Narcotoline

Last updated
Narcotoline
Narcotoline structure.png
Names
Preferred IUPAC name
(3S)-3-[(5R)-4-Hydroxy-6-methyl-5,6,7,8-tetrahydro-2H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,7-dimethoxy-2-benzofuran-1(3H)-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.559 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-313-6
KEGG
PubChem CID
UNII
  • InChI=1S/C21H21NO7/c1-22-7-6-10-8-13-20(28-9-27-13)17(23)14(10)16(22)18-11-4-5-12(25-2)19(26-3)15(11)21(24)29-18/h4-5,8,16,18,23H,6-7,9H2,1-3H3/t16-,18+/m1/s1 X mark.svgN
    Key: LMGZCSKYOKDBES-AEFFLSMTSA-N X mark.svgN
  • InChI=1/C21H21NO7/c1-22-7-6-10-8-13-20(28-9-27-13)17(23)14(10)16(22)18-11-4-5-12(25-2)19(26-3)15(11)21(24)29-18/h4-5,8,16,18,23H,6-7,9H2,1-3H3/t16-,18+/m1/s1
    Key: LMGZCSKYOKDBES-AEFFLSMTBE
  • CN1CCC2=CC3=C(C(=C2[C@@H]1[C@@H]4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)O)OCO3
Properties
C21H21NO7
Molar mass 399.399 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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, [1] and has also been used in tissue culture media. [2]

Contents

Sources

It can be obtained from the opium poppy, Papaver somniferum . It is present at much higher levels in culinary strains (cultivars) of P. somniferum used for poppy seed production than in high-morphine pharmaceutical strains used for opium production. [3]

Related Research Articles

Opium Dried latex obtained from the opium poppy

Opium is dried latex obtained from the seed capsules of the opium poppy Papaver somniferum. Approximately 12 percent of opium is made up of the analgesic alkaloid morphine, which is processed chemically to produce heroin and other synthetic opioids for medicinal use and for the illegal drug trade. The latex also contains the closely related opiates codeine and thebaine, and non-analgesic alkaloids such as papaverine and noscapine. The traditional, labor-intensive method of obtaining the latex is to scratch ("score") the immature seed pods (fruits) by hand; the latex leaks out and dries to a sticky yellowish residue that is later scraped off and dehydrated. The word "meconium" historically referred to related, weaker preparations made from other parts of the opium poppy or different species of poppies.

Thebaine Chemical compound

Thebaine (paramorphine), also known as codeine methyl enol ether, is an opiate alkaloid, its name coming from the Greek Θῆβαι, Thēbai (Thebes), an ancient city in Upper Egypt. A minor constituent of opium, thebaine is chemically similar to both morphine and codeine, but has stimulatory rather than depressant effects. At high doses, it causes convulsions similar to strychnine poisoning. The synthetic enantiomer (+)-thebaine does show analgesic effects apparently mediated through opioid receptors, unlike the inactive natural enantiomer (−)-thebaine. While thebaine is not used therapeutically, it is the main alkaloid extracted from Papaver bracteatum and can be converted industrially into a variety of compounds, including hydrocodone, hydromorphone, oxycodone, oxymorphone, nalbuphine, naloxone, naltrexone, buprenorphine and etorphine. Butorphanol can also be derived from thebaine.

Poppy Species of flowering plant in the family Papaveraceae

A poppy is a flowering plant in the subfamily Papaveroideae of the family Papaveraceae. Poppies are herbaceous plants, often grown for their colourful flowers. One species of poppy, Papaver somniferum, is the source of the narcotic drug opium which contains powerful medicinal alkaloids such as morphine and has been used since ancient times as an analgesic and narcotic medicinal and recreational drug. It also produces edible seeds. Following the trench warfare in the poppy fields of Flanders, Belgium during World War I, poppies have become a symbol of remembrance of soldiers who have died during wartime.

<i>Papaver</i> genus of flowering plants in the poppy family Papaveraceae

Papaver is a genus of 70–100 species of frost-tolerant annuals, biennials, and perennials native to temperate and cold regions of Eurasia, Africa and North America. It is the type genus of the poppy family, Papaveraceae.

