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A thick, syrupy, colorless alkaloid, C17H21NO4, extracted from plants such as henbane and used primarily as a mydriatic and sedative, and to treat nausea and prevent motion sickness. Also called hyoscine.
[New Latin Scopolia, plant genus (after Giovanni Antonio Scopoli (1723–1788), Italian naturalist) + –AMINE.]
Definition
Scopolamine, also called hyoscine hydrobromide, is used in cancer treatment to prevent nausea and vomiting that results from movement of the head.
Purpose
Chemotherapy causes nausea and vomiting in many people. These conditions can occur for several different reasons. Scopolamine is used to treat nausea and vomiting that result from movement of the head. In many ways, this type of nausea is similar to motion sickness.
Other uses of scopolamine include pre-anesthesia sedation. In combination with morphine, scopolamine may be given to women in childbirth to induce "twilight sleep." Lastly, scopolamine is used in an ophthalmic solution to dilate the pupil of the eye before an eye examination.
Description
Scopolamine is a natural product and is familiar to many people as a motion sickness medicine. In its most common form, it comes as a patch that a person with motion sickness wears behind the ear. It is also known by the brand names Transderm-Scop and Transderm-V.
As a motion sickness drug, scopolamine has been used for many years with few side effects. It is approved by the United States Food and Drug Administration (FDA), and its cost is usually covered by insurance. In cancer treatment, scopolamine is used to treat a particular type of nausea and vomiting that occur as a result of chemotherapy.
Scopolamine is classified as an anticholinergic drug. This means it works by blocking the nerve impulses that send information from the part of the inner ear that controls the sense of balance. In motion sickness, a person vomits because conflicting information arrives in the brain from the inner ear and the eye. Some chemotherapy drugs also cause the brain to receive conflicting information, so that when patients move their head, they feel nauseated. People vary in their sensitivity to this condition. This drug is effective in helping most people control nausea and vomiting that arises from this source.
Recommended Dosage
Scopolamine comes in a patch that the patient applies behind the ear. The patch stays in place for three days and releases a continuous supply of the drug. To be effective, the patch must be applied at least four hours before chemotherapy is begun. After three days, the patch is removed. Unused patches should be stored at room temperature.
Precautions
People applying or removing a scopolamine patch should wash their hands well immediately after handling the patch so that they do not accidentally transfer any of the drug to other parts of their body (for example, by rubbing their eyes). Scopolamine should not be used in children, should be kept away from pets, and should be used with caution in the elderly.
The patch should be used with caution in patients with a history of either seizures or psychosis, because scopolamine may make either of these disorders worse.
Side Effects
About 65% of the people who use scopolamine get a dry mouth. About 17% of people report feeling drowsy from the drug. Other less common side effects include blurred vision, disorientation, restlessness, confusion, dizziness, difficulty urinating, constipation, skin rash, dry red itchy eyes, extreme sensitivity to light, and narrow-angle glaucoma.
Interactions
Many drugs interact with nonprescription (over-thecounter) drugs and herbal remedies. Patients should always tell their health care providers about these remedies, as well as prescription drugs they are taking. Patients should also mention if they are on a special diet such as low salt or high protein.
Scopolamine interferes with the absorption of ketoconazole (Nizoral), an antifungal drug, sometimes used to treat prostate cancer. It may also interact with other anticholinergic drugs (drugs that block nerve impulses), antidepressants, and antihistamines. Scopolamine decreases the absorption of phenothiazines (antipsychotic drugs), and interfers with the effectiveness of levodopa, a drug given to treat Parkinson's disease.
Resources
Books
Beers, Mark H., MD, and Robert Berkow, MD, editors. "Drugs in Pregnancy." Section 18, Chapter 249 In The Merck Manual of Diagnosis and Therapy. Whitehouse Station, NJ: Merck Research Laboratories, 2002.
Beers, Mark H., MD, and Robert Berkow, MD, editors. "Motion Sickness." Section 20, Chapter 282 In The Merck Manual of Diagnosis and Therapy. Whitehouse Station, NJ: Merck Research Laboratories, 2002.
