Lobelanidine

Last updated
Lobelanidine
Lobelanidine.svg
Names
Preferred IUPAC name
(1R)-2-{(2R,6S)-6-[(2S)-2-Hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl}-1-phenylethan-1-ol
Other names
8,10-Diphenyllobelidiol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C22H29NO2/c1-23-19(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/h2-7,9-12,19-22,24-25H,8,13-16H2,1H3/t19-,20+,21-,22+
    Key: OWGJQNXIWMMDTH-COPRSSIGSA-N
  • CN1[C@H](CCC[C@H]1C[C@@H](C2=CC=CC=C2)O)C[C@H](C3=CC=CC=C3)O
Properties
C22H29NO2
Molar mass 339.479 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Lobelanidine is a chemical analog of lobeline. [1]

Related Research Articles

<span class="mw-page-title-main">England</span> Country within the United Kingdom

England is a country that is part of the United Kingdom. It is located on the island of Great Britain, of which it covers about 62%, and more than 100 smaller adjacent islands. It has land borders with Scotland to the north and Wales to the west, and is otherwise surrounded by the North Sea to the east, the English Channel to the south, the Celtic Sea to the south-west, and the Irish Sea to the west. Continental Europe lies to the south-east, and Ireland to the west. At the 2021 census, the population was 56,490,048. London is both the largest city and the capital.

<span class="mw-page-title-main">Piperidine</span> Chemical compound

Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless liquid with an odor described as objectionable, typical of amines. The name comes from the genus name Piper, which is the Latin word for pepper. Although piperidine is a common organic compound, it is best known as a representative structure element within many pharmaceuticals and alkaloids, such as natural-occurring solenopsins.

<i>Lobelia</i> Genus of flowering plants

Lobelia is a genus of flowering plants in the family Campanulaceae comprising 415 species, with a subcosmopolitan distribution primarily in tropical to warm temperate regions of the world, a few species extending into cooler temperate regions. They are known generally as lobelias.

<span class="mw-page-title-main">Barack Obama</span> President of the United States from 2009 to 2017

Barack Hussein Obama II is an American politician and lawyer who served as the 44th president of the United States from 2009 to 2017. A member of the Democratic Party, he was the first African-American president in U.S. history. Obama previously served as a U.S. senator representing Illinois from 2005 to 2008 and as an Illinois state senator from 1997 to 2004.

<span class="mw-page-title-main">Receptor (biochemistry)</span> Protein molecule receiving signals for a cell

In biochemistry and pharmacology, receptors are chemical structures, composed of protein, that receive and transduce signals that may be integrated into biological systems. These signals are typically chemical messengers which bind to a receptor and produce physiological responses such as change in the electrical activity of a cell. For example, GABA, an inhibitory neurotransmitter, inhibits electrical activity of neurons by binding to GABAA receptors. There are three main ways the action of the receptor can be classified: relay of signal, amplification, or integration. Relaying sends the signal onward, amplification increases the effect of a single ligand, and integration allows the signal to be incorporated into another biochemical pathway.

<span class="mw-page-title-main">Campanulaceae</span> Family of flowering plants comprising bellflowers

The family Campanulaceae, of the order Asterales, contains nearly 2400 species in 84 genera of herbaceous plants, shrubs, and rarely small trees, often with milky sap. Among them are several familiar garden plants belonging to the genera Campanula (bellflower), Lobelia, and Platycodon (balloonflower). Campanula rapunculus and Codonopsis lanceolata are eaten as vegetables. Lobelia inflata, L. siphilitica and L. tupa and others have been used as medicinal plants. Campanula rapunculoides may be a troublesome weed, particularly in gardens, while Legousia spp. may occur in arable fields.

ATC code V04Diagnostic agents is a therapeutic subgroup of the Anatomical Therapeutic Chemical Classification System, a system of alphanumeric codes developed by the World Health Organization (WHO) for the classification of drugs and other medical products. Subgroup V04 is part of the anatomical group V Various.

