Scopolamine

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Scopolamine
L-Scopolamin.svg
Scopolamine structure.png
Clinical data
Trade names Transdermscop, Kwells, others
Other namesHyoscine [1]
AHFS/Drugs.com Monograph
MedlinePlus a682509
License data
Pregnancy
category
  • AU:B2
Routes of
administration 		By mouth, transdermal, ophthalmic, subcutaneous, intravenous, sublingual, rectal, buccal, transmucosal, intramuscular
Drug class
ATC code
Legal status
Legal status
Pharmacokinetic data
Metabolism Liver
Elimination half-life 4.5 hours [6]
Excretion Kidney
Identifiers
  • (–)-(S)-3-Hydroxy-2-phenylpropionic acid (1R,2R,4S,5S,7α,9S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl ester
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.083 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C17H21NO4
Molar mass 303.358 g·mol−1
3D model (JSmol)
  • OC[C@H](c1ccccc1)C(=O)O[C@@H]2C[C@H]3N(C)[C@@H](C2)[C@@H]4O[C@H]34
  • InChI=1S/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3/t11-,12-,13-,14+,15-,16+/m1/s1 Yes check.svgY
  • Key:STECJAGHUSJQJN-FWXGHANASA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Scopolamine, also known as hyoscine, [7] or Devil's Breath, [8] is a natural or synthetically produced tropane alkaloid and anticholinergic drug that is used as a medication to treat motion sickness [9] and postoperative nausea and vomiting. [10] [1] It is also sometimes used before surgery to decrease saliva. [1] When used by injection, effects begin after about 20 minutes and last for up to 8 hours. [1] It may also be used orally and as a transdermal patch since it has been long known to have transdermal bioavailability. [1] [11]

Contents

Scopolamine is in the antimuscarinic family of drugs and works by blocking some of the effects of acetylcholine within the nervous system. [1] Scopolamine was first written about in 1881 and started to be used for anesthesia around 1900. [12] [13] Scopolamine is also the main active component produced by certain plants of the nightshade family, which historically have been used as psychoactive drugs (known as deliriants ) due to their antimuscarinic-induced hallucinogenic effects in higher doses. [10] In these contexts, its mind-altering effects have been utilized for recreational and occult purposes. [14] [15] [16] The name "scopolamine" is derived from one type of nightshade known as Scopolia , while the name "hyoscine" is derived from another type known as Hyoscyamus niger , or black henbane. [17] [18] It is on the World Health Organization's List of Essential Medicines. [19]

Medical uses

Scopolamine has a number of formal uses in modern medicine where it is used in its isolated form and in low doses to treat: [20] [21]

It is sometimes used as a premedication, (especially to reduce respiratory tract secretions) in surgery, most commonly by injection. [20] [21] Common side effects include sleepiness, blurred vision, dilated pupils, and dry mouth. [1] It is not recommended in people with angle-closure glaucoma or bowel obstruction. [1] Whether its use during pregnancy is safe remains unclear, and use during breastfeeding is still cautioned by health professionals and manufacturers of the drug. [27]

Breastfeeding

Scopolamine enters breast milk by secretion. Although no human studies exist to document the safety of scopolamine while nursing, the manufacturer recommends that caution be taken if scopolamine is administered to a breastfeeding woman. [27]

Elderly

The likelihood of experiencing adverse effects from scopolamine is increased in the elderly, relative to younger people. This phenomenon is especially true for older people who are also on several other medications. Scopolamine use should be avoided in this age group because of these potent anticholinergic adverse effects, which have also been linked to an increased risk for dementia. [28] [29]

Adverse effects

Adverse effect incidence: [5] [30] [31] [32]

Uncommon (0.1–1% incidence) adverse effects include:

Rare (<0.1% incidence) adverse effects include:

Unknown frequency adverse effects include:

Overdose

Physostigmine, a cholinergic drug that readily crosses the blood–brain barrier, has been used as an antidote to treat the central nervous system depression symptoms of a scopolamine overdose. [33] Other than this supportive treatment, gastric lavage and induced emesis (vomiting) are usually recommended as treatments for oral overdoses. [32] The symptoms of overdose include: [31] [32]

