Psilocin Ester, The phosphate ester in psilocybin is delicate,
- Psilocin Ester, The phosphate ester in psilocybin is delicate, and analysis of psilocybin-containing substrates by standard analytical techniques is therefore problematic. 2 Psilocybin 2. Specifically, the disclosure provides ester derivatives of psilocin and related tryptamines, and methods for treating neurological diseases or disorders, including neurodegenerative diseases, pain, and/or psychiatric disorders that comprise the Know about technical details of Psilocin phosphate ester like: chemical name, chemistry structure, formulation, uses, toxicity, action, side effects and more at Pharmacompass. The study successfully identified several psilocin ester prodrugs and psilocin salts that exhibited desirable characteristics, including storage and handling stability, rapid metabolic conversion to psilocin, and easy synthesis, with potential advantages over psilocybin. Hallucinogenic effects set in rapidly within less than an hour of ingestion and are probably mediated via the serotonergic receptors. These compounds are useful for the treatment or prevention of mental health disorders, such as major depressive disorder, anxiety and addiction disorders, among Here, the authors provide structural and mechanistic insights into psilocybin biosynthesis enzymes, encompassing L-tryptophan-specific decarboxylase PsiD, 4-hydroxytryptamine kinase PsiK, and IUPAC Standard InChIKey: QVDSEJDULKLHCG-UHFFFAOYSA-N Copy CAS Registry Number: 520-52-5 Chemical structure: This structure is also available as a 2d Mol file Other names: Psilocybin; 1H-Indol-4-ol, 3- [2- (dimethylamino)ethyl]-, dihydrogen phosphate (ester); Indol-4-ol, 3- [2- (dimethylamino)ethyl]-, dihydrogen phosphate (ester); Cy 39; Indocybin; 3- [2- (Dimethylamino)ethyl]indol-4-ol This screen revealed fifteen prodrugs that produced measurable levels of psilocin in vitro, with ester and thiocarbonate-based prodrug derivatives significantly represented. 1 Freebase Psilocin 2. Specifically, the disclosure provides ester derivatives of psilocin and related tryptamines, and methods for treating neurological diseases or disorders, including neurodegenerative diseases, pain, and/or psychiatric disorders that comprise the compounds or compositions thereof. Psilocin is a potent serotonin 2a agonist, and is the primary origin of its psychoactive properties (Geiger et al. [20] The elimination half-life of psilocin was approximately 30 minutes and did not differ between 4-AcO-DMT and psilocybin. Psilocybin mushrooms are any of several species of hallucinogenic fungi, across a number of genera. 1) are naturally occurring tryptamines found in a variety of mushroom-forming fungi colloquially known as “magic mushrooms” or “shrooms”. 1. e. 4,5 Psilocybin and psilocin differ from each other at position 4, having a phosphate and hydroxyl group, respectively. Psilocin is defined as the bioactive agent formed from the dephosphorylation of psilocybin, an indole alkaloid derived from certain fungi, and it is structurally analogous to serotonin, binding to various serotonin receptors and disrupting serotonergic neurotransmission. Other adverse effects include severe nausea, vomiting, cardiovascular side effects, hyperthermia, dilated pupils, and convulsions. [5] Psilocin ester prodrugs like 4-AcO-DMT are cleaved into psilocin by esterase enzymes. cubensis. [28][20] Psilocin is chemically related to the neurotransmitter serotonin and acts as a non-selective agonist of the serotonin receptors. The present application relates to cost-effective, practical and scalable synthetic routes for the syntheses for psilocybin (Formula I) and its major metabolite psilocybin (Formula II) and their pharmaceutically acceptable salts. Abstract A simple aqueous extraction method for the isolation and identification of psilocin from Psilocybe cubensis mushrooms is reported. It has a biologically relevant affinity for serotonin receptors and is responsible for the observable acute behavioral effects after psilocybin administration. Psilocin (1) is a minor hallucinogenic component isolatedl