CAS 102518-79-6 manufacturers and suppliers on PharmaCompass

CAS 102518-79-6

CAS 102518-79-6

Chemistry

Chemistry

Manufacturers/Suppliers

1 Suppliers

1 Suppliers

Also known as: (-)-huperzine a, 102518-79-6, (-)-huperazine a, Selagine, L-huperzine a, (-)-selagine

Molecular Formula

C₁₅H₁₈N₂O

Molecular Weight

242.32 g/mol

InChI Key

ZRJBHWIHUMBLCN-YQEJDHNASA-N

FDA UNII

0111871I23

(1R,9R,13E)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0,]trideca-2,4,6,10-tetraen-5-ol is a natural product found in Phlegmariurus varius, Phlegmariurus tetrastichus, and Phlegmariurus phlegmaria with data available.

1 2D Structure

CAS 102518-79-6

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,9R,13E)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,10-trien-5-one

2.1.2 InChI

InChI=1S/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)/b11-3+/t10-,15+/m0/s1

2.1.3 InChI Key

ZRJBHWIHUMBLCN-YQEJDHNASA-N

2.1.4 Canonical SMILES

CC=C1C2CC3=C(C1(CC(=C2)C)N)C=CC(=O)N3

2.1.5 Isomeric SMILES

C/C=C/1\[C@@H]2CC3=C([C@]1(CC(=C2)C)N)C=CC(=O)N3

2.2 Other Identifiers

2.2.1 UNII

0111871I23

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Huperzine A, (5alpha,9beta,11z)-(-)-isomer

2.3.2 Depositor-Supplied Synonyms

1. (-)-huperzine A

2. 102518-79-6

3. (-)-huperazine A

4. Selagine

5. L-huperzine A

6. (-)-selagine

7. Hup A

8. Chembl395280

9. Chebi:78330

10. (5r,9r,e)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1h)-one

11. Dsstox_cid_26038

12. Dsstox_rid_81302

13. Dsstox_gsid_46038

14. 0111871i23

15. Huperizine A

16. (+)-huperzine A

17. (5r,9r,11e)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1h)-one

18. Cas-102518-79-6

19. (-)-huperzine A (hupa)

20. 120786-18-7

21. Cerebra

22. Hyperazzine A

23. Kimpukan A

24. 1vot

25. Ncgc00159362-02

26. (-)-huperazinea

27. Hup

28. Huperaine A

29. Huperzine A [mi]

30. Huperzine A [vandf]

31. Huperzine A [who-dd]

32. Schembl136368

33. Spectrum1505255

34. (−)-huperzine A

35. Dtxsid8046038

36. Chebi:94624

37. Zinc9411213

38. Tox21_111603

39. Bdbm50199522

40. Ccg-40292

41. Unii-0111871i23

42. Akos016842839

43. Tox21_111603_1

44. (+-)-ha

45. Db04864

46. Sdccgmls-0066755.p001

47. Ncgc00263655-01

48. As-15723

49. H1700

50. Q425198

51. Q-100029

52. Brd-k62240499-001-02-6

53. (-)-1-amino-13-ethylidene-11-methyl-6-aza-tricyclo[7.3.1.0*2,7*]trideca-2(7),3,10-trien-5-one(huperzine A)

54. (-)1-amino-13-ethylidene-11-methyl-6-aza-tricyclo[7.3.1.0*2,7*]trideca-2(7),3,10-trien-5-one( (-)-huperzine A)

55. (1r,9r)-1-amino-13-eth-(e)-ylidene-11-methyl-6-aza-tricyclo[7.3.1.0*2,7*]trideca-2(7),3,10-trien-5-one

56. (5r,9r,11e)-5-amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta(b)pyridin-2(1h)-one

57. (huperazine A)(-)-1-amino-13-ethylidene-11-methyl-6-aza-tricyclo[7.3.1.0*2,7*]trideca-2(7),3,10-trien-5-one

58. (r)-1-amino-13-eth-(e)-ylidene-11-methyl-6-aza-tricyclo[7.3.1.0*2,7*]trideca-2(7),3,10-trien-5-one

59. (r)-1-amino-13-ethylidene-11-methyl-6-aza-tricyclo[7.3.1.0*2,7*]trideca-2(7),3,10-trien-5-one

60. 1-amino-13-eth-(e)-ylidene-11-methyl-6-aza-tricyclo[7.3.1.0*2,7*]trideca-2(7),3,10-trien-5-one

61. 1-amino-13-eth-(z)-ylidene-11-methyl-6-aza-tricyclo[7.3.1.0*2,7*]trideca-2(7),3,10-trien-5-one

62. 1-amino-13-ethylidene-11-methyl-6-aza-tricyclo[7.3.1.0*2,7*]trideca-2(7),3,10-trien-5-one

63. 1-amino-13-ethylidene-11-methyl-6-aza-tricyclo[7.3.1.0*2,7*]trideca-2(7),3,10-trien-5-one((+/-)-huperzine A)

64. 1-amino-13-ethylidene-11-methyl-6-aza-tricyclo[7.3.1.0*2,7*]trideca-2(7),3,10-trien-5-one((-)-huperzine A)

65. 1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0~2,7~]trideca-2(7),3,10-trien-5-one

66. 1369-64-8

67. 5,9-methanocycloocta(b)pyridin-2(1h)-one, 5-amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-, (5r-(5-alpha,9-beta,11e))-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₈N₂O
Molecular Weight	242.32 g/mol
XLogP3	0
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	242.141913202 g/mol
Monoisotopic Mass	242.141913202 g/mol
Topological Polar Surface Area	55.1 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	551
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in alzheimer's disease.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Huperzine A is an alkaloid derived from Huperzia serrata (which is available as an herbal product in the US). It is under investigation as an acetylcholinesterase inhibitor. Clinical trials in China have shown that huperzine A is comparably effective to the drugs currently on the market, and may even be somewhat safer in terms of side effects.

5.2 MeSH Pharmacological Classification

Cholinesterase Inhibitors

Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system. (See all compounds classified as Cholinesterase Inhibitors.)

Neuroprotective Agents

Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids. (See all compounds classified as Neuroprotective Agents.)

5.3 Mechanism of Action

Huperzine A has been found to be an inhibitor of the enzyme acetylcholinesterase. This is the same mechanism of action of pharmaceutical drugs such as [galantamine] and [donepezil] used to treat Alzheimer's disease.