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Scopolamine



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[3.3.1.02,4]non-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  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

C(US)

Legal status

P(UK) -only(US)

Routes transdermal, ocular, oral, subcutaneous, intravenous

Scopolamine, also known as hyoscine, 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 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.

Additional recommended knowledge

Contents

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.)

Uses

Medical

In medicine scopolamine has 3 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.

Routes of administration

Scopolamine can be administered by transdermal patches, oral, ophthalmic and intravenous. 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).

Nausea

Its use in the form of a transdermal patch to prevent post-operative nausea is perhaps its greatest current use in the US.

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.

Others

  • It can be used as a depressant of the central nervous system, and was formerly used as a bedtime sleep aid (see below).
  • Anesthetic; Its use in general anesthesia is favored by some[citation needed] 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.
  • 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.[1]
  • Due to its effectiveness against sea-sickness it has become commonly used by scuba divers.

Other Uses

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 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].

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 Bogotá have been attributed to scopolamine.[2]

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,[3] the most common act being the clandestine drugging of a victim's drink[4]. 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.[5]

Adverse effects

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.[6] However, scopolamine induced anisocoria clears up usually within 3 days.

Use in scuba diving 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.

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 1950's 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.[7]

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")

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.

  • (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.
  • (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.
  • (1990) Scopolamine is mentioned by the villain Cain as one of the cutting agents of the drug Nuke in Robocop 2
  • (1990s) The X-Files Red Museum shows Scopolamine as a suspect agent in usage for kidnappings.
  • (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.

References

  1. ^ 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.
  2. ^ Wall Street Journal, July 3, 1995
  3. ^ http://www.sobercircle.com/index.asp?node=resources§ion=articles&fileid=8| Retrieved 20/11/07
  4. ^ http://www.sobercircle.com/index.asp?node=resources§ion=articles&fileid=8| Retrieved 20/11/07
  5. ^ 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.
  6. ^ Elias M, Abouleish E (1997). "Scopolamine patch can be confusing to the patient and anesthesiologist: a case report". Anesthesiology 86 (3): 743-4. PMID 9066342.
  7. ^ The Business of Being Born, [1]
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Scopolamine". A list of authors is available in Wikipedia.
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