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Organic chemistry

Organic chemistry
Structure of the organic methane molecule, the simplest hydrocarbon compound Organic chemistry is a chemistry subdiscipline involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.[1][2] Study of structure includes using spectroscopy and other physical and chemical methods to determine the chemical composition and constitution of organic compounds and materials.[3] Study of properties includes both physical properties and chemical properties, and uses similar methods as well as methods to evaluate chemical reactivity, with the aim to understand the behavior of the organic matter in its pure form (when possible), but also in solutions, mixtures, and fabricated forms. The study of organic reactions includes both their preparation—by synthesis or by other means—as well as their subsequent reactivities, both in the laboratory and via theoretical (in silico) study.

Amanita muscaria Amanita muscaria, commonly known as the fly agaric or fly amanita, is a mushroom and psychoactive basidiomycete fungus, one of many in the genus Amanita. Native throughout the temperate and boreal regions of the Northern Hemisphere, Amanita muscaria has been unintentionally introduced to many countries in the Southern Hemisphere, generally as a symbiont with pine plantations, and is now a true cosmopolitan species. It associates with various deciduous and coniferous trees. Although it is generally considered poisonous, reports of human deaths resulting from eating the mushroom are extremely rare. Taxonomy and naming[edit] The name of the mushroom in many European languages is thought to be derived from its use as an insecticide when sprinkled in milk. Buttons Classification[edit] Amanita muscaria var. formosa sensu Thiers, southern Oregon Coast Amanita muscaria varies considerably in its morphology, and many authorities recognise several subspecies or varieties within the species.

Ergoline Ergoline is a chemical compound whose structural skeleton is contained in a diverse range of alkaloids. Ergoline derivatives are used clinically for the purpose of vasoconstriction (5-HT1 receptor agonists—ergotamine) and in the treatment of migraines (used with caffeine) and Parkinson's disease. Some ergoline alkaloids found in ergot fungi are implicated in the condition ergotism, which causes convulsive and gangrenous symptoms. Others include psychedelic drugs (e.g., LSD and some alkaloids in Ipomoea tricolor and related species[citation needed]). Uses[edit] In addition to the naturally occurring ergonovine (used as an oxytocic) and ergotamine (a vasoconstrictor used to control migraine), synthetic derivatives of importance are the oxytocic methergine, the anti-migraine drugs dihydroergotamine and methysergide, hydergine (a mixture of dihydroergotoxine mesylates, INN: ergoline mesylates), and bromocriptine, used for numerous purposes including treatment of Parkinson's disease.

Mescaline Mescaline or 3,4,5-trimethoxyphenethylamine is a naturally occurring psychedelic alkaloid of the phenethylamine class, known for its hallucinogenic effects similar to those of LSD and psilocybin. It shares strong structural similarities with the catecholamine dopamine. It occurs naturally in the peyote cactus (Lophophora williamsii),[1] the San Pedro cactus[2] (Echinopsis pachanoi) and in the Peruvian torch (Echinopsis peruviana), and as well in a number of 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.[3] Naturally derived mescaline powder extract. History and usage[edit] Peyote has been used for at least 5700 years by Native Americans in Mexico.[4] Europeans noted use of peyote in Native American religious ceremonies upon early contact, notably by the Huichols in Mexico. Potential medical usage[edit] Notable users[edit] Biosynthesis of mescaline[edit] Synthetic Mescaline[edit]

Tabernanthe iboga Tabernanthe iboga or simply iboga is a perennial rainforest shrub and psychedelic, native to western Central Africa. Iboga stimulates the central nervous system when taken in small doses and induces visions in larger doses. In parts of Africa where the plant grows the bark of the root is chewed for various pharmacological or ritualistic purposes. Normally growing to a height of 2 m, T. iboga may eventually grow into a small tree up to 10 m tall, given the right conditions. Traditional use[edit] Bark of Tabernanthe iboga. The Iboga tree is the central pillar of the Bwiti spiritual practice in West-Central Africa, mainly Gabon, Cameroon and the Republic of the Congo, which uses the alkaloid-containing roots of the plant in a number of ceremonies. In lower doses Iboga has a stimulant effect and is used to maintain alertness while hunting.[1][2] Addiction treatment[edit] Legal status[edit] Exportation of iboga from Gabon is illegal since the passage of a 1994 cultural protection law.[5]

Dimethyltryptamine History[edit] Another historical milestone is the discovery of DMT in plants frequently used by Amazonian natives as additive to the vine Banisteriopsis caapi to make ayahuasca decoctions. Biosynthesis[edit] Biosynthetic pathway for N,N-dimethyltryptamine This transmethylation mechanism has been repeatedly and consistently proven by radiolabeling of SAM methyl group with carbon-14 (14C-CH3)SAM).[22][20][24][25][26] Evidence in mammals[edit] In 2013, researchers first reported DMT in the pineal gland microdialysate of rodents.[28] A study published in 2014 reported the biosynthesis of N,N-dimethyltryptamine (DMT) in the human melanoma cell line SK-Mel-147 including details on its metabolism by peroxidases. [29] In a 2014 paper, a group first demonstrated the immunomodulatory potential of DMT and 5-MeO-DMT through the Sigma-1_receptor of human immune cells. INMT[edit] Endogenous DMT[edit] The first claimed detection of mammalian endogenous DMT was published in June 1965: German researchers F.

