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Revision as of 09:50, 3 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL').← Previous edit Latest revision as of 09:07, 27 December 2024 edit undoJohnbtarrphd (talk | contribs)485 editsm →Chemistry 
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{{Short description|Anticholinergic medication used as antidote for nerve agent poisoning}}
{{Drugbox| Verifiedfields = changed
{{Drugbox
| Watchedfields = changed
| Verifiedfields = changed
| verifiedrevid = 408786288
| Watchedfields = changed
| IUPAC_name = (''RS'')-(8-methyl-8-azabicyclooct-3-yl) 3-hydroxy-2-phenylpropanoate
| verifiedrevid = 458781584
| image = Atropine.svg
| image = Atropine.svg
| image2 = Atropine-D-and-L-isomers-from-DL-xtal-2004-3D-balls.png
| alt =
| width2 = 260
| caption =
| image2 = Atropine-D-and-L-isomers-from-DL-xtal-2004-3D-balls.png
| width2 = 260
| alt2 = <!--Clinical data-->
| tradename = Atropen, others
| synonyms = Daturin<ref>{{cite book|url=https://archive.org/details/mobot31753000788254 |page= |title=Medical Flora; Or, Manual of the Medical Botany of the United States of ... - Constantine Samuel Rafinesque - Internet Archive |publisher=Atkinson & Alexander |access-date=2012-11-07|year=1828| vauthors = Rafinesque CS }}</ref>
| Drugs.com = {{drugs.com|monograph|atropine}}
| MedlinePlus = a682487
| licence_EU =
| licence_US =
| DailyMedID = Atropine
| pregnancy_AU = A
| routes_of_administration = ], ], ], ], ]
| class = ] (anticholinergic)
| ATC_prefix = A03
| ATC_suffix = BA01
| ATC_supplemental = {{ATC|S01|FA01}}


<!-- Legal status -->| pregnancy_category =
<!--Clinical data-->
| legal_AU = S4
| tradename = Atropen
| legal_AU_comment =<ref>{{cite web | title=AusPAR: Atropine sulfate monohydrate | website=Therapeutic Goods Administration (TGA) | date=31 May 2022 | url=https://www.tga.gov.au/auspar/auspar-atropine-sulfate-monohydrate | access-date=12 June 2022 | archive-date=31 May 2022 | archive-url=https://web.archive.org/web/20220531202918/http://www.tga.gov.au/auspar/auspar-atropine-sulfate-monohydrate | url-status=live }}</ref>
| Drugs.com = {{drugs.com|monograph|atropine}}
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| MedlinePlus = a682487
| pregnancy_US = C | legal_BR_comment =
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_status = R<sub>x</sub> only
| legal_CA_comment =
| routes_of_administration = Oral, ], ], rectal
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment =
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_UK_comment =
| legal_US = Rx-only
| legal_US_comment =<ref name="Atropine sulfate FDA label" /><ref>{{cite web | title=Atropine- atropine sulfate solution/ drops | website=DailyMed | date=22 February 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=127a7e32-a150-01d6-a66a-b7708d85809f | access-date=16 March 2022 | archive-date=16 March 2022 | archive-url=https://web.archive.org/web/20220316210929/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=127a7e32-a150-01d6-a66a-b7708d85809f | url-status=live }}</ref>
| legal_EU =
| legal_EU_comment =
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment =
| legal_status = <!-- For countries not listed above -->


<!--Pharmacokinetic data--> <!-- Pharmacokinetic data -->| bioavailability = 25%
| metabolism = ≥50% ]d to ] and ]
| bioavailability = 25%
| onset = c. 1 minute<ref name=Bar2009/>
| metabolism = 50% ]d to ] and ]
| elimination_half-life = 2 hours | elimination_half-life = 2 hours
| duration_of_action = 30 to 60 min<ref name=Bar2009/>
| excretion = 50% excreted unchanged in urine
| excretion = 15–50% excreted unchanged in urine


<!--Identifiers--> <!--Identifiers-->| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 51-55-8
| CAS_number_Ref = {{cascite|correct|??}}
| PubChem = 174174
| CAS_number = 51-55-8
| IUPHAR_ligand = 320
| ATC_prefix = A03
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| ATC_suffix = BA01
| DrugBank = DB00572
| ATC_supplemental = {{ATC|S01|FA01}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| PubChem = 174174
| ChemSpiderID = 10194105
| IUPHAR_ligand = 320
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7C0697DR9I
| DrugBank = DB00572
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00113
| ChemSpiderID = 10194105
| UNII_Ref = {{fdacite|correct|FDA}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16684
| UNII = 7C0697DR9I
| ChEMBL_Ref =
| KEGG_Ref = {{keggcite|correct|kegg}}
| ChEMBL = 517712
| KEGG = D00113

