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Psilocybin, also known as 4-phosphoryloxy-N,N-dimethyltryptamine (4-PO-DMT),[a] is a naturally occurring tryptamine alkaloid and investigational drug found in more than 200 species of mushrooms, with hallucinogenic and serotonergic effects.[20][25] Effects include euphoria, changes in perception, a distorted sense of time,[26] and perceived spiritual experiences. It can also cause adverse reactions such as nausea and panic attacks.[27]

Psilocybin is a prodrug of psilocin.[20] That is, the compound itself is biologically inactive but quickly converted by the body to psilocin.[20] Psilocybin is transformed into psilocin by dephosphorylation mediated via phosphatase enzymes.[28][20] Psilocin is chemically related to the neurotransmitter serotonin and acts as a non-selective agonist of the serotonin receptors.[20] Activation of one serotonin receptor, the serotonin 5-HT2A receptor, is specifically responsible for the hallucinogenic effects of psilocin and other serotonergic psychedelics.[20] Psilocybin is usually taken orally.[20] By this route, its onset is about 20 to 50 minutes, peak effects occur in about 1 to 2 hours, and its duration is about 4 to 6 hours.[11][19][20][14]

Psilocybin mushrooms were used ritualistically in pre-Columbian Mexico, but claims of their widespread ancient use are largely exaggerated and shaped by modern idealization and ideology.[29] In 1958, the Swiss chemist Albert Hofmann isolated psilocybin and psilocin from the mushroom Psilocybe mexicana. His employer, Sandoz, marketed and sold pure psilocybin to physicians and clinicians worldwide for use in psychedelic therapy. Increasingly restrictive drug laws of the 1960s and the 1970s curbed scientific research into the effects of psilocybin and other hallucinogens, but its popularity as an entheogen grew in the next decade, owing largely to the increased availability of information on how to cultivate psilocybin mushrooms. Buy Psilocybin (4-PO-DMT) Cas-520-52-5

Possession of psilocybin-containing mushrooms has been outlawed in most countries, and psilocybin has been classified as a Schedule I controlled substance under the 1971 United Nations Convention on Psychotropic Substances. Psilocybin is being studied as a possible medicine in the treatment of psychiatric disorders such as depressionsubstance use disordersobsessive–compulsive disorder, and other conditions such as cluster headaches.[30] Psilocybin was approved for treatment-resistant depression in Australia in 2023.[31][32] It is in late-stage clinical trials in the United States for treatment-resistant depression.[33][34][35] A decision on approval of psilocybin for this indication is expected by the end of 2026.[36] Especially at higher doses and combined with psychological support, single doses of psilocybin can produce rapid and long-lasting antidepressant effects that generally outperform placebo, though they show only modest advantages over conventional continuous antidepressants like selective serotonin reuptake inhibitor (SSRIs); the quality of evidence is generally low and trial bias is common.[37][38][39][40][41]

Psilocybin is a hallucinogenic agent that binds to the serotonin receptor and produces psilocybin-induced visual distortions, changes in perception, and alterations in mood. It is used as a pharmacological treatment for psychological disorders such as anxiety, depression, and obsessive compulsive disorder. In humans, psilocybin increases metabolic rate and monoamine neurotransmitter levels in the occipital cortex. The effects of this drug are dose-dependent with low doses producing perceptual changes, while higher doses produce euphoria and hallucinations. Psilocybin has been shown to be an effective treatment for treatment-resistant symptoms of obsessive compulsive disorder with significantly reduced symptoms after six months of therapy.Buy Psilocybin (4-PO-DMT) Cas-520-52-5

Uses

Psilocybin is used recreationallyspiritually (as an entheogen), and medically.[42] It is primarily taken orally, but other routes of administration, such as intravenous injection, are sometimes employed by licensed medical researchers using pharmaceutical-grade psilocybin powder designed for injection. Injection should never be attempted by unlicensed people.[7]

