R-(+)-Cotinine

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for R-(+)-Cotinine are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the R-(+)-Cotinine?

The molecule R-(+)-Cotinine presents a molecular formula of C₁₀H₁₂N₂O and its IUPAC name is (5R)-1-methyl-5-pyridin-3-ylpyrrolidin-2-one.

R-(+)-Cotinine is a molecule that belongs in the tobacco plant. It is the main alkaloid in tobacco and is responsible for the addictive nature of smoking. Cotinine is also found in smaller amounts in other plants, including the nightshade family of plants..

Cotinine is a colorless, oily liquid that is insoluble in water. It has a strong, unpleasant odor. Cotinine is formed when tobacco is burned and inhaled. It is also a breakdown product of nicotine..

Cotinine is absorbed through the skin, mucous membranes, and the gastrointestinal tract. It is metabolized in the liver and excreted in the urine..

Cotinine has a half-life of 16-19 hours. This means that it takes 16-19 hours for the body to eliminate half of the cotinine that is in the body..

Cotinine is a nicotinic acetylcholine receptor agonist. This means that it binds to and activates the nicotinic acetylcholine receptors. These receptors are found in the brain and other parts of the nervous system..

Activation of the nicotinic acetylcholine receptors leads to an increase in the release of the neurotransmitter dopamine. Dopamine is a neurotransmitter that is associated with pleasure and reward. This is one of the mechanisms that contributes to the addictive nature of smoking..

Cotinine also has other effects on the body. It can increase heart rate and blood pressure. It can also cause bronchodilation..

There are a number of ways to measure cotinine levels in the body. These include blood tests, urine tests, and hair tests..

Cotinine levels can be used to determine exposure to tobacco smoke. They can also be used to monitor smoking cessation programs..

High levels of cotinine can be toxic. Symptoms of cotinine toxicity include nausea, vomiting, diarrhea, abdominal pain, and seizures..

Cotinine is a molecule that belongs in the tobacco plant. It is the main alkaloid in tobacco and is responsible for the addictive nature of smoking. Cotinine is also found in smaller amounts in other plants, including the nightshade family of plants..

3D structure

Cartesian coordinates

Geometry of R-(+)-Cotinine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

Molecule descriptors

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

Reference codes for other databases

• CAS number (Chemical Abstracts Service Registry Number) is a unique identifier is assigned to every chemical compound indexed in the CAS database.
• Beilstein: The Beilstein database is a comprehensive source of information on organic chemistry, including information on chemical structures, properties, and reactions. The Beilstein database assigns unique identifiers which can be used to identify compounds in scientific literature and other sources.
• ChEBI (Chemical Entities of Biological Interest): ChEBI is a database of small chemical molecules that are of interest in the field of biology.
• PubChem CID (Compound Identifier): PubChem is a database of chemical compounds that is maintained by the National Institutes of Health (NIH).
• RTECS number (Registry of Toxic Effects of Chemical Substances): The RTECS is a database of information on the toxic effects of chemicals, including information on their structures and properties.
• ChEMBL (Compound Bioactivity Data): ChEMBL is a database of bioactivity data for small molecules, including information on their properties and structures.
• CompTox Dashboard (Environmental Protection Agency): The CompTox Dashboard is a database of information on the toxicology and environmental effects of chemicals.

Physico-Chemical properties

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (K_ow) data is applied in toxicology and drug research. K_ow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(K_ow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Ų are required. Thus, molecules with a polar surface area greater than 140 Ų tend to be poorly permeable to cell membranes.