Alkaloids

thumb|250px|The first individual alkaloid, morphine, was isolated in 1804 from the opium poppy (Papaver somniferum).

Imidazole (ImH) is an organic compound with the formula . It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. It can be classified as a heterocycle, specifically as a diazole.

Colchicine is a medication used to prevent and treat gout, to treat familial Mediterranean fever and Behçet's disease, and to reduce the risk of myocardial infarction. The American College of Rheumatology recommends colchicine, nonsteroidal anti-inflammatory drugs (NSAIDs) or steroids in the treatment of gout. Other uses for colchicine include the management of pericarditis.

thumb|Amanita muscaria

Physostigmine (also known as eserine from éséré, the West African name for the Calabar bean) is a highly toxic parasympathomimetic alkaloid, specifically, a reversible cholinesterase inhibitor. It occurs naturally in the Calabar bean and the fruit of the Manchineel tree.

Muscimol, also known as agarin, pantherine, or pyroibotenic acid, is a GABAA receptor agonist with sedative and hallucinogenic effects and the principal psychoactive constituent of Amanita mushrooms such as Amanita muscaria (fly agaric) and Amanita pantherina (panther cap). It is a 3-hydroxyisoxazole alkaloid and is closely related structurally to the neurotransmitter γ-aminobutyric acid (GABA). The compound is widely used as a ligand and agonist of the GABAA receptor in scientific research. Muscimol is typically taken orally, but may also be smoked. Peak effects occur after 1 to 3hours orally

Arecoline is a cholinergic agent, stimulant, and naturally occurring alkaloid found in areca (betel) nuts of the areca palm (Areca catechu) found in South and Southeast Asia. Its effects, depending on the dose, include stimulation, alertness, increased concentration, cognitive enhancement, elation, euphoria, pro-sexual effects, relaxation, reduced anxiety, and sedation, as well as addiction and withdrawal symptoms upon discontinuation. Its effects are described as subtle and it has been likened to a strong cup of coffee. There are also other active constituents of areca nuts, but arecoline is

Orellanine or orellanin is a mycotoxin found in a group of mushrooms known as the Orellani within the family Cortinariaceae. Structurally, it is a bipyridine N-oxide compound somewhat related to the herbicide diquat.

Trigonelline is an alkaloid with chemical formula . It is a zwitterion formed by the methylation of the nitrogen atom of niacin (vitamin B3). Trigonelline is a product of niacin metabolism that is excreted in the urine of mammals.

Neurine is an alkaloid found in egg yolk, brain, bile and in cadavers. It is formed during putrefaction of biological tissues by the dehydration of choline. It is a poisonous, syrupy liquid with a fishy odor.

Cordycepin, or '''3'-deoxyadenosine''', is a derivative of the nucleoside adenosine, differing from the latter by the replacement of the hydroxy group in the 3' position with a hydrogen. It was initially extracted from the fungus Cordyceps militaris, but can now be produced synthetically.

thumb|right|150px|class=skin-invert-image|The lysergamide core, with common substitution positions denoted.

chemical compound

Midostaurin, sold under the brand name Rydapt by Novartis, is a multi-targeted protein kinase inhibitor that has been investigated for the treatment of acute myeloid leukemia (AML), myelodysplastic syndrome (MDS) and advanced systemic mastocytosis. It is a semi-synthetic derivative of staurosporine, an alkaloid from the bacterium Streptomyces staurosporeus.

Sinapine is an alkaloidal amine found in some seeds, particularly oil seeds of plants in the family Brassicaceae. It is the choline ester of sinapic acid.

