Portal:Alkaloids
Portal maintenance status: (October 2018)
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Introduction
Alkaloids are a class of naturally occurring organic compounds that mostly contain basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed 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. They can be purified from crude extracts of these organisms by acid-base extraction. Alkaloids have a wide range of pharmacological activities including antimalarial (e.g. quinine), antiasthma (e.g. ephedrine), anticancer (e.g. homoharringtonine), cholinomimetic (e.g. galantamine), vasodilatory (e.g. vincamine), antiarrhythmic (e.g. quinidine), analgesic (e.g. morphine), antibacterial (e.g. chelerythrine), and antihyperglycemic activities (e.g. piperine). Many have found use in traditional or modern medicine, or as starting points for drug discovery. Other alkaloids possess psychotropic (e.g. psilocin) and stimulant activities (e.g. cocaine, caffeine, nicotine, theobromine), and have been used in entheogenic rituals or as recreational drugs. Alkaloids can be toxic too (e.g. atropine, tubocurarine). Although alkaloids act on a diversity of metabolic systems in humans and other animals, they almost uniformly evoke a bitter taste.
Selected general articles
Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is an organic chemical of the catecholamine and phenethylamine families that plays several important roles in the brain and body. 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 controlling the release of various hormones. These pathways and cell groups form a dopamine system which is neuromodulatory.
In popular culture and media, dopamine is often seen as the main chemical of pleasure, but the current opinion in pharmacology is that dopamine instead confers motivational salience; in other words, dopamine signals the perceived motivational prominence (i.e., the desirability or aversiveness) of an outcome, which in turn propels the organism's behavior toward or away from achieving that outcome. Read more...
Tyramine (/ˈtaɪrəmiːn/ TY-rə-meen) (also spelled tyramin), also known by several other names is a naturally occurring trace amine derived from the amino acid tyrosine. Tyramine acts as a catecholamine releasing agent. Notably, it is unable to cross the blood-brain barrier, resulting in only non-psychoactive peripheral sympathomimetic effects following ingestion. A hypertensive crisis can result, however, from ingestion of tyramine-rich foods in conjunction with monoamine oxidase inhibitors (MAOIs). Read more...
Tryptamine is a monoamine alkaloid. It contains an indole ring structure, and is structurally similar to the amino acid tryptophan, from which the name derives. Tryptamine is found in trace amounts in the brains of mammals and is hypothesized to play a role as a neuromodulator or neurotransmitter. Similar to other trace amines, tryptamine binds to human trace amine-associated receptor 1 (TAAR1) as an agonist.
Tryptamine is the common functional group in a set of compounds termed collectively substituted tryptamines. This set includes many biologically active compounds, including neurotransmitters and psychedelic drugs. Read more...
Coniine refers to a poisonous chemical compound, an alkaloid present in and isolable from poison hemlock (Conium maculatum), where its presence has been a source of significant economic, medical, and historico-cultural interest; coniine is also produced by the yellow pitcher plant (Sarracenia flava), and fool's parsley (Aethusa cynapium). Its ingestion and extended exposure are toxic to humans and all classes of livestock; its mechanism of poisoning involves disruption of the central nervous system, with death caused by respiratory paralysis. The biosynthesis of coniine contains as its penultimate step the non-enzymatic cyclisation of 5-oxooctylamine to γ-coniceine, a Schiff base differing from coniiine only by its carbon-nitrogen double bond in the ring. This pathway results in natural coniine that is a mixture—a racemate—composed of two enantiomers, the stereoisomers (S)-(+)-coniine and (R)-(−)-coniine, depending on the direction taken by the chain that branches from the ring. Both enantiomers are toxic, with the (R)-enantiomer being the more biologically active and toxic of the two in general. Coniine holds a place in organic chemistry history as being the first of the important class of alkaloids to be synthesized, by Albert Ladenburg in 1886, and it has been synthesized in the laboratory in a number of unique ways through to modern times.
Hemlock poisoning has been a periodic human concern, a regular veterinary concern, and has had significant occurrences in human and cultural history. Notably, in 399 BC, Socrates, when he was sentenced to death, chose to die by drinking a coniine-containing mixture of poison hemlock. Read more...