Salvia divinorum Salvia divinorum (also known as Diviner's Sage,[2] Ska María Pastora,[3] Seer's Sage,[4] and by its genus name Salvia) is a psychoactive plant which can induce "visions" and other hallucinatory experiences. Its native habitat is in cloud forest in the isolated Sierra Mazateca of Oaxaca, Mexico, where it grows in shady and moist locations.[5][6] The plant grows to over a meter high,[1] has hollow square stems, large leaves, and occasional white flowers with violet calyxes. Botanists have not determined whether Salvia divinorum is a cultigen or a hybrid; native plants reproduce vegetatively, rarely producing viable seed.[7][8] Mazatec shamans have a long and continuous tradition of religious use of Salvia divinorum, using it to facilitate visionary states of consciousness during spiritual healing sessions.[1] Most of the plant's local common names allude to the Mazatec belief that the plant is an incarnation of the Virgin Mary, with its ritual use also invoking that relationship. History

Salvinorin A Salvinorin A is the main active psychotropic molecule in Salvia divinorum, a Mexican plant which has a long history of use as an entheogen by indigenous Mazatec shamans. Salvinorin A is considered a dissociative exhibiting atypically psychedelic effects. Salvinorin A can produce psychoactive experiences in humans with a typical duration of action being several minutes to an hour or so, depending on the method of ingestion.[2] History[edit] Salvinorin A was first described and named in 1982 by Alfredo Ortega and colleagues in Mexico. They used a combination of spectroscopy and x-ray crystallography to determine the chemical structure of the compound, which was shown to have a bicyclic diterpene structure.[3] Around the same time, Leander Julián Valdés III independently isolated the molecule as part of his PhD research, published in 1983.[4] Valdés named the chemical divinorum, and also isolated an analog that he named divinorum B. Pharmacology[edit] Potency and selectivity[edit] Salvinorin A

Ibogaine Ibogaine is a naturally occurring psychoactive substance found in plants in the Apocynaceae family such as Tabernanthe iboga, Voacanga africana and Tabernaemontana undulata. A psychedelic with dissociative properties, the substance is banned in some countries; in other countries it is used by proponents of psychedelic therapy to treat addiction to methadone, heroin, alcohol, cocaine, methamphetamine, anabolic steroids, and other drugs. Ibogaine is also used to treat depression and post traumatic stress disorder. Derivatives of ibogaine that lack the substance's psychedelic properties are under development.[1] Ibogaine-containing preparations are used for medicinal and ritual purposes within African spiritual traditions of the Bwiti, who claim to have learned it from the Pygmy peoples. Ibogaine is an indole alkaloid that is obtained either by extraction from the iboga plant or by semi-synthesis from the precursor compound voacangine,[3][4] another plant alkaloid. History[edit]

Ergotamine Ergotamine is an ergopeptine and part of the ergot family of alkaloids; it is structurally and biochemically closely related to ergoline. It possesses structural similarity to several neurotransmitters, and has biological activity as a vasoconstrictor. It is used medicinally for treatment of acute migraine attacks (sometimes in combination with caffeine). Mechanism of action[edit] Biosynthesis[edit] Ergotamine is a secondary metabolite (natural product) and the principal alkaloid produced by the ergot fungus, Claviceps purpurea, and related fungi in the family Clavicipitaceae.[7] Its biosynthesis in these fungi requires the amino acid L-tryptophan and dimethylallyl diphosphate. Drug uses[edit] Ergotamine produces vasoconstriction peripherally as well as damages the peripheral epithelium. Ergotamine continues to be prescribed for migraines. Availability and dosage[edit] See also[edit] References[edit] ^ Jump up to: a b Sanders, SW; Haering N, Mosberg H, Jaeger H (1986).