Interactions

Due to interactions with metabolism of other drugs, scopolamine can cause significant unwanted side effects or unpredictable synergies when taken with other medications or compounds. Specific attention should be paid to other medications in the same pharmacologic class as scopolamine, also known as anticholinergics. The following compounds could also potentially interact with the metabolism of scopolamine: receptor-binding analgesic/pain medication such as gabapentinoids or opioids, ethanol, cannabinoids, zolpidem, thiazide diuretics, nicotine, benzodiazepines, buprenorphine, and especially anticholinergic drugs such as tiotropium, diphenhydramine, dimenhydrinate, etc. Nicotine in particular likely has a counteracting effect on the effects of scopolamine due to its opposing effect on acetylcholine signaling.[ citation needed ]

Route of administration

Scopolamine can be taken by mouth, subcutaneously, in the eye, and intravenously, as well as via a transdermal patch. [34]

Pharmacokinetic

Scopolamine undergoes first-pass metabolism and about 2.6% is excreted unchanged in urine. Grapefruit juice decreases metabolism of scopolamine, consequently increasing plasma concentration. [35]

Pharmacodynamics

The pharmacological effects of scopolamine are mediated through the drug's competitive antagonism of the peripheral and central muscarinic acetylcholine receptors. Scopolamine acts as a nonspecific muscarinic antagonist at all four (M1, M2, M3, and M4) receptor sites. [36] [37]

In doses higher than intended for medicinal use; the hallucinogenic alteration of consciousness, as well as the deliriousness in particular are tied to the compound's activity at the M1 muscarinic receptor. M1 receptors are located primarily in the central nervous system and are involved in perception, attention and cognitive functioning. Delirium is only associated with the antagonism of postsynaptic M1 receptors and currently other receptor subtypes have not been implicated. [38] Peripheral muscarinic receptors are part of the autonomic nervous system. M2 receptors are located in the brain and heart, M3 receptors are in salivary glands and M4 receptors are in the brain and lungs. [38] Due to the drug's inhibition of various signal transduction pathways, the decrease in acetylcholine signaling is what leads to many of the cognitive deficits, mental impairments and delirium associated with psychoactive doses. Medicinal effects appear to mostly be tied to activation of the peripheral receptors and only from marginal decreases in acetylcholine signaling. [39]

Although often broadly referred to as simply being 'anticholinergic', antimuscarinic would be more specific and accurate terminology to use for scopolamine, as, for example, it is not known to block nicotinic receptors. [38]

Biosynthesis in plants

Scopolamine is among the secondary metabolites of plants from Solanaceae (nightshade) family of plants, such as henbane (Hyoscyamus niger), jimson weed ( Datura ), angel's trumpet ( Brugmansia ), deadly nightshade ( Belladonna ), mandrake ( Mandragora officinarum ), and corkwood ( Duboisia ). [40] [17]

Biochemistry of tropane class compounds. Hyoscyamine and scopolamine are present and labeled. Tropane alkaloids biochemistry.png
Biochemistry of tropane class compounds. Hyoscyamine and scopolamine are present and labeled.

The biosynthesis of scopolamine begins with the decarboxylation of L-ornithine to putrescine by ornithine decarboxylase. Putrescine is methylated to N-methylputrescine by putrescine N-methyltransferase. [41]

A putrescine oxidase that specifically recognizes methylated putrescine catalyzes the deamination of this compound to 4-methylaminobutanal, which then undergoes a spontaneous ring formation to N-methyl-pyrrolium cation. In the next step, the pyrrolium cation condenses with acetoacetic acid yielding hygrine. No enzymatic activity could be demonstrated to catalyze this reaction. Hygrine further rearranges to tropinone. [41]

Subsequently, tropinone reductase I converts tropinone to tropine, which condenses with phenylalanine-derived phenyllactate to littorine. A cytochrome P450 classified as Cyp80F1 [42] oxidizes and rearranges littorine to hyoscyamine aldehyde. In the final step, hyoscyamine undergoes epoxidation catalyzed by 6beta-hydroxyhyoscyamine epoxidase yielding scopolamine. [41]

Scopolamine biosynthesis.svg

History

Plants naturally containing scopolamine such as Atropa belladonna (deadly nightshade), Brugmansia (angels trumpet), Datura (Jimson weed), Hyoscyamus niger , Mandragora officinarum , Scopolia carniolica , Latua and Duboisia myoporoides have been known about and used for various purposes in both the New and Old Worlds since ancient times. [43] [44] [45] Being one of the earlier alkaloids isolated from plant sources, scopolamine has been in use in its purified forms (such as various salts, including hydrochloride, hydrobromide, hydroiodide, and sulfate) since its official isolation by the German scientist Albert Ladenburg in 1880, [46] and as various preparations from its plant-based form since antiquity and perhaps prehistoric times. Following the description of the structure and activity of scopolamine by Ladenburg, the search for synthetic analogues, and methods for total synthesis, of scopolamine and atropine in the 1930s and 1940s resulted in the discovery of diphenhydramine, an early antihistamine and the prototype of its chemical subclass of these drugs, and pethidine, the first fully synthetic opioid analgesic, known as Dolantin and Demerol amongst many other trade names.[ citation needed ]