from the mushroom species Psilocybe mexicana withthe accompanying phosphorylation product psilocybin (2) and is the active species in the central nervous system (Figure 1),1,2 In spite of its interesting physiological activities and its rather have been reported so far e syn PDSP2_001375 psilocibina psilocibina; psilocybine; psilocybinum psilocin phosphate ester Psilocine phosphate Psilocybin-d10 Psilocybin-d10 (exempt preparation) Important for clinical studies, psilocin time-concentration curves varied but psilocin levels were closely associated with psychedelic experience. Click here to learn more! Psilocybin and psilocin Psilocybin and Psilocin (4-HO-DMT) (Fig. 5,6 This is because psilocin is more susceptible to oxidation due to the lack of the phosphate group that is present in psilocybin. Psilocin, hallucinogenic principle contained in certain mushrooms, notably the Mexican species Psilocybe mexicana and P. Psilocin Psilocin Systematic (IUPAC) name 4-Hydroxy-N,N-dimethyl-tryptamine Identifiers CAS number 520-53-6 ATC code ? PubChem 4980 Chemical data Formula The world-famous chemists Albert Hofmann and Alexander and Ann Shulgin have said that psilocin on its own is an unstable compound compared to psilocybin. Also provided are methods for preparing the compounds described The indoles psilocin and its phosphate ester psilocybin are structural analogues of serotonin (5-hydroxytryptamine) and act on the 5-HT2 receptors. Psilocin, also called N,N-dimethyl-4-hydroxytryptamine, is a psychoactive substance that was first isolated in 1958 by Albert Hofmann and co-workers at Sandoz (Basel, Switzerland; now part of Novartis) from the psychedelic mushroom Psilocybe mexicana. Psilocybin is the phosphoric acid ester of psilocin and, as such, is the first and hitherto only phosphoric-acid-containing indole compound discovered in nature. Herein, we Psilocybin is the most well-known compound found in psychedelic mushrooms (aka psilocybin mushrooms or magic mushrooms). In vivo, psilocybin is rapidly dephosphorylated to psilocin which induces psychedelic effects by interacting with the 5-HT2A receptor. Oct 16, 2023 · The disclosure relates to compounds, compositions, methods and uses relating to activation of one or more serotonin receptors (i. Three patents-focused on controlled-release delivery systems, ester analogs, and acetal/ketal derivatives-present novel approaches to enhancing the stability, bioavailability, and efficacy of psilocin and related compounds. Some other mushroom species also contain these products [2, 3, 4]. As I had discussed in the CZ-74 to CEY-19 entries in 4-HO-DET, there is no proof that the ester goes to the indolol metabolically, but it is a good guess, and there have been no demonstrated differences in their 1 Brief overview - What is Bufotenine? 2 Chemical and physical properties 2. The OK item is the casual equation between the hydroxy compound psilocin, the acetate ester, and the phosphate ester, psilocybin. This method employs a dephosphorylation of the phosphate ester to psilocin, which facilitates a greater product yield and simplifies identification. These mushrooms produce psychoactive compounds psilocybin and psilocin, which can have mind-altering effects. 33. Pharmaceutically acceptable salts, esters and conjugates of psilocin and compositions and methods for their production and use in treating diseases or conditions treatable with psilocin or psilocybin are provided. Also provided are methods for preparing the compounds described The study successfully identifiedseveral psilocin ester prodrugs and psilocin salts that exhibited desirable characteristics, including storage and handling stability, rapid metabolic conversion to psilocin, and easy synthesis, with potential advantages over psilocybin. Current medical-grade psilocybin production is inefficient and relies on a complicated multistep synthesis. Psilocin, also known as 4-hydroxy-N,N-dimethyltryptamine (4-HO-DMT), is a psychedelic drug and fungal alkaloid of the tryptamine and 4-hydroxytryptamine families. This means that psilocin mimics the shape of serotonin and can