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Chemistry

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Also known as: Psilocybin, Indocybin, Psilocibin, Teonanacatl, 520-52-5, Psilocin phosphate ester
Molecular Formula
C12H17N2O4P
Molecular Weight
284.25  g/mol
InChI Key
QVDSEJDULKLHCG-UHFFFAOYSA-N
FDA UNII
2RV7212BP0

Psilocybine
The major of two hallucinogenic components of Teonanacatl, the sacred mushroom of Mexico, the other component being psilocin. (From Merck Index, 11th ed)
1 2D Structure

Psilocybine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[3-[2-(dimethylamino)ethyl]-1H-indol-4-yl] dihydrogen phosphate
2.1.2 InChI
InChI=1S/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)
2.1.3 InChI Key
QVDSEJDULKLHCG-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN(C)CCC1=CNC2=C1C(=CC=C2)OP(=O)(O)O
2.2 Other Identifiers
2.2.1 UNII
2RV7212BP0
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Psilocibin

2. Psilocybin

2.3.2 Depositor-Supplied Synonyms

1. Psilocybin

2. Indocybin

3. Psilocibin

4. Teonanacatl

5. 520-52-5

6. Psilocin Phosphate Ester

7. Psilotsibin

8. Psilocibina

9. Psilocybinum

10. O-phosphoryl-4-hydroxy-n,n-dimethyltryptamine

11. Cy 39

12. Cy-39

13. 3-(2-dimethylaminoethyl)indol-4-yl Dihydrogen Phosphate

14. 4-phosphoryloxy-n,n-dimethyltryptamine

15. 3-2'-dimethylaminoethylindol-4-phosphate

16. 3-(2-(dimethylamino)ethyl)-1h-indol-4-ol Dihydrogen Phosphate Ester

17. Chebi:8614

18. Chembl194378

19. 3-[2-(dimethylamino)ethyl]-1h-indol-4-yl Dihydrogen Phosphate

20. 2rv7212bp0

21. 1h-indol-4-ol, 3-(2-(dimethylamino)ethyl)-, Dihydrogen Phosphate (ester)

22. Ncgc00247732-01

23. Indol-4-ol, 3-(2-(dimethylamino)ethyl)-, Dihydrogen Phosphate

24. Psylocybin

25. Psilocybinum [inn-latin]

26. Psilocibina [inn-spanish]

27. Hsdb 7365

28. Einecs 208-294-4

29. Brn 0273158

30. Psilocybine [inn:ban:dcf]

31. Unii-2rv7212bp0

32. [3-[2-(dimethylamino)ethyl]-1h-indol-4-yl] Dihydrogen Phosphate

33. 4-phosphoryloxy-omega-n,n-dimethyltryptamine

34. Dea No. 7437

35. (3-(2-(dimethylamino)ethyl)-1h-indol-4-yl) Dihydrogen Phosphate

36. 1h-indol-4-ol, 3-[2-(dimethylamino)ethyl]-, Dihydrogen Phosphate (ester)

37. Psilocybin [mi]

38. Psilocybine [inn]

39. Psilocybine [hsdb]

40. Dsstox_cid_28824

41. Dsstox_rid_83093

42. Psilocybine [mart.]

43. Dsstox_gsid_48898

44. Psilocybine [who-dd]

45. 4-22-00-05665 (beilstein Handbook Reference)

46. Constituent Of Magic Mushrooms

47. Schembl158945

48. Cy39

49. Dtxsid0048898

50. Zinc1530830

51. Tox21_112898

52. Bdbm50171269

53. Pdsp1_001391

54. Pdsp2_001375

55. Db11664

56. Sb18760

57. Cas-520-52-5

58. C07576

59. P-7825

60. Q208118

61. 3-[2-(dimethylamino)ethyl]indol-4-yl Dihydrogen Phosphate

62. ({3-[2-(dimethylamino)ethyl]-1h-indol-4-yl}oxy)phosphonic Acid

63. 1h-indol-4-ol, 3-[2-(dimethylamino)ethyl]-, Dihydrogen Phosphate

64. 3-[2-(dimethylamino)ethyl]-1h-indol-4-yl Dihydrogen Phosphate #

65. 3-[2-(dimethylamino)ethyl]indol-4-ol Dihydrogen Phosphate Ester

66. Indol-4-ol, 3-[2-(dimethylamino)ethyl]-, Dihydrogen Phosphate (ester)

2.4 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 284.25 g/mol
Molecular Formula C12H17N2O4P
XLogP3-1.6
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count5
Exact Mass284.09259403 g/mol
Monoisotopic Mass284.09259403 g/mol
Topological Polar Surface Area85.8 Ų
Heavy Atom Count19
Formal Charge0
Complexity347
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Hallucinogens

Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations, and other alterations of mood and thinking. Despite the name, the feature that distinguishes these agents from other classes of drugs is their capacity to induce states of altered perception, thought, and feeling that are not experienced otherwise. (See all compounds classified as Hallucinogens.)


