14-Hydroxy-LSD
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14-Hydroxy-LSD
14-Hydroxy-LSD is a lysergamide and a metabolite of the psychedelic drug lysergic acid diethylamide (LSD). It is formed via aromatic hydroxylation at position 14 of the lysergic acid moiety and is subsequently excreted as a glucuronide conjugate. 14-Hydroxy-LSD is a major metabolite of LSD in rats and guinea pigs, where it is excreted predominantly as a glucuronide in bile and urine. In contrast, it appears only as a minor metabolite in rhesus monkeys and humans. Studies using human liver microsomes and urine samples have confirmed its presence in humans, but in low concentrations that are often below quantification limits. The specific enzymes involved in the formation of hydroxylated LSD metabolites like 14-hydroxy-LSD remain unidentified. As of 2016, David E. Nichols noted that the pharmacology of hydroxylated LSD metabolites, including 14-hydroxy-LSD, had not been studied. Notably, 14-hydroxy-LSD does not induce LSD-like changes in the EEG of rabbits, in contrast to LSD and ...
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Substituted Lysergamide
Lysergamides, also known as ergoamides or as lysergic acid amides, are amides of lysergic acid (LA). They are ergolines, with some lysergamides being found naturally in ergot as well as other fungi. Lysergamides are notable in containing embedded phenethylamine and tryptamine moieties within their ergoline ring system. The simplest lysergamides are ergine (lysergic acid amide; LSA) and isoergine (iso-lysergic acid amide; iso-LSA). In terms of pharmacology, the lysergamides include numerous serotonin and dopamine receptor agonists, most notably the psychedelic drug lysergic acid diethylamide (LSD) but also a number of pharmaceutical drugs like ergometrine, methylergometrine, methysergide, and cabergoline. Various analogues of LSD, such as the psychedelics ALD-52 (1A-LSD), ETH-LAD, LSZ, and 1P-LSD and the non-hallucinogenic 2-bromo-LSD (BOL-148), have also been developed. Ergopeptines like ergotamine, dihydroergotamine, and bromocriptine are also lysergamides, but with a ...
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2-Oxo-3-hydroxy-LSD
2-Oxo-3-hydroxy-LSD, or 2-oxy-3-hydroxy-LSD, also known as O-H-LSD or OH-LSD, as well as more fully as 2-oxo-3-hydroxy-2,3-dihydro-LSD, is a lysergamide and the major metabolite of the psychedelic drug lysergic acid diethylamide (LSD). LSD is eliminated 13% as O-H-LSD in urine within 24hours and urinary concentrations of O-H-LSD are 4 to 40times those of LSD in humans. The specific enzymes responsible for the formation of O-H-LSD from LSD are unclear. However, subsequent research found involvement of several cytochrome P450 enzymes. O-H-LSD is thought to form from other LSD metabolites like 2-oxo-LSD and 3-hydroxy-LSD. It is unknown whether O-H-LSD is pharmacologically active. However, O-H-LSD showed profoundly reduced albeit still detectable activity at the serotonin 5-HT2 receptors, including the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors, compared to LSD ''in vitro''. O-H-LSD was first described in the scientific literature by at least the 1990s. See also * Substi ...
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2-Oxo-LSD
2-Oxo-LSD, also known as 2-oxy-LSD or 2-keto-LSD, or more fully as 2-oxo-2,3-dihydro-LSD, is a lysergamide and metabolite of the psychedelic drug lysergic acid diethylamide (LSD). It is a metabolite of LSD in both humans and various animal species, although there are important differences in LSD metabolism and relative proportions of metabolites between species. Metabolism It is formed directly from LSD in the body and is also possibly an intermediate in the generation of LSD's major metabolite 2-oxo-3-hydroxy-LSD (O-H-LSD), which is present in urine at concentrations 4 to 40times those of LSD in humans. However, O-H-LSD may also form from other metabolites, such as 3-hydroxy-LSD. The specific enzymes responsible for the generation of individual LSD metabolites like 2-oxo-LSD are largely unknown. However, several cytochrome P450 enzymes were investigated and implicated in the formation of O-H-LSD in 2019. Pharmacology 2-Oxo-LSD showed absence of various pharmacological eff ...