The vesicular monoamine transporter (VMAT) is a transport protein integrated into the membranes of synaptic vesicles of presynaptic neurons. It transports monoamine neurotransmitters – such as dopamine, serotonin, norepinephrine, epinephrine, and histamine – into the vesicles, which release the neurotransmitters into synapses, as chemical messages to postsynaptic neurons. VMATs utilize a proton gradient generated by V-ATPases in vesicle membranes to power monoamine import.

<i>Lobelia cardinalis</i> Species of flowering plant

Lobelia cardinalis, the cardinal flower, is a species of flowering plant in the bellflower family Campanulaceae native to the Americas, from southeastern Canada south through the eastern and southwestern United States, Mexico and Central America to northern Colombia.

<i>Lobelia tupa</i> Species of plant

Lobelia tupa is a species of Lobelia native to central Chile from Valparaíso south to Los Lagos regions.

<span class="mw-page-title-main">Lobeline</span> Chemical compound

Lobeline is a piperidine alkaloid found in a variety of plants, particularly those in the genus Lobelia, including Indian tobacco, Devil's tobacco, great lobelia, Lobelia chinensis, and Hippobroma longiflora. In its pure form, it is a white amorphous powder which is freely soluble in water.

A nicotinic agonist is a drug that mimics the action of acetylcholine (ACh) at nicotinic acetylcholine receptors (nAChRs). The nAChR is named for its affinity for nicotine.

Elbert D. Glover is an American researcher and author in the field of tobacco addiction and smoking cessation. He retired as professor emeritus at the University of Maryland at College Park School of Public Health where he served as Chairperson of the Department of Behavioral and Community Health from 2005 to his retirement in 2015. He was an entrepreneur, editor, publisher, co-founder and principal owner of Health Behavior and Policy Review, and co-founder, owner, editor, and publisher of American Journal of Health Behavior and Tobacco Regulatory Science. Glover was the founder of the American Academy of Health Behavior and served as its first president from 1997 to 2001.

<i>Hippobroma</i> Genus of plants

Hippobroma longiflora, also called Star of Bethlehem or madamfate, is a flowering plant in the family Campanulaceae. It is the only species in the genus Hippobroma. It is endemic to the West Indies, but has become naturalized across the American tropics and Oceania.

<span class="mw-page-title-main">Michael Jackson</span> American singer (1958–2009)

Michael Joseph Jackson was an American singer, songwriter, dancer, and philanthropist. Dubbed the "King of Pop", he is regarded as one of the most significant cultural figures of the 20th century. Over a four-decade career, his world record music achievements broke racial barriers in America and his publicized personal life made him a global figure. Through songs, stages, and fashion, he proliferated visual performance for singers in pop music; popularizing street dance moves including the moonwalk, the robot, and the anti-gravity lean. Guinness World Records named him the most successful entertainer of all-time.

<i>Lobelia chinensis</i> Species of flowering plant

Lobelia chinensis, commonly known as Asian lobelia, Chinese lobelia, and Herba Lobellae Chinensis, is a species of flowering plant in the family Campanulaceae. It is one of the 50 fundamental herbs used in traditional Chinese medicine, where it has the name.

Lobel is a surname. Notable people with the surname include:

<span class="mw-page-title-main">Lobelanine</span> Chemical compound

Lobelanine is a chemical precursor in the biosynthesis of lobeline.

<span class="mw-page-title-main">Piperidine alkaloids</span> Class of chemical compounds

Piperidine alkaloids are naturally occurring chemical compounds from the group of alkaloids, which are chemically derived from piperidine.

References

  1. Chênevert R, Morin P (2009). "Synthesis of (−)-lobeline via enzymatic desymmetrization of lobelanidine". Bioorg. Med. Chem. 17 (5): 1837–9. doi:10.1016/j.bmc.2009.01.055. PMID   19217305.