Cytisine
Encyclopedia
Cytisine, also known as baphitoxine and sophorine, is a pyridine
-like alkaloid
. In medical use, it improves the rate of smoking cessation. It is less effective but much cheaper (≥$6 for a course of treatment) than similar products. Its structure is similar to nicotine
and has similar pharmacological effects. In large doses, it can interfere with breathing and cause death.
subfamily, including Laburnum
, Anagyris
, Thermopsis
, Cytisus
, Genista
and Sophora
. It is also present in Gymnocladus
of the Caesalpinioideae
subfamily.
Māmane (Sophora chrysophylla) can contain amounts of cytisine that are lethal to most animals. The palila
(Loxioides bailleui, a bird
), Uresiphita polygonalis virescens
and Cydia species (moth
s), and possibly sheep
and goat
s are not affected by the toxin for various reasons, and use māmane, or parts thereof, as food. U. p. virescens caterpillars are possibly able to sequester the cytisine to give themselves protection from getting eaten; they have aposematic
coloration which would warn off potential predators.
agonist
, and as a pharmaceutical preparation, it is available for the treatment of tobacco smoking
. It is extracted from the seeds of Cytisus laborinum L. (Golden Rain acacia) and has been available in former socialist economy (FSE) countries for more than 40 years as an aid to smoking cessation under the brand name Tabex produced by the Bulgarian pharmaceutical company Sopharma AD. It was first marketed in Bulgaria in 1964 and then became widely available in FSE countries.
The cytisine derivative varenicline was approved in 2006 as a smoking cessation drug.
In 2011, a randomized controlled trial with 740 patients found cytisine improved 12-month abstinence from nicotine from 2.4% with placebo to 8.4% with cytisine.
Plants containing cytisine, including the common broom and mescalbean
, have also been used recreationally
. Positive effects are reported to include a mild intoxication and heightened awareness of color
. However, this practice is not recommended, since negative side effects can include nausea
, vomiting
, convulsions, heart pain, headache
and, in larger dose
s, even death
via respiratory failure
.
Pyridine
Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N. It is structurally related to benzene, with one C-H group replaced by a nitrogen atom...
-like alkaloid
Alkaloid
Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...
. In medical use, it improves the rate of smoking cessation. It is less effective but much cheaper (≥$6 for a course of treatment) than similar products. Its structure is similar to nicotine
Nicotine
Nicotine is an alkaloid found in the nightshade family of plants that constitutes approximately 0.6–3.0% of the dry weight of tobacco, with biosynthesis taking place in the roots and accumulation occurring in the leaves...
and has similar pharmacological effects. In large doses, it can interfere with breathing and cause death.
Sources
Plants that contain the alkaloid in various concentrations include those from several genera of the FaboideaeFaboideae
Faboideae is a subfamily of the flowering plant family Fabaceae or Leguminosae. One acceptable alternative name for the subfamily is Papilionoideae....
subfamily, including Laburnum
Laburnum
Laburnum is a genus of two species of small trees in the subfamily Faboideae of the pea family Fabaceae, Laburnum anagyroides and L. alpinum . They are native to the mountains of southern Europe from France to the Balkan Peninsula...
, Anagyris
Anagyris
Anagyris is a genus of flowering plants in the legume family, Fabaceae. It belongs to the sub family Faboideae....
, Thermopsis
Thermopsis
Thermopsis is a genus of 8 to 23 species of legumes, native to temperate North America and east Asia. They are herbaceous perennials and are known as goldenbanners.-Species:* Thermopsis alpina...
, Cytisus
Cytisus
Cytisus is a genus of flowering plants in the legume family, Fabaceae. It belongs to the subfamily Faboideae.-Selected species:* Cytisus arboreus DC.* Cytisus ardoini E.Fourn.* Cytisus baeticus Steud....
, Genista
Genista
Genista is a genus of legumes which includes many species of broom. Many of these brooms are notorious as noxious weeds.Species include:*Genista aetnensis - Mount Etna broom*Genista anglica - petty whin, needle furze*Genista canariensis...
and Sophora
Sophora
Sophora is a genus of about 45 species of small trees and shrubs in the subfamily Faboideae of the pea family, Fabaceae. The species are native to southeast Europe, southern Asia, Australasia, various islands in the Pacific Ocean, western South America, the western United States, the Southern US...
. It is also present in Gymnocladus
Kentucky coffeetree
The Kentucky Coffeetree, Gymnocladus dioicus, is a tree in the subfamily Caesalpinioideae of the pea family Fabaceae, native to the midwest of North America.-Introduction:...
of the Caesalpinioideae
Caesalpinioideae
Caesalpinioideae is a botanical name at the rank of subfamily, placed in the large family Fabaceae or Leguminosae. Its name is formed from the generic name Caesalpinia....
subfamily.
Māmane (Sophora chrysophylla) can contain amounts of cytisine that are lethal to most animals. The palila
Palila
The Palila is a critically endangered finch-billed species of Hawaiian honeycreeper. It has a golden-yellow head and breast, with a light belly, gray back, and greenish wings and tail...
(Loxioides bailleui, a bird
Bird
Birds are feathered, winged, bipedal, endothermic , egg-laying, vertebrate animals. Around 10,000 living species and 188 families makes them the most speciose class of tetrapod vertebrates. They inhabit ecosystems across the globe, from the Arctic to the Antarctic. Extant birds range in size from...