Medical

In 2023, the Therapeutic Goods Administration (TGA) approved psilocybin for treatment of treatment-resistant depression in Australia.[43][44][45] It is also under development for the treatment of depression and for various other indications elsewhere, such as the United States and Europe, but has not yet been approved in other countries (see below).[10][30][35]

Dosing

Psilocybin is used as a psychedelic at doses of 5 to 40 mg orally.[14][46] Low doses are 5 to 10 mg, an intermediate or “good effect” dose is 20 mg, and high or ego-dissolution doses are 30 to 40 mg.[14][46] Psilocybin’s effects can be subjectively perceived at a dose as low as 3 mg per 70 kg body weight.[46][47] Microdosing involves the use of subthreshold psilocybin doses of less than 2.5 mg.[14][46]

When psilocybin is used in the form of psilocybin-containing mushrooms, microdoses are 0.1 g to 0.3 g and psychedelic doses are 1.0 g to 3.5–5.0 g in the case of dried mushrooms.[48][49][7] The preceding 1.0 to 5.0 g range corresponds to psilocybin doses of about 10 to 50 mg.[7] Psilocybin-containing mushrooms vary in their psilocybin and psilocin content, but are typically around 1% of the dried weight of the mushrooms (in terms of total or combined psilocybin and psilocin content).[49][50][21][7][28][51][52][53] Psilocin is about 1.4 times as potent as psilocybin because of the two compounds’ difference in molecular weight.[21][54][55]

“Lemon tek” or “lemon tekking” is a method sometimes used by recreational psilocybin users.[56][57][58] It involves soaking psilocybin-containing mushrooms in citric acid-containing lemon juice to supposedly convert their psilocybin content into psilocin before administration.[56][57][58] This is claimed to hasten their onset, cause a sharper and more intense peak, and shorten their duration.[56][57][58]

Available forms

Psilocybin is most commonly consumed in the form of psilocybin-containing mushrooms, such as Psilocybe species like Psilocybe cubensis. It may also be prepared synthetically, but outside of research settings it is not typically used in this form. Regardless of form, psilocybin is usually taken orally. The psilocybin present in certain species of mushrooms can be ingested in several ways: by consuming fresh or dried fruit bodies, by preparing an herbal tea, or by combining with other foods to mask the bitter taste.[59] In rare cases people have intravenously injected mushroom extracts, with serious medical complications such as systemic mycological infection and hospitalization.[60][61][62][63] Another form of psilocybin (as well as of related psychedelics like 4-AcO-DMT) is mushroom edibles such as chocolate bars and gummies, which may be purchased at psychedelic mushroom stores.

Psilocybin, an indole derivative and alkaloid found in certain mushrooms, is a naturally occurring hallucinogenic drug. It has been used for centuries by Mesoamerican natives, particularly in spiritual ceremonies, and is described as an entheogen, a substance used to raise spiritual consciousness. Although psilocybin possession is now outlawed in most countries, its illicit use remains widespread. Buy Psilocybin (4-PO-DMT) Cas-520-52-5

520-52-5

  • 520-52-5 Structure
  • Basic information

    1. Product Name: psilocybine
    2. Synonyms: INDOL-4-OL,3-(2-DIMETHYLAMINO)ETHYL)-DIHYDROGENPHOSPHATE;3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol 4-Dihydrogen Phosphate Ester;4-Phosphoryl-N,N-dimethyltryptamine;Cy 39;Indocybin;O-Phosphoryl-4-hydroxy-N,N-dimethyltryptamine;Psilocine Phosphate;3-[2-(Dimethylamino)ethyl]-1H-indol-4-yl phosphate
    3. CAS NO:520-52-5
    4. Molecular Formula: C12H17N2O4P
    5. Molecular Weight: 284.25
    6. EINECS: 208-294-4
    7. Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Phosphorylating and Phosphitylating Agents;Indole Derivatives
    8. Mol File: 520-52-5.mol
  • Chemical Properties

