Sparteine: Difference between revisions

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'''Sparteine''' is a class 1a [[antiarrhythmic agent]], a type of [[alkaloid]]. It is an [[isomer]] of [[lupinine]]. It is named after the [[Scotch broom]] (Cytisus scoparius), which is also known as "Sparteine broom" because it is one of the plant species that contains it.
{{Short description|An alkaloid with various pharmacological effects}}
{{Use dmy dates|date=October 2023}}


==Chemistry==
'''Sparteine''' is a naturally occurring [[alkaloid]] found in various species of the [[Fabaceae]] family, particularly in the [[genus]] ''[[Cytisus]]''. It is known for its pharmacological properties and has been used in traditional medicine as well as in modern pharmacology.
Sparteine is a [[bicyclic]] [[alkaloid]] that is classified as a [[quinolizidine]]. It is a [[chiral molecule]], with two [[stereocenters]], which means it has four possible [[stereoisomer]]s. The natural form of sparteine is a mixture of two of these stereoisomers, known as the (-)-sparteine and (+)-sparteine.


==Pharmacology==
==Chemical Structure and Properties==
Sparteine works as an [[antiarrhythmic agent]], which means it is used to treat and prevent abnormal heart rhythms. It is classified as a class 1a antiarrhythmic agent, which means it works by blocking the fast inward [[sodium channel]], slowing the influx of sodium ions into the [[cardiomyocyte]]. This decreases the rate of depolarization, slows conduction velocity, and prolongs the refractory period, helping to restore normal rhythm.
Sparteine is a [[quinolizidine]] alkaloid with the chemical formula C<sub>15</sub>H<sub>26</sub>N<sub>2</sub>. It is a bicyclic compound, consisting of two nitrogen atoms within its structure. Sparteine is a colorless, oily liquid at room temperature and is known for its bitter taste.


==Toxicity==
==Sources==
Sparteine can be toxic if consumed in large amounts. Symptoms of sparteine poisoning can include [[nausea]], [[vomiting]], [[abdominal pain]], [[arrhythmia]], and in severe cases, [[seizures]] or [[death]]. It is also a [[teratogen]], which means it can cause birth defects if consumed during pregnancy.
Sparteine is primarily extracted from plants of the ''Cytisus'' genus, such as ''[[Cytisus scoparius]]'' (commonly known as [[Scotch broom]]). It can also be found in other members of the Fabaceae family, including ''[[Lupinus]]'' species.


==See also==
==Pharmacological Effects==
Sparteine has several pharmacological effects, including:
 
* '''Cardiovascular effects''': Sparteine acts as a [[cardiac depressant]], affecting the heart's conduction system. It has been used historically to treat certain types of [[arrhythmias]].
* '''Oxytocic effects''': Sparteine can stimulate uterine contractions, which has led to its use in obstetrics to induce labor.
* '''Neuromuscular effects''': It has a mild [[neuromuscular blocking]] effect, which can influence muscle relaxation.
 
==Medical Uses==
Historically, sparteine was used in the treatment of [[cardiac arrhythmias]] due to its ability to modulate heart rhythm. However, its use has declined with the development of more effective and safer antiarrhythmic drugs.
 
In obstetrics, sparteine was used to induce labor due to its ability to stimulate uterine contractions. However, its use in modern medicine is limited due to the availability of more controlled and predictable agents.
 
==Metabolism and Pharmacokinetics==
Sparteine is metabolized in the liver by the [[cytochrome P450]] enzyme system, particularly by the CYP2D6 isoenzyme. There is significant genetic variability in the metabolism of sparteine, with some individuals being "poor metabolizers" due to genetic polymorphisms in the CYP2D6 gene.
 
==Toxicity and Side Effects==
Sparteine can be toxic in high doses, leading to symptoms such as nausea, vomiting, dizziness, and [[hypotension]]. Due to its narrow therapeutic index, careful dosing and monitoring are required when it is used therapeutically.
 
==Related Compounds==
Sparteine is related to other quinolizidine alkaloids such as [[lupanine]] and [[cytisine]], which also have pharmacological activities.
 
==Related Pages==
* [[Alkaloid]]
* [[Alkaloid]]
* [[Antiarrhythmic agent]]
* [[Cytisus scoparius]]
* [[Quinolizidine]]
* [[Cardiac arrhythmia]]
* [[Sodium channel]]
* [[Cytochrome P450]]


[[Category:Alkaloids]]
[[Category:Alkaloids]]
[[Category:Antiarrhythmic agents]]
[[Category:Pharmacology]]
[[Category:Quinolizidines]]
[[Category:Fabaceae]]
[[Category:Sodium channel blockers]]
 
{{stub}}
<gallery>
File:(_)-Sparteine.svg|Structure of (_)-Sparteine
File:BiosynthesisofSparteine.png|Biosynthesis pathway of Sparteine
File:BiosynthesisSparteine2.png|Detailed biosynthesis of Sparteine
File:GeneralbiosynthesisSparteine.gif|General biosynthesis of Sparteine
</gallery>

Revision as of 17:42, 18 February 2025

An alkaloid with various pharmacological effects



Sparteine is a naturally occurring alkaloid found in various species of the Fabaceae family, particularly in the genus Cytisus. It is known for its pharmacological properties and has been used in traditional medicine as well as in modern pharmacology.

Chemical Structure and Properties

Sparteine is a quinolizidine alkaloid with the chemical formula C15H26N2. It is a bicyclic compound, consisting of two nitrogen atoms within its structure. Sparteine is a colorless, oily liquid at room temperature and is known for its bitter taste.

Sources

Sparteine is primarily extracted from plants of the Cytisus genus, such as Cytisus scoparius (commonly known as Scotch broom). It can also be found in other members of the Fabaceae family, including Lupinus species.

Pharmacological Effects

Sparteine has several pharmacological effects, including:

  • Cardiovascular effects: Sparteine acts as a cardiac depressant, affecting the heart's conduction system. It has been used historically to treat certain types of arrhythmias.
  • Oxytocic effects: Sparteine can stimulate uterine contractions, which has led to its use in obstetrics to induce labor.
  • Neuromuscular effects: It has a mild neuromuscular blocking effect, which can influence muscle relaxation.

Medical Uses

Historically, sparteine was used in the treatment of cardiac arrhythmias due to its ability to modulate heart rhythm. However, its use has declined with the development of more effective and safer antiarrhythmic drugs.

In obstetrics, sparteine was used to induce labor due to its ability to stimulate uterine contractions. However, its use in modern medicine is limited due to the availability of more controlled and predictable agents.

Metabolism and Pharmacokinetics

Sparteine is metabolized in the liver by the cytochrome P450 enzyme system, particularly by the CYP2D6 isoenzyme. There is significant genetic variability in the metabolism of sparteine, with some individuals being "poor metabolizers" due to genetic polymorphisms in the CYP2D6 gene.

Toxicity and Side Effects

Sparteine can be toxic in high doses, leading to symptoms such as nausea, vomiting, dizziness, and hypotension. Due to its narrow therapeutic index, careful dosing and monitoring are required when it is used therapeutically.

Related Compounds

Sparteine is related to other quinolizidine alkaloids such as lupanine and cytisine, which also have pharmacological activities.

Related Pages