| ChEBI_Ref = {{ebicite|changed|EBI}}
<!--Chemical data-->| drug_name =
| ChEBI = 16684
| type =
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| IUPAC_name = (''RS'')-(8-Methyl-8-azabicyclooct-3-yl) 3-hydroxy-2-phenylpropanoate
| ChEMBL = <!-- blanked - oldvalue: 195 -->
| C=17 | H=23 | N=1 | O=3 | C = 17
| H = 23
| molecular_weight = 289.369
| N = 1
| smiles = CN31CC3C(C1)OC(=O)C(CO)c2ccccc2
| O = 3
| InChI = 1/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16?
| smiles = CN31CC3C(C1)OC(=O)C(CO)c2ccccc2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16?
| StdInChI = 1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16?
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RKUNBYITZUJHSG-SPUOUPEWSA-N
| StdInChIKey = RKUNBYITZUJHSG-SPUOUPEWSA-N
}} }}
<!-- Definition and medical uses -->
'''Atropine''' is a naturally occurring ] extracted from ] (''Atropa belladonna''), ] (''Datura stramonium''), ] (''Mandragora officinarum'') and other plants of the family ]. It is a ] of these plants and serves as a ] with a wide variety of effects. It is a ] for the ]. It is classified as an ] (]). The species name "belladonna" comes from the original use of deadly nightshade as a way of dilating women's pupils to make them beautiful. Both atropine and the genus name for deadly nightshade derive from ], one of the three ] who, according to Greek mythology, chose how a person was to die. Atropine is a ''core'' medicine in the ]'s "]", which is a list of minimum medical needs for a basic health care system.<ref name="essentialWHO">{{cite web
'''Atropine''' is a ] and ] medication used to treat certain types of ] and ]s as well as some types of ], and to decrease ] production during surgery.<ref name=AHFS2015>{{cite web|title=Atropine|url=https://www.drugs.com/monograph/atropine.html|publisher=The American Society of Health-System Pharmacists|access-date=Aug 13, 2015|url-status=live|archive-url=https://web.archive.org/web/20150712191611/http://www.drugs.com/monograph/atropine.html|archive-date=2015-07-12}}</ref> It is typically given ] or by injection ].<ref name=AHFS2015/> ] are also available which are used to treat ] and early ].<ref name=Ric2014>{{cite book| vauthors = Hamilton RJ, Duffy AN, Stone D, Spencer A |title=Tarascon pharmacopoeia|date=2014|isbn=9781284056716|page=386|publisher=Jones & Bartlett Publishers |edition=15|url=https://books.google.com/books?id=F6YdAwAAQBAJ&pg=PA386|url-status=live|archive-url=https://web.archive.org/web/20151002131018/https://books.google.ca/books?id=F6YdAwAAQBAJ&pg=PA386|archive-date=2015-10-02}}</ref><ref name="National Eye Institute 2019">{{cite web | title=Amblyopia (Lazy Eye) | website=National Eye Institute | date=2019-07-02 | url=https://www.nei.nih.gov/learn-about-eye-health/eye-conditions-and-diseases/amblyopia-lazy-eye | access-date=2020-01-31 | quote=Putting special eye drops in the stronger eye. A once-a-day drop of the drug atropine can temporarily blur near vision, which forces the brain to use the other eye. For some children, this treatment works as well as an eye patch, and some parents find it easier to use (for example, because young children may try to pull off eye patches). | archive-date=2020-01-31 | archive-url=https://web.archive.org/web/20200131061230/https://www.nei.nih.gov/learn-about-eye-health/eye-conditions-and-diseases/amblyopia-lazy-eye | url-status=live }}</ref> The intravenous solution usually begins working within a minute and lasts half an hour to an hour.<ref name=Bar2009>{{cite book| vauthors = Barash PG |title=Clinical anesthesia|date=2009|publisher=Wolters Kluwer/Lippincott Williams & Wilkins|location=Philadelphia|isbn=9780781787635|page=525|edition=6th|url=https://books.google.com/books?id=-YI9P2DLe9UC&pg=PA525|url-status=live|archive-url=https://web.archive.org/web/20151124084028/https://books.google.ca/books?id=-YI9P2DLe9UC&pg=PA525|archive-date=2015-11-24}}</ref> Large doses may be required to treat some poisonings.<ref name=AHFS2015/>
| year = March 2005
| url = http://whqlibdoc.who.int/hq/2005/a87017_eng.pdf
| title = WHO Model List of Essential Medicines
| format = PDF
| publisher = World Health Organization
| accessdate = 2006-03-12
}}</ref>


== Physiological effects and uses == <!-- Side effects and mechanism -->
Common ] include ], ], ], ], and a ].<ref name=AHFS2015/> It should generally not be used in people with ].<ref name=AHFS2015/> While there is no evidence that its use during pregnancy causes ], this has not been well studied so sound clinical judgment should be used.<ref name=Breast2015/> It is likely safe during breastfeeding.<ref name=Breast2015>{{cite web|title=Atropine Pregnancy and Breastfeeding Warnings|url=https://www.drugs.com/pregnancy/atropine.html|access-date=14 August 2015|url-status=live|archive-url=https://web.archive.org/web/20150906151324/http://www.drugs.com/pregnancy/atropine.html|archive-date=6 September 2015}}</ref> It is an ] (a type of anticholinergic) that works by inhibiting the ].<ref name=AHFS2015/>


<!-- History, society and culture -->
Atropine increases firing of the ] (SA) and conduction through the ] (AV) of the ], opposes the actions of the ], blocks ] ] sites, and decreases ] ]s.
Atropine occurs naturally in a number of plants of the ], including ] (belladonna), ], and ].<ref>{{cite book| vauthors = Brust JC |title=Neurological aspects of substance abuse|date=2004|publisher=Elsevier|location=Philadelphia|isbn=9780750673136|page=310|edition=2|url=https://books.google.com/books?id=fOfxoQm_a7MC&pg=PA310|url-status=live|archive-url=https://web.archive.org/web/20151002123816/https://books.google.ca/books?id=fOfxoQm_a7MC&pg=PA310|archive-date=2015-10-02}}</ref> It was first isolated in 1833,<ref>{{cite book| vauthors = Ainsworth S |title=Neonatal Formulary: Drug Use in Pregnancy and the First Year of Life|date=2014|publisher=John Wiley & Sons|isbn=9781118819593|page=94|url=https://books.google.com/books?id=VOLhBQAAQBAJ&pg=PA94|url-status=live|archive-url=https://web.archive.org/web/20151002140026/https://books.google.ca/books?id=VOLhBQAAQBAJ&pg=PA94|archive-date=2015-10-02}}</ref> It is on the ].<ref name="WHO22nd">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }}</ref> It is available as a ].<ref name=AHFS2015/><ref>{{cite book| vauthors = Hamilton RJ |title=Tarascon pharmacopoeia|date=2014|isbn=9781284056716|page=386|publisher=Jones & Bartlett Publishers |edition=15|url=https://books.google.com/books?id=F6YdAwAAQBAJ&pg=PA386|url-status=live|archive-url=https://web.archive.org/web/20151002131018/https://books.google.ca/books?id=F6YdAwAAQBAJ&pg=PA386|archive-date=2015-10-02}}</ref><ref>{{cite web | title=Competitive Generic Therapy Approvals | website=U.S. ] (FDA) | date=29 June 2023 | url=https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | access-date=29 June 2023 | archive-date=29 June 2023 | archive-url=https://web.archive.org/web/20230629233651/https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | url-status=live }}</ref>


== Medical uses ==
In general, atropine lowers the ] activity of all ]s and ]s regulated by the ]. This occurs because atropine is a ] of the muscarinic ]s (] being the main ] used by the ] nervous system). Therefore, it may cause swallowing difficulties and reduced secretions.
] containing atropine injection 0.5mg/1mL]]


