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1-alpha-H,5-alpha-H-Tropan-3-alpha-ol (+-)-tropate (ester) (8CI)
Also known as: Dl-hyoscyamine, Tropine tropate, Atropen, Atropin, 51-55-8, Dl-tropyltropate
Molecular Formula
C17H23NO3
Molecular Weight
289.4  g/mol
InChI Key
RKUNBYITZUJHSG-PJPHBNEVSA-N
FDA UNII
7C0697DR9I

An alkaloid, originally from Atropa belladonna, but found in other plants, mainly SOLANACEAE. Hyoscyamine is the 3(S)-endo isomer of atropine.
Atropine is an Anticholinergic and Cholinergic Muscarinic Antagonist. The mechanism of action of atropine is as a Cholinergic Antagonist and Cholinergic Muscarinic Antagonist.
1 2D Structure

1-alpha-H,5-alpha-H-Tropan-3-alpha-ol (+-)-tropate (ester) (8CI)

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate
2.1.2 InChI
InChI=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?
2.1.3 InChI Key
RKUNBYITZUJHSG-PJPHBNEVSA-N
2.1.4 Canonical SMILES
CN1C2CCC1CC(C2)OC(=O)C(CO)C3=CC=CC=C3
2.1.5 Isomeric SMILES
CN1[C@@H]2CC[C@H]1CC(C2)OC(=O)C(CO)C3=CC=CC=C3
2.2 Other Identifiers
2.2.1 UNII
7C0697DR9I
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Anhydrous, Atropine Sulfate

2. Atropen

3. Atropin Augenl

4. Atropine Sulfate

5. Atropine Sulfate Anhydrous

6. Atropinol

7. Augenl, Atropin

8. Sulfate Anhydrous, Atropine

9. Sulfate, Atropine

2.3.2 Depositor-Supplied Synonyms

1. Dl-hyoscyamine

2. Tropine Tropate

3. Atropen

4. Atropin

5. 51-55-8

6. Dl-tropyltropate

7. Atropinol

8. Eyesules

9. Isopto-atropine

10. Troyl Tropate

11. Hyoscyamine

12. Atropina

13. Atropin-flexiolen

14. (+,-)-tropyl Tropate

15. Atropin [german]

16. Atropina [italian]

17. (+-)-hyoscyamine

18. Tropine, Tropate (ester)

19. (+-)-atropine

20. Tropic Acid, Ester With Tropine

21. (+/-)-atropine

22. (+/-)-hyoscyamine

23. Ccris 3080

24. Atropine (usp)

25. Tropic Acid, 3-alpha-tropanyl Ester

26. Atropinum

27. Hsdb 2199

28. Dl-tropanyl 2-hydroxy-1-phenylpropionate

29. 2-phenylhydracrylic Acid 3-alpha-tropanyl Ester

30. (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl Tropate

31. Ai3-60219

32. Beta-phenyl-gamma-oxypropionsaure-tropyl-ester [german]

33. Dl-tropyl Tropate

34. (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 3-hydroxy-2-phenylpropanoate

35. 1alphah,5alphah-tropan-3alpha-ol (+-)-tropate (ester)

36. Beta-phenyl-gamma-oxypropionsaeure-tropyl-ester [german]

37. Tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate

38. 8-methyl-8-azabicyclo[3.2.1]oct-3-yl Tropate

39. Mls000069795

40. Chebi:16684

41. 7c0697dr9i

42. 8-methyl-8-azabicyclo[3.2.1]oct-3-yl 3-hydroxy-2-phenylpropanoate

43. [(1s,5r)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-hydroxy-2-phenyl-propanoate

44. Alpha-(hydroxymethyl)benzeneacetic Acid 8-methyl-8-azabicyclo(3.2.1)oct-3-yl Ester

45. Endo-(+/-)-alpha-(hydroxymethyl)benzeneacetic Acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl Ester

46. Benzeneacetic Acid, Alpha-(hydroxymethyl)-8-methyl-8-azabicyclo(3,2,1)oct-3-yl Ester, Endo-(+-)-

47. Ncgc00017333-03

48. Smr000058248

49. Dsstox_cid_113

50. Ab00694549-11

51. Dsstox_rid_75375

52. Dsstox_gsid_20113

53. Benzeneacetic Acid, Alpha-(hydroxymethyl)-, 8-methyl-8-azabicyclo(3.2.1)oct-3-yl Ester, Endo-(+-)-

54. Cas-51-55-8

55. Atropen (tn)

56. Protamine & Atropine

57. Atropine [usp:ban]

58. Einecs 200-104-8

59. Tropine (+/-)-tropate

60. Ropine Tropate

61. Unii-7c0697dr9i

62. (3-endo)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl Tropate

63. Atropine Solution

64. (1r,3r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate

65. Ncgc00159345-02

66. 3-tropoyloxytropane

67. 1-alpha-h,5-alpha-h-tropan-3-alpha-ol (+-)-tropate (ester)