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14-Methoxy-LSD
14-Methoxy-LSD is a lysergamide related to lysergic acid diethylamide (LSD). It is the derivative of LSD with a methoxy group at the 14 position and is the ''O''-methyl ether of 14-hydroxy-LSD. Unlike 13-hydroxy-LSD and 13-methoxy-LSD and other related compounds like 12-hydroxy-LSD and 12-methoxy-LSD, 14-hydroxy-LSD and 14-methoxy-LSD did not produce LSD-like electroencephalogram (EEG) changes in rabbits. 14-Methoxy-LSD was first described in the scientific literature by 1979. See also * Substituted lysergamide * 14-Hydroxy-LSD 14-Hydroxy-LSD is a lysergamide and a metabolite of the psychedelic drug lysergic acid diethylamide (LSD). It is formed via aromatic hydroxylation at position 14 of the lysergic acid moiety and is subsequently excreted as a glucuronide conjugate. ... * 13-Methoxy-LSD * 12-Methoxy-LSD * 7-MeO-DMT References Diethylamino compounds Lysergamides Methoxy compounds {{Organic-compound-stub ...
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12-Hydroxy-LSD
12-Hydroxy-LSD is a drug of the ergoline and lysergamide families and a derivative of lysergic acid diethylamide (LSD). In terms of chemical structure, 12-hydroxy-LSD is to LSD as bufotenin (5-HO-DMT) is to dimethyltryptamine (DMT), with 12-hydroxy-LSD notably containing bufotenin within its rigidified structure. 12-Hydroxy-LSD produces psychedelic-like effects in animals, whereas reports on its activities in humans are very limited and have been conflicting. Pharmacology 12-Hydroxy-LSD is known to be pharmacologically active in animal studies. The drug's effects in rabbits include antiserotonergic activity (25% of that of LSD) and hyperthermia (dose ratio relative to of 1:44 for 12-hydroxy-LSD and 1:725 for LSD). In addition, like LSD, it is highly potent in terms of lethality, with a median lethal dose (LD50) of 0.3mg/kg in rabbits (relative to 0.1mg/kg for LSD). 12-Hydroxy-LSD also produces LSD-like electroencephalogram (EEG) changes in rabbits. According to Robert C. Pfa ...
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Lysergamides
Lysergamides, also known as ergoamides or as lysergic acid amides, are amides of lysergic acid (LA). They are ergolines, with some lysergamides being found natural product, naturally in ergot as well as other fungi. Lysergamides are notable in containing embedded substituted phenethylamine, phenethylamine and substituted tryptamine, tryptamine moiety (chemistry), moieties within their ergoline ring system (chemistry), ring system. The simplest lysergamides are ergine (lysergic acid amide; LSA) and isoergine (iso-lysergic acid amide; iso-LSA). In terms of pharmacology, the lysergamides include numerous serotonin and dopamine receptor (biochemistry), receptor agonists, most notably the psychedelic drug lysergic acid diethylamide (LSD) but also a number of pharmaceutical drugs like ergometrine, methylergometrine, methysergide, and cabergoline. Various analogues of LSD, such as the psychedelics ALD-52 (1A-LSD), ETH-LAD, LSZ, and 1P-LSD and the non-hallucinogenic 2-bromo-LSD (BOL-148) ...