=== Ophthalmic use === === Eyes ===
] atropine is used as a ], to temporarily paralyze the ], and as a ], to dilate the ]s. Atropine degrades slowly, typically wearing off in 7 to 14 days, so it is generally used as a therapeutic ], whereas ] (a shorter-acting ] antagonist) or ] (an α-adrenergic agonist) is preferred as an aid to ] examination. Atropine induces ] by blocking contraction of the circular ] muscle, which is normally stimulated by acetylcholine release, thereby allowing the radial ] ] to contract and dilate the ]. Atropine induces ] by paralyzing the ]s, whose action inhibits accommodation to allow accurate refraction in children, helps to relieve pain associated with ], and treats ciliary block (malignant) ]. Atropine is ] in patients pre-disposed to narrow angle ]. ] atropine is used as a ], to temporarily paralyze the ], and as a ], to dilate the ]s.<ref name="pmid29132914"/> Atropine degrades slowly, typically wearing off in 7 to 14 days, so it is generally used as a therapeutic ], whereas ] (a shorter-acting ] antagonist) or ] (an α-adrenergic agonist) is preferred as an aid to ] examination.<ref name="pmid29132914">{{cite journal | vauthors = Yazdani N, Sadeghi R, Momeni-Moghaddam H, Zarifmahmoudi L, Ehsaei A | title = Comparison of cyclopentolate versus tropicamide cycloplegia: A systematic review and meta-analysis | journal = Journal of Optometry | volume = 11 | issue = 3 | pages = 135–143 | date = 2018 | pmid = 29132914 | pmc = 6039578 | doi = 10.1016/j.optom.2017.09.001 }}</ref>


In refractive and accommodative ], when occlusion is not appropriate sometimes atropine is given to induce blur in the good eye.<ref>{{cite journal | vauthors = Georgievski Z, Koklanis K, Leone J | year = 2008 | title = Fixation behavior in the treatment of amblyopia using atropine | journal = Clinical and Experimental Ophthalmology | volume = 36 | issue = Suppl 2| pages = A764–A765 }}</ref> Evidence suggests that atropine penalization is just as effective as occlusion in improving visual acuity.<ref>{{Cite journal |last= |date=2019-12-05 |title=A patch or eye drops are similarly effective for the treatment of "lazy eye" in children |url=https://evidence.nihr.ac.uk/alert/a-patch-or-eye-drops-are-similarly-effective-for-the-treatment-of-lazy-eye-in-children |journal=NIHR Evidence |type=Plain English summary |publisher=National Institute for Health and Care Research |doi=10.3310/signal-000849 |s2cid=243130859 |access-date=2022-09-16 |archive-date=2024-05-26 |archive-url=https://web.archive.org/web/20240526050121/https://evidence.nihr.ac.uk/alert/a-patch-or-eye-drops-are-similarly-effective-for-the-treatment-of-lazy-eye-in-children/ |url-status=live }}</ref><ref>{{cite journal | vauthors = Li T, Qureshi R, Taylor K | title = Conventional occlusion versus pharmacologic penalization for amblyopia | journal = The Cochrane Database of Systematic Reviews | volume = 8 | pages = CD006460 | date = August 2019 | issue = 8 | pmid = 31461545 | pmc = 6713317 | doi = 10.1002/14651858.CD006460.pub3 }}</ref>
Atropine can be given to patients who have direct globe trauma.


Antimuscarinic topical medication is effective in slowing myopia progression in children; accommodation difficulties and papillae and follicles are possible side effects.<ref>{{Cite journal|vauthors=Walline JJ, Lindsley KB, Vedula SS, Cotter SA, Mutti DO, Ng SM, Twelker JD|date=13 Jan 2020|title=Interventions to slow progression of myopia in children|journal=Cochrane Database Syst Rev|volume=1|issue=9|pages=CD004916|doi=10.1002/14651858.CD004916.pub4|pmid=31930781|pmc=6984636}}</ref> All doses of atropine appear similarly effective, while higher doses have greater side effects.<ref name="Gong2017">{{cite journal | vauthors = Gong Q, Janowski M, Luo M, Wei H, Chen B, Yang G, Liu L | title = Efficacy and Adverse Effects of Atropine in Childhood Myopia: A Meta-analysis | journal = JAMA Ophthalmology | volume = 135 | issue = 6 | pages = 624–630 | date = June 2017 | pmid = 28494063 | pmc = 5710262 | doi = 10.1001/jamaophthalmol.2017.1091 }}</ref> The lower dose of 0.01% is thus generally recommended due to fewer side effects and potential less rebound worsening when the atropine is stopped.<ref name="Gong2017" /><ref>{{cite journal | vauthors = Fricke T, Hurairah H, Huang Y, Ho SM | title = Pharmacological interventions in myopia management | journal = Community Eye Health | volume = 32 | issue = 105 | pages = 21–22 | date = 2019 | pmid = 31409953 | pmc = 6688412 }}</ref>
=== Resuscitation ===
]s of atropine are used in the treatment of ] (an extremely low heart rate). Atropine blocks the action of the ], a part of the parasympathetic system of the heart whose main action is to decrease heart rate. Therefore, its primary function in this circumstance is to increase the heart rate. Atropine was previously included in international resuscitation guidelines for use in cardiac arrest associated with ] and ], but was removed from these guidelines in 2010 due to a lack of evidence.<ref>{{cite journal |author=Field JM, Hazinski MF, Sayre MR, ''et al.'' |title=Part 1: executive summary: 2010 American Heart Association Guidelines for Cardiopulmonary Resuscitation and Emergency Cardiovascular Care |journal=Circulation |volume=122 |issue=18 Suppl 3 |pages=S640–56 |year=2010 |month=November |pmid=20956217 |doi=10.1161/CIRCULATIONAHA.110.970889 |url=http://circ.ahajournals.org/cgi/content/full/122/18_suppl_3/S640}}</ref> For symptomatic bradycardia, the usual dosage is 0.5 to 1&nbsp;mg IV push, may repeat every 3 to 5 minutes up to a maximum dose of 3&nbsp;mg.<ref>* {{cite book | first =Bledsoe | last =Bryan E | authorlink = | coauthors = Robert S. Porter, Richard A. Cherry | year = 2004| month = | title = Intermediate Emergency Care | chapter = Ch. 3| editor = | others = | edition = | pages = 260 | publisher = Pearson Prentice Hill| location =Upper Saddle River, NJ | isbn = 0-13-113607-0| url = }}</ref>


=== Heart ===
Atropine is also useful in treating ], and also ] with a high ] or ] ]. It is usually not effective in ], and in third-degree heart block with a low Purkinje or ventricular escape rhythm. Atropine is contraindicated in ]-induced conduction block, because the drug increases ] demand of the AV nodal tissue, thereby aggravating ischemia and the resulting ].
]s of atropine are used in the treatment of symptomatic or unstable ].


