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Chemistry

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Also known as: Psilocine, 4-hydroxy-n,n-dimethyltryptamine, 520-53-6, Psilotsin, Psilocyn, 3-[2-(dimethylamino)ethyl]-1h-indol-4-ol

Molecular Formula

C₁₂H₁₆N₂O

Molecular Weight

204.27 g/mol

InChI Key

SPCIYGNTAMCTRO-UHFFFAOYSA-N

FDA UNII

CMS88KUW0G

psilocin is a natural product found in Conocybe velutipes, Conocybe tenera, and other organisms with data available.

1 2D Structure

Psilocin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-[2-(dimethylamino)ethyl]-1H-indol-4-ol

2.1.2 InChI

InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3

2.1.3 InChI Key

SPCIYGNTAMCTRO-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN(C)CCC1=CNC2=C1C(=CC=C2)O

2.2 Other Identifiers

2.2.1 UNII

CMS88KUW0G

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (3-(2-dimethylamino)ethyl)indol-4-ol

2. Psilocin Hydrochloride

3. Psilocin Tartrate (1:1)

2.3.2 Depositor-Supplied Synonyms

1. Psilocine

2. 4-hydroxy-n,n-dimethyltryptamine

3. 520-53-6

4. Psilotsin

5. Psilocyn

6. 3-[2-(dimethylamino)ethyl]-1h-indol-4-ol

7. 3-(2-(dimethylamino)ethyl)indol-4-ol

8. N,n-dimethyl-4-hydroxytryptamine

9. 3-(2-(dimethylamino)ethyl)-1h-indol-4-ol

10. Cms88kuw0g

11. 4-ho-dmt

12. Chembl65547

13. Chebi:8613

14. Ncgc00247728-01

15. 1h-indol-4-ol, 3-[2-(dimethylamino)ethyl]-

16. 3-[2-(dimethylamino)ethyl]-1~{h}-indol-4-ol

17. Indol-4-ol, 3-(2-(dimethylamino)ethyl)-

18. Indol-4-ol, 3-[2-(dimethylamino)ethyl]-

19. Cx-59

20. Einecs 208-296-5

21. Unii-cms88kuw0g

22. Brn 0160503

23. Dea No. 7438

24. 91q

25. Psilocin [mi]

26. Psilocin [mart.]

27. Psilocin [who-dd]

28. 4-oh-dmt

29. Magic Mushrooms (salt/mix)

30. Dsstox_cid_28825

31. Dsstox_rid_83094

32. Dsstox_gsid_48899

33. 5-22-12-00014 (beilstein Handbook Reference)

34. Schembl194899

35. Psilocin/psilocybin (salt/mix)

36. Zinc2001

37. Dtxsid5048899

38. Gtpl11291

39. Spciygntamctro-uhfffaoysa-

40. Cx 59

41. Tox21_112894

42. Bdbm50081701

43. Akos022505992

44. En-0002

45. 3-[2-(dimethylamino)ethyl]-indol-4-ol

46. Cas-520-53-6

47. 3-[2-(dimethylamino)ethyl]-1h-indol-4-ol #

48. C08312

49. P-7800

50. 4-hydroxy-n,n-dimethyltryptamine Psilocin

51. L000675

52. Q409150

53. Psilocin, Vial Of 5 Mg, Certified Reference Material

54. Psilocin Solution, 100 Mug/ml In Methanol, Drug Standard

55. Psilocin Solution, 1.0 Mg/ml In Acetonitrile, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₆N₂O
Molecular Weight	204.27 g/mol
XLogP3	2.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	3
Exact Mass	204.126263138 g/mol
Monoisotopic Mass	204.126263138 g/mol
Topological Polar Surface Area	39.3 Å²
Heavy Atom Count	15
Formal Charge	0
Complexity	208
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 Metabolism/Metabolites

Psilocin has known human metabolites that include (2S,3S,4S,5R)-6-[[3-[2-(dimethylamino)ethyl]-1H-indol-4-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

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