Theobromine, formerly known as xantheose, is a bitter alkaloid of the cacao plant, with the chemical formula C7H8N4O2. It is found in chocolate, as well as in a number of other foods, including the leaves of the tea plant, and the kola nut. It is classified as a xanthine alkaloid, others of which include theophylline and caffeine. The compounds differ in that caffeine has an extra methyl group (see under Pharmacology section).
Despite its name, the compound contains no bromine—theobromine is derived from Theobroma, the name of the genus of the cacao tree (which itself is made up of the Greek roots theo ("god") and broma ("food"), meaning "food of the gods") with the suffix -ine given to alkaloids and other basic nitrogen-containing compounds. Read more...
Cocaine, also known as coke, is a strong stimulant mostly used as a recreational drug. It is commonly snorted, inhaled as smoke, or dissolved and injected into a vein. Mental effects may include loss of contact with reality, an intense feeling of happiness, or agitation. Physical symptoms may include a fast heart rate, sweating, and large pupils. High doses can result in very high blood pressure or body temperature. Effects begin within seconds to minutes of use and last between five and ninety minutes. Cocaine has a small number of accepted medical uses such as numbing and decreasing bleeding during nasal surgery.
Cocaine is addictive due to its effect on the reward pathway in the brain. After a short period of use, there is a high risk that dependence will occur. Its use also increases the risk of stroke, myocardial infarction, lung problems in those who smoke it, blood infections, and sudden cardiac death. Cocaine sold on the street is commonly mixed with local anesthetics, cornstarch, quinine, or sugar, which can result in additional toxicity. Following repeated doses a person may have decreased ability to feel pleasure and be very physically tired. Read more...
Serotonin (/ˌsɛrəˈtoʊnɪn,ˌsɪərə-/) or 5-hydroxytryptamine (5-HT) is a monoamine neurotransmitter that has a popular image as a contributor to feelings of well-being and happiness. Biochemically, the indoleamine molecule derives from the amino acid tryptophan. Serotonin is primarily found in the enteric nervous system located in the gastrointestinal tract (GI tract). However, it is also produced in the central nervous system (CNS), specifically in the Raphe nuclei located in the brainstem. Additionally, serotonin is stored in blood platelets and is released during agitation and vasoconstriction, where it then acts as an agonist to other platelets.
Approximately 90% of the human body's total serotonin is located in the enterochromaffin cells in the GI tract, where it regulates intestinal movements. The serotonin is secreted luminally and basolaterally, which leads to increased serotonin uptake by circulating platelets and activation after stimulation, which gives increased stimulation of myenteric neurons and gastrointestinal motility. The remainder is synthesized in serotonergic neurons of the CNS, where it has various functions. These include the regulation of mood, appetite, and sleep. Serotonin also has some cognitive functions, including memory and learning. Modulation of serotonin at synapses is thought[by whom?] to be a major action of several classes of pharmacological antidepressants. Read more...
Solanine is a glycoalkaloid poison found in species of the nightshade family within the genus Solanum, such as the potato (Solanum tuberosum), the tomato (Solanum lycopersicum), and the eggplant (Solanum melongena). It can occur naturally in any part of the plant, including the leaves, fruit, and tubers. Solanine has pesticidal properties, and it is one of the plant's natural defenses. Solanine was first isolated in 1820 from the berries of the European black nightshade (Solanum nigrum), after which it was named. It belongs to the chemical family of saponins. Read more...
Muscarine, L-(+)-muscarine, or muscarin is a natural product found in certain mushrooms, particularly in Inocybe and Clitocybe species, such as the deadly C. dealbata. Mushrooms in the genera Entoloma and Mycena have also been found to contain levels of muscarine which can be dangerous if ingested. Muscarine has been found in harmless trace amounts in Boletus, Hygrocybe, Lactarius and Russula. Muscarine is only a trace compound in the fly agaric Amanita muscaria; the pharmacologically more relevant compounds from this mushroom are ibotenic acid and muscimol. A. muscaria fruitbodies contain a variable dose of muscarine, usually around 0.0003% fresh weight. This is very low and toxicity symptoms occur very rarely. Inocybe and Clitocybe contain muscarine concentrations up to 1.6%.