Atropine was previously included in international resuscitation guidelines for use in cardiac arrest associated with ] and ] but was removed from these guidelines in 2010 due to a lack of evidence for its effectiveness.<ref>{{cite journal | vauthors = Field JM, Hazinski MF, Sayre MR, Chameides L, Schexnayder SM, Hemphill R, Samson RA, Kattwinkel J, Berg RA, Bhanji F, Cave DM, Jauch EC, Kudenchuk PJ, Neumar RW, Peberdy MA, Perlman JM, Sinz E, Travers AH, Berg MD, Billi JE, Eigel B, Hickey RW, Kleinman ME, Link MS, Morrison LJ, O'Connor RE, Shuster M, Callaway CW, Cucchiara B, Ferguson JD, Rea TD, Vanden Hoek TL | display-authors = 6 | title = Part 1: executive summary: 2010 American Heart Association Guidelines for Cardiopulmonary Resuscitation and Emergency Cardiovascular Care | journal = Circulation | volume = 122 | issue = 18 Suppl 3 | pages = S640-56 | date = November 2010 | pmid = 20956217 | doi = 10.1161/CIRCULATIONAHA.110.970889 | s2cid = 1031566 | doi-access = }}</ref> For symptomatic bradycardia, the usual dosage is 0.5 to 1&nbsp;mg IV push; this may be repeated every 3 to 5 minutes, up to a total dose of 3&nbsp;mg (maximum 0.04&nbsp;mg/kg).<ref>* {{cite book | vauthors = Bledsoe BE, Porter RS, Cherry RA | year = 2004| title = Intermediate Emergency Care | chapter = Ch. 3| page = 260 | publisher = Pearson Prentice Hill| location =Upper Saddle River, NJ | isbn = 0-13-113607-0}}</ref>
One of the main actions of the ] is to stimulate the ] in the heart, but atropine inhibits this action.


Atropine is also useful in treating ], and also ] with a high ] or ] ]. It is usually not effective in ], and in ] with a low Purkinje or ventricular escape rhythm.{{citation needed|date=January 2022}}
=== Secretions and bronchoconstriction ===
Atropine's actions on the parasympathetic nervous system inhibits salivary and mucus glands. The drug may also inhibit sweating via the sympathetic nervous system. This can be useful in treating ], and can prevent the ] of dying patients. Even though atropine has not been officially indicated for either of these purposes by the FDA, it has been used by physicians for these purposes.<ref></ref>


Atropine has also been used to prevent a low heart rate during ] of children; however, the evidence does not support this use.<ref>{{cite journal | vauthors = de Caen AR, Berg MD, Chameides L, Gooden CK, Hickey RW, Scott HF, Sutton RM, Tijssen JA, Topjian A, van der Jagt ÉW, Schexnayder SM, Samson RA | display-authors = 6 | title = Part 12: Pediatric Advanced Life Support: 2015 American Heart Association Guidelines Update for Cardiopulmonary Resuscitation and Emergency Cardiovascular Care | journal = Circulation | volume = 132 | issue = 18 Suppl 2 | pages = S526-42 | date = November 2015 | pmid = 26473000 | pmc = 6191296 | doi = 10.1161/cir.0000000000000266 }}</ref>
=== Treatment for organophosphate poisoning ===
Atropine is not an actual antidote for organophosphate poisoning. However, by blocking the action of ] at ] receptors, atropine also serves as a treatment for poisoning by ] ]s and ]es, such as ] (GA), ] (GB), ] (GD) and ]. Troops who are likely to be attacked with ]s often carry ]s with atropine and ], which can be quickly injected into the ]. Atropine is often used in conjunction with ].


=== Secretions ===
Atropine is given as a treatment for ] (], ], ], ], ] motility, ]) symptoms caused by organophosphate poisoning. Another mnemonic is DUMBBELSS, which stands for diarrhea, urination, miosis, bradycardia, bronchoconstriction, excitation (as of muscle in the form of fasciculations and CNS), lacrimation, salivation, and sweating (only sympathetic innervation using Musc receptors).
Atropine's actions on the parasympathetic nervous system inhibit salivary and mucous glands. The drug may also inhibit sweating via the sympathetic nervous system. This can be useful in treating ], and can prevent the ] of dying patients. Even though atropine has not been officially indicated for either of these purposes by the FDA, it has been used by physicians for these purposes.<ref>{{cite web | title=Death Rattle and Oral Secretions, 2nd ed | website=eperc.mcw.edu | url=http://www.eperc.mcw.edu/EPERC/FastFactsIndex/ff_109.htm | archive-url=https://web.archive.org/web/20140414033606/http://www.eperc.mcw.edu/EPERC/FastFactsIndex/ff_109.htm | archive-date=2014-04-14 | url-status=dead | access-date=2019-10-20}}</ref>


=== Poisonings ===
Some of the nerve agents attack and destroy ] by phosphorylation, so the action of acetylcholine becomes prolonged, pralidoxime (2-PAM) is the cure for organophosphate poisoning because it can cleave this phosphorylation. Atropine can be used to reduce the effect of the poisoning by blocking muscarinic acetylcholine receptors, which would otherwise be overstimulated by excessive acetylcholine accumulation.
Atropine is not an actual ] for ]. However, by blocking the action of ] at ] receptors, atropine also serves as a treatment for poisoning by ] ]s and ]s, such as ] (GA), ] (GB), ] (GD), and ]. Troops who are likely to be attacked with ]s often carry ]s with atropine and ], for rapid injection into the muscles of the thigh. In a developed case of nerve gas poisoning, maximum atropinization is desirable. Atropine is often used in conjunction with the oxime ].


Some of the nerve agents attack and destroy ] by ], so the action of acetylcholine becomes excessive and prolonged. Pralidoxime (2-PAM) can be effective against organophosphate poisoning because it can re-cleave this phosphorylation. Atropine can be used to reduce the effect of the poisoning by blocking muscarinic acetylcholine receptors, which would otherwise be overstimulated, by excessive acetylcholine accumulation.
=== Optical penalisation ===
In refractive and accommodative ], when occlusion is not appropriate sometimes atropine is given to induce blur in the good eye.<ref>Georgievski Z, Koklanis K, Leone J. Fixation behaviour in the treatment of amblyopia using atropine. Clinical and Experimental Ophthalmology 2008; 36 (Suppl 2): A764–A765.</ref>


Atropine or ] can be used to treat ] intoxication.{{medcn|date=March 2022}}
=== Side-effects and overdose ===
Adverse reactions to atropine include ventricular ], supraventricular or ventricular ], ], ], blurred vision, loss of balance, dilated pupils, ], dry mouth and potentially extreme ], dissociative ]s and ] especially amongst the elderly. These latter effects are because atropine is able to cross the ]. Because of the ] properties, some have used the drug ], though this is potentially dangerous and often unpleasant.