Beers, Mark H., MD, and Robert Berkow, MD, editors. "Ophthalmologic Disorders." Section 8, Chapter 96 In The Merck Manual of Diagnosis and Therapy. Whitehouse Station, NJ: Merck Research Laboratories, 2002.
Karch, A. M. Lippincott's Nursing Drug Guide.Springhouse, PA: Lippincott Williams & Wilkins, 2003.
Periodicals
Spinks, A. B., J. Wasiak, E. V. Villanueva, and V. Bernath. "Scopolamine for Preventing and Treating Motion Sickness." Cochrane Database Systems Review 3 (2004): CD002851.
Organizations
United States Food and Drug Administration (FDA). 5600 Fishers Lane, Rockville, MD 20857-0001. (888) INFO-FDA.
—Tish Davidson, A.M.; Rebecca J. Frey, PhD
An alkaloid found in the leaves and seeds of Atropa belladonna and other solanaceous plants having an action similar to atropine and used when spasmolytic or antisecretory effects are desired.
Brand names: Isopto® Hyoscine, Maldemar™, Scopace®, Transderm Scop®
Chemical formula:
Scopolamine skin patches
What are scopolamine skin patches?
SCOPOLAMINE (Transderm Scop®) patches help prevent nausea and vomiting associated with motion sickness. Generic scopolamine skin patches are not yet available.
What should I tell my health care provider before I take this medicine?
They need to know if you have any of these conditions:
• difficulty passing urine
• heart or blood vessel disease, high blood pressure
• hiatal hernia
• glaucoma
• liver disease
• nervous system disease
• over active thyroid
• stomach obstruction
• ulcerative colitis
• an unusual or allergic reaction (especially skin allergy) to scopolamine, atropine, other medicines, foods, dyes, or preservatives
• pregnant or trying to get pregnant
• breast-feeding
How should I use this medicine?
Scopolamine skin patches are for external use only. Follow the directions on the prescription label. Use exactly as directed. One patch contains enough scopolamine to prevent motion sickness for up to 3 days. Apply the patch at least 4 hours before you need it and only wear one disc at a time. Choose an area behind the ear, that is clean, dry, hairless and free from any cuts or irritation. Wipe the area with a clean dry tissue. Peel off the plastic backing of the skin patch, trying not to touch the adhesive side with your hands. Firmly apply to the area you have chosen, with the metallic side of the patch to the skin and the tan-colored side showing. Once firmly in place, wash your hands well with soap and water. Remove the disc after 3 days, or sooner if you no longer need it. If you need to use a second patch after you remove the first, place it behind the other ear.
Contact your pediatrician or health care professional regarding the use of this medicine in children. Special care may be needed.
What drug(s) may interact with scopolamine?
• alcohol
• amantadine
• benztropine
• bethanechol
• cisapride
• digoxin
• donepezil
• erythromycin
• galantamine
• glutethimide
• ketoconazole
• levodopa
• medicines for hay fever and other allergies
• medicines for mental depression
• medicines for mental problems and psychotic disturbances
• medicine for anxiety or sleeping problems (such as diazepam, or temazepam)
• meperidine
• metoclopramide
• quinidine
• rivastigmine
• tacrine
• tegaserod
Tell your prescriber or health care professional about all other medicines you are taking, including nonprescription medicines, nutritional supplements, or herbal products. Also tell your prescriber or health care professional if you are a frequent user of drinks with caffeine or alcohol, if you smoke, or if you use illegal drugs. These may affect the way your medicine works. Check with your health care professional before stopping or starting any of your medicines.
What should I watch for while taking scopolamine?
Check with your prescriber or health care professional as soon as you can if you get pain in your eye, or reddening of the whites of your eye.
Keep the patch dry, if possible, to prevent it from falling off. Limited contact with water, however, as in bathing or swimming, will not affect the system. If the patch falls off, throw it away and put a new one behind the other ear.
You may get drowsy, dizzy, or have blurred vision. Do not drive, use machinery, or do anything that needs mental alertness until you know how scopolamine affects you. To reduce the risk of dizzy or fainting spells, do not sit or stand up quickly, especially if you are an older patient. Alcohol can make you more drowsy, avoid alcoholic drinks.
Your mouth may get dry. Chewing sugarless gum or sucking hard candy, and drinking plenty of water will help.
