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Also known as: Thip, 64603-91-4, Gaboxadolum, Gaboxadolum [latin], 4,5,6,7-tetrahydroisoxazolo(5,4-c)pyridin-3-ol, Mk-0928

Molecular Formula

C₆H₈N₂O₂

Molecular Weight

140.14 g/mol

InChI Key

ZXRVKCBLGJOCEE-UHFFFAOYSA-N

FDA UNII

K1M5RVL18S

Gaboxadol also known as 4,5,6,7-tetrahydroisoxazolo(5,4-c)pyridin-3-ol (THIP) is an experimental sleep aid drug developed by Lundbeck and Merck, who reported increased deep sleep without the reinforcing effects of benzodiazepines. Development of Gaboxadol was stopped in March 2007 after concerns regarding safety and efficacy. It acts on the GABA system, but in a seemingly different way from benzodiazepines and other sedatives.

1 2D Structure

Gaboxadol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4,5,6,7-tetrahydro-[1,2]oxazolo[5,4-c]pyridin-3-one

2.1.2 InChI

InChI=1S/C6H8N2O2/c9-6-4-1-2-7-3-5(4)10-8-6/h7H,1-3H2,(H,8,9)

2.1.3 InChI Key

ZXRVKCBLGJOCEE-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CNCC2=C1C(=O)NO2

2.2 Other Identifiers

2.2.1 UNII

K1M5RVL18S

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4,5,6,7-tetrahydroisoxazolo(5,4-c)pyridin-3-ol

2. Lu 2030

3. Lu-2-030

4. Thip

2.3.2 Depositor-Supplied Synonyms

1. Thip

2. 64603-91-4

3. Gaboxadolum

4. Gaboxadolum [latin]

5. 4,5,6,7-tetrahydroisoxazolo(5,4-c)pyridin-3-ol

6. Mk-0928

7. Lu 02-030

8. 4,5,6,7-tetrahydro-[1,2]oxazolo[5,4-c]pyridin-3-one

9. 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-ol

10. Lu-02-030

11. Prestwick-13b03

12. Lu-02030

13. Chebi:34373

14. 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3(2h)-one

15. K1m5rvl18s

16. Zinc19795995

17. Nsc-759585

18. Ncgc00015982-05

19. Isoxazolo(5,4-c)pyridin-3(2h)-one, 4,5,6,7-tetrahydro-

20. Isoxazolo[5,4-c]pyridin-3(2h)-one, 4,5,6,7-tetrahydro-

21. Gaboxadol [usan:inn]

22. Dsstox_cid_25206

23. Dsstox_rid_80750

24. Dsstox_gsid_45206

25. Gaboxadol [inn]

26. Cas-64603-91-4

27. Gaboxadol (usan/inn)

28. Einecs 264-963-0

29. Unii-k1m5rvl18s

30. 4,5,6,7-tetrahydroisoxazolo(5,4-c)pyridin-3(2h)-one

31. Ei7

32. 4,5,6,7-tetrahydroisoxazole(5,4-c)pyridin-3-ol

33. Spectrum_001484

34. Tocris-0807

35. Gaboxadol [mi]

36. Lopac-t-101

37. Gaboxadol [usan]

38. Prestwick0_000972

39. Prestwick1_000972

40. Prestwick2_000972

41. Prestwick3_000972

42. Spectrum2_001590

43. Spectrum3_000728

44. Spectrum4_000172

45. Spectrum5_001907

46. Biomol-nt_000235

47. Gaboxadol [who-dd]

48. Lopac0_001233

49. Bspbio_001003

50. Bspbio_002256

51. Kbiogr_000683

52. Kbioss_001964

53. Divk1c_000211

54. Spbio_001560

55. Spbio_002914

56. Bpbio1_000420

57. Bpbio1_001105

58. Chembl312443

59. Gtpl4322

60. Dtxsid0045206

61. Bdbm82002

62. Kbio1_000211

63. Kbio2_001964

64. Kbio2_004532

65. Kbio2_007100

66. Kbio3_001476

67. Ninds_000211

68. Bcp07031

69. Nsc_3448

70. Tox21_110271

71. Bdbm50224809

72. Mfcd05664626

73. Ov-101

74. Akos006282519

75. Tox21_110271_1

76. Ccg-205307

77. Db06554

78. Nsc 759585

79. Sb18782

80. Sdccgsbi-0051200.p004

81. Idi1_000211

82. Ncgc00015982-01

83. Ncgc00015982-02

84. Ncgc00015982-03

85. Ncgc00015982-04

86. Ncgc00015982-06

87. Ncgc00015982-07

88. Ncgc00015982-13

89. Ncgc00024801-01

90. Ncgc00024801-02

91. Ncgc00024801-03

92. Ncgc00263653-01

93. Hy-10232

94. Sy253214

95. Sbi-0051200.p003

96. Cas_64603-91-4

97. Ab00053777

98. Cs-0002507

99. Ft-0774669

100. D04282

101. Ab00053777_07

102. 4,5,6,7-tetrahydro-isoxazolo[5,4-c]pyridin-3-ol

103. 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-one

104. 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridine-3-ol

105. 4h,5h,6h,7h-[1,2]oxazolo[5,4-c]pyridin-3-ol

106. Q4130924

107. 2h,3h,4h,5h,6h,7h-[1,2]oxazolo[5,4-c]pyridin-3-one

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₆H₈N₂O₂
Molecular Weight	140.14 g/mol
XLogP3	-0.9
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	0
Exact Mass	140.058577502 g/mol
Monoisotopic Mass	140.058577502 g/mol
Topological Polar Surface Area	50.4 Å²
Heavy Atom Count	10
Formal Charge	0
Complexity	210
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 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in sleep disorders and insomnia.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

GABA Agonists

Endogenous compounds and drugs that bind to and activate GAMMA-AMINOBUTYRIC ACID receptors (RECEPTORS, GABA). (See all compounds classified as GABA Agonists.)

Analgesics

Compounds capable of relieving pain without the loss of CONSCIOUSNESS. (See all compounds classified as Analgesics.)

Anticonvulsants

Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)

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