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Atropine
Atropine
is a medication to treat certain types of nerve agent and pesticide poisonings as well as some types of slow heart rate and to decrease saliva production during surgery.[3] It is typically given intravenously or by injection into a muscle.[3] Eye drops are also available which are used to treat uveitis and early amblyopia.[4] The intravenous solution usually begins working within a minute and lasts half an hour to an hour.[2] Large doses may be required to treat some poisonings.[3] Common side effects include a dry mouth, large pupils, urinary retention, constipation, and a fast heart rate.[3] It should generally not be used in people with angle closure glaucoma.[3] While there is no evidence that its use during pregnancy causes birth defects, it has not been well studied.[5] It is likely safe during breastfeeding.[5] It is an antimuscarinic (a type of anticholinergic) that works by inhibiting the parasympathetic nervous system.[3] Atropine
Atropine
occurs naturally in a number of plants of the nightshade family including deadly nightshade, Jimson weed, and mandrake.[6] It was first isolated in 1833.[7] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[8] It is available as a generic medication and is not very expensive.[3][9] A one-milligram vial costs between US$0.06 and US$0.44, wholesale, in the developing world.[10]

Contents

1 Medical uses

1.1 Eyes 1.2 Heart 1.3 Secretions 1.4 Poisonings

2 Side-effects 3 Contraindications 4 Mechanism of action 5 Chemistry
Chemistry
and pharmacology 6 History 7 Natural sources 8 Synthesis

8.1 Biosynthesis

9 Name 10 See also 11 References 12 External links

Medical uses[edit]

An ampoule containing atropine injection 1mL/0.5mg.

