Scopolamine
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The fictional truth drug Hyoscine-pentothal does not describe real hyoscine accurately.

Scopolamine
Systematic (IUPAC) name
(-)-(S)-3-Hydroxy-2-phenyl-propionic acid (1R,2R,4S,7S,9S)-9-methyl-3-oxa-9-aza-tricyclo[3.3.1.02,4non-7-yl ester
Identifiers
CAS number	51-34-3
ATC code	A04AD01 N05CM05, S01FA02
PubChem	5184
DrugBank	APRD00616
Chemical data
Formula	C17H21NO4
Mol. mass	303.353 g/mol
Pharmacokinetic data
Bioavailability	10 - 50% [1]
Metabolism	?
Half life	4.5 hours[1]
Excretion	?
Therapeutic considerations
Pregnancy cat.	C(US)
Legal status	P(UK) ℞-only(US)
Routes	transdermal, ocular, oral, subcutaneous, intravenous

Scopolamine, also known as hyoscine and "Devils Breath", is a tropane alkaloid drug with muscarinic antagonist effects. It is obtained from plants of the family Solanaceae (nightshades), such as henbane or jimson weed (Datura species). It is among the secondary metabolites of these plants. The drug can be highly toxic due its powerful anticholinergic properties and has legitimate medical applications in very minute doses. As an example, in the treatment of motion sickness, the dose, gradually released from a transdermal patch, is only 330 micrograms (µg) per day.

An overdose can cause delirium, delusions, paralysis, stupor and death.

Etymology

Scopolamine is named after the plant genus Scopolia. The name "hyoscine" is from the scientific name for henbane, Hyoscyamus niger.

Physiology

Scopolamine acts as a competitive antagonist at specific muscarinic acetylcholine receptors, specifically M1 receptors; it is thus classified as an anticholinergic, or, more specifically, as an anti-muscarinic drug. (See the article on the parasympathetic nervous system for details of this physiology.)

Medical use

In medicine, scopolamine has three primary uses: treatment of nausea and motion sickness, treatment of intestinal cramping, and for ophthalmic purposes. Use as a general depressant and adjunct to narcotic painkillers is also common. The drug is less commonly used as a preanesthetic agent and uncommonly for some forms of Parkinsonism. Scopolamine is also used as an adjunct to narcotic analgesia, such as the product Twilight Sleep which contained morphine and scopolamine, some of the original formulations of Percodan and some European brands of methadone injection, as well as use of tablets or patches to combat nausea as well as enhance the pain-killing ability of various opioids. Scopolamine can be used as an occasional sleep aid and was available in some over the counter products in the United States for this purpose until November 1990.

Nausea

Its use as an antiemetic in the form of a transdermal patch is the drug's most common medical application in the United States.^{citation needed}

Ophthalmic

The drug is used in eye drops to induce mydriasis (pupillary dilation) and cycloplegia (paralysis of the eye focusing muscle), primarily in the treatment of eye disorders that benefit from its prolonged effect, e.g. uveitis, iritis, iridocyclitis, etc.

Memory research

Because of its anticholinergic effects, scopolamine has been shown to prevent the activation of medial temporal lobe structures for novel stimuli during working memory tasks.

Nicotine addiction

Scopolamine is being investigated for its possible usefulness alone or in conjunction with other drugs in assisting people in breaking the nicotine habit. The mechanism by which it mitigates withdrawal symptoms appears to be at least partially different from that of clonidine meaning that the two drugs can be used together without duplicating or cancelling out the effects of each other.

Other medical uses

• It can be used as a depressant of the central nervous system, and was formerly used as a bedtime sleep aid.
• Anesthetic; Its use in general anesthesia is favored by some^{citation needed} due to its amnesic effect. Scopolamine causes memory impairments to a similar degree as diazepam.^[2]
• In otolaryngology it is used to dry the upper airway (anti-sialogogue action) prior to instrumentation of the airway.
• In October 2006 researchers at the US National Institute of Mental Health found that scopolamine reduced symptoms of depression within a few days, and the improvement lasted for at least a week after switching to a placebo.^[3]
• Due to its effectiveness against sea-sickness it has become commonly used by scuba divers.