Atropine was added to cafeteria salt shakers in an attempt to poison the staff of ] during the ].<ref>The Battle Over Hearts and Minds
In overdoses, atropine is ]ous. Atropine is sometimes added to potentially addictive drugs, particularly anti-diarrhea opioid drugs such as ] or ], wherein the secretion-reducing effects of the atropine can also aid the anti-diarrhea effects.
A Cold War of Spies: Episode 4 |https://www.imdb.com/title/tt27484449/?ref_=ttep_ep4 {{Webarchive|url=https://web.archive.org/web/20240526050120/https://www.imdb.com/title/tt27484449/?ref_=ttep_ep4 |date=2024-05-26 }}</ref><ref>{{cite web | url=https://www.pbsamerica.co.uk/series/a-cold-war-of-spies/#7749 | title=A Cold War of Spies {{pipe}} PBS America {{pipe}} UK | access-date=2024-02-11 | archive-date=2024-02-16 | archive-url=https://web.archive.org/web/20240216182829/https://www.pbsamerica.co.uk/series/a-cold-war-of-spies/#7749 | url-status=live }}</ref>


=== Irinotecan-induced diarrhea ===
Although atropine treats ] (slow heart rate) in emergency settings, it can cause paradoxical heart rate slowing when given at very low doses, presumably as a result of central action in the CNS.<ref>* {{cite book | first = | last =Rang HP, Dale MM, Ritter JM, Flower RJ| authorlink = | coauthors = | year = 2007| month = | title = Rang and Dale's Pharmacology | chapter = Ch. 10| editor = | others = | edition = | pages = 153 | publisher = Elsevier Churchill Livingstone| location = | isbn = 0-443-06911-5| url = }}</ref>
Atropine has been observed to prevent or treat ] induced acute diarrhea.<ref>{{cite journal | vauthors = Yumuk PF, Aydin SZ, Dane F, Gumus M, Ekenel M, Aliustaoglu M, Karamanoglu A, Sengoz M, Turhal SN | display-authors = 6 | title = The absence of early diarrhea with atropine premedication during irinotecan therapy in metastatic colorectal patients | journal = International Journal of Colorectal Disease | volume = 19 | issue = 6 | pages = 609–610 | date = November 2004 | pmid = 15293062 | doi = 10.1007/s00384-004-0613-5 | s2cid = 11784173 }}</ref>


==Side effects==
Atropine is incapacitating at doses of 10 to 20&nbsp;mg per person. Its LD<sub>50</sub> is estimated to be 453&nbsp;mg per person (per oral) with a probit slope of 1.8.<ref>* {{cite book | first = | last =Goodman E| authorlink = | coauthors = | year = 2010| month = | title = Historical Contributions to the Human Toxicology of Atropine | chapter = | editor = Ketchum J, Kirby R| others = | edition = | pages = 120 | publisher = Eximdyne| location = | isbn = 978-0-9677264-3-4| url = }}</ref>
Adverse reactions to atropine include ventricular ], supraventricular or ], ], ], blurred vision, loss of balance, dilated pupils, ], dry mouth and potentially extreme ], deliriant ]s, and ] especially among the elderly. These latter effects are because atropine can cross the ]. Because of the ] properties, some have used the drug ], though this is potentially dangerous and often unpleasant.{{medcn|date=December 2015}}
The antidote to atropine is ] or ].


In overdoses, atropine is ]ous.{{medcn|date=March 2022}} Atropine is sometimes added to potentially addictive drugs, particularly antidiarrhea opioid drugs such as ] or ], wherein the secretion-reducing effects of the atropine can also aid the antidiarrhea effects.{{medcn|date=March 2022}}
A common ] used to describe the physiologic manifestations of atropine overdose is: as per Jon Blinkey "hot as a hare, blind as a bat, dry as a bone, red as a beet, and mad as a hatter".<ref name="holzman">{{cite journal|url=http://www.anesthesiology.org/pt/re/anes/fulltext.00000542-199807000-00030.htm;jsessionid=GSJKLv9vLCdQSmpp6vH3xdhnzWN1hy3s7JqMNFpWkHhLbKJT5vLM!741375937!-949856145!8091!-1#P89|title=The Legacy of Atropos|author=Robert S. Holzman, MD|journal=Anesthesiology|volume=89|issue=1|date=1998-07|pages=241–249|accessdate=2007-05-21|pmid=9667313}} citing J. Arena, Poisoning: Toxicology-Symptoms-Treatments, 3rd edition. Springfield, Charles C. Thomas, 1974, p 345</ref> These associations reflect the specific changes of warm, dry skin from decreased sweating, blurry vision, decreased sweating/lacrimation, vasodilation, and central nervous system effects on ] receptors, type 4 and 5. This set of symptoms is known as ], and may also be caused by other drugs with anticholinergic effects, such as ], ] ]s and ].<ref>{{cite web | url = http://www.intox.org/databank/documents/treat/treate/trt05_e.htm | title = Acute anticholinergic syndrome | author = Szajewski J | year = 1995 | publisher = IPCS Intox Databank | accessdate = 2007-05-22}}</ref>


Although atropine treats ] (slow heart rate) in emergency settings, it can cause paradoxical heart rate slowing when given at very low doses (i.e. <0.5&nbsp;mg),<ref>{{cite web |url=http://www.uptodate.com/contents/atropine-drug-information |title=Atropine Drug Information|url-access=subscription |website=uptodate.com|access-date=2014-02-02 |url-status=live |archive-url=https://web.archive.org/web/20140220062212/http://www.uptodate.com/contents/atropine-drug-information?source=search_result&search=atropine&selectedTitle=1~150 |archive-date=2014-02-20 }}</ref> presumably as a result of central action in the CNS.<ref>* {{cite book |vauthors=Rang HP, Dale MM, Ritter JM, Flower RJ | year = 2007| title = Rang and Dale's Pharmacology |url=https://archive.org/details/rangdalespharmac0006dale |url-access=registration | chapter = Ch. 10| page = | publisher = Elsevier Churchill Livingstone| isbn = 978-0-443-06911-6}}</ref> One proposed mechanism for atropine's paradoxical bradycardia effect at low doses involves blockade of inhibitory presynaptic muscarinic ]s, thereby blocking a system that inhibits the parasympathetic response.<ref>{{cite book| vauthors = Laurence B |title=Goodman & Gilman's Pharmacological Basis of Therapeutics, 12th Edition|date=2010|publisher=McGraw-Hill|isbn=978-0-07-162442-8}}</ref>
== Chemistry and pharmacology==
Atropine is a ] mixture of ]-] and ''l''-hyoscyamine, with most of its physiological effects due to ''l''-hyoscyamine. Its pharmacological effects are due to binding to muscarinic ]s. It is an antimuscarinic agent. Significant levels are achieved in the CNS within 30 minutes to 1 hour and disappears rapidly from the blood with a half-life of 2 hours. About 60% is excreted unchanged in the urine, most of the rest appears in urine as hydrolysis and conjugation products. Effects on the iris and ciliary muscle may persist for longer than 72 hours.


