant women to limit consumption to the equivalent of two cups of coffee per day or less. The American Congress of Obstetricians and Gynecologists (ACOG) concluded in 2010 that caffeine consumption is safe up to 200 mg per day in pregnant women. Caffeine has pressor and mild diuretic effects when administered to people who are not used to it, but regular users develop a tolerance to this effect, and studies have generally failed to support the common notion that ordinary consumption contributes significantly to dehydration. With heavy use, tolerance develops rapidly to autonomic effects such as elevated heart rate and muscle twitching, but not to the cognitive or arousal effects of caffeine. The degree to which caffeine can produce clinically significant dependency and addiction remains a subject of controversy in the medical literature.
Alkaloids are a group of naturally occurring chemical compounds, that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure are also attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
Alkaloids are produced by a large variety of organisms, including bacteria, fungi, plants, and animals, and are part of the group of natural products (also called secondary metabolites). Many alkaloids can be purified from crude extracts by acid-base extraction. Many alkaloids are toxic to other organisms. They often have pharmacological effects and are used as medications, as recreational drugs, or in entheogenic rituals. Examples are the local anesthetic and stimulant cocaine; the psychedelic psilocin; the stimulant caffeine; nicotine; the analgesic morphine; the antibacterial berberine; the anticancer compound vincristine; the antihypertension agent reserpine; the cholinomimeric galantamine; the spasmolysis agent atropine; the vasodilator vincamine; the anti-arhythmia compound quinidine; the anti-asthma therapeutic ephedrine; and the antimalarial drug quinine. Although alkaloids act on a diversity of metabolic systems in humans and other animals, they almost uniformly invoke a bitter taste.
The boundary between alkaloids and other nitrogen-containing natural compounds is not clear-cut. Compounds like amino acid peptides, proteins, nucleotides, nucleic acid, amines, and antibiotics are usually not called alkaloids. Natural compounds containing nitrogen in the exocyclic position (mescaline, serotonin, dopamine, etc.) are usually attributed to amines rather than alkaloids. Some authors, however, consider alkaloids a special case of amines.
Alkaloids are often divided into the following major groups:
"True alkaloids", which contain nitrogen in the heterocycle and originate from amino acids. Their characteristic examples are atropine, nicotine, and morphine. This group also includes some alkaloids that besides nitrogen heterocycle contain terpene (e.g., evonine ) or peptide fragments (e.g. ergotamine ). This group also includes piperidine alkaloids coniine and coniceine although they do not originate from amino acids.
"Protoalkaloids", which contain nitrogen and also originate from amino acids. Examples include mescaline, adrenaline and ephedrine.
Polyamine alkaloids – derivatives of putrescine, spermidine, and spermine.
Peptide and cyclopeptide alkaloids.
Pseudalkaloids – alkaloid-like compounds that do not originate from amino acids. This group includes, terpene-like and steroid-like alkaloids, as well as purine-like alkaloids such as caffeine, theobromine, theacrine and theophylline. Some authors classify as pseudoalkaloids such compounds such as ephedrine and cathinone. Those originate from the amino acid phenylalanine, but acquire their nitrogen atom not from the amino acid but through transamination.
--------------
How does one define the difference between Cocoa, and Coca?
Cocoa is the common name for the bean of the cacao plant (note the different spelling) and the products that result from processing those beans after drying, roasting and grinding, not unlike the process for coffee. You are correct that cocoa is the primary ingredient in chocolate, in the form of cocoa powder, cocoa butter and cocoa solids.
The leaves of the coca plant (which is completely different from and in no way related to the cacao plant) contain a variety of naturally occurring chemical compounds called alkaloids, and one of the alkaloids found in the coca leaf is cocaine, a powerful and highly addictive stimulant. Coca leaves are used medicinally by the local peoples of western South America in teas and by chewing them, but of course it is most popularly used to produce cocaine.
The formula for Coca-cola originally contained an extract from the coca leaf, but not actual cocaine as we know it. Coca-cola was originally developed as a medicinal tonic, so the inclusion of coca extract and caffeine produced a stimulant effect, which made the drinker feel better, at least for a little while.
