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Lysergol API

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Synopsis

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Chemistry

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Also known as: 602-85-7, Lysergole, Ntr684z1az, Chembl39947, 1413-67-8, Chebi:60528

Molecular Formula

C₁₆H₁₈N₂O

Molecular Weight

254.33 g/mol

InChI Key

BIXJFIJYBLJTMK-MEBBXXQBSA-N

FDA UNII

NTR684Z1AZ

Lysergol is an alkaloid of the ergoline family that occurs as a minor constituent in some species of fungi (most within Claviceps), and in the morning glory family of plants (Convolvulaceae), including the hallucinogenic seeds of Rivea corymbosa (ololiuhqui), Argyreia nervosa (Hawaiian baby woodrose) and Ipomoea violacea. As it is derived from dimethylergoline, it is referred to as a clavine. Lysergol can be utilized as an intermediate in the manufacture of some ergoloid medicines. Long term exposure to some ergoline alkaloids can cause ergotism, a disease causing convulsive and gangrenous symptoms. (L1918, L1928)

1 2D Structure

Lysergol API

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]methanol

2.1.2 InChI

InChI=1S/C16H18N2O/c1-18-8-10(9-19)5-13-12-3-2-4-14-16(12)11(7-17-14)6-15(13)18/h2-5,7,10,15,17,19H,6,8-9H2,1H3/t10-,15-/m1/s1

2.1.3 InChI Key

BIXJFIJYBLJTMK-MEBBXXQBSA-N

2.1.4 Canonical SMILES

CN1CC(C=C2C1CC3=CNC4=CC=CC2=C34)CO

2.1.5 Isomeric SMILES

CN1C[C@@H](C=C2[C@H]1CC3=CNC4=CC=CC2=C34)CO

2.2 Other Identifiers

2.2.1 UNII

NTR684Z1AZ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 9,10-didehydro-6-methylergoline-8b-methanol

2. Isolysergol

3. Lysergol, (8alpha)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 602-85-7

2. Lysergole

3. Ntr684z1az

4. Chembl39947

5. 1413-67-8

6. Chebi:60528

7. [(6ar,9r)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinolin-9-yl]methanol

8. ((6ar,9r)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-yl)methanol

9. (6-methyl-9,10-didehydroergolin-8beta-yl)methanol

10. 9,10-didehydro-6-methyl-8-hydroxymethylergoline

11. (7-methyl-4,6,6a,7,8,9-hexahydro-indolo(4,3-fg)quinolin-9-yl)-methanol

12. (7-methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinolin-9-yl)-methanol

13. [(6ar,9r)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-yl]methanol

14. Lol

15. Prestwick_308

16. Prestwick0_000454

17. Prestwick1_000454

18. Prestwick2_000454

19. Prestwick3_000454

20. Unii-ntr684z1az

21. Bspbio_000528

22. Gtpl123

23. Cid_14987

24. Mls001049075

25. Divk1c_000515

26. Schembl178071

27. Spbio_002467

28. Bpbio1_000582

29. Megxp0_001732

30. Acon0_000797

31. Acon1_000057

32. Hms501j17

33. Kbio1_000515

34. Ninds_000515

35. Hms1569k10

36. Hms2096k10

37. Hms2271m04

38. Hy-n6809

39. Tnp00316

40. Zinc3983953

41. Bdbm50016479

42. Akos030490884

43. Phytochem 12: 2435 (1973)

44. Idi1_000515

45. Smp1_000185

46. Ncgc00017367-01

47. As-18087

48. Smr000386913

49. Cs-0092658

50. E75857

51. A923435

52. Sr-01000758923

53. Q6710130

54. Sr-01000758923-3

55. Brd-k27871032-001-02-6

56. Brd-k27871032-001-04-2

57. ((6ar)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-yl)methanol

2.3.3 Other Synonyms

1. Lysergol Api

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₁₈N₂O
Molecular Weight	254.33 g/mol
XLogP3	2.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	1
Exact Mass	g/mol
Monoisotopic Mass	g/mol
Topological Polar Surface Area	39.3
Heavy Atom Count	19
Formal Charge	0
Complexity	394
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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

Antipsychotic Agents

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus. (See all compounds classified as Antipsychotic Agents.)

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