(-)-Lobeline hydrochloride
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(-)-Lobeline hydrochloride
structure -
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CAS No:
134-63-4
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Formula:
C22H27NO2.ClH
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Chemical Name:
(-)-Lobeline hydrochloride
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Synonyms:
Ethanone,2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methyl-2-piperidinyl]-1-phenyl-,hydrochloride (1:1);Lobeline,hydrochloride;Ethanone,2-[6-(2-hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl]-1-phenyl-,hydrochloride,[2R-[2α,6α(S*)]]-;Ethanone,2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methyl-2-piperidinyl]-1-phenyl-,hydrochloride;(-)-Lobeline hydrochloride;Lobelin hydrochloride;(-)-α-Lobeline hydrochloride;Zoolobelin;Lobron;VUF 10751
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CAS No:
Description
Lobeline hydrochloride, a nicotinic receptor agonist, acting as a potent antagonist at both α3β2 and α4β2 neuronal nicotinic receptor subtypes.
(-)-Lobeline hydrochloride Basic Attributes
373.92
373.180847
205-150-2
757421
ROSETTES OF SLENDER NEEDLES FROM ALC
Characteristics
40.5
4.97590
white to off-white powder
178-180 °C
510.5°C at 760 mmHg
247.5ºC
-57.5 ° (C=1, H2O)
H2O: 25 mg/mL
Store at RT
3.02E-11mmHg at 25°C
D20 -43° (c = 2)
WATER SOLN ARE SLIGHTLY ACID TO LITMUS
186 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
Safety Information
III
6.1(b)
UN 1544 6.1/PG 3
3
23/25
36/37/39-45
OJ8490100
T
P261-P301 + P310-P311
H301 + H331
|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P301+P310, P304+P340, P311, P321, P330, P403+P233, P405, and P501|Aggregated GHS information provided by 42 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Lobelia urens (aerid lobelia) is the only poisonous species of this family found wild in the UK. It is localized to heaths in Cornwall and Dorset. /Lobelia urens/
Toxicity
FROM HERB & SEEDS OF LOBELIA INFLATA L, LOBELIACEAE (INDIAN TOBACCO).|The lobelias contain several closely related alkaloids, the most important being lobeline.
Drug Information
HAS BEEN USED AS A RESPIRATORY STIMULANT; ALSO FOR TREATING TOBACCO ADDICTION. THE WATER-SOL HYDROCHLORIDE & SULFATE HAVE BEEN ADMIN BY PARENTERAL ROUTES.|(VET) HAS BEEN USED AS A RESPIRATORY STIMULANT, RUMINATORIC /LOBELINE/
TWO NATURAL ALKALOIDS, NICOTINE & LOBELINE, OWE MUCH OF THEIR PHARMACOLOGICAL ACTIVITY TO THEIR ACTIONS AT AUTONOMIC GANGLIA. ... LOBELINE HAS MANY OF THE SAME ACTIONS IN THE BODY AS NICOTINE BUT IS LESS POTENT. /LOBELINE/|... Lobeline ... resembles nicotine and coniine in its action, causing first stimulation then paralysis of autonomic ganglia. /Lobeline/
HUMANS HAVE TOLERATED 8 MG BY MOUTH BUT SOME REPORTED NAUSEA & EPIGASTRIC PAIN. AS WITH NICOTINE, CENTRAL NERVOUS STIMULATION IS FOLLOWED BY SEVERE DEPRESSION & SOMETIMES DEATH IN RESPIRATORY PARALYSIS. /LOBELINE (& SALTS)/
(-)-Lobeline hydrochloride Use and Manufacturing
A neuronal nicotinic acetylcholine receptor agonist. A CNS stimulant.
Commercial preprations to cure smoking (containing lobeline) are of marginal value. /Lobeline/
Computed Properties
Molecular Weight:373.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:6
Exact Mass:373.1808568
Monoisotopic Mass:373.1808568
Topological Polar Surface Area:40.5
Heavy Atom Count:26
Complexity:412
Undefined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes
Drug Function and Efficacy
It stimulates the carotid sinus and aortic body chemoreceptors (both N1 receptors), reflexively excites the respiratory center and speeds up breathing, but has no direct excitatory effect on the respiratory center. It also has a reflex excitatory effect on the vagus nerve center and vasomotor center; it first excites the autonomic ganglia and then blocks them.
Registered Holders
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China Resources Double-Crane Pharmaceutical Co., Ltd.
Active
China
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Shanghai Wonder Pharmaceutical Co., Ltd.
Active
China
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Beijing Yanjing Pharmaceutical Co., Ltd.
Active
China
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