Muscarine is a nonselective agonist of the muscarinic acetylcholine receptor. Read more...
Ephedrine is a medication and stimulant. It is often used to prevent low blood pressure during spinal anesthesia. It has also been used for asthma, narcolepsy, and obesity but is not the preferred treatment. It is of unclear benefit in nasal congestion. It can be taken by mouth or by injection into a muscle, vein, or just under the skin. Onset with intravenous use is fast, while injection into a muscle can take 20 minutes, and by mouth can take an hour for effect. When given by injection it lasts about an hour and when taken by mouth it can last up to four hours.
Common side effects include trouble sleeping, anxiety, headache, hallucinations, high blood pressure, fast heart rate, loss of appetite, and inability to urinate. Serious side effects include stroke, heart attack, and abuse. While likely safe in pregnancy its use in this population is poorly studied. Use during breastfeeding is not recommended. Ephedrine works by increasing the activity of the α and β adrenergic receptors. Read more...
Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine which acts as a central nervous system stimulant in humans.
Phenethylamine functions as a monoaminergic neuromodulator and, to a lesser extent, a neurotransmitter in the human central nervous system. It is biosynthesized from the amino acid L-phenylalanine by enzymatic decarboxylation via the enzyme aromatic L-amino acid decarboxylase. In addition to its presence in mammals, phenethylamine is found in many other organisms and foods, such as chocolate, especially after microbial fermentation. It is sold as a dietary supplement for purported mood and weight loss-related therapeutic benefits; however, in orally ingested phenethylamine, a significant amount is metabolized in the small intestine by monoamine oxidase B (MAO-B) and then aldehyde dehydrogenase (ALDH), which convert it to phenylacetic acid. This means that for significant concentrations to reach the brain, the dosage must be higher than for other methods of administration. Read more...
Hyoscyamine (also known as daturine) is a tropane alkaloid. It is a secondary metabolite found in certain plants of the family Solanaceae, including henbane (Hyoscyamus niger), mandrake (Mandragora officinarum), jimsonweed (Datura stramonium), tomato (Solanum lycopersicum) and deadly nightshade (Atropa belladonna). It is the levorotary isomer of atropine (third of the three major nightshade alkaloids) and thus sometimes known as levo-atropine.
Brand names for hyoscyamine include Symax, HyoMax, Anaspaz, Egazil, Buwecon, Cystospaz, Levsin, Levbid, Levsinex, Donnamar, NuLev, Spacol T/S and Neoquess. Read more...
Reserpine (also known by trade names Raudixin, Serpalan, Serpasil) is an indole alkaloid, antipsychotic, and antihypertensive drug that has been used for the control of high blood pressure and for the relief of psychotic symptoms, although because of the development of better drugs for these purposes and because of its numerous side-effects, it is rarely used today. The antihypertensive actions of reserpine are a result of its ability to deplete catecholamines (among other monoamine neurotransmitters) from peripheral sympathetic nerve endings. These substances are normally involved in controlling heart rate, force of cardiac contraction and peripheral vascular resistance.
Reserpine-mediated depletion of monoamine neurotransmitters in the synapses is often cited as evidence to the theory that depletion of the monoamine neurotransmitters causes subsequent depression in humans (c.f. monoamine hypothesis). However, this claim is not without controversy. The reserpine-induced depression is considered by some researchers to be a myth, while others claim that teas made out of the plant roots containing reserpine have a calming, sedative action that can actually be considered antidepressant. Notably, reserpine was the first compound shown to be an effective antidepressant in a randomized placebo-controlled trial. Read more...
5-MeO-DMT (5-methoxy-N,N-dimethyltryptamine) is a psychedelic of the tryptamine class. It is found in a wide variety of plant species, and at least one toad species, the Sonora Desert toad. Like its close relatives DMT and bufotenin (5-HO-DMT), it has been used as an entheogen in South America. Read more...
Nicotine is an antiherbivory alkaloid and potent parasympathomimetic stimulant and found in plants, mostly those in the nightshade family. Nicotine acts as a receptor agonist at most nicotinic acetylcholine receptors (nAChRs), except at two nicotinic receptor subunits (nAChRα9 and nAChRα10) where it acts as a receptor antagonist.