---------------
Cocaine
Cocaine (INN) (benzoylmethylecgonine, an ecgonine derivative) is a crystalline tropane alkaloid that is obtained from the leaves of the coca plant. The name comes from "coca" and the alkaloid suffix "-ine", forming "cocaine". It is a stimulant, an appetite suppressant, and a nonspecific voltage gated sodium channel blocker, which in turn causes it to produce anaesthesia at low doses. Biologically, cocaine acts as a serotonin–norepinephrine–dopamine reuptake inhibitor, also known as a triple reuptake inhibitor (TRI). It is addictive because of its effect on the mesolimbic reward pathway. It is markedly more dangerous than other CNS stimulants, including the entire amphetamine drug class, at high doses due to its effect on sodium channels, as blockade of Nav1.5 can cause sudden cardiac death.
Unlike most molecules, cocaine has pockets with both high hydrophilic and lipophilic efficiency, violating the rule of hydrophilic-lipophilic balance. This causes it to cross the blood–brain barrier far better than other psychoactive chemicals and may even induce blood-brain barrier breakdown.
It is controlled internationally by the Single Convention on Narcotic Drugs (Schedule I, preparation in Schedule III).
----------------
Atropine
Atropine is a naturally occurring tropane alkaloid extracted from deadly nightshade (Atropa belladonna), Jimson weed (Datura stramonium), mandrake (Mandragora officinarum) and other plants of the family Solanaceae. It is a secondary metabolite of these plants and serves as a drug with a wide variety of effects.
In general, atropine counters the "rest and digest" activity of glands regulated by the parasympathetic nervous system. This occurs because atropine is a competitive antagonist of the muscarinic acetylcholine receptors (acetylcholine being the main neurotransmitter used by the parasympathetic nervous system). Atropine dilates the pupils, increases heart rate, and reduces salivation and other secretions.
Atropine is a core medicine in the World Health Organization's "Essential Drugs List", which is a list of minimum medical needs for a basic health care system.
------------------
Nicotine
Nicotine is a potent parasympathomimetic alkaloid found in the nightshade family of plants (Solanaceae) and a stimulant drug. It is a nicotinic acetylcholine receptor agonist. It is made in the roots and accumulates in the leaves of the plants. It constitutes approximately 0.6–3.0% of the dry weight of tobacco and is present in the range of 2–7 µg/kg of various edible plants. It functions as an antiherbivore chemical; consequently, nicotine was widely used as an insecticide in the past and nicotine analogs such as imidacloprid are currently widely used.
In smaller doses (an average cigarette yields about 1 mg of absorbed nicotine), the substance acts as a stimulant in mammals, while high amounts (500–1000 mg) can be harmful. This stimulant effect is likely a major contributing factor to the dependence-forming properties of tobacco smoking. According to the American Heart Association, nicotine addiction has historically been one of the hardest addictions to break, while the pharmacological and behavioral characteristics that determine tobacco addiction are similar to those determining addiction to heroin and cocaine. The nicotine content of popular American-brand cigarettes has slowly increased over the years, and one study found that there was an average increase of 1.78% per year between the years of 1998 and 2005. This was found for all major market categories of cigarettes.
Research in 2011 found that nicotine inhibits chromatin-modifying enzymes (class I and II histone deacetylases); this inhibition has been shown to increase the ability of cocaine to cause an addiction.
-----------------
Morphine
Morphine (INN) (/ˈmɔrfiːn/; MS Contin, MSIR, Avinza, Kadian, Oramorph, Roxanol, Kapanol) is a potent opiate analgesic drug that is used to relieve severe pain. It was first isolated in 1804 by Friedrich Sertürner, which is generally believed to be the first ever isolation of a natural plant alkaloid in history. It was first distributed by him in 1817; and first commercially sold by Merck in 1827, which at the time was a single small chemists' shop. It was more widely used after the invention of the hypodermic needle in 1857. Sertürner originally named the substance morphium after the Greek god of dreams Morpheus (Greek: Μορφεύς) for its tendency to cause sleep.
After it was isolated from opium by Sertürner, the traditional way to obtain morphine had been by chemical processing of opium. In India, opium harvested by licensed poppy farmers is dehydrated to uniform levels of hydration at government processing centers, and then sold to pharmaceutical companies, which extract morphine from the opium. However in Turkey and Tasmania morphine is obtained by harvesting and processing the fully mature dry seed pods, with attached stalks, called poppy straw. By not harvesting opium at all, and by obtaining morphine only from the dry poppy straw, and not from opium, and by using a large scale industrial process to do so, at factories located near the poppy farms, opportunities for illicitly diverting opium from the crop, and for illicit production of morphine, and heroin from the opium, are reduced. In Turkey, a water extraction process is used. In Tasmania, a solvent extraction process is used.