Delphinine is a toxic diterpenoid alkaloid found in plants from the Delphinium (larkspur) and Atragene (a clematis) genera, both in the family Ranunculaceae. Delphinine is the principal alkaloid found in Delphinium staphisagria seeds – at one time, under the name stavesacre, a very well known herbal treatment for body lice. It is related in structure and has similar effects to aconitine, acting as an allosteric modulator of voltage gated sodium channels, and producing low blood pressure, slowed heart rate and abnormal heart rhythms. These effects make it highly poisonous ( 1.5–3.0 mg/kg i

Anatoxin-a, also known as Very Fast Death Factor (VFDF), is a secondary, bicyclic amine alkaloid and cyanotoxin with acute neurotoxicity. It was first discovered in the early 1960s in Canada, and was isolated in 1972. The toxin is produced by multiple genera of cyanobacteria and has been reported in North America, South America, Central America, Europe, Africa, Asia, and Oceania. Symptoms of anatoxin-a toxicity include loss of coordination, muscular fasciculations, convulsions and death by respiratory paralysis. Its mode of action is through the nicotinic acetylcholine receptor (nAchR) where i

Substitution of the heterocycle isoquinoline at the C1 position by a benzyl group provides 1‑benzylisoquinoline, the most widely examined of the numerous benzylisoquinoline structural isomers. The 1-benzylisoquinoline moiety can be identified within numerous compounds of pharmaceutical interest, such as moxaverine; but most notably it is found within the structures of a wide variety of plant natural products, collectively referred to as benzylisoquinoline alkaloids. This class is exemplified in part by the following compounds: papaverine, noscapine, codeine, morphine, apomorphine, berberine, t

Leonurine (also known as SCM-198 in research) is a pseudoalkaloid that has been isolated from Leonotis leonurus, Leonotis nepetifolia, Leonurus japonicus, Leonurus cardiaca (motherwort), Leonurus sibiricus, as well as other plants of family Lamiaceae. Leonurine is easily extracted into water.

Pseudopelletierine is the main alkaloid derived from the root-bark of the pomegranate tree (Punica granatum), along with at least three other alkaloids: pelletierine, isopelletierine, and methylpelletierine (C9H17ON), which yield 1.8, 0.52, 0.01, and 0.20 grams per kilogram of raw bark.

Ricinine is a toxic alkaloid found in the castor plant. It can serve as a biomarker of ricin poisoning. It was first isolated from the castor seeds by Tuson in 1864.

thumb|right|Histrionicotoxin 283A

'''Palau'amine' is a toxic chlorinated alkaloid compound synthesized naturally by certain species of sea sponges. The name of the molecule derives from the island nation of Palau, near where the first sponge species discovered to produce it, Stylotella agminata, is found. It has since been isolated in other sponges, including Stylissa massa''.

Guvacine is a tetrahydropyridine alkaloid found in areca nuts. It is the N-demethylated derivative of arecaidine and the product of ester hydrolysis of guvacoline, both of which are also found in areca nuts as well. The compound is a potent and selective GABA reuptake inhibitor via GABA transporter 1 (GAT-1) inhibition. It shows poor blood–brain barrier penetration. Lime hydrolyzes guvacoline to guvacine.

Theacrine, also known as 1,3,7,9-tetramethyluric acid, is a purine alkaloid found in cupuaçu (Theobroma grandiflorum) and in a Chinese kucha tea () (Camellia assamica var. kucha). It shows anti-inflammatory and analgesic effects and appears to affect adenosine signalling in a manner similar to caffeine. In kucha leaves, theacrine is synthesized from caffeine in what is thought to be a three-step pathway. Theacrine and caffeine are structurally similar.

pure basic form of an amine, as opposed to its salt form

Slaframine is an bicyclic alkaloid mycotoxin that causes salivation (slobbers) in most animals. It is usually produced by the fungus Rhizoctonia leguminicola which is a common fungal pathogen of red clover (Trifolium pratense) that causes black patch disease in the plant. Slaframine has the molecular formula C10H18N2O2. Wet and humid weather are the favorable environmental condition for the growth of the fungus and production of slaframine. Legume hays contaminated with slaframine cause slobber syndrome and various animals are sensitive to its effects.

Rhoeadine (rheadine) is an alkaloid derived from the flowers of the corn poppy (Papaver rhoeas). It has been studied for its potential use in the treatment of morphine dependence.

Catharanthine is a terpene indole alkaloid produced by the medicinal plant Catharanthus roseus and Tabernaemontana divaricata. Catharanthine is derived from strictosidine, but the exact mechanism by which this happens is currently unknown. Catharanthine is one of the two precursors that form vinblastine, the other being vindoline.