Eyes[edit] Topical
Topical
atropine is used as a cycloplegic, to temporarily paralyze the accommodation reflex, and as a mydriatic, to dilate the pupils. Atropine
Atropine
degrades slowly, typically wearing off in 7 to 14 days, so it is generally used as a therapeutic mydriatic, whereas tropicamide (a shorter-acting cholinergic antagonist) or phenylephrine (an α-adrenergic agonist) is preferred as an aid to ophthalmic examination. In refractive and accommodative amblyopia, when occlusion is not appropriate sometimes atropine is given to induce blur in the good eye.[11] Evidence suggests that atropine penalization is just as effective as occlusion in improving visual acuity.[12] Atropine
Atropine
eye drops have been shown to be effective in slowing the progression of myopia in children in several studies, but it is not available for this use, and side effects would limit its use.[13] Heart[edit] Injections of atropine are used in the treatment of bradycardia (a heart rate < 60 beats per minute). Atropine
Atropine
was previously included in international resuscitation guidelines for use in cardiac arrest associated with asystole and PEA, but was removed from these guidelines in 2010 due to a lack of evidence for its effectiveness.[14] For symptomatic bradycardia, the usual dosage is 0.5 to 1 mg IV push, may repeat every 3 to 5 minutes up to a total dose of 3 mg (maximum 0.04 mg/kg).[15] Atropine
Atropine
is also useful in treating second-degree heart block Mobitz type 1 (Wenckebach block), and also third-degree heart block with a high purkinje or AV-nodal escape rhythm. It is usually not effective in second-degree heart block Mobitz type 2, and in third-degree heart block with a low Purkinje or ventricular escape rhythm. Atropine
Atropine
has also been used in an effort to prevent a low heart rate during intubation of children; however, evidence does not support this use.[16] Secretions[edit] Atropine's actions on the parasympathetic nervous system inhibit salivary and mucus glands. The drug may also inhibit sweating via the sympathetic nervous system. This can be useful in treating hyperhidrosis, and can prevent the death rattle 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.[17] Poisonings[edit] Atropine
Atropine
is not an actual antidote for organophosphate poisoning. However, by blocking the action of acetylcholine at muscarinic receptors, atropine also serves as a treatment for poisoning by organophosphate insecticides and nerve gases, such as tabun (GA), sarin (GB), soman (GD) and VX. Troops who are likely to be attacked with chemical weapons often carry autoinjectors with atropine and obidoxime, for rapid injection into the muscles of the thigh. In a developed case of nerve-gas poisoning, maximum atropinization is desirable. Atropine
Atropine
is often used in conjunction with pralidoxime chloride. Atropine
Atropine
is given as a treatment for SLUDGE syndrome (salivation, lacrimation, urination, diaphoresis, gastrointestinal motility, emesis) 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 muscarinic receptors). Some of the nerve agents attack and destroy acetylcholinesterase by phosphorylation, 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
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. Side-effects[edit] Adverse reactions to atropine include ventricular fibrillation, supraventricular or ventricular tachycardia, dizziness, nausea, blurred vision, loss of balance, dilated pupils, photophobia, dry mouth and potentially extreme confusion, deliriant hallucinations and excitation especially amongst the elderly. Most of available ampules are carried on sulphate which can cause histamine release and anaphylaxis to susceptible patients or patients with allergy to sulpha products. These latter effects are because atropine is able to cross the blood–brain barrier. Because of the hallucinogenic properties, some have used the drug recreationally, though this is potentially dangerous and often unpleasant.[medical citation needed] In overdoses, atropine is poisonous. Atropine
Atropine
is sometimes added to potentially addictive drugs, particularly anti-diarrhea opioid drugs such as diphenoxylate or difenoxin, wherein the secretion-reducing effects of the atropine can also aid the anti-diarrhea effects. Although atropine treats bradycardia (slow heart rate) in emergency settings, it can cause paradoxical heart rate slowing when given at very low doses (i.e. <0.5 mg),[18] presumably as a result of central action in the CNS.[19] One proposed mechanism for atropine's paradoxical bradycardia effect at low doses involves blockade of inhibitory presynaptic muscarinic autoreceptors, thereby blocking a system that inhibits the parasympathetic response.[20] Atropine
Atropine
is incapacitating at doses of 10 to 20 mg per person. Its LD50 is estimated to be 453 mg per person (by mouth) with a probit slope of 1.8.[21] The antidote to atropine is physostigmine or pilocarpine. A common mnemonic 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".[22] 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 muscarinic receptors, type 4 and 5. This set of symptoms is known as anticholinergic toxidrome, and may also be caused by other drugs with anticholinergic effects, such as hyoscine hydrobromide (scopolamine), diphenhydramine, phenothiazine antipsychotics and benztropine.[23] Contraindications[edit] Atropine
Atropine
is contraindicated in patients pre-disposed to narrow angle glaucoma.[medical citation needed] Mechanism of action[edit] In general, atropine counters the "rest and digest" activity of glands regulated by the parasympathetic nervous system. This occurs because atropine is a competitive, reversible antagonist of the muscarinic acetylcholine receptors (acetylcholine being the main neurotransmitter used by the parasympathetic nervous system). Atropine
Atropine
is a competitive antagonist of the muscarinic acetylcholine receptor types M1, M2, M3, M4 and M5.[24] It is classified as an anticholinergic drug (parasympatholytic). In cardiac uses, it works as a nonselective muscarinic acetylcholinergic antagonist, increasing firing of the sinoatrial node (SA) and conduction through the atrioventricular node (AV) of the heart, opposes the actions of the vagus nerve, blocks acetylcholine receptor sites, and decreases bronchial secretions.[medical citation needed] In the eye, atropine induces mydriasis by blocking contraction of the circular pupillary sphincter muscle, which is normally stimulated by acetylcholine release, thereby allowing the radial iris dilator muscle to contract and dilate the pupil. Atropine
Atropine
induces cycloplegia by paralyzing the ciliary muscles, whose action inhibits accommodation to allow accurate refraction in children, helps to relieve pain associated with iridocyclitis, and treats ciliary block (malignant) glaucoma.[medical citation needed] Chemistry
Chemistry
and pharmacology[edit] Atropine
Atropine
is an enantiomeric mixture of d-hyoscyamine and l-hyoscyamine, with most of its physiological effects due to l-hyoscyamine. Its pharmacological effects are due to binding to muscarinic acetylcholine receptors. 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. The most common atropine compound used in medicine is atropine sulfate (monohydrate) (C17H23NO3)2·H2SO4·H2O, the full chemical name is 1α H, 5α H-Tropan-3-α ol (±)-tropate(ester), sulfate monohydrate. 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
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. Increases in vagal activities 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 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 on 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
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[edit] Mandragora (mandrake) was described by Theophrastus
Theophrastus
in the fourth century B.C. for treatment of wounds, gout, and sleeplessness, and as a love potion. By the first century A.D. Dioscorides
Dioscorides
recognized wine of mandrake as an anaesthetic for treatment of pain or sleeplessness, to be given prior to surgery or cautery.[22] The use of Solanaceae containing tropane alkaloids for anesthesia, often in combination with opium, persisted throughout the Roman and Islamic Empires and continued in Europe until superseded by the use of ether, chloroform, and other modern anesthetics. Atropine
Atropine
extracts from the Egyptian henbane were used by Cleopatra
Cleopatra
in the last century B.C. to dilate her pupils, in the hope that she would appear more alluring. In the Renaissance, women used the juice of the berries of Atropa belladonna
Atropa belladonna
to enlarge the pupils of their eyes, for cosmetic reasons. This practice resumed briefly in the late nineteenth- and early twentieth-century in Paris. The mydriatic effects of atropine were studied among others by the German chemist Friedlieb Ferdinand Runge
Friedlieb Ferdinand Runge
(1795–1867). In 1831, the German pharmacist Heinrich F. G. Mein (1799-1864)[25] succeeded in preparing atropine in pure crystalline form.[26] [27] The substance was first synthesized by German chemist Richard Willstätter
Richard Willstätter
in 1901.[28] Natural sources[edit]