Morphine is the most abundant opiate found in opium, the dried latex extracted by shallowly slicing the unripe seedpods of the Papaver somniferum poppy. Morphine was the first active principle purified from a plant source and is one of at least 50 alkaloids of several different types present in opium, poppy straw concentrate, and other poppy derivatives. Morphine is generally 8 to 14 percent of the dry weight of opium, although specially bred cultivars reach 26 percent or produce little morphine at all (under 1 percent, perhaps down to 0.04 percent). The latter varieties, including the 'Przemko' and 'Norman' cultivars of the opium poppy, are used to produce two other alkaloids, thebaine and oripavine, which are used in the manufacture of semi-synthetic and synthetic opioids like oxycodone and etorphine and some other types of drugs. P. bracteatum does not contain morphine or codeine, or other narcotic phenanthrene-type, alkaloids. This species is rather a source of thebaine. Occurrence of morphine in other Papaverales and Papaveraceae, as well as in some species of hops and mulberry trees has not been confirmed. Morphine is produced most predominantly early in the life cycle of the plant. Past the optimum point for extraction, various processes in the plant produce codeine, thebaine, and in some cases negligible amounts of hydromorphone, dihydromorphine, dihydrocodeine, tetrahydro-thebaine, and hydrocodone (these compounds are rather synthesized from thebaine and oripavine). The human body produces endorphins, which are endogenous opioid peptides that function as neurotransmitters and have similar effects.
In clinical medicine, morphine is regarded as the gold standard, or benchmark, of opioid analgesics used to relieve severe or agonizing pain and suffering. Like other opioids, such as oxycodone, hydromorphone, and diacetylmorphine (heroin), morphine acts directly on the central nervous system (CNS) to relieve pain.
Morphine has a high potential for addiction; tolerance and psychological dependence develop rapidly, although physiological dependence may take several months to develop.
Tolerance to respiratory depression and euphoria develops more rapidly than tolerance to analgesia, and many chronic pain patients are being maintained on a stable dose, for many years.
--------------
Caffeine
Caffeine is a bitter, white crystalline xanthine alkaloid and a stimulant drug. Caffeine is found in varying quantities in the seeds, leaves, and fruit of some plants, where it acts as a natural pesticide that paralyzes and kills certain insects feeding on the plants, as well as enhancing the reward memory of pollinators. It is most commonly consumed by humans in infusions extracted from the seed of the coffee plant and the leaves of the tea bush, as well as from various foods and drinks containing products derived from the kola nut. Other sources include yerba maté, guarana berries, guayusa, and the yaupon holly.
In humans, caffeine acts as a central nervous system stimulant, temporarily warding off drowsiness and restoring alertness. Studies have shown that caffeine potentially induces chromosomal aberrations, and shows both teratogenic and mutagenic properties. It is the world's most widely consumed psychoactive drug, but unlike many other psychoactive substances, it is legal and unregulated in nearly all parts of the world. Beverages containing caffeine, such as coffee, tea, soft drinks, and energy drinks, enjoy great popularity. In North America, 90% of adults consume caffeine daily.
Part of the reason caffeine is classified by the Food and Drug Administration as GRAS (generally recognized as safe) is that toxic doses (over 10 grams for an average adult) are much higher than typically used doses (less than 500 milligrams). Ordinary consumption can have low health risks, even when carried on for years – there may be a modest protective effect against some diseases, including Parkinson's disease, and certain types of cancer. Some people experience sleep disruption if they consume caffeine, especially during the evening hours, but others show little disturbance and the effect of caffeine on sleep is highly variable.
Evidence of a risk to pregnancy is equivocal, but some authorities have concluded that prudent advice is for pregnant women to limit consumption to the equivalent of two cups of coffee per day or less. The American Congress of Obstetricians and Gynecologists (ACOG) concluded in 2010 that caffeine consumption is safe up to 200 mg per day in pregnant women. Caffeine has pressor and mild diuretic effects when administered to people who are not used to it, but regular users develop a tolerance to this effect, and studies have generally failed to support the common notion that ordinary consumption contributes significantly to dehydration. With heavy use, tolerance develops rapidly to autonomic effects such as elevated heart rate and muscle twitching, but not to the cognitive or arousal effects of caffeine. The degree to which caffeine can produce clinically significant dependency and addiction remains a subject of controversy in the medical literature.
