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Chemistry

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Also known as: 1019-45-0, 5-methoxy-n,n-dimethyltryptamine, Methoxybufotenin, O-methylbufotenine, 5-meo-dmt, Meodmt

Molecular Formula

C₁₃H₁₈N₂O

Molecular Weight

218.29 g/mol

InChI Key

ZSTKHSQDNIGFLM-UHFFFAOYSA-N

FDA UNII

X0MKX3GWU9

Compounds that contain the biogenic monoamine tryptamine and are substituted with one methoxy group and two methyl groups. Members of this group include several potent serotonergic hallucinogens found in several unrelated plants, skins of certain toads, and in mammalian brains. They are possibly involved in the etiology of schizophrenia.

1 2D Structure

Mebufotenin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine

2.1.2 InChI

InChI=1S/C13H18N2O/c1-15(2)7-6-10-9-14-13-5-4-11(16-3)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3

2.1.3 InChI Key

ZSTKHSQDNIGFLM-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN(C)CCC1=CNC2=C1C=C(C=C2)OC

2.2 Other Identifiers

2.2.1 UNII

X0MKX3GWU9

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5 Methoxy N,n Dimethyltryptamine

2. 5-methoxy-n,n-dimethyltryptamine

3. Methoxydimethyltryptamine

4. Methoxydimethyltryptamines

5. Methylbufotenin

6. N,n Dimethyl 5 Methoxytryptamine

2.3.2 Depositor-Supplied Synonyms

1. 1019-45-0

2. 5-methoxy-n,n-dimethyltryptamine

3. Methoxybufotenin

4. O-methylbufotenine

5. 5-meo-dmt

6. Meodmt

7. Methylbufotenine

8. 5-methoxydimethyltryptamine

9. 3-(2-dimethylaminoethyl)-5-methoxyindole

10. Bufotenine, O-methyl-

11. 2-(5-methoxy-1h-indol-3-yl)-n,n-dimethylethanamine

12. 1h-indole-3-ethanamine, 5-methoxy-n,n-dimethyl-

13. Ct 4334

14. Methoxydimethyltryptamines

15. 5-methoxy-n,n-dimethyl-1h-indole-3-ethanamine

16. Nsc 88624

17. 5-methoxy-n,n-dimethyl-1h-indole-3-ethylamine

18. Indole, 3-(2-(n,n-dimethylamino)ethyl)-5-methoxy-

19. X0mkx3gwu9

20. 3-(2-(n,n-dimethyl)aminoethyl)-5-methoxyindole

21. Chembl7257

22. Mls000069438

23. Chebi:2086

24. Indole, 3-(2-(dimethylamino)ethyl)-5-methoxy-

25. Indole, 3-[2-(dimethylamino)ethyl]-5-methoxy-

26. 3-[2-(n,n-dimethylamino)ethyl]-5-methoxy-indole

27. Nsc-88624

28. Smr000059066

29. 3-(2-(n,n-dimethylamino)ethyl)-5-methoxyindole

30. 3-[2-(n,n-dimethylamino)ethyl]-5-methoxyindole

31. 5-ome-dmt

32. Einecs 213-813-2

33. Unii-x0mkx3gwu9

34. Brn 0164771

35. Maybridge3_000045

36. Lopac-m-2381

37. Cid_1832

38. Lopac0_000724

39. Oprea1_596468

40. Gtpl145

41. 5-22-12-00027 (beilstein Handbook Reference)

42. Schembl132733

43. 2-(5-methoxy-1h-indol-3-yl)-n,n-dimethyl-ethanamine

44. Bdbm30707

45. Zinc57152

46. Dtxsid70144324

47. [2-(5-methoxy-1h-indol-3-yl)-ethyl]-dimethyl-amine

48. Hms1431c01

49. Hms2235c20

50. Hms3370m04

51. N,n-dimethyl-5-methoxy Tryptamine

52. Nsc88624

53. Pdsp1_000032

54. Pdsp1_000447

55. Pdsp2_000032

56. Pdsp2_000445

57. Stk368074

58. 5-methoxy-n-dimethyltryptamine

59. Akos005203483

60. Bufotenine, 5-methoxydimethyltryptamine

61. Ccg-204809

62. Db14010

63. Sdccgmls-0003129.p003

64. Idi1_011432

65. Wln: T56 Bmj D2n1&1 Go1

66. Ncgc00015654-01

67. Ncgc00015654-02

68. Ncgc00015654-03

69. Ncgc00015654-04

70. Ncgc00015654-05

71. Ncgc00015654-06

72. Ncgc00023288-03

73. Ncgc00023288-04

74. Indole,n-dimethylamino)ethyl]-5-methoxy-

75. Db-005455

76. N,n-dimethyl-5-methoxytryptamine, Free Base

77. C08309

78. D-5380

79. [2-(5-methoxy-1h-indol-3-yl)ethyl]dimethylamine

80. 019d450

81. 2-(5-methoxy-1h-indol-3-yl)ethyl-dimethyl-amine

82. 5-methoxyindole 3-(2-(n,n-dimethylamino)ethyl)

83. L000724

84. Q570757

85. 2-(5-methoxy-1h-indol-3-yl)-ethyl-dimethyl-amine

86. Brd-k34224286-001-07-1

87. 2-(5-methoxy-1h-indol-3-yl)-n,n-dimethylethanamine #

88. 5-meo-dmt Solution, 1.0 Mg/ml In Methanol, Certified Reference Material

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₃H₁₈N₂O
Molecular Weight	218.29 g/mol
XLogP3	1.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	4
Exact Mass	218.141913202 g/mol
Monoisotopic Mass	218.141913202 g/mol
Topological Polar Surface Area	28.3 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	220
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 Metabolism/Metabolites

N,n-dimethyl-5-methoxytryptamine has known human metabolites that include Bufotenine.

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

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