Atropa belladonna

Atropine
Atropine
is found in many members of the Solanaceae
Solanaceae
family. The most commonly found sources are Atropa belladonna, Datura innoxia, D. metel, and D. stramonium. Other sources include members of the Brugmansia
Brugmansia
and Hyoscyamus
Hyoscyamus
genera. Synthesis[edit] Atropine
Atropine
can be synthesized by the reaction of tropine with tropic acid in the presence of hydrochloric acid. Biosynthesis[edit]

Biosynthesis of atropine starting from L-Phenylalanine

The biosynthesis of atropine starting from l-phenylalanine first undergoes a transamination forming phenylpyruvic acid which is then reduced to phenyl-lactic acid.[29] Coenzyme A then couples phenyl-lactic acid with tropine forming littorine, which then undergoes a radical rearrangement initiated with a P450
P450
enzyme forming hyoscyamine aldehyde.[29] A dehydrogenase then reduces the aldehyde to a primary alcohol making (−)-hyoscyamine, which upon racemization forms atropine.[29] Name[edit] The species name "belladonna" ("beautiful woman" in Italian) 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 Atropos, one of the three Fates who, according to Greek mythology, chose how a person was to die. See also[edit]

Apoatropine Mark I Nerve Agent Antidote Kit

References[edit]

^ Medical Flora; Or, Manual of the Medical Botany of the United States of ... - Constantine Samuel Rafinesque - Google Books. Books.google.com. 1828. Retrieved 2012-11-07.  ^ a b c Barash, Paul G. (2009). Clinical anesthesia (6th ed.). Philadelphia: Wolters Kluwer/Lippincott Williams & Wilkins. p. 525. ISBN 9780781787635. Archived from the original on 2015-11-24.  ^ a b c d e f g "Atropine". The American Society of Health-System Pharmacists. Archived from the original on 2015-07-12. Retrieved Aug 13, 2015.  ^ design, Richard J. Hamilton ; Nancy Anastasi Duffy, executive editor ; Daniel Stone, production editor ; Anne Spencer, cover (2014). Tarascon pharmacopoeia (15 ed.). p. 386. ISBN 9781284056716. Archived from the original on 2015-10-02.  ^ a b " Atropine
Atropine
Pregnancy and Breastfeeding Warnings". Archived from the original on 6 September 2015. Retrieved 14 August 2015.  ^ Brust,, John C. M. (2004). Neurological aspects of substance abuse (2 ed.). Philadelphia: Elsevier. p. 310. ISBN 9780750673136. Archived from the original on 2015-10-02.  ^ Ainsworth, Sean (2014). Neonatal Formulary: Drug Use in Pregnancy and the First Year of Life. John Wiley & Sons. p. 94. ISBN 9781118819593. Archived from the original on 2015-10-02.  ^ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived (PDF) from the original on 13 December 2016. Retrieved 8 December 2016.  ^ Hamilton, Richard J. (2014). Tarascon pharmacopoeia (15 ed.). p. 386. ISBN 9781284056716. Archived from the original on 2015-10-02.  ^ " Atropine
Atropine
Sulfate". International Drug Price Indicator Guide. Retrieved 13 August 2015.  ^ Georgievski Z, Koklanis K, Leone J (2008). "Fixation behavior in the treatment of amblyopia using atropine". Clinical and Experimental Ophthalmology. 36 (Suppl 2): A764–A765.  ^ Li T, Shotton K (2009). "Conventional occlusion versus pharmacologic penalization for amblyopia". Cochrane Database Syst Rev. 4: CD006460. doi:10.1002/14651858.CD006460.pub2. PMC 3804306 . PMID 19821369.  ^ Walline JJ, Lindsley K, Vedula SS, Cotter SA, Mutti DO, Twelker JD (2011). "Interventions to slow progression of myopia in children". Cochrane Database Syst Rev (12): CD004916. doi:10.1002/14651858.CD004916.pub3. PMC 4270373 . PMID 22161388.  ^ Field JM, Hazinski MF, Sayre MR, et al. (November 2010). "Part 1: executive summary: 2010 American Heart
Heart
Association Guidelines for Cardiopulmonary Resuscitation and Emergency Cardiovascular Care". Circulation. 122 (18 Suppl 3): S640–56. doi:10.1161/CIRCULATIONAHA.110.970889. PMID 20956217. Archived from the original on 2010-11-14.  ^ * Bryan E, Bledsoe; Robert S. Porter; Richard A. Cherry (2004). "Ch. 3". Intermediate Emergency Care. Upper Saddle River, NJ: Pearson Prentice Hill. p. 260. ISBN 0-13-113607-0.  ^ 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 (3 November 2015). "Part 12: Pediatric Advanced Life Support: 2015 American Heart
Heart
Association Guidelines Update for Cardiopulmonary Resuscitation and Emergency Cardiovascular Care". Circulation. 132 (18 Suppl 2): S526–42. doi:10.1161/cir.0000000000000266. PMID 26473000.  ^ Death Rattle and Oral Secretions Archived 2014-04-14 at the Wayback Machine. ^ "Archived copy". Archived from the original on 2014-02-20. Retrieved 2014-02-02.  ^ * Rang HP, Dale MM, Ritter JM, Flower RJ (2007). "Ch. 10". Rang and Dale's Pharmacology. Elsevier Churchill Livingstone. p. 153. ISBN 0-443-06911-5.  ^ Laurence, Brunton (2010). Goodman & Gilman's Pharmacological Basis of Therapeutics, 12th Edition. McGraw-Hill. ISBN 978-0-07-162442-8.  ^ * Goodman E (2010). Ketchum J, Kirby R, eds. Historical Contributions to the Human Toxicology of Atropine. Eximdyne. p. 120. ISBN 978-0-9677264-3-4.  ^ a b Robert S. Holzman, MD (July 1998). "The Legacy of Atropos". Anesthesiology. 89 (1): 241–249. doi:10.1097/00000542-199807000-00030. PMID 9667313. Retrieved 2007-05-21.  citing J. Arena, Poisoning: Toxicology-Symptoms-Treatments, 3rd edition. Springfield, Charles C. Thomas, 1974, p 345 ^ Szajewski J (1995). "Acute anticholinergic syndrome". IPCS Intox Databank. Archived from the original on 2 July 2007. Retrieved 2007-05-22.  ^ Rang, Dale, Ritter and More: Pharmacology, p. 139. Elsevier 2003. ^ Biography of Heinrich Friedrich Georg Mein (1799-1864) (in German). ^ Heinrich Friedrich Georg Mein (1831) "Ueber die Darstellung des Atropins in weissen Kristallen" Archived 2016-05-15 at the Wayback Machine. (On the preparation of atropine as white crystals), Annalen der Pharmacie, 6(1): 67-72. ^ Atropine
Atropine
was also independently isolated in 1833 by Geiger and Hesse:

Geiger and Hesse (1833) "Darstellung des Atropins" Archived 2016-05-14 at the Wayback Machine. (Preparation of atropine), Annalen der Pharmacie, 5: 43-81. Geiger and Hesse (1833) "Fortgesetzte Versuche über Atropin" Archived 2016-06-10 at the Wayback Machine. (Continued experiments on atropine), Annalen der Pharmacie, 6: 44-65.

^ See:

Willstätter Richard (1901). "Synthese des Tropidins" [Synthesis of tropidine]. Berichte der Deutschen chemischen Gesellschaft zu Berlin. 34: 129–144. doi:10.1002/cber.19010340124. Archived from the original on 2013-03-01.  Willstätter Richard (1901). "Umwandlung von Tropidin in Tropin" [Conversion of tropidine into tropine]. Berichte der Deutschen chemischen Gesellschaft zu Berlin. 34: 3163–3165. doi:10.1002/cber.190103402289. Archived from the original on 2013-01-26. 

^ a b c Dewick, Paul M. (2009). Medicinal natural products: A biosynthetic approach (3rd ed.). Chichester: A John Wiley & Sons. ISBN 978-0470741672

External links[edit]

Media related to Atropine
Atropine
at Wikimedia Commons U.S. National Library of Medicine: Drug Information Portal
Portal
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Aconitum
Aconitum
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Atropa belladonna
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medical use

Castoreum Coca Conium
Conium
(hemlock) Datura innoxia
Datura innoxia
(thorn-apple) Datura metel
Datura metel
(devil's trumpet) Hyoscyamus
Hyoscyamus
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Quaternary ammonium compounds

Benzilone Mepenzolate Pipenzolate Glycopyrronium Oxyphenonium Penthienate Methantheline Propantheline Otilonium Tridihexethyl Isopropamide Hexocyclium Poldine Bevonium Diphemanil Tiemonium Prifinium Timepidium Fenpiverinium

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Belladonna and derivatives (antimuscarinics)

Tertiary amines: Atropine Hyoscyamine

Quaternary ammonium
Quaternary ammonium
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Epinephrine
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Book:Emergency medicine Category:Emergency medicine

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25x-NBx

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25B-NB3OMe 25C-NB3OMe 25D-NB3OMe 25E-NB3OMe 25H-NB3OMe 25I-NB3OMe 25N-NB3OMe 25P-NB3OMe 25T2-NB3OMe 25T4-NB3OMe 25T7-NB3OMe 25TFM-NB3OMe

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25B-NB4OMe 25C-NB4OMe 25D-NB4OMe 25E-NB4OMe 25H-NB4OMe 25I-NB4OMe 25N-NB4OMe 25P-NB4OMe 25T2-NB4OMe 25T4-NB4OMe 25T7-NB4OMe 25TFM-NB4OMe