In 1899, a Dr. Schneiderlin recommended the use of scopolamine and morphine for surgical anaesthesia, and it started to be used sporadically for that purpose. [12] [47] The use of this combination in obstetric anesthesiology (childbirth) was first proposed by Richard von Steinbuchel in 1902 and was picked up and further developed by Carl Gauss in Freiburg, Germany, starting in 1903. [48] The method, which was based on a drug synergy between both scopolamine and morphine came to be known as Dämmerschlaf ("twilight sleep") or the "Freiburg method". [47] [48] It spread rather slowly, and different clinics experimented with different dosages and ingredients; in 1915, the Canadian Medical Association Journal reported, "the method [was] really still in a state of development". [47] It remained widely used in the US until the 1960s, when growing chemophobia and a desire for more natural childbirth led to its abandonment. [49]

Society and culture

Names

Hyoscine hydrobromide is the international nonproprietary name, and scopolamine hydrobromide is the United States Adopted Name. Other names include levo-duboisine, devil's breath, and burundanga. [15] [50]

Australian bush medicine

A bush medicine developed by Aboriginal peoples of the eastern states of Australia from the soft corkwood tree ( Duboisia myoporoides ) was used by the Allies in World War II to stop soldiers from getting seasick when they sailed across the English Channel on their way to France during the Invasion of Normandy. Later, the same substance was found to be usable in the production of scopolamine and hyoscyamine, which are used in eye surgery, and a multimillion-dollar industry was built in Queensland based on this substance. [51]

Recreational and religious use

While it has been occasionally used recreationally for its hallucinogenic properties, the experiences are often unpleasant, mentally and physically. It is also physically dangerous and officially classified as a deliriant drug, so repeated recreational use is rare. [52] In June 2008, more than 20 people were hospitalized with psychosis in Norway after ingesting counterfeit rohypnol tablets containing scopolamine. [53] In January 2018, 9 individuals were hospitalized in Perth, Western Australia, after reportedly ingesting scopolamine. [54] However, the alkaloid scopolamine, when taken recreationally for its psychoactive effect is usually taken in the form of preparations from plants of the genera Datura or Brugmansia , often by adolescents or young adults in order to achieve hallucinations and an altered state of consciousness induced by muscarinic antagonism. [55] [56] In circumstances such as these, the intoxication is usually built on a synergistic, but even more toxic mixture of the additional alkaloids in the plants which includes atropine and hyoscyamine.

Historically, the various plants that produce scopolamine have been used psychoactively for spiritual and magical purposes, particularly by witches in western culture and indigenous groups throughout the Americas such as Native American tribes like the Chumash. [16] [57] [58] [59] When entheogenic preparations of these plants were used, scopolamine was considered to be the main psychoactive compound and was largely responsible for the hallucinogenic effects, particularly when the preparation was made into a topical ointment (most notably flying ointment). [60] Scopolamine is reported to be the only active alkaloid within these plants that can effectively be absorbed through the skin to cause effects. [11] Different recipes for these ointments were explored in European witchcraft at least as far back as the Early Modern period and included multiple ingredients to help with the transdermal absorption of scopolamine (such as animal fat), as well as other possible ingredients to counteract its noxious and dysphoric effects. [60]

In the Bible, there are multiple mentions of Mandrake, a psychoactive and hallucinogenic plant root that contains scopolamine. It was associated with fertility and (sexual) desire where it was yearned for by Rachel, who apparently was "barren" (infertile) but trying to conceive. [61] [62]

Interrogation

The effects of scopolamine were studied for use as a truth serum in interrogations in the early 20th century, [63] but because of the side effects, investigations were dropped. [64] In 2009, the Czechoslovak state security secret police were proven to have used scopolamine at least three times to obtain confessions from alleged antistate dissidents. [65]