68. Atropine [mi]

69. Atropine [vandf]

70. Atropinum [hpus]

71. Opera_id_1088

72. Atropine [mart.]

73. Beta-phenyl-gamma-oxypropionsaure-tropyl-ester

74. Atropine [usp-rs]

75. Atropine [who-dd]

76. Bmse000649

77. Beta-phenyl-gamma-oxypropionsaeure-tropyl-ester

78. Schembl2812

79. [(1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate

80. Atropine, Analytical Standard

81. Gtpl320

82. Benzeneacetic Acid, Alpha-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl Ester

83. Mls001148094

84. Mls002695888

85. Atropine [green Book]

86. Atnaa Component Atropine

87. Atropine [ep Impurity]

88. Atropine [orange Book]

89. Chembl254656

90. Chembl475124

91. Chembl517712

92. Cid_174174

93. Megxp0_001878

94. Atropine [ep Monograph]

95. Atropine ((+/-))

96. Atropine [usp Monograph]

97. Atropine, (+/-)-

98. Dtxsid4020113

99. Acon1_000046

100. Chebi:78734

101. Duodote Component Atropine

102. Atropine, >=95.0% (nt)

103. Atropine Component Of Atnaa

104. Bdbm200229

105. Dtxsid601141720

106. Hms2089a16

107. Hms2231g17

108. Hms3259m13

109. Bcp15060

110. Hy-b1205

111. Atropine Component Of Duodote

112. Atropine, >=99% (tlc), Powder

113. Tox21_110816

114. Tox21_111590

115. Tox21_200487

116. 1-alpha-h,5-alpha-h-tropan-3-alpha-ol (+-)-tropate (ester) (8ci)

117. Bdbm50403547

118. S4713

119. Akos015955538

120. Cs-4834

121. Db00572

122. Nc00493

123. Ncgc00017333-02

124. Ncgc00017333-04

125. Ncgc00017333-05

126. Ncgc00017333-06

127. Ncgc00142514-01

128. Ncgc00142514-03

129. Ncgc00258041-01

130. Ncgc00385525-01

131. As-56020

132. Benzeneacetic Acid, Alpha-(hydroxymethyl)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl Ester, Endo-(+-)-

133. Atropine, Meets Usp Testing Specifications

134. C1504

135. Ft-0627165

136. C01479

137. D00113

138. Q26272

139. Ab00694549-12

140. Ab00694549_14

141. Rac-tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate

142. Brd-a27290375-001-01-8

143. Brd-a27290375-330-01-1

144. Atropine, European Pharmacopoeia (ep) Reference Standard

145. Homatropine Hydrobromide Impurity D [ep Impurity]

146. 1.alpha.h,5.alpha.h-tropan-3.alpha.-ol (+/-)-tropate (ester)

147. (3-exo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl Alpha-(hydroxymethyl)benzeneacetate

148. [(1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenyl-propanoate

149. [(1s,5r)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenyl-propanoate

150. Alpha-hydroxymethylphenylacetic Acid (1r,5s)-8-methyl-8-azabicyclo[3.2.1]octane-3-yl Ester

151. Atropine For Peak Identification, European Pharmacopoeia (ep) Reference Standard

152. Rac-(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 3-hydroxy-2-phenylpropanoate

153. (1beta,3alpha,5beta)-3-[(3-hydroxy-1-oxo-2-phenylpropyl)oxy]-8-methyl-8-azabicyclo[3.2.1]octane

154. 16175-85-2

155. Benzeneacetic Acid, .alpha.-(hydroxymethyl)-(3-endo)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl Ester

156. Benzeneacetic Acid, .alpha.-(hydroxymethyl)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl Ester, Endo-(+/-)-

157. Benzeneacetic Acid, Alpha-(hydroxymethyl)- (3-endo)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl Ester

158. Benzeneacetic Acid, Alpha-(hydroxymethyl)-, 8-methyl-8-azabicyclo(3.2.1)oct-3-yl Ester, Endo-(+/-)-

2.4 Create Date
2005-06-01
3 Chemical and Physical Properties
Molecular Weight 289.4 g/mol
Molecular Formula C17H23NO3
XLogP31.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Exact Mass289.16779360 g/mol
Monoisotopic Mass289.16779360 g/mol
Topological Polar Surface Area49.8 Ų
Heavy Atom Count21
Formal Charge0
Complexity353
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameAtropen
PubMed HealthAtropine (Injection)
Drug ClassesAnesthetic Adjunct, Cholinergic Antagonist, Gastrointestinal Agent, Nerve Gas Antidote, Urinary Antispasmodic
Drug LabelEach prefilled auto-injector provides a dose of the antidote atropine in a self-contained unit, specially designed for self or caregiver administration. Four strengths of AtroPen are available; they are AtroPen 0.25 mg, AtroPen 0.5 mg, AtroPen...
Active IngredientAtropine
Dosage FormInjectable
RouteInjection
Strengtheq 0.25mg sulfate/0.3ml; eq 1mg sulfate/0.7ml; eq 0.5mg sulfate/0.7ml; eq 2mg sulfate/0.7ml
Market StatusPrescription
CompanyMeridian Medcl