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25x-NBMD

25B-NBMD 25C-NBMD 25D-NBMD 25E-NBMD 25F-NBMD 25H-NBMD 25I-NBMD 25P-NBMD 25T2-NBMD 25T7-NBMD 25TFM-NBMD

25x-NBOH

25B-NBOH 25C-NBOH 25CN-NBOH 25D-NBOH 25E-NBOH 25F-NBOH 25H-NBOH 25I-NBOH 25P-NBOH 25T2-NBOH 25T7-NBOH 25TFM-NBOH

25x-NBOMe

25B-NBOMe 25C-NBOMe 25CN-NBOMe 25D-NBOMe 25E-NBOMe 25F-NBOMe 25G-NBOMe 25H-NBOMe 25I-NBOMe 25iP-NBOMe 25N-NBOMe 25P-NBOMe 25T2-NBOMe 25T4-NBOMe 25T7-NBOMe 25TFM-NBOMe

Atypical structures

25I-NB34MD 2CBCB-NBOMe 2CBFly-NBOMe NBOMe-mescaline

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4C-x

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DOx

DOT DOB DOC DOEF DOET DOF DOI DOiPR DOM DON DOPR DOTFM MEM

HOT-x

HOT-2 HOT-7 HOT-17

MDxx

DMMDA DMMDA-2 Lophophine MDA MMDA MMDA-2 MMDA-3a MMDMA

Mescaline
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(subst.)

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TMA TMA-2 TMA-3 TMA-4 TMA-5 TMA-6

Others

2C-B-BUTTERFLY 2C-B-DragonFLY 2CB-5-hemifly 2-TOM 5-TOET 5-TOM 2CB-Ind 2CD-5EtO BOB BOD βk-2C-B βk-2C-I DESOXY DMCPA DMBMPP DOB-FLY Fenfluramine Ganesha Macromerine MMA TCB-2 TOMSO

Piperazines

BZP pFPP

Tryptamines

alpha-alkyltryptamines

4,5-DHP-α-MT 5-MeO-α-ET 5-MeO-α-MT α-ET α-MT

x-DALT

(Daltocin) 4-HO-DALT (Daltacetin) 4-AcO-DALT 5-MeO-DALT DALT

x-DET

(Ethacetin) 4-AcO-DET (Ethocin) 4-HO-DET 5-MeO-DET (T-9) DET (Ethocybin) 4-PO-DET

x-DiPT

1-Me-5-MeO-DiPT (Ipracetin) 4-AcO-DiPT (Iprocin) 4-HO-DiPT (Foxy Methoxy) 5-MeO-DiPT DiPT

x-DMT

4,5-DHP-DMT 2,N,N-TMT 4-AcO-DMT 4-HO-5-MeO-DMT 4,N,N-TMT 4-Propionyloxy-DMT 5,6-diBr-DMT 5-AcO-DMT 5-Bromo-DMT 5-MeO-2,N,N-TMT 5-MeO-4,N,N-TMT 5-MeO-α,N,N-TMT 5-MeO-DMT 5-N,N-TMT 7,N,N-TMT α,N,N-TMT (Bufotenin) 5-HO-DMT DMT Norbaeocystin (Psilocin) 4-HO-DMT (Psilocybin) 4-PO-DMT

x-DPT

(Depracetin) 4-AcO-DPT (Deprocin) 4-HO-DPT 5-MeO-DPT (The Light) DPT

Ibogaine-related

18-MAC 18-MC Coronaridine Ibogaine Ibogamine ME-18-MC Noribogaine Tabernanthine Voacangine

x-MET

(Metocin) 4-HO-MET (Metocetin) 4-AcO-MET 5-MeO-MET MET

x-MiPT

(Mipracetin) 4-AcO-MiPT (Miprocin) 4-HO-MiPT 5-Me-MiPT (Moxy) 5-MeO-MiPT MiPT

Others

4-HO-DBT 4-HO-EPT 4-HO-McPT (Lucigenol) 4-HO-MPMI (Meprocin) 4-HO-MPT 5-MeO-EiPT 5-MeO-MALT 5-MeO-MPMI Aeruginascin Baeocystin DBT DCPT EiPT EPT MPT PiPT

Others

5-MeO-DiBF AL-38022A ALPHA Dimemebfe Efavirenz Lorcaserin M-ALPHA RH-34 Also empathogens in general (e. g.: 5-APB, 5-MAPB, 6-APB
6-APB
and other substituted benzofurans, MDAI, MDMA).

