Scopolamine

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Scopolamine, also known as hyoscine,<ref name=Huo2001>Template:Cite book</ref> or Devil's Breath,<ref>Template:Cite news</ref> is a medication used to treat motion sickness<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> and postoperative nausea and vomiting.<ref name="Springer Science & Business Media">Template:Cite book</ref><ref name=AHFS2016/> It is also sometimes used before surgery to decrease saliva.<ref name=AHFS2016/> When used by injection, effects begin after about 20 minutes and last for up to 8 hours.<ref name=AHFS2016/> It may also be used orally and as a transdermal patch since it has been long known to have transdermal bioavailability.<ref name=AHFS2016>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name="W.B. Saunders">Template:Cite book</ref>

Scopolamine is in the antimuscarinic family of drugs and works by blocking some of the effects of acetylcholine within the nervous system.<ref name=AHFS2016/>

Scopolamine was first written about in 1881 and started to be used for anesthesia around 1900.<ref name=Keys>Template:Cite book</ref><ref name=Fis2006>Template:Cite book</ref> 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.<ref name="Springer Science & Business Media"/> In these contexts, its mind-altering effects have been utilized for recreational and occult purposes.<ref name="Kennedy 2014">Template:Cite book</ref><ref name="Uribe_et_al_2005"/><ref name="Raetsch">Template:Cite book</ref> 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.<ref name=Chambers>Template:Cite book</ref><ref name="Cattell1910">Template:Cite book</ref> It is on the World Health Organization's List of Essential Medicines.<ref name="WHO23rd">Template:Cite book</ref>

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:<ref name="BNF">Template:Cite book</ref><ref name="AMH">Template:Cite book</ref>

• Postoperative nausea and vomiting
• Motion sickness, including sea sickness, leading to its use by scuba divers (where it is often applied as a transdermal patch behind the ear)<ref name="pmid1853467">Template:Cite journal</ref><ref name="pmid3363755">Template:Cite journal</ref><ref>Template:Cite journal</ref><ref>{{#invoke:citation/CS1|citation

|CitationClass=web }}</ref>

• Gastrointestinal spasms
• Renal or biliary spasms
• Aid in gastrointestinal radiology and endoscopy
• Irritable bowel syndrome
• Clozapine-induced drooling
• Bowel colic
• Eye inflammation<ref>{{#invoke:citation/CS1|citation

|CitationClass=web }}</ref> It is sometimes used as a premedication, especially to reduce respiratory tract secretions in surgery, most commonly by injection.<ref name = BNF/><ref name = AMH/> Common side effects include sleepiness, blurred vision, dilated pupils, and dry mouth.<ref name=AHFS2016/> It is not recommended in people with angle-closure glaucoma or bowel obstruction.<ref name=AHFS2016/> Whether its use during pregnancy is safe remains unclear, and use during breastfeeding is still cautioned by health professionals and manufacturers of the drug.<ref name="Briggs 1994">Template:Cite book</ref>

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.<ref name="Briggs 1994"/>

Adverse effects

Adverse effect incidence:<ref name="Transderm Scop FDA label" /><ref name=TGAin>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name=EMCBut>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name=EMChyd>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

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

• Dry mouth
• Anhidrosis (reduced ability to sweat to cool off)
• Tachycardia (usually occurs at higher doses and is succeeded by bradycardia)
• Bradycardia
• Urticaria (hives)
• Pruritus (itching)

Rare (<0.1% incidence) adverse effects include:

• Constipation
• Urinary retention
• Hallucinations
• Agitation
• Confusion
• Restlessness
• Seizures

Unknown frequency adverse effects include:

• Anaphylactic shock or reactions
• Dyspnea (shortness of breath)
• Rash
• Erythema
• Other hypersensitivity reactions
• Blurred vision
• Mydriasis (dilated pupils)
• Drowsiness
• Dizziness
• Somnolence

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.<ref>Template:Cite book</ref> Other than this supportive treatment, gastric lavage and induced emesis (vomiting) are usually recommended as treatments for oral overdoses.<ref name = EMChyd/> The symptoms of overdose include:<ref name = EMCBut/><ref name = EMChyd/>

