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Psilocin | |
| Systematic (IUPAC) name | |
| 4-Hydroxy-N,N-dimethyl-tryptamine | |
| Identifiers | |
| CAS number | |
| ATC code | ? |
| PubChem | |
| Chemical data | |
| Formula | C12H16N2O |
| Mol. mass | 204. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs It is controlled by the WHO Collaborating Centre for Drug PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 Nitrogen (ˈnaɪtɹəʤɪn is a Chemical element that has the symbol N and Atomic number 7 and Atomic weight 14 Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the The molecular mass (abbreviated m of a substance, more commonly referred to as molecular weight and abbreviated as MW, is the Mass of one 27 g/mol |
| SMILES | & |
| Physical data | |
| Melt. point | 173–176 °C (343–349 °F) |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | Liver |
| Half life | 2-3 hours |
| Excretion | Kidneys/Urine |
| Therapeutic considerations | |
| Pregnancy cat. | ? |
| Legal status | Prohibited (S9)(AU) Schedule III(CA) Class A(UK) Schedule I(US) |
| Routes | Oral, IV |
Psilocin (4-HO-DMT) sometimes also (mis)spelled psilocine, psilocyn, or psilotsin, is a psychedelic (hallucinogenic) mushroom alkaloid. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. In Pharmacology, bioavailability is used to describe the fraction of an administered Dose of unchanged drug that reaches the Systemic circulation, one of Drug metabolism is the Metabolism of drugs, their Biochemical modification or degradation usually through specialized enzymatic systems The biological half-life of a substance is the time it takes for a substance (drug radioactive nuclide or other to lose half of its pharmacologic physiologic or radiologic activity Excretion is the process of eliminating waste products of Metabolism and other non-useful materials The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical if it is used as directed by the mother during The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction The Standard for the Uniform Scheduling of Drugs and Poisons, abbreviated SUSDP, is a document used in the regulation of drugs and poisons in Australia. For a topic outline on this subject see List of basic Australia topics. The Controlled Drugs and Substances Act is Canada 's federal drug control statute Country to "Dominion of Canada" or "Canadian Federation" or anything else please read the Talk Page The Misuse of Drugs Act 1971 (c38 is an Act of Parliament, by which the United Kingdom aims to control the possession and supply of numerous drugs The United Kingdom of Great Britain and Northern Ireland, commonly known as the United Kingdom, the UK or Britain,is a Sovereign state located The Controlled Substances Act ( CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control The United States of America —commonly referred to as the In Pharmacology and Toxicology, a route Psychedelic drugs are Psychoactive drugs whose primary action is to alter the thought processes of the brain and perception of the mind The general group of pharmacological agents commonly known as hallucinogens can be divided into three broad categories Psychedelics, Dissociatives A mushroom is the fleshy Spore -bearing Fruiting body of a Fungus, typically produced above ground on soil or on its food source This article is about the chemical compounds alkaloids For the Pharmaceutical company in the Republic of Macedonia see Alkaloid (company. It is found in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocybin (IPA /saɪləˈsaɪbɪn/ (also known as psilocybine) is a psychedelic Indole of the Tryptamine family found in Psilocybin Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. The Convention on Psychotropic Substances is a United Nations Treaty designed to control Psychoactive drugs such as Amphetamines Barbiturates [1]
Contents |
History