Papaveraceae family of flowering plants

The Papaveraceae are an economically important family of about 42 genera and approximately 775 known species of flowering plants in the order Ranunculales, informally known as the poppy family. The family is cosmopolitan, occurring in temperate and subtropical climates, but almost unknown in the tropics. Most are herbaceous plants, but a few are shrubs and small trees. The family currently includes two groups that have been considered to be separate families: Fumariaceae and Pteridophyllaceae.

<i>Papaver somniferum</i> Species of flowering plant in the family Papaveraceae

Papaver somniferum, commonly known as the opium poppy or breadseed poppy, is a species of flowering plant in the family Papaveraceae. It is the species of plant from which both opium and poppy seeds are derived and is also a valuable ornamental plant, grown in gardens. Its native range is probably the eastern Mediterranean, but is now obscured by ancient introductions and cultivation, being naturalized across much of Europe and Asia.

Papaverine

Papaverine is an opium alkaloid antispasmodic drug, used primarily in the treatment of visceral spasm and vasospasm, and occasionally in the treatment of erectile dysfunction. It is used in the treatment of acute mesenteric ischemia. While it is found in the opium poppy, papaverine differs in both structure and pharmacological action from the analgesic morphine-like compounds.

Noscapine

Noscapine is a benzylisoquinoline alkaloid, of the phthalideisoquinoline structural subgroup, which has been isolated from numerous species of the family Papaveraceae. It lacks significant hypnotic, euphoric, or analgesic effects affording it with very low addictive potential. This agent is primarily used for its antitussive (cough-suppressing) effects.

Poppy tea

Poppy tea is a herbal tea infusion brewed from poppy straw or seeds of several species of poppy. The species most commonly used for this purpose is Papaver somniferum, which produces opium as a natural defense against predators. In the live flower, opium is released when the surface of the bulb, called the seed pod, is pierced or scraped. For the purpose of the tea, dried pods are more commonly used than the pods of the live flower. The walls of the dried pods contain opiate alkaloids, primarily consisting of morphine.

Scoulerine Chemical compound

Scoulerine, also known as discretamine and aequaline, is a benzylisoquinoline alkaloid (BIA) that is derived directly from (S)-reticuline through the action of berberine bridge enzyme. It is a precursor of other BIAs, notably berberine, noscapine, (S)-tetrahydropalmatine, and (S)-stylopine, as well as the alkaloids protopine, and sanguinarine. It is found in many plants, including opium poppy, Croton flavens, and certain plants in the genus Erythrina.

Laudanosine Chemical compound

Laudanosine or N-methyltetrahydropapaverine is a recognized metabolite of 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.

Meconic acid Chemical compound

Meconic acid, also known as acidum meconicum and poppy acid, is a chemical substance found in certain plants of the poppy family, Papaveraceae, such as Papaver somniferum and Papaver bracteatum. Meconic acid constitutes about 5% of opium and can be used as an analytical marker for the presence of opium. Meconic acid has erroneously been described as a mild narcotic, but it has little or no physiological activity, and is not used medicinally. Meconic acid forms salts with alkaloids and metals. These salts as well as meconic acid esters are called meconates. Meconic acid was first isolated by Friedrich Sertürner in 1805.

<i>Papaver bracteatum</i> Species of flowering plant

Papaver bracteatum, also known as the Iranian poppy and Persian poppy and the great scarlet poppy is a sturdy hardy perennial poppy with large deep red flowers up to 8 inches (20 cm) diameter on stiff stalks up to 4 feet high with a prominent black spot near the base of the petals. It is closely related to the commonly cultivated oriental poppy, Papaver orientale and is sometimes recorded as the varietal form Papaver orientale var. bracteatum.

Canadine Chemical compound

(S)-Canadine, also known as (S)-tetrahydroberberine and xanthopuccine, is a benzylisoquinoline alkaloid (BIA), of the protoberberine structural subgroup, and is present in many plants from the family Papaveraceae, such as Corydalis yanhusuo and C. turtschaninovii.

Legal cultivation of opium for medicinal purposes is carried out in India, only in selected areas, under free licensing conditions. India is the world's largest manufacturer of legal opium for the pharmaceutical industry according to the CIA World Factbook. India is one among 12 countries in world where legal cultivation for medical use is permissible within the ambit of United Nations, Single Convention on Narcotic Drugs 1961. In India legal cultivation is done primarily in Madhya Pradesh, Rajasthan and Uttar Pradesh. Despite producing poppy for opium production India depends heavily on imports to meet need of Poppy seed for edible purposes and domestic Codeine demand for medical purposes . Opium is heavily imported from its top producing nations like Afghanistan. There is also an account of Opium black marketing in India.