Routes of administration

Scopolamine can be administered by transdermal patches,^[4] oral, subcutaneous, ophthalmic and intravenous routes. The transdermal patch for prevention of nausea and motion sickness employs scopolamine base. The oral, ophthalmic and intravenous forms are usually scopolamine hydrobromide (for example in Donnatal).

Recreational use

Scopolamine, in common with the large percentage of anticholinergics which cross the blood-brain barrier such as diphenhydramine, dicyclomine, trihexyphenidyl and related drugs, is said to produce euphoria at and around therapeutic doses as well as to potentiate this and other effects of morphine, methadone, hydromorphone, oxycodone and other opioids. It is therefore occasionally seen as a recreational drug. The use of medical scopolamine (most often in the form of tablets) for euphoria is uncommon but does exist and can be seen in conjunction with opioid use.

Another separate group of users prefer dangerously high doses, especially in the form of datura or belladonna preparations, for the deliriant and hallucinogenic effects. The hallucinations produced by scopolamine, in common with other potent anticholinergics, are especially real-seeming and create a perception of a new world filled with frenzied energy. The difference in realism of hallucinations caused by anticholinergics such as scopolamine and other hallucinogens such as the phenethylamines or dissociatives like PCP is quite large. Additionally, an overdose of scopolamine can quite often be fatal, unlike other more commonly used hallucinogens. For these reasons, naturally occurring anticholinergics are rarely used for recreational purposes.

Potential use in interrogation

The use of scopolamine as a truth drug was investigated in the 1950s by various intelligence agencies, including the CIA as part of Project MKULTRA. Nazi doctor Josef Mengele experimented on scopolamine as an interrogation drug.^{citation needed}

Criminal use

Traces of scopolamine were found in the body found in the cellar of Hawley Harvey Crippen, executed for the murder of his wife. It is unclear whether this caused death, and there is said to be some doubt that the body found was that of his wife.

Scopolamine has been used under the name burundanga in Venezuelan and Thailand resorts in order to drug and then rob tourists. While there are unfounded rumours that delivery mechanisms include using pamphlets and flyers laced with the drug, not enough is readily absorbed through the skin to have an effect. However, spiked alcoholic drinks are occasionally used. ^[5][6]

In recent years the criminal use of scopolamine has become an epidemic. Approximately fifty percent of emergency room admissions for poisoning in Bogotá have been attributed to scopolamine.^[7]

Victims of this crime are often admitted to a hospital in police custody, under the assumption that the patient is experiencing a psychotic episode. A telltale sign is a fever accompanied by a lack of sweat.^{citation needed}

Scopolamine is used criminally as a date rape drug and as an aid to robbery,^[8] the most common act being the clandestine drugging of a victim's drink^[9]. It is preferred because it induces anterograde amnesia, or an inability to recall events a certain amount of time after its administration or during the time of intoxication.

In June 2008, more than 20 people were hospitalized with psychosis in Norway after ingesting counterfeit Rohypnol tablets containing Scopolamine. 11

Shamanic use

In Colombia a plant admixture containing scopolamine called Burundanga has been used shamanically for decades.^{citation needed}

Adverse effects

The common side effects are related to the anticholinergic effect on parasympathetic postsynaptic receptors: dry mouth, throat and nasal passages in overdose cases progressing to impaired speech which can reach the extreme of the victim only being able to emit noises which sound like the vocalisations of a raccoon, thirst, blurred vision and sensitivity to light, constipation, difficulty urinating and tachycardia. Other effects include flushing and fever, as well as excitement, restlessness, hallucinations, or delirium, especially with higher doses. These side effects are commonly observed with oral or parenteral uses of the drug and generally not with topical ophthalmic use. An extreme adverse reaction to ultra-high doses of drugs and other preparations containing scopolamine is temporary blindness which can last up to 72 hours.

The fever and dryness associated with scopolamine has caused some recreational users to stumble into bodies of water and drown on occasion.

Sometimes side effects of scopolamine can be mistaken for symptoms of cancer because of the nausea and anisocoria associated with brain tumors. However, scopolamine induced anisocoria clears up usually within 3 days.

Use in scuba diving to prevent sea sickness has led to the discovery of another side effect^{citation needed}. In deep water, below 50–60 feet, some divers have reported pain in the eyes that subsides quickly if the diver ascends to a depth of 40 feet or less. Mydriatics can precipitate an attack of glaucoma in susceptible patients, so the medication should be used with extra caution among divers who intend to go below 50 feet.