Scopolamine may cause dry eyes and blurred vision. If you wear contact lenses you may feel some discomfort. Lubricating drops may help. See your ophthalmologist if the problem does not go away or is severe.
When you remove a patch, fold it in half (sticky side in) and throw away out of reach of children or pets.
If you are going to have a MRI procedure, let your MRI technician know about the use of these patches. Some drug patches contain an aluminized backing that can become heated when exposed to MRI and may cause burns. You may need to temporarily remove the patch during the MRI procedure.
What side effects may I notice from using scopolamine?
Side effects that you should report to your prescriber or health care professional as soon as possible:
• agitation, nervousness, confusion
• blurred vision and other eye problems
• dizziness, drowsiness
• hallucinations (seeing and hearing things that are not really there)
• pain or difficulty passing urine
• skin rash, itching
• vomiting
Side effects that usually do not require medical attention (report to your prescriber or health care professional if they continue or are bothersome):
• dry mouth
• headache
• nausea
Where can I keep my medicine?
Keep out of the reach of children.
Store at room temperature between 15 and 30 degrees C (59 and 86 degrees F). Throw away any unused medicine after the expiration date.
Last updated: 7/1/2002
Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.
An anticholinergic alkaloid derived from various plants, used as the hydrobromide in parasympathetic blockade and as a central nervous system depressant.
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Scopolamine
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| Systematic (IUPAC) name | |
| (-)-(S)-3-Hydroxy-2-phenyl-propionic acid (1R,2R,4S,7S,9S)-9-methyl-3-oxa-9-aza-tricyclo[3.3.1.02,4]non-7-yl ester | |
| Identifiers | |
| CAS number | |
| ATC code | A04 N05CM05, S01FA02 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C17H21NO4 |
| Mol. mass | 303.353 g/mol |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
C(US) |
| Legal status | |
| Routes | transdermal, ocular, oral, subcutaneous, intravenous |
Scopolamine, also known as hyoscine, is a tropane alkaloid drug 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 and should be used in minute doses. As an example, in the treatment of motion sickness, the dose, gradually released from a transdermal patch, is only 0.33 milligram of scopolamine per day. An overdose can cause delirium, delusions, paralysis, stupor and death.
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 specific muscarinic acetylcholine receptors ("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.)
In medicine scopolamine has 3 primary uses: treatment of nausea and motion sickness, treatment of intestinal cramping, and for ophthalmic purposes. Its use in the form of a transdermal patch to prevent post-operative nausea is perhaps its greatest current use in the US. The drug is less commonly used as a preanesthetic agent and uncommonly for some forms of Parkinsonism. The oral, ophthalmic and intravenous forms are usually scopolamine hydrobromide (for example in Donnatal). The transdermal patch for prevention of nausea and motion sickness employs scopolamine base. 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. It can be used as a depressant of the central nervous system, and was formerly used as a bedtime sleep aid (see below). Its use in general anesthesia is favored by some due to its amnesic effect. In otolaryngology it has been used to dry the upper airway (anti-sialogogue action) prior to instrumentation of the airway.
The common side effects are related to the anticholinergic effect on parasympathetic postsynaptic receptors: dry mouth, throat and nasal passages, 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 [citation needed].
Sometimes side effects of scopolamine can be mistaken for symptoms of cancer because of the nausea and anisocoria associated with brain tumors.[1] However, scopolamine induced anisocoria clears up usually within 3 days.
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.
Scopolamine was one of the active ingredients in Asthmador, an over the counter smoking preparation marketed in the 1950's and 60's claiming to combat asthma and bronchitis.
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.
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.[2]
Due to its effectiveness against sea-sickness it has become commonly used by scuba divers. However, this 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, but the pain 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.
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. The euphoria is the result of changes in dopamine and acetylcholine levels and ratios [citation needed] and appears to be related to some part of the chemical structure of the drug [citation needed] and other factors known or unknown -- even closely related drugs like atropine and hyoscyamine do not produce euphoria whilst the others listed above certainly appear to [citation needed].
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, violent 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.
