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Lobeline Sulfate

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Chemistry

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Also known as: 134-64-5, Lobeline sulphate, Lobelin sulphate, 4cj480v2hp, Bantron, Lobeline (sulfate)

Molecular Formula

C₄₄H₅₆N₂O₈S

Molecular Weight

773.0 g/mol

InChI Key

GRZMOSSVIPFGFF-GNJLJDPWSA-N

FDA UNII

4CJ480V2HP

An alkaloid that has actions similar to NICOTINE on nicotinic cholinergic receptors but is less potent. It has been proposed for a variety of therapeutic uses including in respiratory disorders, peripheral vascular disorders, insomnia, and smoking cessation.

1 2D Structure

Lobeline Sulfate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone;sulfuric acid

2.1.2 InChI

InChI=1S/2C22H27NO2.H2O4S/c2*1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18;1-5(2,3)4/h2*2-7,9-12,19-21,24H,8,13-16H2,1H3;(H2,1,2,3,4)/t2*19-,20+,21-;/m00./s1

2.1.3 InChI Key

GRZMOSSVIPFGFF-GNJLJDPWSA-N

2.1.4 Canonical SMILES

CN1C(CCCC1CC(=O)C2=CC=CC=C2)CC(C3=CC=CC=C3)O.CN1C(CCCC1CC(=O)C2=CC=CC=C2)CC(C3=CC=CC=C3)O.OS(=O)(=O)O

2.1.5 Isomeric SMILES

CN1[C@@H](CCC[C@@H]1CC(=O)C2=CC=CC=C2)C[C@@H](C3=CC=CC=C3)O.CN1[C@@H](CCC[C@@H]1CC(=O)C2=CC=CC=C2)C[C@@H](C3=CC=CC=C3)O.OS(=O)(=O)O

2.2 Other Identifiers

2.2.1 UNII

4CJ480V2HP

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Lobeline

2. Smokeless

3. Sulfate, Lobeline

2.3.2 Depositor-Supplied Synonyms

1. 134-64-5

2. Lobeline Sulphate

3. Lobelin Sulphate

4. 4cj480v2hp

5. Bantron

6. Lobeline (sulfate)

7. Lobelin Sulfate

8. 2-[(2r,6s)-6-[(2s)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone;sulfuric Acid

9. 2-(6-(2-hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl)-1-phenylethanone Sulfate

10. Einecs 205-151-8

11. Unii-4cj480v2hp

12. Smokeless (tn)

13. Lobeline, Sulfate (2:1) (salt)

14. Inflatine Sulfate

15. Inflatine Sulphate

16. Lobeline Sulfate, Aldrichcpr

17. Lobeline Sulfate [mi]

18. Schembl3686934

19. .alpha.-lobeline Sulfate

20. .alpha.-lobeline Sulphate

21. Dtxsid80158452

22. Lobeline Sulfate [mart.]

23. Lobeline Sulfate [who-dd]

24. Hms3886l05

25. Mfcd00135592

26. S5844

27. Akos032428277

28. Ethanone, 2-(6-(2-hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenyl-, (2theta-(2alpha,6alpha(s)))-, Sulfate (2:1) (salt)

29. Hy-128420

30. Cs-0099255

31. D08138

32. J-006568

33. Q27259407

34. 2-(6-(.beta.-hydroxyphenethyl)-1-methyl-2-piperidyl)acetophenone Sulfate

35. 2-(6-(.beta.-hydroxyphenethyl)-1-methyl-2-piperidyl)acetophenone Sulphate

36. 2-((2r,6s)-6-((2s)-2-hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenylethanone Sulfate

37. 2-((2r,6s)-6-((2s)-2-hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenylethanone Sulphate

38. 2-((2r,6s)-6-((s)-2-hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl)-1-phenylethanone Hemisulfate

2.4 Create Date

2005-07-19

3 Chemical and Physical Properties

Molecular Formula	C₄₄H₅₆N₂O₈S
Molecular Weight	773.0 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	12
Exact Mass	772.37573792 g/mol
Monoisotopic Mass	772.37573792 g/mol
Topological Polar Surface Area	164 Å²
Heavy Atom Count	55
Formal Charge	0
Complexity	494
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Respiratory System Agents

Drugs used for their effects on the respiratory system. (See all compounds classified as Respiratory System Agents.)

Nicotinic Agonists

Drugs that bind to and activate nicotinic cholinergic receptors (RECEPTORS, NICOTINIC). Nicotinic agonists act at postganglionic nicotinic receptors, at neuroeffector junctions in the peripheral nervous system, and at nicotinic receptors in the central nervous system. Agents that function as neuromuscular depolarizing blocking agents are included here because they activate nicotinic receptors, although they are used clinically to block nicotinic transmission. (See all compounds classified as Nicotinic Agonists.)

Ganglionic Stimulants

Agents that mimic neural transmission by stimulation of the nicotinic receptors on postganglionic autonomic neurons. Drugs that indirectly augment ganglionic transmission by increasing the release or slowing the breakdown of acetylcholine or by non-nicotinic effects on postganglionic neurons are not included here nor are the nonspecific cholinergic agonists. (See all compounds classified as Ganglionic Stimulants.)

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