Atropine is incapacitating at doses of 10 to 20&nbsp;mg per person. Its LD<sub>50</sub> is estimated to be 453&nbsp;mg per person (by mouth) with a probit slope of 1.8.<ref>* {{cite book | vauthors = Goodman E | year = 2010| title = Historical Contributions to the Human Toxicology of Atropine |veditors=Ketchum J, Kirby R | page = 120 | publisher = Eximdyne| isbn = 978-0-9677264-3-4}}</ref>
The most common atropine compound used in medicine is atropine ] (]<sub>17</sub>]<sub>23</sub>]]<sub>3</sub>)<sub>2</sub>·]·], the full chemical name is 1α H, 5α H-Tropan-3-α ol (±)-tropate(ester), sulfate monohydrate.
The antidote to atropine is ] or ].{{medcn|date=March 2022}}


A common ] used to describe the physiologic manifestations of atropine overdose is: "hot as a hare, blind as a bat, dry as a bone, red as a beet, and mad as a hatter".<ref name="holzman">{{cite journal | vauthors = Holzman RS | title = The legacy of Atropos, the fate who cut the thread of life | journal = Anesthesiology | volume = 89 | issue = 1 | pages = 241–9 | date = July 1998 | pmid = 9667313 | doi = 10.1097/00000542-199807000-00030 | url = http://www.anesthesiology.org/pt/re/anes/fulltext.00000542-199807000-00030.htm;jsessionid=GSJKLv9vLCdQSmpp6vH3xdhnzWN1hy3s7JqMNFpWkHhLbKJT5vLM!741375937!-949856145!8091!-1#P89 | access-date = 2007-05-21 | s2cid = 28327277 | doi-access = free }} citing J. Arena, Poisoning: Toxicology-Symptoms-Treatments, 3rd edition. Springfield, Charles C. Thomas, 1974, p 345</ref> These associations reflect the specific changes of warm, dry skin from decreased sweating, blurry vision, decreased lacrimation, vasodilation, and central nervous system effects on ] receptors, type 4 and 5. This set of symptoms is known as ], and may also be caused by other drugs with anticholinergic effects, such as ] (scopolamine), ], ] ]s and ].<ref>{{cite web | url = http://www.intox.org/databank/documents/treat/treate/trt05_e.htm | title = Acute anticholinergic syndrome | author = Szajewski J | year = 1995 | publisher = IPCS Intox Databank | access-date = 2007-05-22| archive-url= https://web.archive.org/web/20070702175337/http://www.intox.org/databank/documents/treat/treate/trt05_e.htm| archive-date= 2 July 2007 | url-status= live}}</ref>
The vagus (parasympathetic) nerves that innervate the heart release acetylcholine (ACh) as their primary neurotransmitter. ACh binds to muscarinic receptors (M2) that are found principally on cells comprising the sinoatrial (SA) and atrioventricular (AV) nodes. Muscarinic receptors are coupled to the Gi-protein; therefore, vagal activation decreases cAMP. Gi-protein activation also leads to the activation of KACh channels that increase potassium efflux and hyperpolarizes the cells.


==Contraindications==
Increases in vagal activity to the SA node decreases the firing rate of the pacemaker cells by decreasing the slope of the pacemaker potential (phase 4 of the action potential); this decreases heart rate (negative chronotropy). The change in phase 4 slope results from alterations in potassium and calcium currents, as well as the slow-inward sodium current that is thought to be responsible for the pacemaker current (If). By hyperpolarizing the cells, vagal activation increases the cell's threshold for firing, which contributes to the reduction the firing rate. Similar electrophysiological effects also occur at the AV node; however, in this tissue, these changes are manifested as a reduction in impulse conduction velocity through the AV node (negative dromotropy). In the resting state, there is a large degree of vagal tone on the heart, which is responsible for low resting heart rates.
It is generally ] in people with ], ], or ], except in doses ordinarily used for preanesthesia.<ref name="Atropine sulfate FDA label">{{cite web |title=Atropine sulfate |url=https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=910cb308-36c6-4330-8f25-45998ec3cde7 |website=dailymed.nlm.nih.gov |publisher=U.S. National Library of Medicine |access-date=30 October 2019 |archive-date=26 July 2020 |archive-url=https://web.archive.org/web/20200726132945/https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=910cb308-36c6-4330-8f25-45998ec3cde7 |url-status=live }}</ref>


==Chemistry==
There is also some vagal innervation of the atrial muscle, and to a much lesser extent, the ventricular muscle. Vagus activation, therefore, results in modest reductions in atrial contractility (inotropy) and even smaller decreases in ventricular contractility.
{{More medical citations needed|date=January 2022}}
Atropine, a ], is an ]ic mixture of '']''-] and ''l''-hyoscyamine<ref name="PubChem">{{cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/Atropine_-sulfate-_2_1 | title=PubChem: Atropine, sulfate (2:1) | publisher=National Library of Medicine, National Institutes of Health }}</ref>, with most of its physiological effects due to ''l''-hyoscyamine, the 3(S)-endo isomer of atropine. Its pharmacological effects are due to binding to ]s. It is an antimuscarinic agent. Significant levels are achieved in the CNS within 30 minutes to 1 hour and disappear rapidly from the blood with a half-life of 2 hours. About 60% is excreted unchanged in the urine, and most of the rest appears in the urine as hydrolysis and conjugation products. Noratropine (24%), atropine-N-oxide (15%), tropine (2%), and tropic acid (3%) appear to be the major metabolites, while 50% of the administered dose is excreted as apparently unchanged atropine. No conjugates were detectable. Evidence that atropine is present as (+)-hyoscyamine was found, suggesting that stereoselective metabolism of atropine probably occurs.<ref>{{cite journal | vauthors = Van der Meer MJ, Hundt HK, Müller FO | title = The metabolism of atropine in man | journal = The Journal of Pharmacy and Pharmacology | volume = 38 | issue = 10 | pages = 781–4 | date = October 1986 | pmid = 2879005 | doi = 10.1111/j.2042-7158.1986.tb04494.x | s2cid = 27306334 }}</ref> Effects on the iris and ciliary muscle may persist for longer than 72 hours.