Poppy straw

Poppy straw is derived from opium poppies that are harvested when fully mature and dried by mechanical means, minus the ripe poppy seeds. Opium poppy straw today can be one of several different things. It is what remains after the poppy seed harvest, that is, the dried stalks, stem and leaves of poppies grown for their seeds. The dried leaves and stalks are harvested after the seed pods have been used for traditional opium extraction. The field dried leaves, stalk and seed pod are used in commercial manufacture of morphine or other poppy alkaloid derived drugs, by first processing the material to make poppy straw separating the seeds then making concentrate of poppy straw, where no extraction using traditional methods of latex extraction has been made. The straw was originally considered an agricultural by-product of the mechanised poppy seed harvest, which was primarily grown for its edible and oil-producing seed. This changed in 1927 when János Kabay developed a chemical process to extract morphine from the crushed capsule. Concentrated poppy straw consisting mainly of the crushed capsule without the seeds soon became a valuable source of morphine. Today, concentrate of poppy straw is a major source of many opiates and other alkaloids. It is the source of 90% of the world supply of legal morphine and in some countries it also is a source of illegal morphine, which could be processed into illegal heroin.

Opiate substance derived from opium

Opiate is a term classically used in pharmacology to mean a substance derived from opium. Opioid, a more modern term, is used to designate all substances, both natural and synthetic, that bind to opioid receptors in the brain. Opiates are alkaloid compounds naturally found in the opium poppy plant Papaver somniferum. The psychoactive compounds found in the opium plant include morphine, codeine, and thebaine. Opiates have long been used for a variety of medical conditions with evidence of opiate trade and use for pain relief as early as the eighth century AD. Opiates are considered drugs with moderate to high abuse potential and are listed on various "Substance-Control Schedules" under the Uniform Controlled Substances Act of the United States of America.

Narceine Chemical compound

Narceine is an opium alkaloid produced by the Papaver somniferum plant. It is a bitter, crystalline compound with narcotic effects. It was formerly used as a substitute for morphine. Its name is derived from the Greek νάρκη (nárkē), meaning numbness, and the postfix -ine referring to an alkaloid.

Salutaridinol Chemical compound

Salutaridinol is a modified benzyltetrahydroisoquinoline alkaloid with the formula C19H23NO4. It is produced in the secondary metabolism of the opium poppy Papaver somniferum (Papaveraceae) as an intermediate in the biosynthetic pathway that generates morphine. As an isoquinoline alkaloid, it is fundamentally derived from tyrosine as part of the shikimate pathway of secondary metabolism. Salutaridinol is a product of the enzyme salutaridine: NADPH 7-oxidoreductase and the substrate for the enzyme salutaridinol 7-O-acetyltransferase, which are two of the four enzymes in the morphine biosynthesis pathway that generates morphine from (R)-reticuline. Salutaridinol's unique position adjacent to two of the four enzymes in the morphine biosynthesis pathway gives it an important role in enzymatic, genetic, and synthetic biology studies of morphine biosynthesis. Salutaridinol levels are indicative of the flux through the morphine biosynthesis pathway and the efficacy of both salutaridine: NADPH 7-oxidoreductase and salutaridinol 7-O-acetyltransferase.

Papaver somniferum × Papaver bracteatum, also known as Sagan's poppy is a hybrid between the opium poppy and the Iranian poppy.

References

  1. Karlsson, MO; Dahlström, B; Neil, A (1988). "Characterization of high-affinity binding sites for the antitussive 3Hnoscapine in guinea pig brain tissue". European Journal of Pharmacology. 145 (2): 195–203. doi:10.1016/0014-2999(88)90230-0. PMID   3350041.
  2. US 2004063205 "Composition and method for culturing potentially regenerative cells and functional tissue-organs in vitro"
  3. Frick, S; Kramell, R; Schmidt, J; Fist, AJ; Kutchan, TM (2005). "Comparative qualitative and quantitative determination of alkaloids in narcotic and condiment Papaver somniferum cultivars". Journal of Natural Products. 68 (5): 666–73. doi:10.1021/np0496643. PMID   15921406.