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Benzylisoquinoline information


Benzylisoquinoline
Names
Preferred IUPAC name
1-Benzylisoquinoline
Systematic IUPAC name
1-(Phenylmethyl)isoquinoline
Identifiers
CAS Number
  • 6907-59-1 ☒N
3D model (JSmol)
  • Interactive image
ChemSpider
  • 21830 checkY
PubChem CID
  • 23345
UNII
  • UF5CSU3HA6 checkY
CompTox Dashboard (EPA)
  • DTXSID90219124 Edit this at Wikidata
InChI
  • InChI=1S/C16H13N/c1-2-6-13(7-3-1)12-16-15-9-5-4-8-14(15)10-11-17-16/h1-11H,12H2 checkY
    Key: IZTUINVRJSCOIR-UHFFFAOYSA-N checkY
SMILES
  • c13ccccc3ccnc1Cc2ccccc2
Properties
Chemical formula
C16H13N
Molar mass 219.28112 g/mol
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

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, tubocurarine.

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Benzylisoquinoline

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group provides 1‑benzylisoquinoline, the most widely examined of the numerous benzylisoquinoline structural isomers. The 1-benzylisoquinoline moiety can be...

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Benzylisoquinoline alkaloids

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The benzylisoquinoline alkaloids are natural products that can be classified as isoquinoline alkaloids and are derived from benzylisoquinoline. They also...

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Noscapine

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Narcotine, Nectodon, Nospen, Anarcotine and (archaic) Opiane) is a benzylisoquinoline alkaloid, of the phthalideisoquinoline structural subgroup, which...

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Tubocurarine chloride

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Tubocurarine (also known as d-tubocurarine or DTC) is a toxic benzylisoquinoline alkaloid historically known for its use as an arrow poison. In the mid-1900s...

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Sanguinaria

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berberine and protopine, among other minor alkaloids. Bloodroot produces benzylisoquinoline alkaloids, primarily the toxin sanguinarine. The alkaloids are transported...

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Nelumbo nucifera

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nucifera. The plant also contains nuciferine, neferine, and many other benzylisoquinoline alkaloids with medicinal properties. All parts of Nelumbo nucifera...

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Berberine

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Berberine is a quaternary ammonium salt from the protoberberine group of benzylisoquinoline alkaloids, occurring naturally as a secondary metabolite in some plants...

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Tetrandrine

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Tetrandrine, a bis-benzylisoquinoline alkaloid, is a calcium channel blocker. It is isolated from the plant Stephania tetrandra, and other Chinese and...

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Morphine

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agonist–antagonist drugs have also been developed.[citation needed] Morphine is a benzylisoquinoline alkaloid with two additional ring closures. As Jack DeRuiter of the...

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Protopine

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Fumaria officinalis. Protopine is metabolically derived from the benzylisoquinoline alkaloid (S)-Reticuline through a progressive series of five enzymatic...

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Papaver somniferum

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secondary metabolism, synthesized through the metabolic pathway of benzylisoquinoline. First, the amino acid phenylalanine, through the enzyme phenylalanine...

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Canadine

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(S)-Canadine, also known as (S)-tetrahydroberberine and xanthopuccine, is a benzylisoquinoline alkaloid (BIA), of the protoberberine structural subgroup, and is...

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Gunnerales

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eudicotyledons, and also with Buxales and Trochodendrales, are an absence of benzylisoquinoline alkaloids, euAP3 + TM6 genes (gene duplication paleoAP3: Class B)...

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Higenamine

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chest tightness. (S)-Norcoclaurine/Higenamine is at the center of benzylisoquinoline alkaloid (BIA) biosynthesis. In spite of large structure diversity...

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Isoquinoline

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isoquinoline is used to make reference to isoquinoline derivatives. 1-Benzylisoquinoline is the structural backbone in many naturally occurring alkaloids such...

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Morphinan

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Naloxone Naloxegol The following structures are related to morphinan: Benzylisoquinoline Hasubanan Hasubanonine Brunton L L, Blumenthal D K, Murri N, Dandan...

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Papaver armeniacum

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family Papaveraceae, native to the Caucasus region. It produces the benzylisoquinoline alkaloid armepavine (6 7 methoxy 1 (4' hydroxy benzyl) 1234 tetrahydro...

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Aristolochic acid

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relationship with norlaudanosoline (tetrahydropapaveroline) or related benzylisoquinoline precursors, which in turn are derived from tyrosine (2). Feeding studies...

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Aporphine alkaloids

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occurring chemical compounds from the group of alkaloids. After the benzylisoquinoline alkaloids they are the second largest group of isoquinoline alkaloids...

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List of poisonous plants

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canadensis bloodroot Papaveraceae The rhizome contains morphine-like benzylisoquinoline alkaloids, primarily the toxin sanguinarine. Sanguinarine kills animal...

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Opiate

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attributed to opioids. Opiates belong to the large biosynthetic group of benzylisoquinoline alkaloids, and are so named because they are naturally occurring alkaloids...

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Annonamine

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Annonamine is a benzylisoquinoline alkaloid isolated from Annona muricata (commonly known as soursop, graviola, guanabana, paw-paw and sirsak), a plant...

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Thalictrum

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[better source needed] Typical natural products found in this genus are benzylisoquinoline alkaloids, such as magnoflorine, hernandezine, and the structurally...

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Codeine

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Codeine is an opiate and prodrug of morphine mainly used to treat pain, coughing, and diarrhea. It is also commonly used as a recreational drug. It is...

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Xylopine

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antimicrobial benzylisoquinoline alkaloid. Villar, A; Mares, M; Rios, JL; Canton, E; Gobernado, M (1987). "Antimicrobial activity of benzylisoquinoline alkaloids"...

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Lauraceae

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organisms. Phytochemicals in the Lauraceae are numerous and diverse. Benzylisoquinoline alkaloids include aporphines and oxoaporphines, as well as derivatives...

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Reticuline

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Ocotea fasciculata (also known as Ocotea duckei). It is based on the benzylisoquinoline structure. Reticuline is one of the alkaloids found in opium, and...

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Menispermaceae

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been recorded in Menispermum. The family contains a wide range of benzylisoquinoline compounds (alkaloids) and lignans such as furofuran, flavones and...

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Thalictrum flavum

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N-methyltransferase, which modifies a variety of benzylisoquinoline alkaloids including the eponymous alkaloid pavine. Benzylisoquinoline alkaloids like pavine often have...

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