Benzylisoquinoline
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Benzylisoquinoline
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. Biosynthesis (''S'')-Norcoclaurine (higenamine) has been identified as the central 1-benzyl-tetrahydro-isoquinoline precursor from which numerous complex biosynthetic pathways eventually emerge. These pathways collectively lead to the structurally disparate compounds comprising the broad classification of plant natural products referred to as benzylisoquinoline alkaloids (BIA), ...
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Higenamine
Higenamine (norcoclaurine) is a chemical compound found in a variety of plants including ''Nandina domestica'' (fruit), ''Aconitum carmichaelii'' (root), ''Asarum heterotropioides'', '' Galium divaricatum'' (stem and vine), ''Annona squamosa'', and ''Nelumbo nucifera'' (lotus seeds). Higenamine is found as an ingredient in sports and weight loss dietary supplements sold in the US. The US Food and Drug Administration has received reports of adverse effects from higenamine-containing supplements since 2014, but higenamine's health risks remain poorly understood. Legality Higenamine, also known as norcoclaurine HCl, is legal to use within food supplements in the UK, EU, the USA and Canada. Its main use is within food supplements developed for weight management and sports supplements. Traditional formulations with higenamine have been used for thousands of years within Chinese medicine and come from a variety of sources including fruit and orchids. There are no studies comparing ...
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(S)-norcoclaurine
Higenamine (norcoclaurine) is a chemical compound found in a variety of plants including ''Nandina domestica'' (fruit), ''Aconitum carmichaelii'' (root), ''Asarum heterotropioides'', '' Galium divaricatum'' (stem and vine), ''Annona squamosa'', and ''Nelumbo nucifera'' (lotus seeds). Higenamine is found as an ingredient in sports and weight loss dietary supplements sold in the US. The US Food and Drug Administration has received reports of adverse effects from higenamine-containing supplements since 2014, but higenamine's health risks remain poorly understood. Legality Higenamine, also known as norcoclaurine HCl, is legal to use within food supplements in the UK, EU, the USA and Canada. Its main use is within food supplements developed for weight management and sports supplements. Traditional formulations with higenamine have been used for thousands of years within Chinese medicine and come from a variety of sources including fruit and orchids. There are no studies comparing ...
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Norcoclaurine
Higenamine (norcoclaurine) is a chemical compound found in a variety of plants including ''Nandina domestica'' (fruit), ''Aconitum carmichaelii'' (root), ''Asarum heterotropioides'', '' Galium divaricatum'' (stem and vine), ''Annona squamosa'', and ''Nelumbo nucifera'' (lotus seeds). Higenamine is found as an ingredient in sports and weight loss dietary supplements sold in the US. The US Food and Drug Administration has received reports of adverse effects from higenamine-containing supplements since 2014, but higenamine's health risks remain poorly understood. Legality Higenamine, also known as norcoclaurine HCl, is legal to use within food supplements in the UK, EU, the USA and Canada. Its main use is within food supplements developed for weight management and sports supplements. Traditional formulations with higenamine have been used for thousands of years within Chinese medicine and come from a variety of sources including fruit and orchids. There are no studies comparing ...
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Morphinan
Morphinan is the prototype chemical structure of a large chemical class of psychoactive drugs, consisting of opiate analgesics, cough suppressants, and dissociative hallucinogens, among others. Structure Morphinan has a phenanthrene core structure with the ''A'' ring remaining aromatic and the ''B'' and ''C'' rings being saturated, and an additional nitrogen-containing, six-membered, saturated ring, the ''D'' ring, being attached to carbons 9 and 13 of the core, and with the nitrogen being at position 17 of the composite. Of the major naturally occurring opiates of the morphinan type—morphine, codeine and thebaine—thebaine has no therapeutic properties (it causes seizures in mammals), but it provides a low-cost feedstock for the industrial production of at least four semi-synthetic opiate agonists, including hydrocodone, hydromorphone, oxycodone and oxymorphone, and the opioid antagonist naloxone. Structure-activity relationship The physiological behavior of morphinans ...
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Morphine
Morphine is a strong opiate that is found naturally in opium, a dark brown resin in poppies (''Papaver somniferum''). It is mainly used as a analgesic, pain medication, and is also commonly used recreational drug, recreationally, or to make other illicit drug, illicit opioids. There are numerous methods used to administer morphine: oral; sublingual administration, sublingual; via inhalation; intramuscular, injection into a muscle; by Subcutaneous injection, injection under the skin; intravenously; Intrathecally, injection into the space around the spinal cord; transdermal; or via rectal administration, rectal suppository. It acts directly on the central nervous system (CNS) to induce analgesia and alter perception and emotional response to pain. Physical and psychological dependence and tolerance may develop with repeated administration. It can be taken for both acute pain and chronic pain and is frequently used for pain from myocardial infarction, kidney stones, and during Ch ...
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Noscapine
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 family Papaveraceae (poppy family). 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. Medical uses Noscapine is often used as an antitussive medication. A 2012 Dutch guideline, however, does not recommend its use for acute coughing. Side effects *Nausea *Vomiting *Loss of coordination *Hallucinations (auditory and visual) * Loss of sexual drive * Swelling of prostate *Loss of appetite *Dilated pupils *Increased heart rate * Shaking and muscle spasms *Chest pains *Increased alertness *Loss of any sleepiness *Loss of stereoscopic vision Interactions Noscapine can increase the effects of centrally sedating substances such as ...