The most common atropine compound used in medicine is atropine ] (monohydrate) ({{chem|]|17|]|23|]|]|3}})<sub>2</sub>·]·], the full chemical name is 1α H, 5α H-Tropan-3-α ol (±)-tropate(ester), sulfate monohydrate.

==Pharmacology==
{{More medical citations needed|date=January 2022}}
In general, atropine counters the "rest and digest" activity of ]s regulated by the ], producing clinical effects such as increased heart rate and delayed gastric emptying. This occurs because atropine is a competitive, reversible antagonist of the ]s (] being the main ] used by the parasympathetic nervous system).

Atropine is a ] of the ] types ], ], ], ] and ].<ref>{{cite book | vauthors = Rang HP, Dale MM, Ritter JM, Moore P |title=Pharmacology |page=139 |publisher=Elsevier |year=2003 | isbn = 978-0-443-07145-4 }}</ref> It is classified as an ] (]).

In cardiac uses, it works as a nonselective muscarinic acetylcholinergic antagonist, increasing firing of the ] (SA) and conduction through the ] (AV) of the ], opposes the actions of the ], blocks ] ] sites, and decreases ] ]s.

In the eye, atropine induces ] by blocking the contraction of the circular ] muscle, which is normally stimulated by acetylcholine release, thereby allowing the radial ] to contract and dilate the ]. Atropine induces ] by paralyzing the ]s, whose action inhibits accommodation to allow accurate refraction in children, helps to relieve pain associated with ], and treats ciliary block (malignant) ].

The vagus (parasympathetic) nerves that innervate the heart release acetylcholine (ACh) as their primary neurotransmitter. ACh binds to muscarinic receptors (M2) that are found principally on cells comprising the sinoatrial (SA) and atrioventricular (AV) nodes. Muscarinic receptors are coupled to the ]; therefore, vagal activation decreases cAMP. Gi-protein activation also leads to the activation of ]s that increase potassium efflux and hyperpolarizes the cells.

Increases in vagal activities to the SA node decrease the firing rate of the pacemaker cells by decreasing the slope of the pacemaker potential (phase 4 of the action potential); this decreases heart rate (negative chronotropy). The change in phase 4 slope results from alterations in potassium and calcium currents, as well as the slow-inward sodium current that is thought to be responsible for the pacemaker current (If). By hyperpolarizing the cells, vagal activation increases the cell's threshold for firing, which contributes to the reduction in the firing rate. Similar electrophysiological effects also occur at the AV node; however, in this tissue, these changes are manifested as a reduction in impulse conduction velocity through the AV node (negative dromotropy). In the resting state, there is a large degree of vagal tone in the heart, which is responsible for low resting heart rates.

There is also some vagal innervation of the atrial muscle, and to a much lesser extent, the ventricular muscle. Vagus activation, therefore, results in modest reductions in atrial contractility (inotropy) and even smaller decreases in ventricular contractility.


Muscarinic receptor antagonists bind to muscarinic receptors thereby preventing ACh from binding to and activating the receptor. By blocking the actions of ACh, muscarinic receptor antagonists very effectively block the effects of vagal nerve activity on the heart. By doing so, they increase heart rate and conduction velocity. Muscarinic receptor antagonists bind to muscarinic receptors thereby preventing ACh from binding to and activating the receptor. By blocking the actions of ACh, muscarinic receptor antagonists very effectively block the effects of vagal nerve activity on the heart. By doing so, they increase heart rate and conduction velocity.


== History == == History ==
]
'']'' (mandrake) was described by ] in the fourth century B.C. for treatment of wounds, gout, and sleeplessness, and as a ]. By the first century A.D. ] recognized wine of mandrake as an ] for treatment of pain or sleeplessness, to be given prior to surgery or cautery.<ref name="holzman" /> The use of ] containing ] ]s for anesthesia, often in combination with ], persisted throughout the Roman and Islamic Empires and continued in Europe until superseded by the use of ], ], and other modern anesthetics.


The name ''atropine'' was coined in the 19th century, when pure extracts from the belladonna plant '']'' were first made.<ref>''Goodman and Gilman's Pharmacological Basis of Therapeutics'', q.v. "Muscarinic receptor antagonists - History", p. 163 of the 2001 edition.</ref> The medicinal use of preparations from ] is much older however. ''Mandragora'' (]) was described by ] in the fourth century B.C. for the treatment of wounds, gout, and sleeplessness, and as a love ]. By the first century A.D. ] recognized wine of mandrake as an ] for treatment of pain or sleeplessness, to be given before surgery or cautery.<ref name="holzman" /> The use of nightshade preparations for anesthesia, often in combination with ], persisted throughout the Roman and Islamic Empires and continued in Europe until superseded in the 19th century by modern anesthetics.{{citation needed|date=January 2022}}
Atropine extracts from the Egyptian ] were used by ] in the last century B.C. to dilate her ], in the hope that she would appear more alluring. In the ], women used the juice of the berries of '']'' to enlarge the pupils of their eyes, for cosmetic reasons; "bella donna" is Italian for "beautiful lady". This practice resumed briefly in the late nineteenth- and early twentieth-century in Paris.


Atropine-rich extracts from the Egyptian ] plant (another nightshade) were used by ] in the last century B.C. to dilate the ] of her eyes, in the hope that she would appear more alluring. Likewise in the ], women used the juice of the berries of the nightshade '']'' to enlarge their pupils for cosmetic reasons. This practice resumed briefly in the late nineteenth and early twentieth century in Paris.{{citation needed|date=January 2022}}
The mydriatic effects of atropine were studied among others by the ] ] ] (1795–1867). In 1831, the pharmacist Mein succeeded the pure crystalline isolation of atropine. The substance was first synthesized by German chemist ] in 1901.