• Tachycardia
• Arrhythmia
• Blurred vision
• Photophobia
• Urinary retention
• Drowsiness or paradoxical reaction, which can present with hallucinations
• Cheyne–Stokes respiration
• Dry mouth
• Skin reddening
• Inhibition of gastrointestinal motility

Route of administration

Scopolamine can be taken by mouth, subcutaneously, in the eye, and intravenously, as well as via a transdermal patch.<ref name="White">Template:Cite journal</ref>

Pharmacology

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.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}Template:Ambiguous</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

In doses higher than intended for medicinal use, the hallucinogenic alteration of consciousness, as well as the delirium 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 associated solely with the antagonism of postsynaptic M₁ receptors; currently no other receptor subtypes have been implicated.<ref name="ReferenceC">Template:Cite journal</ref>

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.<ref name="ReferenceC"/> 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.<ref name=":0">Template:Cite journal</ref>

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.<ref name="ReferenceC"/>

Pharmacokinetics

Scopolamine undergoes first-pass metabolism and about 2.6% is excreted unchanged in urine. It has a bioavailability of 20-40%, reaches peak plasma concentration in about 45 minutes, and in healthy subjects has an average half-life of 5 hours (observed range 2 - 10 hours).<ref name="pmid2762223"/> Scopolamine is primarily metabolized by the CYP3A4 enzyme, and grapefruit juice decreases metabolism of scopolamine, consequently increasing plasma concentration.<ref name="pmid16175141"/>

Chemistry

Biosynthesis in plants

Scopolamine is among the secondary metabolites of plants from the Solanaceae (nightshade) family of plants, including henbane (Hyoscyamus niger), jimson weed (Datura), angel's trumpets (Brugmansia), deadly nightshade (Belladonna), mandrake (Mandragora officinarum), and corkwood (Duboisia).<ref name = "Muranaka_1993">Template:Cite journal</ref><ref name=Chambers/>

File:Tropane alkaloids biochemistry.png

The biochemistry of tropane class compounds

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.<ref name="Ziegler2008">Template:Cite journal</ref>

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.<ref name="Ziegler2008" />

Subsequently, tropinone reductase I converts tropinone to tropine, which condenses with phenylalanine-derived phenyllactate to littorine. A cytochrome P450 classified as Cyp80F1<ref>Template:Cite journal</ref> oxidizes and rearranges littorine to hyoscyamine aldehyde. In the final step, hyoscyamine undergoes epoxidation catalyzed by 6β-hydroxyhyoscyamine epoxidase yielding scopolamine.<ref name="Ziegler2008" />

File: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.<ref name="Hunziker Genera">Armando T. Hunziker: The Genera of Solanaceae. A.R.G. Gantner Verlag K.G., Ruggell, Liechtenstein 2001. Template:ISBN</ref><ref name="ReferenceA">Rätsch, Christian, The Encyclopedia of Psychoactive Plants: Ethnopharmacology and Its Applications pub. Park Street Press 2005</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> 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,<ref>Template:Cite journal</ref> and as various preparations from its plant-based form since antiquity and perhaps prehistoric times.

In 1899, Dr. Schneiderlin recommended the use of scopolamine and morphine for surgical anaesthesia, and it started to be used sporadically for that purpose.<ref name=Keys/><ref name=canadian>Template:Cite journal</ref> 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.<ref name=nyt_invest>Template:Cite news</ref> 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".<ref name=canadian/><ref name=nyt_invest/> 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".<ref name=canadian/> It remained widely used in the US until the 1960s, when growing chemophobia and a desire for more natural childbirth led to its abandonment.<ref name=nyt2>Template:Cite news</ref>

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.<ref name="Uribe_et_al_2005">Template:Cite journal</ref><ref name=Wired-2011-03-03>Template:Cite magazine</ref>

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.<ref name=kc2019>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

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.<ref>Template:Cite book</ref> In June 2008, more than 20 people were hospitalized with psychosis in Norway after ingesting counterfeit rohypnol tablets containing scopolamine.<ref>Template:Cite news</ref> In January 2018, 9 individuals were hospitalized in Perth, Western Australia, after reportedly ingesting scopolamine.<ref>Template:Cite news</ref>