4.2 Absorption, Distribution and Excretion

In a clinical study eight volunteers received psilocybin in psychoactive oral doses of 212+ or -25 ug/kg body weight. To investigate the elimination kinetics of psilocin, the first metabolite of psilocybin, urine was collected for 24 hr and psilocin concentrations were determined by high-performance liquid chromatography with column switching and electrochemical detection (HPLC-ECD). Sample workup included protection of the unstable psilocin with ascorbic acid, freeze-drying, and extraction with methanol. Peak psilocin concentrations up to 870 ug/l were measured in urine samples from the 2-4 hr collection interval. The psilocin excretion rate in this period was 55.5+ or -33.8 microg/h. The limit of quantitation (10 ug/L) was usually reached 24 hr after drug administration. Within 24 hr, 3.4+ or -0.9% of the applied dose of psilocybin was excreted as free psilocin. Addition of beta-glucuronidase to urine samples and incubation for 5 hr at 40 degrees C led to twofold higher psilocin concentrations, although 18+ or -7% of the amount of unconjugated PI was decomposed during incubation. /In conclusion/ that in humans psilocin is partially excreted as psilocin-O-glucuronide and that enzymatic hydrolysis extends the time of detectability for psilocin in urine samples.

PMID:12191719 Hasler F et al; J Pharm Biomed Anal 30 (2): 331-9 (2002)


4.3 Metabolism/Metabolites

Psilocybin is rapidly and completely hydrolyzed to psilocin in vivo.

Goldfrank, L.R. (ed). Goldfrank's Toxicologic Emergencies. 7th Edition McGraw-Hill New York, New York 2002., p. 1121


4.4 Mechanism of Action

Psilocybin, which resembles 5-hydroxytryptamine and LSD, inhibits the firing of serotonin-dependent neurons, causing alterations in perception, changes in mood, hallucinations, and a distortion of time.

Dart, R.C. (ed). Medical Toxicology. Third Edition, Lippincott Williams & Wilkins. Philadelphia, PA. 2004., p. 906


The active constituents of hallucinogenic mushrooms probably are indole compounds derived from tryptamine. Psilocybin and its less stable metabolite psilocin are the best known active compounds, but their effects may not entirely explain the range of symptoms caused by hallucinogenic mushrooms. Wide variations occurs in clinical response.

Dart, R.C. (ed). Medical Toxicology. Third Edition, Lippincott Williams & Wilkins. Philadelphia, PA. 2004., p. 1733


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ABOUT THIS PAGE

Psilocybine Manufacturers

A Psilocybine manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Psilocybine, including repackagers and relabelers. The FDA regulates Psilocybine manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Psilocybine API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Psilocybine manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Psilocybine Suppliers

A Psilocybine supplier is an individual or a company that provides Psilocybine active pharmaceutical ingredient (API) or Psilocybine finished formulations upon request. The Psilocybine suppliers may include Psilocybine API manufacturers, exporters, distributors and traders.

click here to find a list of Psilocybine suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Psilocybine USDMF

A Psilocybine DMF (Drug Master File) is a document detailing the whole manufacturing process of Psilocybine active pharmaceutical ingredient (API) in detail. Different forms of Psilocybine DMFs exist exist since differing nations have different regulations, such as Psilocybine USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Psilocybine DMF submitted to regulatory agencies in the US is known as a USDMF. Psilocybine USDMF includes data on Psilocybine's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Psilocybine USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Psilocybine suppliers with USDMF on PharmaCompass.

Psilocybine GMP

Psilocybine Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Psilocybine GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Psilocybine GMP manufacturer or Psilocybine GMP API supplier for your needs.

Psilocybine CoA

A Psilocybine CoA (Certificate of Analysis) is a formal document that attests to Psilocybine's compliance with Psilocybine specifications and serves as a tool for batch-level quality control.

Psilocybine CoA mostly includes findings from lab analyses of a specific batch. For each Psilocybine CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Psilocybine may be tested according to a variety of international standards, such as European Pharmacopoeia (Psilocybine EP), Psilocybine JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Psilocybine USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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