Nicotine is highly addictive. An average cigarette yields about 2 mg of absorbed nicotine, while high amounts (30–60 mg) can be harmful. Nicotine induces both behavioral stimulation and anxiety in animals. Nicotine addiction involves drug-reinforced behavior, compulsive use, and relapse following abstinence. Nicotine dependence involves tolerance, sensitization, physical dependence, and psychological dependence. It is one of the most commonly abused drugs. Read more...
Hyoscine, also known as scopolamine, is a medication used to treat motion sickness and postoperative nausea and vomiting. It is also sometimes used before surgery to decrease saliva. When used by injection, effects begin after about 20 minutes and last for up to 8 hours. It may also be used by mouth and as a skin patch.
Common side effects include sleepiness, blurred vision, dilated pupils, and dry mouth. It is not recommended in people with glaucoma or bowel obstruction. It is unclear if use during pregnancy is safe; however, it appears to be safe during breastfeeding. Hyoscine is in the antimuscarinic family of medications and works by blocking some of the effects of acetylcholine within the nervous system. Read more...
Methamphetamine (contracted from N-methylamphetamine) is a potent central nervous system (CNS) stimulant that is mainly used as a recreational drug and less commonly as a second-line treatment for attention deficit hyperactivity disorder and obesity. Methamphetamine was discovered in 1893 and exists as two enantiomers: levo-methamphetamine and dextro-methamphetamine. Methamphetamine properly refers to a specific chemical, the racemic free base (while INN name metamfetamine refers to single enantiomer, dextromethamphetamine), which is an equal mixture of levomethamphetamine and dextromethamphetamine in their pure amine forms. It is rarely prescribed over concerns involving human neurotoxicity and potential for recreational use as an aphrodisiac and euphoriant, among other concerns, as well as the availability of safer substitute drugs with comparable treatment efficacy. Dextromethamphetamine is a much stronger CNS stimulant than levomethamphetamine.
Both methamphetamine and dextromethamphetamine are illicitly trafficked and sold owing to their potential for recreational use. The highest prevalence of illegal methamphetamine use occurs in parts of Asia, Oceania, and in the United States, where racemic methamphetamine, levomethamphetamine, and dextromethamphetamine are classified as schedule II controlled substances. Levomethamphetamine is available as an over-the-counter (OTC) drug for use as an inhaled nasal decongestant in the United States. Internationally, the production, distribution, sale, and possession of methamphetamine is restricted or banned in many countries, due to its placement in schedule II of the United Nations Convention on Psychotropic Substances treaty. While dextromethamphetamine is a more potent drug, racemic methamphetamine is sometimes illicitly produced due to the relative ease of synthesis and limited availability of chemical precursors. Read more...
Yohimbine (/joʊˈhɪmbiːn/) is an indole alkaloid derived from the bark of the Pausinystalia yohimbe tree in Central Africa. It is a veterinary drug used to reverse sedation in dogs and deer. Yohimbine has been studied as a potential treatment for erectile dysfunction but there is insufficient evidence to rate its effectiveness. Extracts from yohimbe have been marketed as dietary supplements for improving sexual function. Read more...
Codeine is an opiate used to treat pain, as a cough medicine, and for diarrhea. It is typically used to treat mild to moderate degrees of pain. Greater benefit may occur when combined with paracetamol (acetaminophen) or a nonsteroidal anti-inflammatory drug (NSAID) such as aspirin or ibuprofen. Evidence does not support its use for acute cough suppression in children or adults. In Europe it is not recommended as a cough medicine in those under twelve years of age. It is generally taken by mouth. It typically starts working after half an hour with maximum effect at two hours. The total duration of its effects last for about four to six hours.
Common side effects include vomiting, constipation, itchiness, lightheadedness, and drowsiness. Serious side effects may include breathing difficulties and addiction. It is unclear if its use in pregnancy is safe. Care should be used during breastfeeding as it may result in opiate toxicity in the baby. Its use as of 2016 is not recommended in children. Codeine works following being broken down by the liver into morphine. How quickly this occurs depends on a person's genetics. Read more...
