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Scopolamine chemical structure
Scopolamine

(-)-(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
IUPAC name
CAS number
51-34-3
ATC code

A04AD01 ., .

PubChem
5184
DrugBank
APRD00616
Chemical formula {{{chemical_formula}}}
Molecular weight 303.353 g/mol
Bioavailability 10 - 50% [1]
Metabolism
Elimination half-life 4.5 hours[1]
Excretion {{{excretion}}}
Pregnancy category {{{pregnancy_category}}}
Legal status {{{legal_status}}}
Routes of administration 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 [3]). 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.[How to reference and link to summary or text]

Scopolamine has 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 microgrammes (µg) per day. An overdose can cause delirium, delusions, dangerous elevations of body temperature, stupor and death.

EtymologyEdit

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

PhysiologyEdit

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

In medicine, scopolamine has these uses:

NauseaEdit

Its use as an antiemetic in the form of a transdermal patch is the drug's most common medical application in the United States. [How to reference and link to summary or text]

OphthalmicEdit

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.

AddictionEdit

Scopolamine has been used in the past to treat addiction to drugs such as heroin and cocaine. The patient was given frequent doses of scopolamine until they were delerious. This treatment was maintained for 2 to 3 days after which they were treated with pilocarpine. After recovering from this they were said to have lost the acute craving to the drug to which they were addicted. [2]

Currently, scopolamine is being investigated for its possible usefulness alone or in conjunction with other drugs in assisting people in breaking the nicotine habit. [How to reference and link to summary or text] 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 canceling out the effects of each other.[How to reference and link to summary or text]

Other medical usesEdit

Routes of administrationEdit

Scopolamine can be administered by transdermal patches,[7] 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

The use of medical scopolamine/opioid combination preparations 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 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. [How to reference and link to summary or text]

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. [How to reference and link to summary or text]

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. [How to reference and link to summary or text]

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.[How to reference and link to summary or text]

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. [How to reference and link to summary or text]

Scopolamine has been used under the name burundanga in Venezuelan and Thai resorts in order to drug and then rob tourists. [How to reference and link to summary or text]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 one in five emergency room admissions for poisoning in Bogotá have been attributed to scopolamine.[8]

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.[How to reference and link to summary or text]

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.[How to reference and link to summary or text]

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[How to reference and link to summary or text] 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 practice 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. 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.

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.[How to reference and link to summary or text]

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.[9] [How to reference and link to summary or text]

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.


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.
  2. Evelyn Clare Pearce (1941). Pearce's Medical and Nursing Dictionary and Encyclopaedia, Faber & Faber.
  3. 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.
  4. 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.
  5. Bitterman N, Eilender E, Melamed Y (May 1991). Hyperbaric oxygen and scopolamine. Undersea Biomed Res 18 (3): 167–74.
  6. 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.
  7. 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.
  8. Manuel Uribe G., Claudia L. Moreno L, Adriana Zamora S., Pilar J. Acosta (2005) Perfil epidemiológico de la intoxicación con burundanga en la clínica Uribe Cualla S. A. de Bogotá, D. C. Acta Neurol Colomb, 21, 197-201 [1]
  9. The Business of Being Born, [2]

External links Edit


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