The Swiss chemist Albert Hofmann and the laboratory assistant Hans Tscherter from Sandoz Laboratories isolated psilocin and its phosphate ester psilocybin from Psilocybe mushrooms in 1959, guided by self-administration. Albert Hofmann ( January 11 1906 – April 29 2008) was a Swiss scientist best known for having been the first to synthesize Novartis International AG is a multinational Pharmaceutical company based in Basel Switzerland that manufactures drugs such as Clozapine An organophosphate (sometimes abbreviated OP) is the general name for Esters of Phosphoric acid. Psilocybe is a Genus of small Mushrooms growing worldwide This genus is best known for its species with hallucinogenic properties widely
Chemistry
Psilocin can be obtained by dephosphorylation of natural psilocybin under strongly acidic or under alkaline conditions (hydrolysis). Phosphorylation is the addition of a Phosphate (PO4 group to a Protein molecule or a small molecule In Computer science, ACID ( Atomicity Consistency Isolation Durability) is a set of properties that guarantee that Database transactions are In Chemistry, a base is most commonly thought of as an aqueous substance that can accept Protons This refers to the Brønsted-Lowry theory of acids and Hydrolysis is a Chemical reaction during which one or more water molecules are split into hydrogen and hydroxide ions which may go on to participate in further reactions Another synthetic route uses the Speeter-Anthony tryptamine synthesis starting from 4-hydroxyindole. In Chemistry, chemical synthesis is purposeful execution of Chemical reactions in order to get a product, or several products
Psilocin is relatively unstable in solution due to its phenolic hydroxy (-OH) group. In Organic chemistry, phenols, sometimes called phenolics, are a class of Chemical compounds consisting of a Hydroxyl group (- In the presence of oxygen it readily forms bluish and dark black degradation products. Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the Similar products are also formed under acidic conditions in the presence of oxygen and Fe3+ ions (Keller's reagent; FeCl3 / methanol / hydrochloric acid). Iron (ˈаɪɚn is a Chemical element with the symbol Fe (ferrum and Atomic number 26 An ion is an Atom or Molecule which has lost or gained one or more Valence electrons giving it a positive or negative electrical charge Iron chloride redirects here For Iron(II chloride see Iron(II chloride. Methanol, also known as methyl alcohol, carbinol, wood alcohol, wood naphtha or wood spirits, is a Chemical compound Hydrochloric acid is the Solution of Hydrogen chloride ( H[[Chlorine Cl]] in water
Structural analogs
Sulfur analogs are known with a benzothienyl replacement[2] as well as 4-SH-DMT[3]. Sulfur or sulphur (ˈsʌlfɚ see spelling below) is the Chemical element that has the Atomic number 16 Benzothiophene is an Aromatic Organic compound with a molecular formula C8H6S and an odor similar to Naphthalene (mothballs In Organic chemistry, a thiol is a compound that contains the functional group composed of a Sulfur atom and a Hydrogen atom (-SH N1-methylpsilocin is a functionally 5-HT2C receptor prefering agonists. 5-hydroxytryptamine (serotonin receptor 2C, also known as HTR2C, is a 5-HT2 receptor, but also denotes the human Gene encoding it [4] 4-fluoro-N,N-dimethyltryptamine is known. [5]
Pharmacology
Psilocin is the pharmacologically active agent in the body after ingestion of psilocybin or psychedelic mushrooms. Pharmacology (from Greek grc φάρμακον pharmakon, "drug" and grc -λογία -logia) is the study of how Drugs
Psilocybin is rapidly dephosphorylated in the body to psilocin which acts as a 5HT2A, 5HT2C and 5HT1A agonist. Psilocin is structurally similar to serotonin (5-HT)[6], and its effects are thought to come from its ability to mimic serotonin and thereby activate serotonin receptors in the brain. Serotonin (ˌsɛrəˈtoʊnən ( 5-hydroxytryptamine, or 5-HT) is a Monoamine Neurotransmitter synthesized in serotonergic Neurons In the field of Neurochemistry, 5-HT receptors are receptors for the Neurotransmitter and peripheral signal mediator Serotonin, also The brain is the center of the Nervous system in animals All Vertebrates and the majority of Invertebrates have a brain
Psilocin has no significant effect on dopamine receptors (unlike LSD) and only affects the noradrenergic system at very high dosages. Dopamine is a Hormone and Neurotransmitter occurring in a wide variety of animals including both vertebrates and invertebrates [7]