Use in Crime

Scopolamine can render a victim unconscious for 24 hours or more. In large doses, it can cause respiratory failure and death. The most common seems to be recorded in Colombia, where unofficial estimates put the number of annual scopolamine incidents at approximately 50,000. A travel advisory published by the U.S. Overseas Security Advisory Council (OSAC) in 2012 stated:

One common and particularly dangerous method that criminals use in order to rob a victim is through the use of drugs. Scopolamine is most often administered in liquid or powder form in foods and beverages. The majority of these incidents occur in night clubs and bars, and usually men, perceived to be wealthy, are targeted by young, attractive women. It is recommended that, to avoid becoming a victim of scopolamine, a person should never accept food or beverages offered by strangers or new acquaintances, nor leave food or beverages unattended in their presence. Victims of scopolamine or other drugs should seek immediate medical attention. [66]

Between 1998 and 2004, 13% of emergency-room admissions for "poisoning with criminal intentions" in a clinic of Bogotá have been attributed to scopolamine, and 44% to benzodiazepines. [15] Most commonly, the person has been poisoned by a robber who gave the victim a scopolamine-laced beverage, in the hope that the victim would become unconscious or unable to effectively resist the robbery. [15]

Beside robberies, it is also allegedly involved in express kidnappings and sexual assault. [67] The Hospital Clínic in Barcelona introduced a protocol in 2008 to help medical workers identify cases, while Madrid hospitals adopted a similar working document in February 2015. [67] Hospital Clínic has found little scientific evidence to support this use and relies on the victims' stories to reach any conclusion. [67] Although poisoning by scopolamine appears quite often in the media as an aid for raping, kidnapping, killing, or robbery, the effects of this drug and the way it is applied by criminals (transdermal injection, on playing cards and papers, etc.) are often exaggerated, [68] [69] [70] especially skin exposure, as the dose that can be absorbed by the skin is too low to have any effect. [67] Scopolamine transdermal patches must be used for hours to days. [34] There are certain other aspects of the usage of scopolamine in crimes. Powdered scopolamine is referred to as "devil's breath". In popular media and television, it is portrayed as a method to brainwash or control people into being defrauded by their attackers; [71] [72] [73] [74] there is debate whether these claims are true. [75] [76] It is not verified if the powdered form is capable of inducing a suggestive state. The danger is real enough that in addition to the Overseas Security Advisory Council (OSAC) in 2012, the US Department of State, as well as the Government of Canada, published [77] [78] travel advisories warning travelers about the possibility of targeting. Criminals using Devil's Breath often use attractive, young women, including women in dating apps [79] to target men that they believe are wealthy. [80] Nevertheless, the drug is known to produce loss of memory following exposure and sleepiness, similar to the effect of benzodiazepines or alcohol poisoning. [81] [82]

Research

Scopolamine is used as a research tool to study memory encoding. Initially, in human trials, relatively low doses of the muscarinic receptor antagonist scopolamine were found to induce temporary cognitive defects. [83] Since then, scopolamine has become a standard drug for experimentally inducing cognitive defects in animals. [84] [85] Results in primates suggest that acetylcholine is involved in the encoding of new information into long-term memory. [86] Scopolamine has also been shown to exert a greater impairment on episodic memory, event-related potentials, memory retention and free recall compared to DPH (an anticholinergic and antihistamine). [82]

Scopolamine produces detrimental effects on short-term memory, memory acquisition, learning, visual recognition memory, visuospatial praxis, visuospatial memory, visuoperceptual function, verbal recall, and psychomotor speed. [87] [84] [85] It does not seem to impair recognition and memory retrieval, though. [85] Acetylcholine projections in hippocampal neurons, which are vital in mediating long-term potentiation, are inhibited by scopolamine. [85] [88] Scopolamine also inhibits cholinergic-mediated glutamate release in hippocampal neurons, which assist in depolarization, potentiation of action potential, and synaptic suppression. Scopolamine's effects on acetylcholine and glutamate release in the hippocampus favor retrieval-dominant cognitive functioning. [85] Scopolamine has been used to model the defects in cholinergic function for models of Alzheimer's, dementia, fragile X syndrome, and Down syndrome. [85] [89] [90] [91]

Scopolamine has been identified as a psychoplastogen, which refers to a compound capable of promoting rapid and sustained neuroplasticity in a single dose. [92] It has been, and continues to be investigated as a rapid-onset antidepressant, with a number of small studies finding positive results, particularly in female subjects. [93] [94] [95] [96]

NASA agreed to develop a nasal administration method. With a precise dosage, the NASA spray formulation has been shown to work faster and more reliably than the oral form to treat motion sickness. [97]