Dissociatives (NMDAR antagonists)

Arylcyclo‐ hexylamines

Ketamine-related

2-Fluorodeschloroketamine Arketamine
Arketamine
((R)-ketamine) Deschloroketamine Ethketamine
Ethketamine
(N-Ethylnorketamine) Esketamine
Esketamine
((S)-ketamine) Ketamine Methoxetamine Methoxmetamine Methoxyketamine Norketamine Tiletamine

PCP-related

3'-HO-PCP 3'-MeO-PCE 3'-MeO-PCMo 3'-MeO-PCP BDPC Dieticyclidine
Dieticyclidine
(PCDE) Eticyclidine
Eticyclidine
(PCE) Methoxydine
Methoxydine
(4'-MeO-PCP) PCPr Phencyclidine
Phencyclidine
(PCP) Rolicyclidine
Rolicyclidine
(PCPy) Tenocyclidine
Tenocyclidine
(TCP)

Others

BTCP Gacyclidine PRE-084

Diarylethylamines

Diphenidine Ephenidine Fluorolintane Methoxphenidine

Morphinans

Dextrallorphan Dextromethorphan Dextrorphan Racemethorphan Racemorphan

Others

2-EMSB 2-MDP 8A-PDHQ Aptiganel Budipine Delucemine Dexoxadrol Dizocilpine Etoxadrol Herkinorin Ibogaine Midafotel NEFA Neramexane Nitrous oxide Noribogaine Perzinfotel RB-64 Remacemide Salvinorin A Selfotel Xenon

Deliriants (mAChR antagonists)

Atropine Benactyzine Benzatropine Benzydamine Biperiden BRN-1484501 Brompheniramine BZ CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,368 CAR-302,537 CAR-302,668 Chloropyramine Chlorphenamine Clemastine CS-27349 Cyclizine Cyproheptadine Dicycloverine Dimenhydrinate Diphenhydramine Ditran Doxylamine EA-3167 EA-3443 EA-3580 EA-3834 Elemicin Flavoxate Hyoscyamine JB-318 JB-336 Meclozine Mepyramine Myristicin Orphenadrine Oxybutynin Pheniramine Phenyltoloxamine Procyclidine Promethazine Scopolamine Tolterodine Trihexyphenidyl Tripelennamine Triprolidine WIN-2299

Others

Cannabinoids (CB1 agonists)

Natural

THC (Dronabinol) THCV

Synthetic

AM-x

AM-087 AM-251 AM-279 AM-281 AM-356 AM-374 AM-381 AM-404 AM-411 AM-630 AM-661 AM-678 AM-679 AM-694 AM-735 AM-855 AM-881 AM-883 AM-905 AM-906 AM-919 AM-926 AM-938 AM-1116 AM-1172 AM-1220 AM-1221 AM-1235 AM-1241 AM-1248 AM-1710 AM-1714 AM-1902 AM-2201 AM-2212 AM-2213 AM-2232 AM-2233 AM-2389 AM-3102 AM-4030 AM-4054 AM-4056 AM-4113 AM-6545

CP x

CP 47,497 CP 55,244 CP 55,940 (±)-CP 55,940 (+)-CP 55,940 (-)-CP 55,940

HU-x

HU-210 HU-211 HU-239 HU-243 HU-308 HU-320 HU-331 HU-336 HU-345

JWH-x

JWH-007 JWH-015 JWH-018 JWH-019 JWH-030 JWH-047 JWH-048 JWH-051 JWH-057 JWH-073 JWH-081 JWH-098 JWH-116 JWH-120 JWH-122 JWH-133 JWH-139 JWH-147 JWH-148 JWH-149 JWH-149 JWH-161 JWH-164 JWH-166 JWH-167 JWH-171 JWH-175 JWH-176 JWH-181 JWH-182 JWH-184 JWH-185 JWH-192 JWH-193 JWH-193 JWH-194 JWH-195 JWH-196 JWH-197 JWH-198 JWH-199 JWH-200 JWH-203 JWH-205 JWH-210 JWH-210 JWH-213 JWH-220 JWH-229 JWH-234 JWH-249 JWH-250 JWH-251 JWH-253 JWH-258 JWH-300 JWH-302 JWH-307 JWH-336 JWH-350 JWH-359 JWH-387 JWH-398 JWH-424

Misc. designer cannabinoids

4-HTMPIPO 5F-AB-FUPPYCA 5F-AB-PINACA 5F-ADB 5F-ADB-PINACA 5F-ADBICA 5F-AMB 5F-APINACA 5F-CUMYL-PINACA 5F-NNE1 5F-PB-22 5F-SDB-006 A-796,260 A-836,339 AB-001 AB-005 AB-CHFUPYCA AB-CHMINACA AB-FUBINACA AB-PINACA ADAMANTYL-THPINACA ADB-CHMINACA ADB-FUBINACA ADB-PINACA ADBICA ADSB-FUB-187 AMB-FUBINACA APICA APINACA APP-FUBINACA CB-13 CUMYL-PICA CUMYL-PINACA CUMYL-THPINACA DMHP EAM-2201 FAB-144 FDU-PB-22 FUB-144 FUB-APINACA FUB-JWH-018 FUB-PB-22 FUBIMINA JTE 7-31 JTE-907 Levonantradol MDMB-CHMICA MDMB-CHMINACA MDMB-FUBINACA MEPIRAPIM MAM-2201 MDA-19 MN-18 MN-25 NESS-0327 NESS-040C5 Nabilone Nabitan NM-2201 NNE1 Org 28611 Parahexyl PTI-1 PTI-2 PX-1 PX-2 PX-3 QUCHIC QUPIC RCS-4 RCS-8 SDB-005 SDB-006 STS-135 THC-O-acetate THC-O-phosphate THJ-018 THJ-2201 UR-144 WIN 55,212-2 XLR-11

