Systematic (IUPAC) name
(-)-(S)-3-Hydroxy-2-phenyl-propionic acid (1R,2R,4S,7S,9S)-9-methyl-3-oxa-9-aza-tricyclo[,4]non-7-yl ester
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.


Legal status

P(UK) -only(US)

Routes transdermal, ocular, oral, subcutaneous, intravenous, sublingual, rectal, buccal transmucousal, intramuscular

Scopolamine, also known as levo-duboisine and hyoscine, is a tropane alkaloid drug with muscarinic antagonist effects. It is obtained from plants of the family Solanaceae (nightshades), such as henbane, jimson weed and Angel's Trumpets (Datura resp. Brugmansia spec.), and corkwood (Duboisia species [2]). It is among the secondary metabolites of these plants. Therefore, scopolamine is one of three main active components of belladonna and stramonium tinctures and powders used medicinally along with atropine and hyoscyamine. Scopolamine was isolated from plant sources by scientists in 1881 in Germany and description of its structure and activity followed shortly thereafter and much knowledge was acquired prior to 1881 as the alkaloid was known for a number of years as levo-duboisine.

Scopolamine has anticholinergic properties at a level of 92 per cent of the strength of atropine at equivalent doses, 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 microgrammes (µg) per day. An overdose can cause delirium, delusions, paralysis, dangerous elevations of body temperature, stupor and death. The amounts present in combination products such as Donnagel PG can range down to 1 to 2 µg (other ingredients therein do most of the work) whereas tablets and solutions of scopolamine come in doses of 50, 100, 200, and 400 µg, the latter usually an extended-release tablet for nausea and pre-medication for some GI and Ear, Nose & Throat procedures and surgeries. By comparison, the usual therapeutic dose of atropine is 600 µg and hyoscyamine is 125 µg.

All three major belladonna alkaloids are capable of producing complete muscarinic acetylcholine receptor blockade for varying lengths of time and have some impact on nicotinic and other receptors and many neurotransmitter levels; this would be at toxic levels and doses well above those used in medicine for all three and the only therapeutic uses at those levels are some methods of anaesthesia and "atropinisation" (which can also be done less efficiently with the other tropanes and some other anticholinergics) which is a method used to counter organophosphate and some forms of carbamate poisoning (malathion and related, for example) and use of an atropine auto-injector for pre- and/or post-exposure treatment for exposure to many nerve agents such as VX (nerve gas) and BZ (incapacitating agent) in their various forms. Scopolamine itself has been investigated in the past for use as a non-lethal incapacitating agent because of the low doses required to create significant hallucinatory, sedative, and incapacitating effects. As of November 2008, no known development of weaponised scopolamine is known to have been undertaken by any state or organisation.


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


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

Medical useEdit

Scoplamine has about 92 per cent of the muscarinic blocking power of atropine and affects numerous systems in the body. The search for a similar drug that may have fewer side effect led to the discovery of diphenhydramine in 1937, a drug which is about 65 per cent as strong as atropine and is the prototype of the ethanolamine antihistamines, which include phenyltoloxamine, doxylamine, bromodiphenhydramine, orphenadrine and others; the group is also closely related to other non-tropane anticholinergics.

In medicine, scopolamine has these uses:


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]


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 researchEdit

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

Nicotine addictionEdit

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

Other medical usesEdit

Routes of administrationEdit

Scopolamine can be administered by transdermal patches,[6] 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 useEdit

Scopolamine, in common with the large percentage of anticholinergics which cross the blood-brain barrier such as diphenhydramine, orphenadrine, 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 others. It is therefore occasionally seen as a recreational drug. The use of medical scopolamine/opioid combination preparations for euphoria is uncommon but does exist and can be seen in conjunction with opioid use. The euphoria is produced in a fashion quite different from that of the opioids and is thought to be generated by changing the dopamine:acetylcholine ratio in the central nervous system; this effect is similar to that produced by many tricyclic, quaternary ammonium, and tertiary amine anticholinergics including dicycloverine (Bentyl®), trihexyphenidyl (Artane®), and many antihistamines of the ethanolamine, ethylenediamine, and alkylamine classes. Notably, atropine, hyoscyamine, and some other anticholinergics do not produce this effect.

