2-Oxo-3-hydroxy-LSD
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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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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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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-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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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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2,3-Dihydro-LSD
2,3-Dihydro-LSD, or 2,3-DH-LSD, also known as 2,3-dihydrolysergic acid diethylamide, is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD). It is the analogue of LSD in which the 2,3- double bond in the indole ring within the ergoline ring system has been hydrogenated. Use and effects The drug produces similar autonomic and psychoactive effects as LSD in humans, although its hallucinogenic effects are less pronounced. It has been found to possess about one-sixth to one-eighth (i.e., ~15% overall) of the potency of LSD in inducing mydriasis (pupil dilation) and psychedelic effects, respectively, in humans. More specifically, 2,3-dihydro-LSD is psychedelic at doses of 3.0 to 4.5μg/kg (210–315μg for a 70-kg person), while LSD is hallucinogenic at doses of 0.5 to 1.0μg/kg (35–70μg for a 70-kg person). In addition to its greatly reduced potency compared to LSD, 2,3-dihydro-LSD has a delayed onset and time to peak effects relative to LSD ...
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Serotonin Receptor Modulator
5-HT receptors, 5-hydroxytryptamine receptors, or serotonin receptors, are a group of G protein-coupled receptor and ligand-gated ion channels found in multiple tissues including the central and peripheral nervous systems. They mediate both excitatory and inhibitory neurotransmission. The serotonin (i.e., 5-hydroxytryptamine, hence "5-HT") receptors are activated by the neurotransmitter serotonin, which acts as their natural ligand. The serotonin receptors modulate the release of many neurotransmitters, including glutamate, GABA, dopamine, epinephrine / norepinephrine, and acetylcholine, as well as many hormones, including oxytocin, prolactin, vasopressin, cortisol, corticotropin, and substance P, among others. Serotonin receptors influence various biological and neurological processes such as aggression, anxiety, appetite, cognition, learning, memory, mood, nausea, sleep, and thermoregulation. They are the target of a variety of pharmaceutical and recreational drugs, includin ...
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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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Cyclic Ketones
In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone (where R and R' are methyl), with the formula . Many ketones are of great importance in biology and industry. Examples include many sugars (ketoses), many steroids, ''e.g.'', testosterone, and the solvent acetone. Nomenclature and etymology The word ''ketone'' is derived from ''Aketon'', an old German word for ''acetone''. According to the rules of IUPAC nomenclature, ketone names are derived by changing the suffix ''-ane'' of the parent alkane to ''-anone''. Typically, the position of the carbonyl group is denoted by a number, but traditional nonsystematic names are still generally used for the most important ketones, for example acetone and benzophenone. These nonsystematic names are considered retained IUPAC names, although some introdu ...
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Hydroxyarenes
Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it requires careful handling because it can cause chemical burns. It is acutely toxic and is considered a health hazard. Phenol was first extracted from coal tar, but today is produced on a large scale (about 7 million tonnes a year) from petroleum-derived feedstocks. It is an important industrial commodity as a precursor to many materials and useful compounds, and is a liquid when manufactured. It is primarily used to synthesize plastics and related materials. Phenol and its chemical derivatives are essential for production of polycarbonates, epoxies, explosives such as picric acid, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceutical dru ...
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Human Drug Metabolites
Humans (''Homo sapiens'') or modern humans are the most common and widespread species of primate, and the last surviving species of the genus ''Homo''. They are great apes characterized by their hairlessness, bipedalism, and high intelligence. Humans have large brains, enabling more advanced cognitive skills that facilitate successful adaptation to varied environments, development of sophisticated tools, and formation of complex social structures and civilizations. Humans are highly social, with individual humans tending to belong to a multi-layered network of distinct social groups — from families and peer groups to corporations and political states. As such, social interactions between humans have established a wide variety of values, social norms, languages, and traditions (collectively termed institutions), each of which bolsters human society. Humans are also highly curious: the desire to understand and influence phenomena has motivated humanity's developmen ...
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