bind to a serotonin receptor called 5-ht 2a. 1 Psilocybin (Psilocin Phosphate Ester) 3 Effects 4 Pharmacology, toxicity and general safety 5 Plants containing bufotenine 6 Extraction teks 7 Dosages and consumption methods 8 History of usage 9 Analysis of bufotenine 10 Scientific publications 11 Other links of Psilocybin | C12H17N2O4P | CID 10624 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety Under certain conditions (temperature or pH), the ester in 4-acetoxy-DMT may be hydrolyzed into an alcohol and an acid, that is, psilocin and acetic acid. [20] Psilocybin is transformed into psilocin by dephosphorylation mediated via phosphatase enzymes. Neuropsychopharmacology - Plasma psilocin critically determines behavioral and neurobiological effects of psilocybin Here we look at the various differences between the two psychedelic compounds psilocin and psilocybin, found in magic mushrooms. , 5-HT2 receptors). It is a substituted tryptamine and prodrug of psilocin, and the compound that… This guide compares psilocin to psilocybin, highlighting differences and similarities in how they work in the body, their effects, strength, benefits, and legality. The half-life of psilocin remained consistent at around 30 minutes, regardless of whether it originated from psilocybin or psilacetin. [38] A 2025 in-vitro study examined the stability and metabolism of several psilocin ester prodrugs, including 4-AcO-DMT. The body converts the prodrug psilocybin into psilocin. chemical compound 4-PO-DMT O-phosphoryl-4-hydroxy-N,N-dimethyltryptamine 4-phosphoryloxy-N,N-dimethyltryptamine psilocin phosphate ester psilocybine indocybin 3- (2- (dimethylamino)ethyl)-1H-indol-4-ol dihydrogen phosphate ester 3- (2-dimethylaminoethyl)indol-4-yl dihydrogen phosphate So, how does psilocin cause you to have a psychedelic experience? The answer is that psilocin is an agonist for serotonin receptors. Also provided are methods for preparing the compounds described The psychedelic prodrug psilocybin has shown therapeutic benefits for the treatment of numerous psychiatric conditions. Learn more about Psilocybin uses, effectiveness, possible side effects, interactions, dosage, user ratings and products that contain Psilocybin. This method employs adephosphorylation f the phosphate ester o psilocin, which facilitates agreater product yield and simplifies identifica-tion. The phosphoric acid residue does not contribute to the activity, for the phosphoric-acid-free psilocin is just as active as psilocybin, but it makes the molecule more stable. That is, the compound itself is biologically inactive but quickly converted by the body to psilocin. Psilocin primarily undergoes glucuronidation or conversion to 4-hydroxyindole-3-acetic acid (4-HIAA). This current review was conducted following a search, using SciFinder as a database, on methods of synthesizing psilocin or psilocybin. 2. The mass spectrum of derivatized psilocin is given in Fig. Psilocybin is known to break down into psilocin at high temperatures and at high pH. Psilocin is an active metabolite that is formed when psilocybin, a tryptamine, is administered systemically. Psilocin can also be analyzed by GC/MS after derivatization with BSTFA reagent (N, O -bis-trimethylsilyl-acetamide containing 1% trimethylchlorosilane) to covert psilocin to its trimethylsilyl ester (psilocin-1,4-di-trimethylsilyl) (Paul DB unpublished data). , 2009a). Psilocin alters the actions of the neurotransmitter serotonin in the brain. The psilocybin pathway originates from l -tryptophan, which undergoes decarboxylation, oxygenation and phosphate ester formation to yield norbaeocystin, the acceptor substrate for the Other names: Psilocybin; 1H-Indol-4-ol, 3- [2- (dimethylamino)ethyl]-, dihydrogen phosphate (ester); Indol-4-ol, 3- [2- (dimethylamino)ethyl]-, dihydrogen phosphate (ester); Cy 39; Indocybin; 3- [2- (Dimethylamino)ethyl]indol-4-ol dihydrogen phosphate ester; 3- [2- (Dimethylamino)ethyl]indol-4-yl dihydrogen phosphate; 1H-Indol-4-ol, 3- [2 Psilocin, and not psilocybin, is actually responsible for the psychedelic effects of magic mushrooms. [39] Psilocin | C12H16N2O | CID 4980 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety The study successfully identified several psilocin ester prodrugs and psilocin salts that exhibited desirable characteristics, including storage and handling stability, rapid metabolic conversion to psilocin, and easy synthesis, with potential advantages over psilocybin. Considering the two substances’ similar skeletal structure, the authors wondered whether the sample was indeed a mixture of the two substances, or whether perhaps 4-acetoxy-DMT was hydrolyzed to psilocin during the analysis. Psilocin is a 4-hydroxy substituted DMT compound and psilocybin is its phosphorylated product. This study has explored and evaluated psilocin ester prodrugs and psilocin salts as potential alternatives to psilocybin Specifically, the disclosure provides ester derivatives of psilocin and related tryptamines, and methods for treating neurological diseases or disorders, including neurodegenerative diseases, pain, and/or psychiatric disorders that comprise the compounds or compositions thereof. [8][9][2] Along with its phosphate ester psilocybin, it is found in most species of psilocybin-containing mushrooms, such as Psilocybe cubensis and Psilocybe mexicana, and is the Mar 20, 2025 · As interest in using psilocybin therapy for treating mental health disorders intensifies, the need for efficient production methods becomes increasingly important. Jun 16, 2025 · This study has explored and evaluated psilocin ester prodrugs and psilocin salts as potential alternatives to psilocybin, focusing on their ease of synthesis, chemical stability, and metabolic profiles. The first two indole derivatives identified in 1958 and then synthesized in 1959 by Hofmann and co-workers were psilocybin and psilocin [5, 6]. , 2018 ). com. The sample chromatogram showed a mixture of two illicit drugs, 4-acetoxy-DMT and psilocin. . Psilocin extracted by this method is sufficiently concentrated and free of co-contaminants to allow identification by infrared spectroscopy and gas chromatography/mass spectrometry. This screen revealed fifteen prodrugs that produced measurable levels of psilocin in vitro, with ester and thiocarbonate-based prodrug derivatives significantly represented. Despite positive clinical end points targeting depression and anxiety, concerns regarding the duration of the psychedelic experience produced by psilocybin, associated with enduring systemic exposure to the active metabolite psilocin, pose a barrier to its therapeutic Psilocybin is the phosphorylated ester of psilocin (Figure 1). Psilocin causes anxiety, disorientation, depersonalization, psychosis, and hallucinations. The psychedelic prodrug psilocybin has shown therapeutic benefits for the treatment of numerous psychiatric conditions. 1 Psilocin 2. The Hofmann group elucidated the structure of the molecule and synthesized it the same year. Learn more about the effects and history of psilocin. These effects usually last for about 2 h and can be extremely intense and frightening (Beyer et al. Despite positive clinical end points targeting depression and anxiety, concerns regarding the duration of the psychedelic Chemical Structures of Psilocybin and Psilocin Psilocybin and psilocin (Figure 1) are tryptamine alkaloids and structural analogs of the neurotransmitter serotonin (Figure 2). Serotonin is the chemical responsible for regulating brain functions, including mood and emotions. The ester modifications introduced in these analogs improve psilocin’s pharmacokinetic and pharmacodynamic profiles, leading to prolonged therapeutic effects and excellent selectivity for the desired receptor subtypes. Overall, psilocin exposure from 4-AcO-DMT fumarate was approximately 70% of that observed with psilocybin. These fifteen NPDs were further evaluated for pharmacokinetic (PK) profiles in mice, assessing plasma levels of both residual prodrug and resultant psilocin. Psilacetin, 4-acetoxy- N, N -dimethyltryptamine, C 14 H 18 N 2 O 2 (4-AcO-DMT), is a synthetic alternative to psilocybin. uqbf8, 542by, w80on, cmizb, gswfw, wy7xnq, lp1z, grbvq, lmlrw, ybme,