Although a fair amount of research has been applied to scopolamine in the field of medicine, its hallucinogenic (psychoactive) effects as well as the psychoactive effects of other antimuscarinic deliriants haven't been extensively researched or as well understood compared to other types of hallucinogens such as psychedelic and disassociative compounds, despite the alkaloid's long history of usage in mind-altering plant preparations. [98]

Related Research Articles

<i>Datura</i> Genus of poisonous, potentially psychoactive plants

Datura is a genus of nine species of highly poisonous, vespertine-flowering plants belonging to the nightshade family (Solanaceae). They are commonly known as thornapples or jimsonweeds, but are also known as devil's trumpets. Other English common names include moonflower, devil's weed, and hell's bells. All species of Datura are extremely poisonous and psychoactive, especially their seeds and flowers, which can cause respiratory depression, arrhythmias, fever, delirium, hallucinations, anticholinergic syndrome, psychosis, and death if taken internally.

<span class="mw-page-title-main">Acetylcholine</span> Organic chemical and neurotransmitter

Acetylcholine (ACh) is an organic compound that functions in the brain and body of many types of animals as a neurotransmitter. Its name is derived from its chemical structure: it is an ester of acetic acid and choline. Parts in the body that use or are affected by acetylcholine are referred to as cholinergic.

<span class="mw-page-title-main">Atropine</span> Anticholinergic medication used as antidote for nerve agent poisoning

Atropine is a tropane alkaloid and anticholinergic medication used to treat certain types of nerve agent and pesticide poisonings as well as some types of slow heart rate, and to decrease saliva production during surgery. It is typically given intravenously or by injection into a muscle. Eye drops are also available which are used to treat uveitis and early amblyopia. The intravenous solution usually begins working within a minute and lasts half an hour to an hour. Large doses may be required to treat some poisonings.

<i>Atropa belladonna</i> Species of toxic flowering plant in the nightshade family.

Atropa belladonna, commonly known as belladonna or deadly nightshade, is a toxic perennial herbaceous plant in the nightshade family Solanaceae, which also includes tomatoes, potatoes and aubergine (eggplant). It is native to Europe and Western Asia, including Turkey. Its distribution extends from Ireland in the west to western Ukraine and the Iranian province of Gilan in the east. It is also naturalised or introduced in some parts of Canada, North Africa and the United States.

<span class="mw-page-title-main">Hyoscyamine</span> Tropane alkaloid

Hyoscyamine is a naturally occurring tropane alkaloid and plant toxin. It is a secondary metabolite found in certain plants of the family Solanaceae, including henbane, mandrake, angel's trumpets, jimsonweed, the sorcerers' tree, and Atropa belladonna. It is the levorotary isomer of atropine and thus sometimes known as levo-atropine.

Anticholinergics are substances that block the action of the acetylcholine (ACh) neurotransmitter at synapses in the central and peripheral nervous system.

<span class="mw-page-title-main">Chlorphenamine</span> Antihistamine used to treat allergies

Chlorphenamine, also known as chlorpheniramine, is an antihistamine used to treat the symptoms of allergic conditions such as allergic rhinitis. It is taken orally. The medication takes effect within two hours and lasts for about 4–6 hours. It is a first-generation antihistamine and works by blocking the H1 receptor.

<span class="mw-page-title-main">Ipratropium bromide</span> Type of anticholinergic

Ipratropium bromide, sold under the trade name Atrovent among others, is a type of anticholinergic medication which is applied by different routes: inhaler, nebulizer, or nasal spray, for different reasons.

<i>Hyoscyamus niger</i> Species of plant

Henbane is a poisonous plant in the nightshade family Solanaceae. Henbane is native to temperate Europe and Siberia, and naturalised in Great Britain and Ireland.

<span class="mw-page-title-main">Deliriant</span> Class of psychoactive drugs

Deliriants are a subclass of hallucinogen. The term was coined in the early 1980s to distinguish these drugs from psychedelics such as LSD and dissociatives such as ketamine, due to their primary effect of causing delirium, as opposed to the more lucid and less disturbed states produced by other types of hallucinogens. The term generally refers to anticholinergic drugs, which are substances that inhibit the function of the neurotransmitter acetylcholine. Common examples of deliriants include plants of the genera Datura and Brugmansia as well as higher than recommended dosages of diphenhydramine (Benadryl). A number of plant deliriants such as that of the Solanaceae family, particularly in the Americas have been used by some indigenous cultures to reach delirious and altered states for traditions or rituals, such as rites of passage, divination or communicating with the ancestors. Despite their long history of use, deliriants are the least-studied class of hallucinogens in terms of their behavioral and neurological effects.