Quinine is a medication used to treat malaria and babesiosis. This includes the treatment of malaria due to Plasmodium falciparum that is resistant to chloroquine when artesunate is not available. While used for restless legs syndrome, it is not recommended for this purpose due to the risk of side effects. It can be taken by mouth or used intravenously. Malaria resistance to quinine occurs in certain areas of the world. Quinine is also the ingredient in tonic water that gives it its bitter taste.
Common side effects include headache, ringing in the ears, trouble seeing, and sweating. More severe side effects include deafness, low blood platelets, and an irregular heartbeat. Use can make one more prone to sunburn. While it is unclear if use during pregnancy causes harm to the baby, use to treat malaria during pregnancy is still recommended. Quinine is an alkaloid, a naturally occurring chemical compound. How it works as a medicine is not entirely clear. Read more...
Morphine is a pain medication of the opiate family which is found naturally in a number of plants and animals. It acts directly on the central nervous system (CNS) to decrease the feeling of pain. It can be taken for both acute pain and chronic pain. It is frequently used for pain from myocardial infarction and during labor. It can be given by mouth, by injection into a muscle, by injection under the skin, intravenously, injection into the space around the spinal cord, or rectally. Maximum effect is reached after about 20 minutes when given intravenously and after 60 minutes when given by mouth, while duration of effect is 3–7 hours. Long-acting formulations also exist.
Potentially serious side effects include a decreased respiratory effort and low blood pressure. Morphine has a high potential for addiction and abuse. If the dose is reduced after long-term use, withdrawal may occur. Common side effects include drowsiness, vomiting, and constipation. Caution is advised when used during pregnancy or breast feeding, as morphine will affect the baby. Read more...
Atropine is a medication to treat certain types of nerve agent and pesticide poisonings as well as some types of slow heart rate and to decrease saliva production during surgery. It is typically given intravenously or by injection into a muscle. Eye drops are also available which are used to treat uveitis and early amblyopia. The intravenous solution usually begins working within a minute and lasts half an hour to an hour. Large doses may be required to treat some poisonings.
Common side effects include a dry mouth, large pupils, urinary retention, constipation, and a fast heart rate. It should generally not be used in people with angle closure glaucoma. While there is no evidence that its use during pregnancy causes birth defects, it has not been well studied. It is likely safe during breastfeeding. It is an antimuscarinic (a type of anticholinergic) that works by inhibiting the parasympathetic nervous system. Read more...
Theophylline, also known as 1,3-dimethylxanthine, is a methylxanthine drug used in therapy for respiratory diseases such as chronic obstructive pulmonary disease (COPD) and asthma under a variety of brand names. As a member of the xanthine family, it bears structural and pharmacological similarity to theobromine and caffeine, and is readily found in nature, and is present in tea (Camellia sinensis) and cocoa (Theobroma cacao). A small amount of theophylline is one of the products of caffeine metabolic processing in the liver. Read more...
Amphetamine (contracted from alpha-methylphenethylamine) is a potent central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. Amphetamine was discovered in 1887 and exists as two enantiomers: levoamphetamine and dextroamphetamine. Amphetamine properly refers to a specific chemical, the racemic free base, which is equal parts of the two enantiomers, levoamphetamine and dextroamphetamine, in their pure amine forms. The term is frequently used informally to refer to any combination of the enantiomers, or to either of them alone. Historically, it has been used to treat nasal congestion and depression. Amphetamine is also used as an athletic performance enhancer and cognitive enhancer, and recreationally as an aphrodisiac and euphoriant. It is a prescription drug in many countries, and unauthorized possession and distribution of amphetamine are often tightly controlled due to the significant health risks associated with recreational use.
The first amphetamine pharmaceutical was Benzedrine, a brand which was used to treat a variety of conditions. Currently, pharmaceutical amphetamine is prescribed as racemic amphetamine, Adderall, dextroamphetamine, or the inactive prodrug lisdexamfetamine. Amphetamine increases monoamine and excitatory neurotransmission in the brain, with its most pronounced effects targeting the norepinephrine and dopamine neurotransmitter systems. Read more...