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Lysergic Acid Diethylamide
Lysergic acid diethylamide, commonly known as LSD (from German ; often referred to as acid or lucy), is a Semisynthesis, semisynthetic, Hallucinogen, hallucinogenic compound derived from ergot, known for its powerful psychological effects and Serotonin, serotonergic activity. It was historically significant in psychiatry and 1960s counterculture; it is currently legally restricted but experiencing renewed scientific interest and increasing use. When taken orally, LSD has an onset of action within 0.4 to 1.0 hours (range: 0.1–1.8 hours) and a duration of effect lasting 7 to 12 hours (range: 4–22 hours). It is commonly administered via tabs of Blotting paper, blotter paper. LSD is extremely potent, with noticeable effects at doses as low as 20 Microgram, micrograms and is sometimes taken in much smaller amounts for microdosing. Yet no fatal human overdoses have been documented. LSD is mainly used recreationally or for spiritual purposes. LSD can cause mystical experiences. ...
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Pharmacology
Pharmacology is the science of drugs and medications, including a substance's origin, composition, pharmacokinetics, pharmacodynamics, therapeutic use, and toxicology. More specifically, it is the study of the interactions that occur between a living organism and chemicals that affect normal or abnormal biochemical function. If substances have medicinal properties, they are considered pharmaceuticals. The field encompasses drug composition and properties, functions, sources, synthesis and drug design, molecular and cellular mechanisms, organ/systems mechanisms, signal transduction/cellular communication, molecular diagnostics, interactions, chemical biology, therapy, and medical applications and antipathogenic capabilities. The two main areas of pharmacology are pharmacodynamics and pharmacokinetics. Pharmacodynamics studies the effects of a drug on biological systems, and pharmacokinetics studies the effects of biological systems on a drug. In broad terms, pharmacod ...
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Electroencephalogram
Electroencephalography (EEG) is a method to record an electrogram of the spontaneous electrical activity of the brain. The bio signals detected by EEG have been shown to represent the postsynaptic potentials of pyramidal neurons in the neocortex and allocortex. It is typically non-invasive, with the EEG electrodes placed along the scalp (commonly called "scalp EEG") using the International 10–20 system, or variations of it. Electrocorticography, involving surgical placement of electrodes, is sometimes called "intracranial EEG". Clinical interpretation of EEG recordings is most often performed by visual inspection of the tracing or quantitative EEG analysis. Voltage fluctuations measured by the EEG bio amplifier and electrodes allow the evaluation of normal brain activity. As the electrical activity monitored by EEG originates in neurons in the underlying brain tissue, the recordings made by the electrodes on the surface of the scalp vary in accordance with their orie ...
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13-hydroxy-LSD
13-Hydroxy-LSD is a lysergamide and a metabolite of the psychedelic drug lysergic acid diethylamide (LSD). It is a major metabolite of LSD in rats and guinea pigs but a minor metabolite of LSD in monkeys and humans. Following its formation, 13-hydroxy-LSD undergoes further metabolism via glucuronidation. Little is known about the specific enzymes responsible for generation of LSD metabolites such as 13-hydroxy-LSD in humans. According to David E. Nichols in 2016, the pharmacology of hydroxylated metabolites of LSD like 13-hydroxy-LSD has not been studied. Nichols has posited that metabolism of LSD into active metabolites with potent dopamine receptor activity may be responsible for the delayed-onset dopaminergic stimulus effects of LSD in rodent drug discrimination tests. Relatedly, lergotrile's corresponding metabolite 13-hydroxylergotrile is several-fold more potent as a dopamine receptor agonist than lergotrile itself ''in vitro''. However, more research is needed to a ...
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Metabolite
In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, catalytic activity of their own (usually as a cofactor to an enzyme), defense, and interactions with other organisms (e.g. pigments, odorants, and pheromones). A primary metabolite is directly involved in normal "growth", development, and reproduction. Ethylene exemplifies a primary metabolite produced large-scale by industrial microbiology. A secondary metabolite is not directly involved in those processes, but usually has an important ecological function. Examples include antibiotics and pigments such as resins and terpenes etc. Some antibiotics use primary metabolites as precursors, such as actinomycin, which is created from the primary metabolite tryptophan. Some sugars are metabolites, such as fructose or glucose, which ar ...
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