    1. Melting Point: 220-2280C
    2. Boiling Point: 523.4°Cat760mmHg
    3. Flash Point: 2℃
    4. Appearance: /solid
    5. Density: 1.409g/cm3
    6. Vapor Pressure: 8.75E-12mmHg at 25°C
    7. Refractive Index: 1.644
    8. Storage Temp.: −20°C
    9. Solubility: N/A
    10. PKA: 1.25±0.30(Predicted)
    11. CAS DataBase Reference: psilocybine(CAS DataBase Reference)
    12. NIST Chemistry Reference: psilocybine(520-52-5)
    13. EPA Substance Registry System: psilocybine(520-52-5)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. RIDADR: 1544
    5. WGK Germany: 1
    6. RTECS: NM3150000
    7. HazardClass: 6.1(b)
    8. PackingGroup: III
    9. Hazardous Substances Data: 520-52-5(Hazardous Substances Data)

520-52-5 Suppliers

This product is a nationally controlled contraband or patented product, and the Lookchem platform doesn’t provide relevant sales information.

520-52-5 Usage

Uses

Used in Recreational Hallucinations:
Psilocybin is used as a recreational hallucinogen for inducing altered states of consciousness and sensory experiences. Its popularity stems from its ability to provoke vivid hallucinations, changes in perception, and a sense of euphoria.
Used in Spiritual Ceremonies:
In some Native American groups, psilocybin-containing mushroom species are employed in official ceremonies, where they are used as entheogens to facilitate spiritual experiences and connect with the divine.
Used in Psychotherapy (Historic):
During the 1960s and 1970s, psilocybin was investigated for its potential utility in psychotherapy. It was used as an adjunctive treatment to help patients explore their inner psyche and address various psychological issues. However, due to changes in drug laws, this use has been discontinued in mainstream medicine.
Used as a Controlled Substance:
Psilocybin is classified as a controlled substance (hallucinogen) due to its psychoactive effects and potential for abuse. Its regulation aims to prevent misuse and ensure that its use is limited to appropriate contexts, such as research or specific cultural practices.

Safety Profile

Poison by intravenous route. Moderately toxic by intraperitoneal route. Human systemic effects by ingestion and intraperitoneal routes: euphoria, hallucinations, toxic psychosis, muscle weakness, nausea or vomiting, visual field changes. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and POx.

Check Digit Verification of cas no

The CAS Registry Mumber 520-52-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,2 and 0 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 520-52:
(5*5)+(4*2)+(3*0)+(2*5)+(1*2)=45
45 % 10 = 5
So 520-52-5 is a valid CAS Registry Number.

InChI:InChI=1/C12H17N2O4P/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)18-19(15,16)17/h3-5,8,13H,6-7H2,1-2H3,(H2,15,16,17)

520-52-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) – Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name psilocybin

1.2 Other means of identification

Product number
Other names [3-[2-(dimethylamino)ethyl]-1H-indol-4-yl] dihydrogen phosphate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier’s details

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More Details:520-52-5 SDS

520-52-5Downstream Products

520-52-5Relevant academic research and scientific papers

Scalable Hybrid Synthetic/Biocatalytic Route to Psilocybin

Fricke, Janis,Kargbo, Robert,Regestein, Lars,Lenz, Claudius,Peschel, Gundela,Rosenbaum, Miriam A.,Sherwood, Alexander,Hoffmeister, Dirk

, p. 8281 – 8285 (2020)

Psilocybin, the principal indole alkaloid of Psilocybe mushrooms, is currently undergoing clinical trials as a medication against treatment-resistant depression and major depressive disorder. The psilocybin supply for pharmaceutical purposes is met by synthetic chemistry. We replaced the problematic phosphorylation step during synthesis with the mushroom kinase PsiK. This enzyme was biochemically characterized and used to produce one gram of psilocybin from psilocin within 20 minutes. We also describe a pilot-scale protocol for recombinant PsiK that yielded 150 mg enzyme in active and soluble form. Our work consolidates the simplicity of tryptamine chemistry with the specificity and selectivity of enzymatic catalysis and helps provide access to an important drug at potentially reasonable cost.