An oneirogen, from the Greek ὄνειρος óneiros meaning "dream" and gen "to create", is a substance or other stimulus which produces or enhances dreamlike states of consciousness. This is characterized by an immersive dream state similar to REM sleep, which can range from realistic to alien or abstract.

<span class="mw-page-title-main">Hyoscine butylbromide</span> Anticholinergic medication

Hyoscine butylbromide, also known as scopolamine butylbromide and sold under the brandname Buscopan among others, is an anticholinergic medication used to treat abdominal pain, esophageal spasms, bladder spasms, biliary colic, and renal colic. It is also used to improve excessive respiratory secretions at the end of life. Hyoscine butylbromide can be taken by mouth, injection into a muscle, or into a vein.

<span class="mw-page-title-main">Arecoline</span> Stimulant alkaloid

Arecoline is a nicotinic acid-based mild parasympathomimetic stimulant alkaloid found in the areca nut, the fruit of the areca palm. It is an odourless oily liquid. It can bring a sense of enhanced alertness and energy along with mild feelings of euphoria and relaxation. The psychoactive effects are comparable to that of nicotine.

<span class="mw-page-title-main">Muscarinic antagonist</span> Drug that binds to but does not activate muscarinic cholinergic receptors

A muscarinic receptor antagonist (MRA), also called an antimuscarinic, is a type of anticholinergic agent that blocks the activity of the muscarinic acetylcholine receptor. The muscarinic receptor is a protein involved in the transmission of signals through certain parts of the nervous system, and muscarinic receptor antagonists work to prevent this transmission from occurring. Notably, muscarinic antagonists reduce the activation of the parasympathetic nervous system. The normal function of the parasympathetic system is often summarised as "rest-and-digest", and includes slowing of the heart, an increased rate of digestion, narrowing of the airways, promotion of urination, and sexual arousal. Muscarinic antagonists counter this parasympathetic "rest-and-digest" response, and also work elsewhere in both the central and peripheral nervous systems.

Muscarinic acetylcholine receptor M<sub>1</sub> Protein-coding gene in the species Homo sapiens

The muscarinic acetylcholine receptor M1, also known as the cholinergic receptor, muscarinic 1, is a muscarinic receptor that in humans is encoded by the CHRM1 gene. It is localized to 11q13.

<i>N</i>-Methyl-3-piperidyl benzilate Chemical compound

N-Methyl-3-piperidyl benzilate is an anticholinergic drug related to the chemical warfare agent 3-quinuclidinyl benzilate.

<i>N</i>-Ethyl-3-piperidyl benzilate Chemical compound

N-Ethyl-3-piperidyl benzilate (JB-318) is an anticholinergic drug related to the chemical warfare agent 3-Quinuclidinyl benzilate.

<span class="mw-page-title-main">Tropane alkaloid</span> Class of chemical compounds

Tropane alkaloids are a class of bicyclic [3.2.1] alkaloids and secondary metabolites that contain a tropane ring in their chemical structure. Tropane alkaloids occur naturally in many members of the plant family Solanaceae. Certain tropane alkaloids such as cocaine and scopolamine are notorious for their psychoactive effects, related usage and cultural associations. Particular tropane alkaloids such as these have pharmacological properties and can act as anticholinergics or stimulants.

Peripherally selective drugs have their primary mechanism of action outside of the central nervous system (CNS), usually because they are excluded from the CNS by the blood–brain barrier. By being excluded from the CNS, drugs may act on the rest of the body without producing side-effects related to their effects on the brain or spinal cord. For example, most opioids cause sedation when given at a sufficiently high dose, but peripherally selective opioids can act on the rest of the body without entering the brain and are less likely to cause sedation. These peripherally selective opioids can be used as antidiarrheals, for instance loperamide (Imodium).

<span class="mw-page-title-main">Cholinergic blocking drug</span> Drug that block acetylcholine in synapses of cholinergic nervous system

Cholinergic blocking drugs are a group of drugs that block the action of acetylcholine (ACh), a neurotransmitter, in synapses of the cholinergic nervous system. They block acetylcholine from binding to cholinergic receptors, namely the nicotinic and muscarinic receptors.

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