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.<ref>Template:Cite journal</ref><ref name='Preissel'>Template:Cite book</ref> 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.<ref name="Raetsch"/><ref name="The Way of the Shaman">Template:Cite book</ref><ref>Template:Cite book</ref><ref>Template:Cite journal</ref> 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.<ref name="Hansen">Hansen, Harold A. The Witch's Garden pub. Unity Press 1978 Template:ISBN</ref>

Scopolamine is reported to be the only active alkaloid within these plants that can effectively be absorbed through the skin to cause effects.<ref name="W.B. Saunders"/> 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.<ref name="Hansen"/>

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 for which it was yearned by Rachel, who was "barren" (infertile) but trying to conceive.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Interrogation

The effects of scopolamine were studied for use as a truth serum in interrogations in the early 20th century,<ref>Template:Cite journal
Reprinted in: Template:Cite journal</ref> but because of the side effects, investigations were dropped.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> 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.<ref>Template:Cite news</ref>

Use in crime

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Ingestion of scopolamine can render a victim unconscious for 24 hours or more. In large doses, it can cause respiratory failure and death. The highest prevalence of misuse seems to be recorded in Colombia. Unofficial estimates there 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 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 nightclubs 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.<ref>{{#invoke:citation/CS1|citation

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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.<ref name="Uribe_et_al_2005"/> 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.<ref name="Uribe_et_al_2005"/>

Beside robberies, it is also allegedly involved in express kidnappings and sexual assault.<ref name="dom">Template:Cite news</ref> In 2008, the Hospital Clínic in Barcelona introduced a protocol to help medical workers identify cases. In February 2015, Madrid hospitals adopted a similar working document.<ref name="dom"/> Hospital Clínic has found little scientific evidence to support this use and relies on the victims' stories to reach any conclusion.<ref name="dom"/>

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,<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>Template:Cite news</ref><ref>Template:Cite news</ref> especially skin exposure, as the dose that can be absorbed by the skin is too low to have any effect.<ref name="dom" /> Scopolamine transdermal patches must be used for hours to days.<ref name="White" />

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.<ref name="Case" >Template:Cite journal</ref> There is debate whether these claims are true.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>Template:Cite news</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

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.<ref>Template:Cite journal</ref> Since then, scopolamine has become a standard drug for experimentally inducing cognitive defects in animals.<ref name = "Hasselmo_1997">Template:Cite journal</ref><ref name = "More_2016">Template:Cite journal</ref> Results in primates suggest that acetylcholine is involved in the encoding of new information into long-term memory.<ref>Template:Cite journal</ref> Scopolamine has been shown to exert a greater impairment on episodic memory, event-related potentials, memory retention and free recall compared to diphenhydramine (an anticholinergic and antihistamine).<ref name="Differentiating the effects of cent">Template:Cite journal</ref>

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.<ref>Template:Cite journal</ref><ref name = "Hasselmo_1997" /><ref name = "More_2016" /> It does not seem to impair recognition and memory retrieval, though.<ref name = "More_2016" /> Acetylcholine projections in hippocampal neurons, which are vital in mediating long-term potentiation, are inhibited by scopolamine.<ref name = "More_2016" /><ref>Template:Cite journal</ref> Scopolamine 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.<ref name = "More_2016" /> Scopolamine has been used to model the defects in cholinergic function for models of Alzheimer's, dementia, fragile X syndrome, and Down syndrome.<ref name = "More_2016" /><ref>Template:Cite journal</ref><ref>Template:Cite book</ref><ref>Template:Cite journal</ref>

Scopolamine has been identified as a psychoplastogen, which refers to a compound capable of promoting rapid and sustained neuroplasticity in a single dose.<ref>Template:Cite journal</ref> It has been and continues to be investigated as a rapid-onset antidepressant, with many small studies finding positive results, particularly in female subjects.<ref>Template:Cite journal</ref><ref>Template:Cite journal</ref><ref>Template:Cite journal</ref><ref name="pmid27270172">Template:Cite journal</ref>

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.<ref>Template:Cite press release</ref>

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 have not been extensively researched or as well understood compared to other types of hallucinogens such as psychedelic and dissociative compounds, despite the alkaloid's long history of usage in mind-altering plant preparations.<ref name="pubmed.ncbi.nlm.nih.gov">Template:Cite journal</ref>

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