Another separate group of users prefer dangerously high doses, especially in the form of datura preparations, for the deliriant and hallucinogenic effects. The hallucinations produced by scopolamine, in common with other potent anticholinergics, are especially real-seeming, repetitive, boring and unpleasant. An overdose of scopolamine is also physically exceedingly unpleasant and can be fatal, unlike the effect of other more commonly used hallucinogens. For these reasons, naturally occurring anticholinergics are rarely used for recreational purposes.[citation needed]

Scopolamine in transdermal, oral, sublingual, and injectable formulations can produce a cholinergic rebound effect when high doses are stopped. This is the opposite of scopolamine's therapeutic effects: sweating, runny nose, abdominal cramps, nausea, vomiting, vertigo, dizziness, irritability, and diarrhea. Psychological dependence is also possible when the drug is taken for its tranquilizing effects.[citation needed]

Potential use in interrogationEdit

"The Use of Scopolamine in Criminology" by Robert E. House appeared in the Texas State Journal of Medicine in September, 1922 and was reprinted in The American Journal of Police Science, Vol. 2, No. 4, Jul. - Aug., 1931.[citation needed]

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 useEdit

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.[citation needed]

Scopolamine has been used under the name burundanga in Venezuelan and Thai resorts in order to drug and then rob tourists. While there are unfounded rumors 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. In recent years the criminal use of scopolamine has become an epidemic. Approximately half of emergency room admissions for poisoning in Bogotá have been attributed to scopolamine.[7][citation needed]

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]

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

Shamanic useEdit

In Colombia a plant admixture containing scopolamine called Burundanga has been used shamanically for decades.

Witchcraft & SorceryEdit

Scopolamine was one of the active principles in many of the "flying ointments" used by witches, sorcerers and fellow travellers of many countries and cultures from millennia ago ostensibly down to the late XIX. Century or even to the present day. Scopolamine and related tropanes contributed both to the flying sensations and hallucinations sought by users of these compounds. Potions, solids of various types, and other forms were also used in some cases.

These ointments could contain any number of ingredients with belladonna, henbane, and other plants of the belladonna and datura families being present almost invariably; they were applied to the vaginal and/or anal mucosa and/or large areas of the skin and other mucous membranes (often using a broom as an applicator, the origin of the image of a witch riding a broom) with the objective being to see the Devil and/or be transported to the Sabbat.

The hallucinations, sensation of flying, often a rapid increase in libido, and other characteristic effects of this practise are largely attributable to the CNS and peripheral effects of scopolamine and other active drugs present in the ointments such as atropine, hyoscyamine, mandragorine, scopoline, solanine, optical isomers of scopolamine and other tropane alkaloids. Still other active chemicals with psychoactivity are present in other ingredients used in salves, ointments, potions, and other forms of drugs which contained ingredients like "water of aconite", bryony root, valerian, digitalis, wild carrot, sage, wormwood, ephedra, and relatives (Artemisia spp.), tobacco, toxic parts of potato and other plants in the Solanaceae family, thistles and daisies of various types, and other plants and ingredients from animal sources.

The inclusion of belladonna/datura type plants amongst the dozens of ingredients in the Haitian zombie drug is thought by some authorities to be at least somewhat likely, although scopolamine-bearing plant matter is almost certainly not the main active ingredient, which has been theorised to possibly be Tetrodotoxin or a related substance.

Adverse effectsEdit

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, thirst, blurred vision and sensitivity to light, constipation, difficulty urinating and tachycardia. Other effects of overdose include flushing and fever, as well as excitement, restlessness, hallucinations, or delirium. 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 high doses (or lower doses in those with hypersensitity to scopolamine and/or all anticholinergics) of drugs and other preparations containing scopolamine is temporary blindness which can last up to 72 hours. The tendency of scopolamine and related drugs to stop secretions from many glands in the body, resulting in the prominent antisialagogue and antimucinogogue effects that dry out the mouth, throat, nose, and other related parts of the body as well as other effects of tropanes can result in another extreme side effect in which the patient is unable to speak normally for a similar length of time, ranging from difficult, rushed-sounding speech to only being able to emit raccoon-like noises. Extreme supertherapeutic doses of scopolamine can result in the effects on vision (mydriaisis, photophobia, and varying degrees of cycloplaegia) as well as "corner of the eye"-type hallucinations, often of insects to last anywhere from 72 hours to more than five weeks as reported in various references on the use of drugs.

The effects of hyperthermia (fever) along with the aforementioned impact on exocrine glands like sweat and saliva glands can lead to two potentially lethal end-points to a severe scopolamine/tropane alkaloids overdose, namely elevated core body temperature which has in extreme cases involving massive exertion in hot, humid enviromnments, reached or exceeded c.a. 44°C or 110°F -- 41°C/105·8°F is life-threatening and 45°C/113°F is invariably and rapidly fatal -- and drowning from users trying to quench the extreme thirst and/or convinced they are being chased by monsters and the like stumbling into bodies of water and drowning.

