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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

CAS 102518-79-6
(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 Weight 242.32 g/mol
Molecular Formula C15H18N2O
XLogP30
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass242.141913202 g/mol
Monoisotopic Mass242.141913202 g/mol
Topological Polar Surface Area55.1 Ų
Heavy Atom Count18
Formal Charge0
Complexity551
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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.


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