D2 agonists

Apomorphine Aporphine Bromocriptine Cabergoline Lisuride Memantine Nuciferine Pergolide Phenethylamine Piribedil Pramipexole Ropinirole Rotigotine Salvinorin A Also indirect D2 agonists, such as dopamine reuptake inhibitors (cocaine, methylphenidate), releasing agents (amphetamine, methamphetamine), and precursors (levodopa).

GABAA enhancers

CI-966 Eszopiclone Ibotenic acid Muscimol
Muscimol
(Amanita muscaria) Zaleplon Zolpidem Zopiclone

Inhalants (Mixed MOA)

Aliphatic hydrocarbons

Butane Gasoline Kerosene Propane

Aromatic hydrocarbons

Toluene

Ethers

Diethyl ether Enflurane

Haloalkanes

Chlorofluorocarbons Chloroform

κOR agonists

2-EMSB Alazocine Bremazocine Butorphan Butorphanol Cyclazocine Cyclorphan Cyprenorphine Diprenorphine Enadoline Herkinorin Heroin HZ-2 Ibogaine Ketazocine Levallorphan Levomethorphan Levorphanol LPK-26 Metazocine Morphine Nalbuphine Nalmefene Nalorphine Noribogaine Oxilorphan Pentazocine Phenazocine Proxorphan Racemethorphan Racemorphan Salvinorin A Spiradoline Tifluadom U-50488 U-69,593 Xorphanol

Others

Glaucine Isoaminile Noscapine Pukateine

v t e

Ophthalmologicals: mydriasis and cycloplegia (S01F)

Anticholinergics/antimuscarinics

Atropine Scopolamine Methylscopolamine Cyclopentolate Homatropine Tropicamide

Sympathomimetics

Phenylephrine Ephedrine Ibopamine

v t e

Drugs used for glaucoma preparations and miosis (S01E)

Sympathomimetics

Apraclonidine Brimonidine
Brimonidine
(+timolol) Clonidine Dipivefrine Epinephrine

Parasympathomimetics

muscarinic

Aceclidine Pilocarpine

muscarinic/nicotinic

Acetylcholine Carbachol

acetylcholinesterase inhibitors

Demecarium Ecothiopate Stigmine
Stigmine
(Fluostigmine Neostigmine Physostigmine) Paraoxon

Carbonic anhydrase inhibitors/ (sulfonamides)

Acetazolamide Brinzolamide
Brinzolamide
(+timolol) Diclofenamide Dorzolamide
Dorzolamide
(+timolol) Methazolamide

Beta blocking agents

Befunolol Betaxolol Carteolol Levobunolol Metipranolol Timolol Mepindolol

Prostaglandin analogues (F2α)

Bimatoprost
Bimatoprost
(+timolol) Latanoprost
Latanoprost
(+timolol) Tafluprost Travoprost
Travoprost
(+timolol) Unoprostone

Other agents

Dapiprazole Guanethidine Ripasudil

v t e

Muscarinic
Muscarinic
acetylcholine receptor modulators

mAChRs

Agonists

77-LH-28-1 AC-42 AC-260,584 Aceclidine Acetylcholine AF30 AF150(S) AF267B Alvameline AQRA-741 Arecoline Bethanechol Bevonium Butyrylcholine Carbachol CDD-0034 CDD-0078 CDD-0097 CDD-0098 CDD-0102 Cevimeline Choline cis-Dioxolane Clozapine Desmethylclozapine
Desmethylclozapine
(norclozapine) Ethoxysebacylcholine Itameline LY-593,039 L-689,660 LY-2,033,298 McNA343 Methacholine Milameline Muscarine NGX-267 Ocvimeline Oxotremorine PD-151,832 Pilocarpine RS86 Sabcomeline SDZ 210-086 Sebacylcholine Suberyldicholine Talsaclidine Tazomeline Thiopilocarpine Vedaclidine VU-0029767 VU-0090157 VU-0152099 VU-0152100 VU-0238429 WAY-132,983 Xanomeline YM-796