Mescaline (3,4,5-trimethoxyphenethylamine) is a naturally occurring psychedelic alkaloid of the phenethylamine class, known for its hallucinogenic effects comparable to those of LSD and psilocybin.
It occurs naturally in the peyote cactus (Lophophora williamsii), the San Pedro cactus (Echinopsis pachanoi), the Peruvian torch (Echinopsis peruviana), and other members of the Cactaceae plant family. It is also found in small amounts in certain members of the Fabaceae (bean) family, including Acacia berlandieri. Read more...
N,N-Dimethyltryptamine (DMT or N,N-DMT) is a tryptamine molecule which occurs in many plants and animals. It can be consumed as a psychedelic drug and has historically been prepared by various cultures for ritual purposes as an entheogen. Rick Strassman labeled it "the spirit molecule". In most countries, DMT is illegal.
DMT has a rapid onset, intense effects and a relatively short duration of action. For those reasons, DMT was known as the "businessman's trip" during the 1960s in the United States, as a user could access the full depth of a psychedelic experience in considerably less time than with other substances such as LSD or magic mushrooms. DMT can be inhaled, injected, vaporized or ingested, and its effects depend on the dose. When inhaled or injected, the effects last a short period of time: about 5 to 15 minutes. Effects can last 3 hours or more when orally ingested along with an MAOI, such as the ayahuasca brew of many native Amazonian tribes. DMT can produce vivid "projections" of mystical experiences involving euphoria and dynamic hallucinations of geometric forms. Read more...
Several alkaloids that function as monoamine oxidase inhibitors (MAOIs) are found in the seeds of Peganum harmala (also known as Harmal or Syrian Rue), as well as tobacco leaves including harmine, harmaline, and harmalol, which are members of a group of substances with a similar chemical structure collectively known as harmala alkaloids. These alkaloids are of interest for their use in Amazonian shamanism, where they are derived from other plants. The harmala alkaloid harmine, once known as telepathine and banisterine, is a naturally occurring beta-carboline alkaloid that is structurally related to harmaline, and also found in the vine Banisteriopsis caapi. Tetrahydroharmine is also found in B. caapi and P. harmala. Dr. Alexander Shulgin has suggested that harmine may be a breakdown product of harmaline. Harmine and harmaline are reversible MAOIs of the MAO-A isoform of the enzyme, and can stimulate the central nervous system by inhibiting the metabolism of monoamine compounds such as serotonin and norepinephrine.
The harmala alkaloids occur in Peganum harmala in concentrations of roughly 3%, though tests have documented anywhere from 2-7% or even higher, as natural sources tend to vary widely in chemical makeup. Harmala alkaloids are also found in the Banisteriopsis caapi vine, the key plant ingredient in the sacramental beverage Ayahuasca, in concentrations that range between 0.31-8.43% for harmine, 0.03-0.83% for harmaline and 0.05-2.94% for tetrahydroharmine.
Although other psychoactive plants are occasionally added to Ayahuasca to achieve visionary states of consciousness, the recipes vary greatly and no single combination is common. Peganum harmala, normally consumed as a tea or used as an incense, is mentioned in classical Persian literature both as a sacred sacrament and as a medicine. The harmala alkaloids are not especially psychedelic, even at higher dosages, when hypnagogic visions, alongside vomiting and diarrhea, become the main effect. Read more...
Psilocin (also known as 4-HO-DMT, 4-hydroxy DMT, psilocine, psilocyn, or psilotsin) is a substituted tryptamine alkaloid and a serotonergic psychedelic substance. It is present in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. The mind-altering effects of psilocin are highly variable, subjective and resemble those of LSD and DMT. Read more...
Cathinone /ˈkæθɪnoʊn/ (also known as benzoylethanamine, or β-keto-amphetamine) is a monoamine alkaloid found in the shrub Catha edulis (khat) and is chemically similar to ephedrine, cathine, methcathinone and other amphetamines. It is probably the main contributor to the stimulant effect of Catha edulis. Cathinone differs from many other amphetamines in that it has a ketone functional group. Other phenethylamines that share this structure include the stimulants methcathinone, MDPV, mephedrone and the antidepressant bupropion among others. Read more...