Drug interactions

When combined with morphine, it produces amnesia and a tranquilized state known as twilight sleep. Although originally used in obstetrics, it is now considered dangerous for that purpose for both mother and baby.

History

Scopolamine was one of the active ingredients in Asthmador, an over the counter smoking preparation marketed in the 1950s and 60's claiming to combat asthma and bronchitis.

Scopolamine was used in the 1940s through the 1960s that put mothers in labor into a kind of "twilight sleep" that didn’t stop pain, but merely eliminated the memory of pain by attacking the brain functions responsible for self-awareness and self-control. Often, this resulted in a kind of psychosis, followed by post-traumatic stress-like memories in thousands of new mothers.^[10]

Scopolamine was an ingredient used in some over-the-counter sleep aids prior to November 1990 in the United States, when the FDA forced several hundred ingredients allegedly not known to be effective off the market. Scopolamine shared a small segment of this market with diphenhydramine, phenyltoloxamine, pyrilamine, doxylamine and other first generation antihistamines, many of which are still used for this purpose in drugs like Sominex, Tylenol PM, NyQuil and so on.

Popular culture

• (1940) In one of crime fiction's all-time classic novels, Farewell, My Lovely (1940) by Raymond Chandler, Marlowe gets shot full of Scopolamine in a private sanitarium in order to both shut him up, and to pump him for knowledge, when he gets too close to the truth on a case, or rather several cases entangled into one another, that he is working on (the idenity of Velma and the whereabouts of Moose Malloy).

"I had been shot full of dope to keep me quiet. Perhaps scopolamine too, to make me talk." (quote by Marlowe in Farewell, My Lovely)

"There's a drug called scopolamine, truth serum, that sometimes makes people talk without their knowing it. It's not sure fire, any more than hypnotism is. But it sometimes works." (quote by Marlowe in "Farewell, My Lovely")

• (1957) In popular culture, scopolamine has achieved a moderate level of notoriety via its mention in the film I Was a Teenage Werewolf, where Dr. Alfred Brandon uses it as part of his endeavor to regress the titular character to his "primitive roots."

• (1961) Scopolamine is featured in the World War II action classic The Guns of Navarone as a Schutzstaffel truth serum.

• (1968) Scopolamine is featured in the World War II action classic Where Eagles Dare as a Schutzstaffel truth serum.

• (1968) In Carlos Castaneda's series of books The Teachings of Don Juan: A Yaqui Way of Knowledge, the Datura plant is the favored shamanic, revelatory drug of the titular character. The book explores, in depth, Castaneda's experiences under the influence of the drug, as well as the rites surrounding its use and preparation.

• (1974) In episode 1 "That'll Be The Day", of the fourth series of the TV Series Callan, Callan is interrogated by the KGB using the drug Scopolamine as a truth serum.

• (1979) Scopolamine is also mentioned several times in Robert Ludlum's Matarese Dynasty, a fictional spy novel in which the drug is known for its uses as a truth serum.

• (1990s) The X-Files Red Museum shows Scopolamine as a suspect agent in usage for kidnappings.

• (1990) Scopolamine is mentioned by the villain Cain as one of the cutting agents of the drug Nuke in Robocop 2

• (1994) In the book Blood Hunt by Ian Rankin (written under the pseudonym Jack Harvey) scopolamine, under the name Burundanga is used by the main Character, Gordon Reeve, to gain information and access to facilities in order to find his brother's killer.^[11]

• (2000) In the pilot episode for Season 1 of CSI: Crime Scene Investigation, a female thief seduces a man to sleep with her. She applies scopolamine to her nipples, which knocks the man out when he ingests it orally. After she robs him and makes her escape, the scopolamine which she absorbed into her skin causes her to pass out as well.

• (2000) Scopolamine was the drug Michael claimed he was injected with either by the military and/or the aliens in "The Mars Records". It might be worth noting in this context that scopolamine can cause confabulation (the mixing of memory and facts).

• (2007) In the episode "Airborne", one character in the TV show House, M.D. is shown wearing a scopolamine patch.

External links

• The Erowid Scopolamine Vault
• Scopolamine Transdermal Patch Information:
• Sober Circle Article on Dangers of Scopolamine

References