Government officials should tell Americans about all domestic uses of Scopolamine.
From Wikipedia, the free encyclopedia
Systematic (IUPAC) name
(–)-(S)-3-hydroxy-2-phenylpropionic acid(1R,2R,4S,7S,9S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl ester
Trade names Transdermscop
Pregnancy cat. C (US)
Legal status ℞-only (US)
Routes transdermal, ocular, oral, subcutaneous, intravenous, sublingual, rectal, buccal transmucousal, intramuscular
Bioavailability 10 – 50%
Half-life 4.5 hours
CAS number 51-34-3
ATC code A04AD01 N05CM05, S01FA02
PubChem CID 5184
IUPHAR ligand 330
Mol. mass 303.353 g/mol
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Scopolamine, also known as levo-duboisine and hyoscine, is a tropane alkaloid drug with muscarinic antagonist effects. It is among the secondary metabolites of plants from Solanaceae (nightshade) family of plants, such as henbane, jimson weed, Angel’s Trumpets (Datura or Brugmansia), and corkwood (Duboisia). Although scopolamine is sometimes portrayed in the media as a dangerous drug, its anticholinergic properties give it some legitimate medical applications in minute doses. An example is the treatment of motion sickness by use of a transdermal patch.
2 Biosynthesis in plants
3 Methods of administration
4 Medical use
4.2 Other medical uses
5 Recreational use
6 Use in interrogation
7 Criminal use and urban legends
8 See also
Scopolamine is named after the plant genus Scopolia. The name “hyoscine” is from the scientific name for henbane, Hyoscyamus niger.
Biosynthesis in plants
The biosynthesis of scopolamine begins with the decarboxylation of L-ornithine to putrescine by ornithine decarboxylase (EC 184.108.40.206). Putrescine is methylated to N-methylputrescine by putrescine N-methyltransferase (EC 220.127.116.11).
A putrescine oxidase (EC 18.104.22.168) that specifically recognizes methylated purtrescine catalizes the deamination of this compound to 4-methylaminobutanal which then undergoes a spontaneous ring formation to N-Methyl-pyrrolium cation. In the next step, the pyrrolium cation condenses with acetoacetic acid yielding hygrine. No enzmyatic activity could be demonstrated that catalyzes this reaction. Hygrine further rearranges to tropinone.
Subsequently, Tropinone reductase I (EC 22.214.171.124) converts tropinone to tropine which condenses with phenylalanine-derived phenyllactate to littorine. A cytochrome P450 classified as Cyp80F1 oxidizes and rearranges littorine to hyoscyamine aldehyde. In the final step, hyoscyamine undergoes epoxidation which is catalyzed by 6beta-hydroxyhyoscyamine epoxidase (EC 126.96.36.199) yielding scopolamine.
Biosynthesis of scopolamine in plants.
Methods of administration
Scopolamine can be administered orally, subcutaneously, opthalmically and intravenously, as well as via a transdermal patch. The transdermal patch (e.g., Transderm Scōp) for prevention of nausea and motion sickness employs scopolamine base, and is effective for up to 3 days.
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 delirious. 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.
Other medical uses
Its primary use is for the treatment of sea-sickness, leading to use by scuba divers.
Scopolamine has been tested as a topical treatment for Aquagenic pruritus and was shown in several cases to be effective.
The drug has been reported as used by astronauts including those on Skylab for the treatment of motion sickness 
Transdermal scopolamine patches are sometimes used to help control excessive saliva and drooling in patients with ALS 
Scopolomine is also used for mild sedation and saliva management in end-of-life care as an adjunct to other comfort medications.
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.
Intravenously administered scopolamine has been found to be effective against major depressive disorder. A phase II clinical trial of its efficacy against both major depressive disorder and depression due to bipolar disorder when administered via transdermal patches is scheduled to finish in September 2011.
While it is occasionally used recreationally for its hallucinogenic properties, the experiences are often extremely mentally and physically unpleasant, and frequently physically dangerous, so repeated use is rare.
Use in interrogation
The effects of scopolamine were studied by criminologists in the early 20th century. In 2009, it was proven that Czechoslovak communist secret police used scopolamine at least three times to obtain confessions from alleged anti-state conspirators. Because of a number of undesirable side effects, scopolamine was shortly disqualified as a truth drug.