), Uresiphita polygonalis virescens
Uresiphita polygonalis
Uresiphita polygonalis is a moth of the Crambidae family. It is found in the Pacific, including Hawaii and New Zealand.The wingspan is about 27 mm. Adults range in color from green to red....
and Cydia species (moth
Moth
A moth is an insect closely related to the butterfly, both being of the order Lepidoptera. Moths form the majority of this order; there are thought to be 150,000 to 250,000 different species of moth , with thousands of species yet to be described...
s), and possibly sheep
Domestic sheep
Sheep are quadrupedal, ruminant mammals typically kept as livestock. Like all ruminants, sheep are members of the order Artiodactyla, the even-toed ungulates. Although the name "sheep" applies to many species in the genus Ovis, in everyday usage it almost always refers to Ovis aries...
and goat
Goat
The domestic goat is a subspecies of goat domesticated from the wild goat of southwest Asia and Eastern Europe. The goat is a member of the Bovidae family and is closely related to the sheep as both are in the goat-antelope subfamily Caprinae. There are over three hundred distinct breeds of...
s are not affected by the toxin for various reasons, and use māmane, or parts thereof, as food. U. p. virescens caterpillars are possibly able to sequester the cytisine to give themselves protection from getting eaten; they have aposematic
Aposematism
Aposematism , perhaps most commonly known in the context of warning colouration, describes a family of antipredator adaptations where a warning signal is associated with the unprofitability of a prey item to potential predators...
coloration which would warn off potential predators.
Uses
Cytisine is a nicotinic acetylcholine receptorNicotinic acetylcholine receptor
Nicotinic acetylcholine receptors, or nAChRs, are cholinergic receptors that form ligand-gated ion channels in the plasma membranes of certain neurons and on the postsynaptic side of the neuromuscular junction...
agonist
Agonist
An agonist is a chemical that binds to a receptor of a cell and triggers a response by that cell. Agonists often mimic the action of a naturally occurring substance...
, and as a pharmaceutical preparation, it is available for the treatment of tobacco smoking
Tobacco smoking
Tobacco smoking is the practice where tobacco is burned and the resulting smoke is inhaled. The practice may have begun as early as 5000–3000 BCE. Tobacco was introduced to Eurasia in the late 16th century where it followed common trade routes...
. It is extracted from the seeds of Cytisus laborinum L. (Golden Rain acacia) and has been available in former socialist economy (FSE) countries for more than 40 years as an aid to smoking cessation under the brand name Tabex produced by the Bulgarian pharmaceutical company Sopharma AD. It was first marketed in Bulgaria in 1964 and then became widely available in FSE countries.
The cytisine derivative varenicline was approved in 2006 as a smoking cessation drug.
In 2011, a randomized controlled trial with 740 patients found cytisine improved 12-month abstinence from nicotine from 2.4% with placebo to 8.4% with cytisine.
Plants containing cytisine, including the common broom and mescalbean
Mescalbean
Calia is a genus of three or four species of shrubs and small trees in the subfamily Faboideae of the pea family, Fabaceae. The genus is native to southwestern North America from western Texas to New Mexico and Arizona in the United States, and south through Chihuahua, Coahuila and Nuevo León in...
, have also been used recreationally
Recreational drug use
Recreational drug use is the use of a drug, usually psychoactive, with the intention of creating or enhancing recreational experience. Such use is controversial, however, often being considered to be also drug abuse, and it is often illegal...
. Positive effects are reported to include a mild intoxication and heightened awareness of color
Color
Color or colour is the visual perceptual property corresponding in humans to the categories called red, green, blue and others. Color derives from the spectrum of light interacting in the eye with the spectral sensitivities of the light receptors...
. However, this practice is not recommended, since negative side effects can include nausea
Nausea
Nausea , is a sensation of unease and discomfort in the upper stomach with an involuntary urge to vomit. It often, but not always, precedes vomiting...
, vomiting
Vomiting
Vomiting is the forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose...
, convulsions, heart pain, headache
Headache
A headache or cephalalgia is pain anywhere in the region of the head or neck. It can be a symptom of a number of different conditions of the head and neck. The brain tissue itself is not sensitive to pain because it lacks pain receptors. Rather, the pain is caused by disturbance of the...
and, in larger dose
Dose (biochemistry)
A dose is a quantity of something that may impact an organism biologically; the greater the quantity, the larger the dose. In nutrition, the term is usually applied to how much of a specific nutrient is in a person's diet or in a particular food, meal, or dietary supplement...
s, even death
Death
Death is the permanent termination of the biological functions that sustain a living organism. Phenomena which commonly bring about death include old age, predation, malnutrition, disease, and accidents or trauma resulting in terminal injury....
via respiratory failure
Respiratory failure
The term respiratory failure, in medicine, is used to describe inadequate gas exchange by the respiratory system, with the result that arterial oxygen and/or carbon dioxide levels cannot be maintained within their normal ranges. A drop in blood oxygenation is known as hypoxemia; a rise in arterial...
.
External links
- Shaman Australis Cytisine pharmacology and information on substance availability in various plants.
- Erowid Library: Golden Guide Hallucinogenic Plants by Richard Evans Schultes More on the dangerous effects of cytisine on health and respiration.
- The Vaults of Erowid : Legal Highs by Adam Gottlieb Information on recreational use.
- Cytisine Is Cheap And Effective In Helping Smokers Quit Information on treatment of tobacco smoking
- Tabex official website