Lobeline

Lobeline Basic information
Product Name:Lobeline
Synonyms:L-lobeline free base;Lobeline;LOBELIDINE95%,98%;LOBELINE HCl, a-(P);Lobeline (base and/or unspecified salts);(-)-α-[(2R,6S)-6-[(S)-β-hydroxyphenethyl]-1-methyl-2-piperidinyl]acetophenone;Inflatine;Lobelin
CAS:90-69-7
MF:C22H27NO2
MW:337.46
EINECS:202-012-3
Product Categories:
Mol File:90-69-7.mol
Lobeline Structure
Lobeline Chemical Properties
Melting point 130-131°
alpha D15 -43° (alc)
Boiling point 473.76°C (rough estimate)
density 1.0909 (rough estimate)
refractive index 1.5614 (estimate)
pka14.34±0.20(Predicted)
Safety Information
Hazard Codes T
Risk Statements 23/24/25
Safety Statements 36/37/39-45
RIDADR 1544
HazardClass 6.1(b)
PackingGroup III
MSDS Information
Lobeline Usage And Synthesis
DescriptionLobeline is mainly present in Lobelia chinensis, Lobelia inflata, Campanula medium, Lobelia hassleri, and Lobelia nicotianaefolia . Lobelia inflata has also been considered as an Indian tobacco and has been used for the treatment of respiratory diseases for a long history. It was also a treatment of asthma by American Aborigines. In the United States during the nineteenth century, doctors use Lobelia inflata as a vomiting agent, to remove the poison from the body. It is also called “vomit grass.” Now Lobelia inflata is still used to clear throat, bronchial, lung, and other respiratory mucus .
Chemical PropertiesCrystalline solid; melts at 130°C (266°F);slightly soluble in water, dissolves readily inhot alcohol, ether, chloroform, and benzene.
Physical propertiesAppearance: White crystalline or granular powder, odorless, and bitter. Solubility: Soluble in ethanol or chloroform, slightly soluble in water. Melting point: 130–131?°C.
HistoryIn the 1930s, the chemical synthesis process of lobeline was completed, and its artificial synthesis was realized, which was found in Lobelia inflata from the North American Campanulaceae. It was commonly used as a lobeline hydrochloride. Because of its structure similar to nicotine, it was initially used for the treatment of respiratory diseases. Further study found that lobeline can selectively excite the carotid sinus peripheral chemoreceptors, then reflect the excitement of the medullary breathing center, and enhance respiratory function. Therefore, it is widely used as a respiratory stimulant .
Although lobeline showed similar biological activity with nicotine, its potency is just only 1/5~1/20 of nicotine. Hence, lobeline was used as a substitute for nicotine in many smoking cessation products. However, in 1993, the Food and Drug Administration (FDA) banned the sale of smoking cessation products containing lobeline because it was ineffective in helping people quit smoking. However, the research of lobeline in drug addiction still continues.
UsesLobeline is the principal lobelia alkaloid.It occurs in the seeds and herb of Indiantobacco (Lobelia inflata and Lobeliaceae). Itis used as a respiratory stimulant. Its sulfatesalt is used in antismoking tablets.
UsesThe action of lobeline is in many respects similar to nicotine; however, it is 50–100 times weaker than nicotine. It is also first, a stimulant, and second, a depressant of sympathetic ganglia, parasympathetic ganglia, adrenal glands, and others. It can be used as a drug to assist with quitting smoking.
IndicationsLobeline was recorded in chemical drug and preparations as lobeline hydrochloride, which is prepared as injection for the treatment of central respiratory inhibition induced by a variety of reasons. In addition, it is also used for the treatment of neonatal stasis, carbon monoxide, opioid poisoning, and so on.
DefinitionChEBI: An optically active piperidine alkaloid having a 2-oxo-2-phenylethyl substituent at the 2-position and a 2-hydroxy-2-phenylethyl group at the 6-position.
Health HazardThe structure of lobeline is different fromthose of nicotine and anabasine. It does nothave a pyridine ring, similar to the lattertwo alkaloids. However, its pharmacologicaction is similar to but less potent than thatof nicotine. Like anabasine, it is a respiratorystimulant. The toxic symptoms includeincreased salivation, nausea, vomiting, diarrhea,and respiratory distress.
PharmacologyThe pharmacological effects of lobeline are extensive, mainly manifested as nicotine-like effect. On the one hand, lobeline can selectively excite the carotid sinus and aortic body chemoreceptors and induce reflective excitement of the respiratory center and vagus center. Lobeline showed better excitatory effect for the respiratory inhibition caused by morphine. There is bronchiectasis effect directly when lobeline is inhaled, hence, against pilocarpine and acetylcholine-induced tracheal contraction. When the dose increased, lobeline can directly stimulate the respiratory center and excite vagal center (reducing heart rate) and vomiting center in medulla oblongata. In addition, lobeline showed dual role in the regulation of ganglion, as manifested excitement and inhibition in chronological order. Lobeline has a zebra-like effect on the striated muscle. In addition, it also has a certain anticancer effect, as manifested by significantly inhibiting the uptake of oxygen in mouse ascites cancer cells .
Clinical UseIt is mainly used in the treatment of (1) neonatal asphyxia, (2) suffocation caused by carbon monoxide, (3) poisoning induced by inhalation of anesthetics and other central inhibitors (such as opioids and barbiturates), and (4) respiratory failure caused by pneumonia, diphtheria, and other infectious diseases.
Side effectsLobeline also showed side effects, such as nausea, vomiting, cough, headache, palpitations, and other adverse reactions.
SynthesisLobeline, 1-methyl-2-(|?-hydroxy-|?-phenylethyl)-6-phenacylpiperidine (13.1.33), is the primary alkaloid of leaves from Lobelia inflata. It is synthesized by condensation of 2,6- dimethylpyridine with two moles of benzaldehyde, giving |á,|á??-distyrylpyridine (13.1.28) [37¨C39]. Exhaustive bromination of this product and subsequent dehydrobromination of the resulting tetrabromo derivative (13.1.29) leads to the formation of |á,|á??-diphenylethinylpyridine (13.1.30). Hydration of the triple bonds of the product (13.1.30) gives |á,|á??- diphenacylpyridine (13.1.31). Reacting this with methyl p-toluenesulfonate gives |á,|á??-diphenacylpyridinium N-methyl-p-toluenesulfonate (13.1.32), which is carefully reduced by hydrogen into the desired lobeline (13.1.33) using simultaneously palladium and platinum catalysts. The product is a racemic mixture from which the levorotatory isomer can be isolated if necessary

Synthesis_90-69-7

Lobeline Preparation Products And Raw materials
(S)-(-)-1-PHENYL-1-DECANOL N-NONANOPHENONE (1S,2S)-(+)-Pseudoephedrine hydrochloride BIS-(3-PHENYL-PROPYL)-AMINE (S)-3-AMINO-1-PHENYL-PROPAN-1-OL 3-(DIMETHYLAMINO)-1-PHENYLPROPAN-1-ONE (R)-(+)-PIPERIDINE-2-ETHANOL OCTANOPHENONE (S)-(-)-1-PHENYL-1-BUTANOL N-METHYLPIPERIDINE-2-ETHANOL pelletierine 1-PHENYL-1-HEPTANOL 3-DIMETHYLAMINO-1-PHENYL-PROPAN-1-OL (R)-(-)-1-Methyl-3-phenylpropylamine (R)-2-Nonanamine CONIINE, D/L-(RG) 2-PHENETHYL-PIPERIDINE N-DECANOPHENONE

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