An Improved, Practical, and Scalable Five-Step Synthesis of Psilocybin

Kargbo, Robert B.,Meisenheimer, Poncho,Sherwood, Alexander M.,Tarpley, Gary

, p. 688 – 694 (2020)

Described herein is an improved synthesis of 3-[2-(dimethylamino)ethyl]-1 H -indol-4-yl dihydrogen phosphate (psilocybin). The protocol outlines: synthesis of multigram quantities of psilocybin, identification of critical in-process parameters, and isolation of psilocybin without the use of chromatography, TLC, or aqueous workup. The synthesis furnishes psilocybin in five steps in 23percent overall yield from an inexpensive acetoxyindole starting material. With specific focus on process control and impurity fate and removal, the improved procedure is amenable to providing high-quality psilocybin.

PREPARATION OF PSILOCYBIN, DIFFERENT POLYMORPHIC FORMS, INTERMEDIATES, FORMULATIONS AND THEIR USE

, (2019/05/02)

This invention relates to the large-scale production of psilocybin for use in medicine. More particularly, it relates to a method of obtaining high purity crystalline psilocybin, particularly, in the form of Polymorph A. It further relates to a method for the manufacture of psilocybin and intermediates in the production thereof and formulations containing psilocybin.

Biocatalytic Production of Psilocybin and Derivatives in Tryptophan Synthase-Enhanced Reactions

Blei, Felix,Baldeweg, Florian,Fricke, Janis,Hoffmeister, Dirk

, p. 10028 – 10031 (2018/07/29)

Psilocybin (4-phosphoryloxy-N,N-dimethyltryptamine) is the main alkaloid of the fungal genus Psilocybe, the so-called “magic mushrooms.” The pharmaceutical interest in this psychotropic natural product as a future medication to treat depression and anxiety is strongly re-emerging. Here, we present an enhanced enzymatic route of psilocybin production by adding TrpB, the tryptophan synthase of the mushroom Psilocybe cubensis, to the reaction. We capitalized on its substrate flexibility and show psilocybin formation from 4-hydroxyindole and l-serine, which are less cost-intensive substrates, compared to the previous method. Furthermore, we show enzymatic production of 7-phosphoryloxytryptamine (isonorbaeocystin), a non-natural congener of the Psilocybe alkaloid norbaeocystin (4-phosphoryloxytryptamine), and of serotonin (5-hydroxytryptamine) by means of the same in vitro approach.

Concise large-scale synthesis of psilocin and psilocybin, principal hallucinogenic constituents of “magic mushroom”

Shirota, Osamu,Hakamata, Wataru,Goda, Yukihiro

, p. 885 – 887 (2007/10/03)

The concise large-scale syntheses of psilocin (1) and psilocybin (2), the principal hallucinogenic constituents of “magic mushroom”, were achieved without chromatographic purification. The key step in the synthesis of 2 was the isolation of the dibenzyl-protected intermediate (7) as a zwitterionic derivative (8), which was completely identified by means of 2D NMR analyses.

Improvements to the synthesis of psilocybin and a facile method for preparing the O-acetyl prodrug of psilocin

Nichols, David E.,Frescas, Stewart

, p. 935 – 938 (2007/10/03)

An improved procedure to accomplish the O-phosphorylation of 4-hydroxy- N,N-dimethyltryptamine (psilocin 5) is reported that utilizes reaction between the O-lithium salt of 5 and tetra-O-benzylpyrophosphate. The O- benzyl groups were removed by catalytic hydrogenation over palladium on carbon to afford N,N-dimethyl-4-phosphoryloxytryptamine (psilocybin, 1). In view of difficulties encountered in the preparation of 1, it is suggested that 4-acetoxy-N,N-dimethyltryptamine (2) may be a useful alternative for pharmacological studies. The latter was obtained following catalytic O- debenzylation of 4-benzyloxy-N,N-dimethyltryptamine in the presence of acetic anhydride and sodium acetate.

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    Psilocybin is described as an entheogen, a substance used to raise spiritual consciousness. Today most countries have outlawed psilocybin possession; however, widespread illicit use continues. The most …

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    • MW: 284.25
    • MF: C12H17N2O4P
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