Tetrahydroisoquinoline alkaloids

Noscapine, also known as narcotine, nectodon, nospen, anarcotine and (archaic) opiane, is a benzylisoquinoline alkaloid of the phthalideisoquinoline structural subgroup, which has been isolated from numerous species of the Papaveraceae (poppy) family. It lacks effects associated with opioids such as sedation, euphoria, or analgesia (pain-relief) and lacks addictive potential. Noscapine is primarily used for its antitussive (cough-suppressing) effects.

Emetine is a drug used as both an anti-protozoal and to induce vomiting. It is produced from the ipecac root. It takes its name from its emetic properties.

chemical compound

Lycorine is a toxic crystalline alkaloid found in various Amaryllidaceae species, such as the cultivated bush lily (Clivia miniata), surprise lilies (Lycoris), and daffodils (Narcissus). It may be highly poisonous, or even lethal, when ingested in certain quantities. Regardless, it is sometimes used medicinally, a reason why some groups may harvest the very popular Clivia miniata.

Dauricine is a plant metabolite, chemically classified as a phenol, an aromatic ether, and an isoquinoline alkaloid. It has been isolated from the Asian vine Menispermum dauricum, Asian moonseed, and the North American vine Menispermum canadense, Canadian moonseed. Scientists Tetsuji Kametani and Keiichiro Fukumoto of Japan are credited with being the first to synthesize dauricine in 1964, using both the Arndt-Eistert reaction and Bischler-Napieralski reaction to do so. Dauricine has been studied in vitro for its potential to inhibit cancer cell growth and to block cardiac transmembrane Na+, K

Hydrastine is an isoquinoline alkaloid which was discovered in 1851 by Alfred P. Durand. Nitric acid induced hydrolysis of hydrastine yields hydrastinine, which was patented by Bayer as a haemostatic drug in the early 1900s. It is present in Hydrastis canadensis (thus the name) and other plants of the family Ranunculaceae.

Dehydroemetine is a synthetically produced antiprotozoal agent similar to emetine in its anti-amoebic properties and structure (they differ only in a double bond next to the ethyl substituent), but it produces fewer side effects. In the United States, it is manufactured by Roche.

Chelidonine is an isolate of Papaveraceae with acetylcholinesterase and butyrylcholinesterase inhibitory activity.

Palmatine is a protoberberine alkaloid found in several plants including Coptis chinensis (Rhizoma coptidis, chinese goldthread), Corydalis yanhusuo, Tinospora cordifolia (gurjo, heart-leaved moonseed), Tinospora sagittata, Phellodendron amurense (amur cork tree), and Stephania yunnanensis.

Dihydrosanguinarine is an alkaloid found in the herbs Corydalis adunca and Lamprocapnos spectabilis. It gets its name from the Sanguinaria canadensis plant in the poppy family Papaveraceae in which it is also found.

Bicuculline is a phthalide-isoquinoline compound that is a light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, and several Corydalis species (all in subfamily Fumarioideae, previously known as family Fumariaceae). Since it blocks the inhibitory action of GABA receptors, the action of bicuculline mimics epilepsy; it also causes convulsions. This property is utilized in laboratories around the world in the in vitro study of epilepsy, generally in hippocampal or

Reticuline is a tetrahydroisoquinoline alkaloid. It is also classified as a benzylisoquinoline alkaloid. It is produced in the opium poppy from the amino acid tyrosine, initially as (S)-reticuline, which is a precursor to alkaloids including papaverine and stylopine. Another large group of alkaloids including morphine are made after (S)-reticuline has been converted in the poppy to its enantiomer, (R)-reticuline.

Coptisine is an alkaloid found in Chinese goldthread (Coptis chinensis), greater celandine, and opium. Famous for the bitter taste that it produces, it is used in Chinese herbal medicine along with the related compound berberine for digestive disorders caused by bacterial infections.

Laudanosine or '''N-methyltetrahydropapaverine''' is a metabolite of the pharmaceutical drugs atracurium and cisatracurium. Laudanosine decreases the seizure threshold, and thus it can induce seizures if present at sufficient threshold concentrations; however, such concentrations are unlikely to be produced consequent to chemodegradable metabolism of clinically administered doses of cisatracurium or atracurium.

Lophophorine, also known as '''N-methylanhalonine', is a tetrahydroisoquinoline alkaloid made by various cacti in the Lophophora'' family. It has been found to lack hallucinogenic effects in humans. Arthur Heffter tried lophophorine at a dose of 20mg resulted in vasodilation, an immediate headache, and a warm flushed feeling, effects which dissipated within an hour. It has also been said to produce nausea in humans. Lophophorine is described as highly toxic and produces strychnine-like convulsions in animals.

Gigantine is a tetrahydroisoquinoline alkaloid found in Carnegiea gigantea and other related cactus species. It was first discovered along with macromerine in 1967. Gigantine is found in significant quantities in many mescaline-containing cactus species, but it is unclear whether it contributes to their psychoactive effects. The compound has been suspected to be hallucinogenic based on animal studies in cats and monkeys, but has not been evaluated in humans.

Cephaeline is an alkaloid that is found in Cephaelis ipecacuanha and other plant species including Psychotria acuminata. Cephaeline induces vomiting by stimulating the stomach lining and is found in commercial products such as syrup of ipecac. Chemically, it is closely related to emetine.

Narcotoline is an opiate alkaloid chemically related to noscapine. It binds to the same receptors in the brain as noscapine to act as an antitussive, and has also been used in tissue culture media.

Anhalonidine, also known as '''N-desmethylpellotine', a naturally occurring tetrahydroisoquinoline alkaloid which can be isolated from certain members of the cactus family, such as Lophophora''. It is structurally related to mescaline. Anhalonidine produced no hallucinogenic effects in humans at doses of up to 250mg. However, it has been reported to have a calming or sedative effect instead, with about one-fourth the potency of pellotine and with marked sedation occurring at doses of 100 to 250mg. Anhalonidine has been found to act as a potent inverse agonist of the serotonin 5-HT7 receptor.

Anhalidine is a naturally occurring tetrahydroisoquinoline based alkaloid which can be isolated from Lophophora williamsii; it has also been detected in other cactii and several species of Acacia. It is part of a family of compounds that are structurally related to mescaline. Anhalidine has been found to act as a potent inverse agonist of the serotonin 5-HT7 receptor.

Anhalamine is a naturally occurring tetrahydroisoquinoline alkaloid which can be isolated from Lophophora williamsii. It is structurally related to mescaline. It has been found to act as a potent inverse agonist of the serotonin 5-HT7 receptor.

Corynoline is an acetylcholinesterase inhibitor isolated from Corydalis incisa.

Pellotine, also known as peyotline or '''N-methylanhalonidine', is a tetrahydroisoquinoline alkaloid found in Lophophora species, in particular L. diffusa. It is the second most common alkaloid found in Lophophora williamsii'' (peyote). Pellotine is slightly sedative, and has been used by Native Americans as a constituent of peyote for sacramental purposes. It was reportedly once marketed for use as a sedative. Pellotine has been sold online.

Michellamines are a group of atropisomeric alkaloid which have been found to be HIV viral replication inhibitors in vitro. It was discovered in the leaves of Ancistrocladus korupensis. There are three michellamines represented as A, B, and C; however, michellamine B is the most active against the NID-DZ strain of HIV-2.