Use in scuba diving to prevent sea sickness has led to the discovery of another side effect. 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: Side Effects And Use Against Pain Edit

Twilight Sleep

When combined with morphine, scopolamine is useful for pre-medication for surgery or diagnostic procedures and was widely used in obstetrics in the past; the mixture also produces amnesia and a tranquillised state known as Twilight Sleep, also the name of a proprietary drug available in the past in ampoules of injectable fluid containing morphine sulphate and scopolamine hydrobromide (and in some cases the phenothiazine anti-nauseants prochlorperazine or promethazine as a third ingredient). Although originally used in obstetrics, it is now considered dangerous for that purpose for both mother and baby.

In current times, diagnostic procedures and surgery requiring a patient to be put in twilight sleep state are performed with sedation provided by a strong short to intermediate-acting benzodiazepine such as midazolam (Versed®) which also has the amnestic effect desired in such cases. Such drugs can be used with or without morphine or a similar agent depending on the instance; it is also common for a patient to receive a moderately high dose of an opioid (sometimes morphine, hydromorphone, or a closely-related drug but also quite often levorphanol, piritramide, oxymorphone, fentanyl, or pethidine) a short time before the procedure begins in order to allay apprehension by means of generating euphoria, co-operativeness, sociability and anxiolysis. Haloperidol or a similar drug may also be used in such instances.

Adjuvant, Atypical & Potentiator for Opioid Therapy for Chronic Pain

A method of mixing scopolamine with opioids which generally uses less scopolamine has found some use in treatment of breakthrough pain in chronic pain patients and some acute cases of severe pain, especially that of neuropathic origin and/or which interferes with sleep. The effect is also of interest to licit and illicit users of morphine and other drugs in that scopolamine, a euphoriant of a different type in its own right, can accentuate the "rush" of injected opioids such as morphine and hydromorphone and potentiate a broad spectrum of narcotic effects of many opioids in general. The subsequent steadier euphoria and sleepiness are also intensified.

Several side effects such as nausea and miosis are also reduced by the comcomitant administration of opioids and scopolamine in most cases. Others such as difficulty concentrating and constipation can be compounded, and in some patients the increase in somnolence or sleepiness as severe enough that administration of a stimulant may be helpful.

The boost in the euphoria and other therapeutic effects of opioids is a synergistic effect which in some patients also results from sublingual administration of hyoscyamine and some other anticholinergics after codeine, dihydrocodeine or similar drugs taken via the oral or rectal route have begun to work. This PRN technique for treatment of sharp, severe nerve pain (which usually complements a preventative strategy which includes the administration of acyclovir with the opioid and perhaps cyclobenzaprine or orphenadrine on a continuing basis for prevention) is equally effective as the above and can actually produce a rush of sorts lasting up to 15 minutes even though both agents were administered by mouth.

The administration of scopolamine with other drugs in a daily schedule of opioids, adjuvants, other drugs for related conditions and side effects for continuing efficacy against chronic neuropathic pain is also useful in that scopolamine fills several niches including anti-nauseant, adjuvant to analgesics, etc. Extended-release tablets or even the scopolamine patch are used for this purpose. Scopolamine can also be used in topical compounds for treatment of nerve pain; these are often creams or gels which can also include many other drugs used for pain and related conditions -- scopolamine can be used in addition to or in place of cyclobenzaprine, amitryptiline, orphenadrine, gabapentin, trazadone, and the like in such mixtures. Acyclovir creams or ointments can serve as intensifiers for topical preparations which contain scopolamine in many of the cases in which the latter is used; acyclovir is also available for prescription compounding in many countries and can be added to the main mixture.

Excessive side effects in such a cases may indicate a change to an adjuvant with milder effects; literally dozens of options are available and come from such pharmacological categories as:

  • first-generation anti-depressants
  • non-steroidal anti-inflammatory drugs (NSAIDs)
  • anticholinergics of certain chemical classes and with predominantly anti-muscarinc activity
  • some quinine-like drugs
  • first-generation antihistamines
  • anti-convulsants
  • beta blockers
  • centrally-acting stimulants
  • caffeine, theobromine and related drugs
  • NMDA antagonists
  • muscle relaxants
  • local anaesthetics
  • non-barbiturate sedative-hypnotics
  • benzodiazepines
  • drugs with action on seritonin and/or norepinephrine re-uptake like duloxetine, tramadol (as either adjuvant or main opioid -- drugs which can be used as the main opioid which combine NMDA antagonist, SSRI and/or SSNI activity include methadone and relatives, levorphanol, piritramide, ketobemidone, other members of the tramadol group and other synthetic opioids); and others,
  • systemic anaesthetics like ketamine or nitrous oxide

...and many other categories.

Side Effects Compounded

In all of these cases as with all instances of simultaneous use of opioids and anticholinergics, close monitoring of bowel function and pre-emptive measures like increase in fibre intake to deal with the possibility of severe constipation and rare complications thereof like paralytic ileus is required.