Caffeine is a central nervous system (CNS) stimulant of the methylxanthine class. It is the world's most widely consumed psychoactive drug. Unlike many other psychoactive substances, it is legal and unregulated in nearly all parts of the world. There are several known mechanisms of action to explain the effects of caffeine. The most prominent is that it reversibly blocks the action of adenosine on its receptor and consequently prevents the onset of drowsiness induced by adenosine. Caffeine also stimulates certain portions of the autonomic nervous system.
Caffeine is a bitter, white crystalline purine, a methylxanthine alkaloid, and is chemically related to the adenine and guanine bases of deoxyribonucleic acid (DNA) and ribonucleic acid (RNA). It is found in the seeds, nuts, or leaves of a number of plants native to Africa, East Asia and South America, and helps to protect them against predator insects and to prevent germination of nearby seeds. The most well-known source of caffeine is the coffee bean, a misnomer for the seed of Coffea plants. Beverages containing caffeine are ingested to relieve or prevent drowsiness and to improve performance. To make these drinks, caffeine is extracted by steeping the plant product in water, a process called infusion. Caffeine-containing drinks, such as coffee, tea, and cola, are very popular; as of 2014, 85% of American adults consumed some form of caffeine daily, consuming 164 mg on average. Read more...
Choline /ˈkoʊliːn/ is a water-soluble vitamin-like essential nutrient. It is a constituent of lecithin, which is present in many plants and animal organs. The term cholines refers to the class of quaternary ammonium salts containing the N,N,N-trimethylethanolammonium cation (X− on the right denotes an undefined counteranion).
The cation appears in the head groups of phosphatidylcholine and sphingomyelin, two classes of phospholipid that are abundant in cell membranes. Choline is the precursor for the neurotransmitter acetylcholine, which is involved in many functions including memory and muscle control. Read more...
Psilocybin (/ˌsaɪləˈsaɪbɪn/ sy-lə-SY-bin) is a naturally occurring psychedelic prodrug compound produced by more than 200 species of mushrooms, collectively known as psilocybin mushrooms. The most potent are members of the genus Psilocybe, such as P. azurescens, P. semilanceata, and P. cyanescens, but psilocybin has also been isolated from about a dozen other genera. As a prodrug, psilocybin is quickly converted by the body to psilocin, which has mind-altering effects similar, in some aspects, to those of LSD, mescaline, and DMT. In general, the effects include euphoria, visual and mental hallucinations, changes in perception, a distorted sense of time, spiritual experiences, and can include possible adverse reactions such as nausea and panic attacks.
Imagery found on prehistoric murals and rock paintings of modern-day Spain and Algeria suggests that human usage of psilocybin mushrooms predates recorded history. In Mesoamerica, the mushrooms had long been consumed in spiritual and divinatory ceremonies before Spanish chroniclers first documented their use in the 16th century. In 1959, the Swiss chemist Albert Hofmann isolated the active principle psilocybin from the mushroom Psilocybe mexicana. Hofmann's employer Sandoz marketed and sold pure psilocybin to physicians and clinicians worldwide for use in psychedelic psychotherapy. Although the increasingly restrictive drug laws of the late 1960s curbed scientific research into the effects of psilocybin and other hallucinogens, its popularity as an entheogen (spirituality-enhancing agent) grew in the next decade, owing largely to the increased availability of information on how to cultivate psilocybin mushrooms. Read more...
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Selected images
Crystals of piperine extracted from black pepper.
The first individual alkaloid, morphine, was isolated in 1804 from the opium poppy (Papaver somniferum).
Strychnine tree. Its seeds are rich in strychnine and brucine.
Friedrich Sertürner, the German chemist who first isolated morphine from opium.
Head of a lamb born to a sheep that ate leaves of the corn lily plant. The cyclopia in the calf is induced by the alkaloid cyclopamine present in the plant.
Bufotenin, an alkaloid from some toads, contains an indole core and is produced in living organisms from the amino acid tryptophan.
The nicotine molecule contains both pyridine (left) and pyrrolidine rings (right).
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