Criminal use and urban legends
In 1910, it was detected in the remains believed to be those of Cora Crippen, wife of Dr. Hawley Harvey Crippen, and was accepted at the time as the cause of her death since her husband was known to have bought some at the start of the year.
Scopolamine poisoning is sometimes reported by the media as method by which people are raped, killed, or robbed, although some of these are unfounded rumors. For example, there have been rumors that robbers in the United States used a transcutaneous delivery mechanism involving business cards, pamphlets or flyers laced with the drug. The use of burundanga (aka scopolamine) impregnated credit cards to attack and to rob isolated people is often propagated by chain emails, although many of these are debunked by sites specialized to do so.
A 2012 example claims small amounts are blown into victims’ faces on the street to turn the victims into “mindless zombies”.
Nevertheless, approximately one in five emergency room admissions for poisoning in Bogotá, Colombia have been attributed to scopolamine. In June 2008, more than 20 people were hospitalized with psychosis in Norway after ingesting counterfeit Rohypnol tablets containing scopolamine.
There have also been reports of tourists being robbed after having scopolamine slipped into their food or drink. Such incidents were reported in Thailand in 2011.
^ a b Putcha, L.; Cintrón, N. M.; Tsui, J.; Vanderploeg, J. M.; Kramer, W. G. (1989). “Pharmacokinetics and Oral Bioavailability of Scopolamine in Normal Subjects”. Pharmacology Research 6 (6): 481–485. doi:10.1023/A:1015916423156. PMID 2762223.
^ Muranaka, T.; Ohkawa, H.; Yamada, Y. (1993). “Continuous Production of Scopolamine by a Culture of Duboisia leichhardtii Hairy Root Clone in a Bioreactor System”. Applied Microbiology and Biotechnology 40 (2–3): 219–223. doi:10.1007/BF00170370.
^ a b The Chambers Dictionary. Allied Publishers. 1998. pp. 788, 1480. ISBN 978-81-86062-25-8.
^ a b White, P. F.; Tang, J.; Song, D. et al. (2007). “Transdermal Scopolamine: An Alternative to Ondansetron and Droperidol for the Prevention of Postoperative and Postdischarge Emetic Symptoms”. Anesthesia and Analgesia 104 (1): 92–96. doi:10.1213/01.ane.0000250364.91567.72. PMID 17179250.
^ Cattell, Henry Ware (1910). Lippincott’s new medical dictionary: a vocabulary of the terms used in medicine, and the allied sciences, with their pronunciation, etymology, and signification, including much collateral information of a descriptive and encyclopedic character. Lippincott. p. 435. Retrieved 25 February 2012.
^ a b c Ziegler, J.; Facchini, P. J. (2008). “Alkaloid Biosynthesis: Metabolism and Trafficking”. Annual Review of Plant Biology 59 (1): 735–769. doi:10.1146/annurev.arplant.59.032607.092730.
^ Li, R.; Reed, D. W.; Liu, E.; Nowak, J.; Pelcher, L. E.; Page, J. E.; Covello, P. S. (2006). “Functional Genomic Analysis of Alkaloid Biosynthesis in Hyoscyamus niger Reveals a Cytochrome P450 Involved in Littorine Rearrangement”. Chemistry & Biology 13 (5): 513–520. doi:10.1016/j.chembiol.2006.03.005.
^ “Transderm Scop patch prescribing information”.
^ Pearce, E. C. (1941). Pearce’s Medical and Nursing Dictionary and Encyclopaedia. Faber & Faber.
^ Bitterman, N.; Eilender, E.; Melamed, Y. (1991). “Hyperbaric Oxygen and Scopolamine”. Undersea Biomedical Research 18 (3): 167–174. PMID 1853467. Retrieved 2008-08-13.
^ Williams, T. H.; Wilkinson, A. R.; Davis, F. M.; Frampton, C. M. (1988). “Effects of Transcutaneous Scopolamine and Depth on Diver Performance”. Undersea Biomedical Research 15 (2): 89–98. PMID 3363755.
^ Greaves, M. W.; Black, A. K.; Eady, R. A.; Coutts, A. (1981). “Aquagenic pruritus”. British Medical Journal (Clinical Research Edition ) 282 (6281): 2008–2010. doi:10.1136/bmj.282.6281.2008. PMC 1505870. PMID 6788168.