Samandaridine is an extremely toxic alkaloid produced by the skin glands of various salamanders.

Hasubanonine is a member of the hasubanan family of alkaloids. The alkaloid with an isoquinoline substructure has the molecular formula of C21H27NO5. The enantiomer of the natural product is being studied as a potential painkiller. Hasubanonine is structurally related to the morphinan class of opioid analgesics.

chemical compound

Alchorneine is an imidazopyrimidine alkaloid found in trees in the genus Alchornea such as Alchornea castaneifolia, Alchornea floribunda or Alchornea cordifolia.

Coronaridine, also known as 18-carbomethoxyibogamine, is an alkaloid found in Tabernanthe iboga and related species, including Tabernaemontana divaricata for which (under the now obsolete synonym Ervatamia coronaria) it was named.

Liberine, also referred to as O(2),1,9-trimethyluric acid, is a purine alkaloid. It is an isolate of coffee beans, tea, kola nuts, guarana, cocoa beans and yerba mate.

Allocryptopine is a bioactive alkaloid found in plants of the Papaveraceae family, including Glaucium arabicum, Argemone mexicana, Eschscholtzia, Corydalis, Fumaria, Chelidonium, Hunnemannia fumariifolia, Eschscholzia lobbii and other Papaveraceae plants.

Dendrobine is an alkaloid found in Dendrobium nobile at an average of 0.5% by weight. It is a colorless solid at room temperature. It is related to the picrotoxin family of natural products. When given a fatal dose, death is usually caused by convulsions. It possesses a molecular structure that attracted interest in its total synthesis by organic chemists.

(−)-Magellanine is a member of the Lycopodium alkaloid class of natural products. It was isolated from the club moss Lycopodium magellanicum in 1976. It has been synthesized five times, with the first synthesis having been completed by the Larry E. Overman group at the University of California, Irvine in 1993. It has also been synthesized by the Leo Paquette group in 1993 at Ohio State University, the Chun-Chen Liao group in 2002 at National Tsing Hua University, the Miyuki Ishikazi and Tamiko Takahashi groups in 2005 at the Josai International University and Tokyo University of Science, and t

Ethocybin also known as '4-phosphoryloxy-N,N-diethyltryptamine (4-PO-DET) or as CEY-19', is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to the psilocybin-containing mushroom alkaloid psilocybin. It is assumed to act as a prodrug of 4-HO-DET (CZ-74) analogously to how psilocybin (4-PO-DMT) acts as a prodrug of psilocin (4-HO-DMT). The drug was first described in the literature by Albert Hofmann and colleagues at Sandoz by 1963.

Vasicine (peganine) is a quinazoline alkaloid. It is found in Justicia adhatoda, after which it is named. It is additionally found in Peganum harmala.

chemical compound

Cryptopine is an opium alkaloid. It is found in plants in the family Papaveraceae, including Argemone mexicana.

Alschomine is an indole alkaloid first identified in the leaves of Alstonia scholaris in 1989.

Methylliberine is an isolate of coffee beans, tea, cola nuts, guarana, cocoa, and yerba mate. It is structurally related to Liberine.

Eritadenine is a chemical compound found in shiitake mushrooms. Eritadenine is an inhibitor of S-adenosyl-L-homocysteine hydrolase (SAHH) and has hypocholesterolemic activity.

Cryogenine, also known as vertine or (10α)-4,5-dimethoxy-2-hydroxylythran-12-one, is a biphenylquinolizidine lactone alkaloid from the plants Sinicuichi (Heimia salicifolia) and H. myrtifolia. The compound has no psychoactive properties in humans up to 310 mg, but has shown anti-inflammatory activity similar to aspirin.

Prajmaline (Neo-gilurythmal) is a class Ia antiarrhythmic agent which has been available since the 1970s. Class Ia drugs increase the time one action potential lasts in the heart. Prajmaline is a semi-synthetic propyl derivative of ajmaline, with a higher bioavailability than its predecessor. It acts to stop arrhythmias of the heart through a frequency-dependent block of cardiac sodium channels.