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Psilocybine

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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

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 Formula	C₁₂H₁₇N₂O₄P
Molecular Weight	284.25 g/mol
XLogP3	-1.6
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	5
Exact Mass	284.09259403 g/mol
Monoisotopic Mass	284.09259403 g/mol
Topological Polar Surface Area	85.8 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	347
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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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