^ Graybiel A.; Miller E.F.;Homick J.L. (1973). “Individual differences in susceptibility to motion sickness among six Skylab astronauts”. Acta Astronautica 2 (1-2): 155–174. PMID 11841091.
^ Stepaniak, P.C.; Ramchandani, S.R.; Jones, J.A. (2007). “Acute Urinary Retention Among Astronauts”. Aviation, Space, and Environmental Medicine 78 (Supplement 1): A5-A8. PMID 17511293.
^ Forshew D.A.; Bromberg M.B. (2003). “A survey of clinicians’ practice in the symptomatic treatment of ALS”. Amyotrophic Lateral Sclerosis 4 (4): 258–263. PMID 14753660.
^ David E. Golan, Armen H. Tashjian, Ehrin J. Armstrong (2011). Principles in Pharmacology. Lippincott Williams & Wilkins (LWW). “Scopolamine is frequently used for the prevention and treatment of motion sickness, as an antiemetic, and, in the hospice setting, as an adjunct to end-of-life comfort care medications to effect mild sedation and management of oral secretions.”
^ Furey, M. L.; Drevets, W. C. (2006). “Antidepressant Efficacy of the Antimuscarinic Drug Scopolamine: A Randomized, Placebo-Controlled Clinical Trial”. Archives of General Psychiatry 63 (10): 1121–1129. doi:10.1001/archpsyc.63.10.1121. PMC 3250308. PMID 17015814.
^ Drevets, W. C.; Furey, M. L. (2010). “Replication of Scopolamine’s Antidepressant Efficacy in Major Depressive Disorder: A Randomized, Placebo-Controlled Clinical Trial”. Biological Psychiatry 67 (5): 432–438. doi:10.1016/j.biopsych.2009.11.021. PMC 3264395. PMID 20074703.
^ ClinicalTrials.gov NCT00369915 The Antidepressant Efficacy of the Anticholinergic Scopolamine
^ Freye, E. (2010). “Toxicity of Datura Stramonium”. Pharmacology and Abuse of Cocaine, Amphetamines, Ecstasy and Related Designer Drugs. Netherlands: Springer. pp. 217–218. doi:10.1007/978-90-481-2448-0_34. ISBN 978-90-481-2447-3.
^ House, R. E. (September 1922). “The Use of Scopolamine in Criminology”. Texas State Journal of Medicine 18: 256–263.
reprinted House, R. E. (1931). “The Use of Scopolamine in Criminology”. American Journal of Police Science (Northwestern University) 2 (4): 328–336. doi:10.2307/1147361. JSTOR 1147361.
^ Gazdík, J.; Navara, L. (2009-08-08). “Svědek: Grebeníček vězně nejen mlátil, ale dával jim i drogy [A witness: Grebeníček not only beat prisoners, he also administered drugs to them]” (in Czech). iDnes. Retrieved 2009-08-10.
^ “”Truth” Drugs in Interrogation”. Central Intelligence Agency. Retrieved 14 June 2012.
^ “The Trial of H.H. Crippen” ed. by Filson Young (Notable British Trials series, Hodge, 1920), p. xxvii; see also evidence, pp. 68-77.
^ “Burundanga Business Card Drug Warning”. Hoax-Slayer.com.
^ “Burundanga Drug Warning”. Urban Legends. About.com.
^ “Burundanga Business Card”. Snopes.com.
^ “The most dangerous drug in the world”. dailymail.co.uk.
^ Uribe-Granja, Manuel; Moreno-López, Claudia L.; Zamora S., Adriana; Acosta, Pilar J. (September 2005). “Perfil epidemiológico de la intoxicación con burundanga en la clínica Uribe Cualla S. A. de Bogotá, D. C” (in Spanish) (pdf). Acta Neurológica Colombiana 21 (3): 197–201.
^ “Bilsykemedisin i falske rohypnol-tabletter”. Aftenposten.no.
^ “Thailand”. Travel Advice. US State Department. Retrieved 2011-11-26.
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Categories: DeliriantsEntheogensEpoxidesMind controlMuscarinic antagonistsNatural tropane alkaloidsPlant toxinsPropionates
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