The pharmacological study of ''belladonna'' extracts was begun by the ] ] ] (1795–1867). In 1831, the German pharmacist Heinrich F. G. Mein (1799-1864)<ref>{{cite web | title=Heinrich Friedrich Georg Mein| website=ostfriesischelandschaft.de | url=http://www.ostfriesischelandschaft.de/fileadmin/php/side.php?news_id=997&part_id=0&navi=11 | archive-url=https://web.archive.org/web/20130511031004/http://www.ostfriesischelandschaft.de/fileadmin/php/side.php?news_id=997&part_id=0&navi=11 | archive-date=2013-05-11 | url-status=unfit | language=de | access-date=2019-10-20}}</ref> succeeded in preparing a pure crystalline form of the active substance, which was named ''atropine''.<ref>{{cite book|author=Heinrich Friedrich Georg Mein|title=Annalen der Pharmacie|url=https://books.google.com/books?id=tT09AAAAcAAJ&pg=PA67|edition=1|volume=6|year=1833|language=de|pages=67–72|chapter=Ueber die Darstellung des Atropins in weissen Kristallen|trans-chapter=On the preparation of atropine as white crystals|access-date=2016-01-05|archive-date=2016-05-15|archive-url=https://web.archive.org/web/20160515150443/https://books.google.com/books?id=tT09AAAAcAAJ&pg=PA67|url-status=live}}</ref><ref>Atropine was also independently isolated in 1833 by Geiger and Hesse:
Atropinic shock therapy, also known as ], is an old and rarely-used method. It consists of induction of atropinic coma by rapid intravenous infusion of atropine. Atropinic shock treatment is considered safe with careful monitoring and preparation, but it entails prolonged coma (between four and five hours), and it has many unpleasant side-effects, such as blurred vision.{{Citation needed|date=May 2008}}
* {{cite book|vauthors=Geiger, Hesse|title=Annalen der Pharmacie|url=https://books.google.com/books?id=pz09AAAAcAAJ&pg=PA43|volume=5|year=1833|language=de|pages=43–81|chapter=Darstellung des Atropins|trans-chapter=Preparation of atropine|access-date=2016-01-05|archive-date=2016-05-14|archive-url=https://web.archive.org/web/20160514231012/https://books.google.com/books?id=pz09AAAAcAAJ&pg=PA43|url-status=live}}
* {{cite book|vauthors=Geiger, Hesse|title=Annalen der Pharmacie|url=https://books.google.com/books?id=tT09AAAAcAAJ&pg=PA44|volume=6|year=1833|language=de|pages=44–65|chapter=Fortgesetzte Versuche über Atropin|trans-chapter=Continued experiments on atropine|access-date=2016-01-05|archive-date=2016-06-10|archive-url=https://web.archive.org/web/20160610162825/https://books.google.com/books?id=tT09AAAAcAAJ&pg=PA44|url-status=live}}</ref> The substance was first synthesized by German chemist ] in 1901.<ref>See:
* {{cite journal | vauthors = Willstätter R | year = 1901 | title = Synthese des Tropidins |trans-title=Synthesis of tropidine | url = http://gallica.bnf.fr/ark:/12148/bpt6k907582/f243.image.langEN | journal = Berichte der Deutschen Chemischen Gesellschaft zu Berlin | volume = 34 | pages = 129–144 | doi = 10.1002/cber.19010340124 | url-status = live | archive-url = https://web.archive.org/web/20130301050307/http://gallica.bnf.fr/ark%3A/12148/bpt6k907582/f243.image.langEN | archive-date = 2013-03-01 |language=de}}
* {{cite journal | vauthors = Willstätter R | year = 1901 | title = Umwandlung von Tropidin in Tropin |trans-title=Conversion of tropidine into tropine | url = http://visualiseur.bnf.fr/ark:/12148/bpt6k90759d | journal = Berichte der Deutschen Chemischen Gesellschaft zu Berlin | volume = 34 | issue = 2| pages = 3163–3165 | doi = 10.1002/cber.190103402289 | url-status = live | archive-url = https://web.archive.org/web/20130126014141/http://visualiseur.bnf.fr/ark%3A/12148/bpt6k90759d | archive-date = 2013-01-26 |language=de }}</ref>


== Natural sources == == Natural sources ==
Atropine is found in many members of the ] family. The most commonly-found sources are '']'', '']'', '']'', and '']''. Other sources include members of the '']'' and '']'' genera. The '']'' genus (including the tobacco plant, '']'') is also found in the Solanaceae family, but these plants do not contain atropine or other tropane alkaloids. Atropine is found in many members of the family ]. The most commonly found sources are '']'' (the ]), '']'', '']'', '']'', and '']''. Other sources include members of the genera '']'' (angel's trumpets) and '']''.<ref name="PubChem"></ref>


==Synthesis== ==Synthesis==
Atropine can be synthesized by the reaction of ] with ] in the presence of hydrochloric acid. Atropine can be synthesized by the reaction of ] with ] in the presence of ].


==See also== ===Biosynthesis===

*]
The biosynthesis of atropine starting from ] first undergoes a ] forming ] which is then reduced to phenyl-lactic acid.<ref name=dewick>{{cite book| vauthors = Dewick PM |title=Medicinal Natural Products: A Biosynthetic Approach|edition=3rd|date=9 March 2009|publisher=A John Wiley & Sons|location=Chichester|isbn=978-0-470-74167-2}}</ref> Coenzyme A then couples phenyl-lactic acid with ] forming ], which then undergoes a radical rearrangement initiated with a ] forming hyoscyamine aldehyde.<ref name=dewick/> A ] then reduces the aldehyde to a primary alcohol making (−)-hyoscyamine, which upon racemization forms atropine.<ref name=dewick/>

==Name==
The species name "belladonna" ('beautiful woman' in ]) comes from the original use of deadly nightshade to dilate the pupils of the eyes for cosmetic effect. Both atropine and the genus name for deadly nightshade derive from ], one of the three ] who, according to Greek mythology, chose how a person was to die.<ref name="holzman" />

== See also ==
* ]
* ]


== References == == References ==
{{Reflist|2}} {{Reflist}}


== External links == == External links ==
* {{Commons category-inline}}
*
* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/atropine | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Atropine }}
* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/atropine%20sulfate | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Atropine sulfate }}


{{Ancient anaesthesia}}
{{Drugs for functional gastrointestinal disorders}} {{Drugs for functional gastrointestinal disorders}}
{{Emergency medicine}}
{{Hallucinogens}}
{{Mydriatics and cycloplegics}} {{Mydriatics and cycloplegics}}
{{Opthalmologicals}} {{Opthalmologicals}}
{{Muscarinic acetylcholine receptor modulators}}
{{Ancient anaesthesia}}
{{Authority control}}
{{Hallucinogens}}
{{Portal bar|Medicine}}
{{Emergency medicine}}
{{Cholinergics}}


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