Psilocin physiological half-life ranges from 2 to 3 hours. [8]
- See psilocybin for more details
Behavioral and Non-behavioral Effects
The general characteristics of the hallucinogenic effects induced by psilocin are virtually identical to those induced by mescaline, except the duration of its effect are comparatively shorter, lasting approximately 6-8 hours. Psilocybin (IPA /saɪləˈsaɪbɪn/ (also known as psilocybine) is a psychedelic Indole of the Tryptamine family found in Psilocybin The general group of pharmacological agents commonly known as hallucinogens can be divided into three broad categories Psychedelics, Dissociatives Mescaline or 345-trimethoxyphenethylamine is a naturally-occurring Psychedelic Alkaloid of the Phenethylamine class [6]
Its physiological effects are similar to a sympathetic arousal state. The Sympathetic Nervous System ( SNS) is a branch of the Autonomic nervous system along with the Enteric nervous system and Parasympathetic nervous Specific effects observed after ingestion can include increased heart rate, dilated pupils, restlessness or arousal, euphoria, open and closed eye visuals (common at medium to high doses), synthesesia (eg. Ingestion is the consumption of a substance by an Organism. In Animals it normally is accomplished by taking in the substance through the Mouth into the Measuring heart rate The Pulse rate (which in most people is identical to the heart rate can be measured at any point on the body where an Artery 's pulsation The pupil is the hole that is located in the center of the iris of the eye and that controls the amount of light that enters the Eye. hearing colours and seeing sounds), increased body temperature, headache, sweating and chills, and nausea. Core temperature, also called core body temperature, is the operating Temperature of an Organism, specifically in deep structures of the body such as the A headache ( cephalalgia in medical terminology is a condition of pain in the Head; sometimes Neck or upper back pain may also be interpreted Nausea ( Latin: Nausea, Greek:, " Sea-sickness " also called wamble) is the sensation of unease and discomfort [6]
There is virtually no direct lethality associated with psilocin. [6] There is virtually no withdrawal syndrome when chronic use of this drug is ceased. Withdrawal, also known as withdrawal/abstinence syndrome, refers to the characteristic signs and symptoms that appear when a drug that causes Physical dependence is A drug, broadly speaking is any chemical substance that when absorbed into the body [6] There is cross tolerance among psilocin, mescaline, and LSD. Cross-tolerance refers to a Pharmacological phenomenon in which a patient being treated with a drug exhibits a physiological resistance to that medication as a result of tolerance [6]
See also
References
- ^ "Green list"
- ^ Chapman (1972) Perkin Trans. 1, 3011
- ^ Hofmann, Swiss 421,960 (1967); CA 68:95680n
- ^ Sard (2005): PMID 16061378
- ^ Cite error: Invalid
<ref>tag; no text was provided for refs namedSard - ^ a b c d e f Diaz, Jaime. Psilocybin (IPA /saɪləˈsaɪbɪn/ (also known as psilocybine) is a psychedelic Indole of the Tryptamine family found in Psilocybin Tryptamine is a Monoamine Alkaloid found in Plants and Animals. Indole is an Aromatic heterocyclic Organic compound. It has a bicyclic structure consisting of a six-membered Benzene ring fused to a five-membered Psychedelic drugs are Psychoactive drugs whose primary action is to alter the thought processes of the brain and perception of the mind A psychoactive drug or psychotropic substance is a Chemical substance that acts primarily upon the Central nervous system where it alters Brain How Drugs Influence Behavior. Englewood Cliffs: Prentice Hall, 1996.
- ^ Psilocybin Investigator’s Brochure
- ^ Psilocybin Investigator’s Brochure
External links
- The Ones That Stain Blue Studies in ethnomycology including the contributions of Maria Sabina, Dr. Albert Hofmann and Dr. Gaston Guzman.
- The Shroomery Detailed information about Psilocybin mushrooms including identification, cultivation and spores, psychedelic images, trip reports, a dosage calculator and an active community.
- 4-HO-DMT entry in TiHKAL
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