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Isoquinoline
Isoquinoline is a heterocyclic aromatic organic compound. It is a structural isomer of quinoline. Isoquinoline and quinoline are benzopyridines, which are composed of a benzene ring fused to a pyridine ring. In a broader sense, the term isoquinoline is used to make reference to isoquinoline derivatives. 1-Benzylisoquinoline is the structural backbone in naturally occurring alkaloids including papaverine. The isoquinoline ring in these natural compound derives from the aromatic amino acid tyrosine. Properties Isoquinoline is a colorless hygroscopic liquid at temperatures above its melting point with a penetrating, unpleasant odor. Impure samples can appear brownish, as is typical for nitrogen heterocycles. It crystallizes in platelets that have a low solubility in water but dissolve well in ethanol, acetone, diethyl ether, carbon disulfide, and other common organic solvents. It is also soluble in dilute acids as the protonated derivative. Being an analog of pyridine, isoquinolin ...
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Tubocurarine
Tubocurarine (also known as ''d''-tubocurarine or DTC) is a toxic alkaloid historically known for its use as an arrow poison. In the mid-1900s, it was used in conjunction with an anesthetic to provide skeletal muscle relaxation during surgery or mechanical ventilation. It is now rarely used as an adjunct for clinical anesthesia because safer alternatives, such as cisatracurium and rocuronium, are available. History Tubocurarine is a naturally occurring mono-quaternary alkaloid obtained from the bark of the Menispermaceae, Menispermaceous South American plant ''Chondrodendron tomentosum'', a climbing vine known to the European world since the Spanish conquest of South America. Curare had been used as a source of arrow poison by South American natives to hunt animals, and they were able to eat the animals' contaminated flesh subsequently without any adverse effects because tubocurarine cannot easily cross mucous membranes. Thus, tubocurarine is effective only if given parenterally, ...
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Morphine
Morphine is a strong opiate that is found naturally in opium, a dark brown resin in poppies (''Papaver somniferum''). It is mainly used as a analgesic, pain medication, and is also commonly used recreational drug, recreationally, or to make other illicit drug, illicit opioids. There are numerous methods used to administer morphine: oral; sublingual administration, sublingual; via inhalation; intramuscular, injection into a muscle; by Subcutaneous injection, injection under the skin; intravenously; Intrathecally, injection into the space around the spinal cord; transdermal; or via rectal administration, rectal suppository. It acts directly on the central nervous system (CNS) to induce analgesia and alter perception and emotional response to pain. Physical and psychological dependence and tolerance may develop with repeated administration. It can be taken for both acute pain and chronic pain and is frequently used for pain from myocardial infarction, kidney stones, and during Ch ...
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Codeine
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 found naturally in the sap of the opium poppy, ''Papaver somniferum''. It is typically used to treat mild to moderate degrees of pain. Greater benefit may occur when combined with paracetamol (acetaminophen) or a nonsteroidal anti-inflammatory drug (NSAID) such as aspirin or ibuprofen. Evidence does not support its use for acute cough suppression in children or adults. In Europe, it is not recommended as a cough medicine in those under 12 years of age. It is generally taken by mouth. It typically starts working after half an hour, with maximum effect at two hours. Its effects last for about four to six hours. Codeine exhibits abuse potential similar to other opioid medications. Common side effects include vomiting, constipation, itchiness, lightheadedness, and drowsiness. Serious side effects may include breathing difficult ...
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Noscapine
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 family Papaveraceae (poppy family). 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. Medical uses Noscapine is often used as an antitussive medication. A 2012 Dutch guideline, however, does not recommend its use for acute coughing. Side effects *Nausea *Vomiting *Loss of coordination *Hallucinations (auditory and visual) * Loss of sexual drive * Swelling of prostate *Loss of appetite *Dilated pupils *Increased heart rate * Shaking and muscle spasms *Chest pains *Increased alertness *Loss of any sleepiness *Loss of stereoscopic vision Interactions Noscapine can increase the effects of centrally sedating substances such as ...
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Papaverine
Papaverine (Latin ''papaver'', "poppy") is an opium alkaloid antispasmodic drug, used primarily in the treatment of visceral spasms and vasospasms (especially those involving the intestines, heart, or brain), occasionally in the treatment of erectile dysfunction and acute mesenteric ischemia. While it is found in the opium poppy, papaverine differs in both structure and pharmacological action from the analgesic morphine and its derivatives (such as codeine). History Papaverine was discovered in 1848 by Georg Merck (1825–1873). Merck was a student of the German chemists Justus von Liebig and August Hofmann, and he was the son of Emanuel Merck (1794–1855), founder of the Merck corporation, a major German chemical and pharmaceutical company. Uses Papaverine is approved to treat spasms of the gastrointestinal tract, bile ducts and ureter and for use as a cerebral and coronary vasodilator in subarachnoid hemorrhage (combined with balloon angioplasty) and coronary artery ...
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