The use of scopolamine as a truth drug was investigated by various intelligence agencies, including the CIA, during the 1950s. see: Project MKULTRA. It was found that, due to the hallucinogenic side effects of the drug, the truth was prone to distortion, and the project was subsequently abandoned [citation needed]. Nazi doctor Josef Mengele experimented on scopolamine as an interrogation drug [citation needed].
In Colombia a plant admixture containing scopolamine called Burundanga has been used
shamanically for decades. In recent years the criminal use of scopolamine has become an
epidemic. Approximately fifty percent of emergency room admissions for poisoning in
Also in Caracas, Venezuela, crime related to burundanga techniques has multiplied in the last years. Targets are easily approached and just with physical contact they administer the drug to the victim. Reports of techniques of administration include wafting the powder to the victim with a puff of air, drugged chewing gum, or even craftily dropping the powder into the collar of a shirt or the front of a woman's low-cut dress [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.
Scopolamine is used criminally as a date rape drug and as an aid to robbery, the most common act being the clandestine drugging of a victim's drink. It is preferred because it induces retrograde amnesia, or an inability to recall events prior to its administration or during the time of intoxication.
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.
Scopolamine (hyoscine) causes memory impairments to a similar degree as diazepam.[3]
"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")
Back in the forties Scopolamine showed promise, and still does today, to some degree, as a "truth serum" although its drawbacks are too many for it to be a surefire "cure" against lying.
| Anesthetic: Ancient anaesthesia | |
|---|---|
| Plants/animals | Aconite • Argyreia speciosa • Beaver • Cannabis • Coca • Deadly nightshade • Henbane • Lactucarium • Mandrake • Metel nut • Opium • Poison hemlock • Saussurea • Toloatzin • Willow |
| People | al-Qasim • al-Razi • Avicenna • Celsus • Dioscorides • Galen • Hippocrates • Susrutha • Theophrastus • Zhang Ji |
| Molecules | Aconitine • Δ9-THC • Atropine • Cocaine • Coniine • Hyoscyamine • Morphine • Salicylate • Scopolamine |
| Antiemetics and antinauseants (A04) | |
|---|---|
| Serotonin (5-HT3) antagonists | Ondansetron • Granisetron • Tropisetron • Dolasetron • Palonosetron |
| Other | Scopolamine • Cerium oxalate • Chlorobutanol • Metopimazine • |
| Ophthalmologicals: mydriatics and cycloplegics (S01F) | |
|---|---|
| Anticholinergics/antimuscarinics | Atropine - Scopolamine - Methylscopolamine - Cyclopentolate - Homatropine - Tropicamide |
| Sympathomimetics | Phenylephrine - Ephedrine - Ibopamine |
| Deliriants (anticholinergic hallucinogens) |
|---|
| 3-quinuclidinyl benzilate, Atropine, Dimenhydrinate, Diphenhydramine, Hyoscyamine, Scopolamine, Cyclizine |
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 | Dictionary. The American Heritage® Dictionary of the English Language, Fourth Edition Copyright © 2007, 2000 by Houghton Mifflin Company. Updated in 2007. Published by Houghton Mifflin Company. All rights reserved. Read more |
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| Oncology Encyclopedia. Gale Encyclopedia of Cancer. Copyright © 2006 by The Gale Group, Inc. All rights reserved. Read more |
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| Dental Dictionary. Mosby's Dental Dictionary. Copyright © 2004 by Elsevier, Inc. All rights reserved. Read more |
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| Drug Info. Gold Standard. Copyright © 2008 by Gold Standard. All rights reserved. Read more |
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| Columbia Encyclopedia. The Columbia Electronic Encyclopedia, Sixth Edition Copyright © 2003, Columbia University Press. Licensed from Columbia University Press. All rights reserved. www.cc.columbia.edu/cu/cup/ Read more |
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| Veterinary Dictionary. Saunders Comprehensive Veterinary Dictionary 3rd Edition. Copyright © 2007 by D.C. Blood, V.P. Studdert and C.C. Gay, Elsevier. All rights reserved. Read more |
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| Word Tutor. Copyright © 2004-present by eSpindle Learning, a 501(c) nonprofit organization. All rights reserved. eSpindle provides personalized spelling and vocabulary tutoring online; free trial. Read more |
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| Wikipedia. This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Scopolamine". Read more |
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