History Edit

Scopolamine was one of the earlier alkaloids isolated from plant sources and has been in use in isolated, purified forms such as free base and various salts, especially hydrochloride, hydrobromide, hydroiodide and sulphate, since its isolation by German chemists in 1881 and in the form of plant-based preparations since antiquity and perhaps pre-historic times.

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 from the 1940s to the 1960s to put mothers in labor into a kind of "twilight sleep" that did not stop pain, but merely eliminated the memory of pain by attacking the brain functions responsible for self-awareness and self-control. Often, this caused a kind of psychosis, followed by post-traumatic stress-like memories in thousands of new mothers.[8][citation needed]

Scopolamine was an ingredient used in some over-the-counter sleep aids before 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, etc.

Popular culture Edit

  • (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 identity 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." According to Dr. Liz Kingsley's film review site And You Call Yourself a Scientist, Brandon's line "Prepare the scopolamine!" is "the only scientifically accurate line in the whole film."
  • 1961 and 1968: Scopolamine is featured in the World War II action classic The Guns of Navarone and the subsequent Where Eagles Dare as a truth serum employed by the villanous SS both movies came from works of Alistair MacLean.
  • 1940s-1960s: In a letter from Tangier to Allen Ginsburg, author, artist, &c. William S. Burroughs recounts an incident in which he shot up a series of ampoules of a methadone preparation containing scopolamine without considering the effect of the latter drug; later in the evening he was reportedly red as a beet, had totally disrobed and was running around yelling and trying to get away from monsters; he needed to be restrained by the owner of the building in which he rented an apartment.
  • 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.
  • 1972: In Fear and Loathing In Las Vegas by Hunter S. Thompson, the narrator's attorney mentions an incident in which he was given an entire datura root as a gift, at the entire thing at once and went blind, had to be taken back to to house in a wheelbarrow and started making noises like a raccoon (Procyon lotor).
  • 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.
  • 1987: Stephen King's novel Misery depicts the protagonist self-administering a morphine-scopolamine injectable to stave off pain and withdrawal symptoms (after being deliberately given narcotic analgesics to produce physical dependence subsequent to being rescued after an automobile crash by a nurse with a huge stash of narcotics who also wanted the main character to re-write pervious novels to suit her ideas about how they should have ended) during an escape attempt.
  • 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.[9]
  • 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.
  • 2008: In the TV series Knight Rider 2008, in episode 4, "A Hard Day's Knight", Mike Knight is poisoned with hyoscine, and needs to find an antidote within 3 hours.
  • 2008: In the TV series My Own Worst Enemy, in episode 2, "The Hummingbird", Henry is poisoned with scopalamine and is told he must have his heart shocked within the next minute or he will die.

References Edit

  1. 1.0 1.1 Putcha L, Cintrón NM, Tsui J, Vanderploeg JM, Kramer WG (June 1989). "Pharmacokinetics and oral bioavailability of scopolamine in normal subjects". Pharm. Res. 6 (6): 481–5. doi:10.1023/A:1015916423156. PMID 2762223. 
  2. Jones DM; Jones ME, Lewis MJ, Spriggs TL. (May 1979). "Drugs and human memory: effects of low doses of nitrazepam and hyoscine on retention.". Br J Clin Pharmacol. 7 (5): 479–83. PMID 475944. 
  3. Furey, ML; Drevets, WC (October 2006). "Antidepressant efficacy of the antimuscarinic drug scopolamine: a randomized, placebo-controlled clinical trial". Archives of General Psychiatry, vol 63, p 1121 63: 1121. doi:10.1001/archpsyc.63.10.1121. PMID 17015814, 
  4. Bitterman N, Eilender E, Melamed Y (May 1991). "Hyperbaric oxygen and scopolamine". Undersea Biomed Res 18 (3): 167–74. PMID 1853467, Retrieved on 13 August 2008. 
  5. Williams TH, Wilkinson AR, Davis FM, Frampton CM (March 1988). "Effects of transcutaneous scopolamine and depth on diver performance". Undersea Biomed Res 15 (2): 89–98. PMID 3363755, Retrieved on 13 August 2008. 
  6. White PF, Tang J, Song D, et al (2007). "Transdermal scopolamine: an alternative to ondansetron and droperidol for the prevention of postoperative and postdischarge emetic symptoms". Anesth. Analg. 104 (1): 92–6. doi:10.1213/01.ane.0000250364.91567.72. PMID 17179250, 
  7. Wall Street Journal, July 3, 1995
  8. The Business of Being Born, [1]
  9. Rankin, Ian. Blood Hunt. Little, Brown and Company, New York: 1994.

External links Edit


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