Muscimol Muscimol (agarin, pantherine) is the major psychoactive alkaloid present in many mushrooms of the Amanita genus. Muscimol is a potent, selective agonist for the GABAA receptors and displays sedative-hypnotic effects. Chemistry[edit] Muscimol is the psychoactive compound responsible for the effects of Amanita muscaria intoxication. Biology[edit] Muscimol is produced naturally in the mushrooms Amanita muscaria and Amanita pantherina, along with muscarine, muscazone, and ibotenic acid.[2][3] A. muscaria and A. pantherina should be eaten with caution and prepared properly to lessen effects of nausea; no official deaths from poisoning have been recorded from A. muscaria and A. pantherina.[4] In A. muscaria, the layer just below the skin of the cap contains the highest amount of muscimol, and is therefore the most psychoactive portion.[5] Pharmacology[edit] During a test involving rabbits connected to an EEG, muscimol showed a distinctly synchronized EEG tracing. Toxicity[edit] Effects[edit]

Lysergic acid diethylamide Lysergic acid diethylamide, abbreviated LSD or LSD-25, also known as lysergide (INN) and colloquially as acid, is a semisynthetic psychedelic drug of the ergoline family, well known for its psychological effects which can include altered thinking processes, closed- and open-eye visuals, synesthesia, an altered sense of time and spiritual experiences, as well as for its key role in 1960s counterculture. It is used mainly as an entheogen, recreational drug, and as an agent in psychedelic therapy. LSD is non-addictive, is not known to cause brain damage, and has extremely low toxicity relative to dose.[3] However, acute adverse psychiatric reactions such as anxiety, paranoia, and delusions are possible.[4] LSD was first synthesized by Albert Hofmann in 1938 from ergotamine, a chemical derived by Arthur Stoll from ergot, a grain fungus that typically grows on rye. Effects Physical LSD can cause pupil dilation, reduced or increased appetite, and wakefulness. Psychological Sensory Potential uses

Dipropyltryptamine Frequent physical effects are nausea, numbness of the tongue or throat, and pupil dilation. Pharmacology[edit] Studies on rodents have found that the effectiveness with which a selective 5-HT2A receptor antagonist blocks the behavioral actions of this compound strongly suggest that the 5-HT2A receptor is an important site of action for DPT, but the modulatory actions of a 5-HT1A receptor antagonist also imply a 5-HT1A-mediated component to the actions of DPT.[2] Chemistry[edit] DPT changes Ehrlich's reagent purple and causes the marquis reagent to turn yellow.[3] Psychedelic properties[edit] While dipropyltryptamine is chemically similar to dimethyltryptamine, its psychoactive effects are markedly different.[4] The most prominent features of the DPT experience are increased significance or intensity of music, colors take on a new intensity or appearance, the body may have a buzz or vibratory feeling, a pleasant sensation of warmth, complete ego loss, apparitions of faces. Religious use[edit]

Ayahuasca Ayahuasca (UK: /ˌaɪ(j)əˈwæskə/, US: /-ˈwɑːskə/) or ayaguasca[1] (in Hispanicized spellings) from Quechua Ayawaska[2] (aya: soul, waska: vine), or yagé (/jɑːˈheɪ, jæ-/), is an entheogenic brew made out of Banisteriopsis caapi vine and other ingredients.[3] The brew is used as a traditional spiritual medicine in ceremonies among the indigenous peoples of the Amazon basin and is known by a number of different names (see below).[4] B. caapi contains several alkaloids that act as monoamine oxidase inhibitors (MAOIs). Another common ingredient in ayahuasca is the shrub Psychotria viridis which contains the primary psychoactive, dimethyltryptamine (DMT). Nomenclature[edit] Ayahuasca is known by many names throughout Northern South America and Brazil. Ayahuasca is the hispanicized spelling of a word in the Quechua languages, which are spoken in the Andean states of Ecuador, Bolivia, Peru, and Colombia. History[edit] Preparation[edit] Traditional usage[edit] Ceremony and the role of shamans[edit]

2C-B History[edit] 2C-B was synthesized from 2,5-dimethoxybenzaldehyde by Alexander Shulgin in 1974. It first saw use among the psychiatric community as an aid during therapy. It was considered one of the best drugs for this purpose because of its short duration, relative absence of side effects, and comparably mild nature.[2] Shortly after becoming popular in the medical community, it became popular recreationally. 2C-B was first sold commercially as an aphrodisiac[3] under the trade name "Eros", which was manufactured by the German pharmaceutical company Drittewelle.[4] For several years, it was available as tablets in Dutch smart shops under the name "Nexus". Internationally, 2C-B is a Schedule II drug under the Convention on Psychotropic Substances.[5] In the Netherlands, 2C-B became a list I substance of the Opium Law despite no health incidents occurring. Patterns of use[edit] Toxicity and dosage[edit] The lethal dosage is unknown. Effects[edit] The effects of 2C-B include:[2][16][17]

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