Antagonists

3-Quinuclidinyl benzilate 4-DAMP Aclidinium bromide
Aclidinium bromide
(+formoterol) Abediterol AF-DX 250 AF-DX 384 Ambutonium bromide Anisodamine Anisodine Antihistamines (first-generation) (e.g., brompheniramine, buclizine, captodiame, chlorphenamine (chlorpheniramine), cinnarizine, clemastine, cyproheptadine, dimenhydrinate, dimetindene, diphenhydramine, doxylamine, meclizine, mepyramine (pyrilamine), mequitazine, perlapine, phenindamine, pheniramine, phenyltoloxamine, promethazine, propiomazine, triprolidine) AQ-RA 741 Atropine Atropine
Atropine
methonitrate Atypical antipsychotics (e.g., clozapine, fluperlapine, olanzapine (+fluoxetine), rilapine, quetiapine, tenilapine, zotepine) Benactyzine Benzatropine
Benzatropine
(benztropine) Benzilone Benzilylcholine mustard Benzydamine BIBN 99 Biperiden Bornaprine Camylofin CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,368 CAR-302,537 CAR-302,668 Caramiphen Cimetropium bromide Clidinium bromide Cloperastine CS-27349 Cyclobenzaprine Cyclopentolate Darifenacin DAU-5884 Desfesoterodine Dexetimide DIBD Dicycloverine
Dicycloverine
(dicyclomine) Dihexyverine Difemerine Diphemanil metilsulfate Ditran EA-3167 EA-3443 EA-3580 EA-3834 Emepronium bromide Etanautine Etybenzatropine
Etybenzatropine
(ethybenztropine) Fenpiverinium Fentonium Fesoterodine Flavoxate Glycopyrronium bromide
Glycopyrronium bromide
(+beclometasone/formoterol, +indacaterol) Hexahydrodifenidol Hexahydrosiladifenidol Hexbutinol Hexocyclium Himbacine HL-031,120 Homatropine Imidafenacin Ipratropium bromide
Ipratropium bromide
(+salbutamol) Isopropamide J-104,129 Hyoscyamine Mamba toxin 3 Mamba toxin 7 Mazaticol Mebeverine Meladrazine Mepenzolate Methantheline Methoctramine Methylatropine Methylhomatropine Methylscopolamine Metixene Muscarinic
Muscarinic
toxin 7 N-Ethyl-3-piperidyl benzilate N-Methyl-3-piperidyl benzilate Nefopam Octatropine methylbromide
Octatropine methylbromide
(anisotropine methylbromide) Orphenadrine Otenzepad (AF-DX 116) Otilonium bromide Oxapium iodide Oxitropium bromide Oxybutynin Oxyphencyclimine Oxyphenonium bromide PBID PD-102,807 PD-0298029 Penthienate Pethidine pFHHSiD Phenglutarimide Phenyltoloxamine Pipenzolate
Pipenzolate
bromide Piperidolate Pirenzepine Piroheptine Pizotifen Poldine Pridinol Prifinium bromide Procyclidine Profenamine
Profenamine
(ethopropazine) Propantheline
Propantheline
bromide Propiverine Quinidine Revefenacin Rociverine RU-47,213 SCH-57,790 SCH-72,788 SCH-217,443 Scopolamine
Scopolamine
(hyoscine) Scopolamine
Scopolamine
butylbromide (hyoscine butylbromide) Silahexacyclium Sofpironium bromide Solifenacin SSRIs (e.g., femoxetine, paroxetine) Telenzepine Terodiline Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin, mirtazapine) Tiemonium iodide Timepidium bromide Tiotropium bromide Tiquizium bromide Tofenacin Tolterodine Tricyclic antidepressants (e.g., amitriptyline (+perphenazine), amitriptylinoxide, butriptyline, cidoxepin, clomipramine, desipramine, desmethyldesipramine, dibenzepin, dosulepin (dothiepin), doxepin, imipramine, lofepramine, nitroxazepine, northiaden (desmethyldosulepin), nortriptyline, protriptyline, quinupramine, trimipramine) Tridihexethyl Trihexyphenidyl Trimebutine Tripitamine (tripitramine) Tropacine Tropatepine Tropicamide Trospium chloride Typical antipsychotics (e.g., chlorpromazine, chlorprothixene, cyamemazine (cyamepromazine), loxapine, mesoridazine, thioridazine) Umeclidinium bromide
Umeclidinium bromide
(+vilanterol) WIN-2299 Xanomeline Zamifenacin

Precursors (and prodrugs)

Acetyl-coA Adafenoxate Choline
Choline
(lecithin) Citicoline Cyprodenate Dimethylethanolamine Glycerophosphocholine Meclofenoxate
Meclofenoxate
(centrophenoxine) Phosphatidylcholine Phosphatidylethanolamine Phosphorylcholine Pirisudanol

See also: Receptor/signaling modulators • Nicotinic
Nicotinic
acetylcholine receptor modulators • Acetylcholine
Acetylcholine
metabolism/transport modulators

Authority control

LCCN: sh85009366 GND: 4143355-5

Pharmacy and pharmacology port

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