2 of 2  
Drug NameAtropen
PubMed HealthAtropine (Injection)
Drug ClassesAnesthetic Adjunct, Cholinergic Antagonist, Gastrointestinal Agent, Nerve Gas Antidote, Urinary Antispasmodic
Drug LabelEach prefilled auto-injector provides a dose of the antidote atropine in a self-contained unit, specially designed for self or caregiver administration. Four strengths of AtroPen are available; they are AtroPen 0.25 mg, AtroPen 0.5 mg, AtroPen...
Active IngredientAtropine
Dosage FormInjectable
RouteInjection
Strengtheq 0.25mg sulfate/0.3ml; eq 1mg sulfate/0.7ml; eq 0.5mg sulfate/0.7ml; eq 2mg sulfate/0.7ml
Market StatusPrescription
CompanyMeridian Medcl

4.2 Therapeutic Uses

Adjuvants, Anesthesia; Anti-Arrhythmia Agents; Antidotes; Bronchodilator Agents; Muscarinic Antagonists; Mydriatics; Parasympatholytics

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


... people poisoned by anticholinesterase organic phosphorus compounds have an increased tolerance for atropine sulfate.

Hayes, W.J., Jr., E.R. Laws, Jr., (eds.). Handbook of Pesticide Toxicology. Volume 2. Classes of Pesticides. New York, NY: Academic Press, Inc., 1991., p. 951


MEDICATION (VET): ...USED ROUTINELY AS ADJUNCT TO GENERAL ANESTHESIA...TO DECR SALIVARY & AIRWAY SECRETIONS. ... USED TO FACILITATE OPHTHALMOSCOPIC EXAM OF INTERNAL OCULAR STRUCTURES & FUNCTIONS &...FOR TREATMENT OF VARIOUS OCULAR DISORDERS. ... ATROPINE IS ESSENTIAL ANTIDOTE TO ANTICHOLINESTERASE OVERDOSAGE & POISONING.

Jones, L.M., et al. Veterinary Pharmacology & Therapeutics. 4th ed. Ames: Iowa State University Press, 1977., p. 159


Adequate doses of atropine can abolish many types of reflex vagal cardiac slowing or asystole--for example, from inhalation of irritant vapors, stimulation of the carotid sinus, pressure on the eyeballs, peritoneal stimulation, or injection of contrast dye during cardiac catheterization. It also prevents or abruptly abolishes bradycardia or asystole caused by choline esters, acetylcholinesterase inhibitors, or other parasympathomimetic drugs, as well as cardiac arrest from electrical stimulation of the vagus.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 165


For more Therapeutic Uses (Complete) data for ATROPINE (24 total), please visit the HSDB record page.


4.3 Drug Warning

FATALITIES FROM ATROPINE...ARE RARE, BUT SOMETIMES OCCUR IN CHILDREN. OF ALL POTENT ALKALOIDS, ATROPINE HAS ONE OF WIDEST MARGINS OF SAFETY. FATAL DOSE... NOT KNOWN; 200-MG DOSE..USED THERAPEUTICALLY FOR MENTAL ILLNESS, &...1000 MG HAVE BEEN SURVIVED. IN CHILDREN, 10 MG OR LESS MAY BE LETHAL.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 522


DRY MOUTH, BLURRED VISION, PHOTOPHOBIA, ANHIDROSIS, & CONSTIPATION ARE UNAVOIDABLE SIDE EFFECTS...

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 840


...CONTRAINDICATED IN PERSONS WHOSE INTRAOCULAR PRESSURE IS...ELEVATED...IN PRESENCE OF PROSTATIC HYPERTROPHY OR ORGANIC PYLORIC STENOSIS. ...USED CAUTIOUSLY IN PT WITH PROSTATISM, URINARY RETENTION, DIABETES, HYPERTHYROIDISM, TACHYCARDIA, IN ELDERLY PERSONS, & CHILDREN UNDER 6 YR OF AGE.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 840


ATROPINE IS OF NO VALUE IN DELAYED TYPE OF MUSHROOM POISONING DUE TO TOXINS OF A PHALLOIDES & CERTAIN OTHER SPECIES OF SAME GENUS.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 531


For more Drug Warnings (Complete) data for ATROPINE (16 total), please visit the HSDB record page.


4.4 Drug Indication

For the treatment of poisoning by susceptible organophosphorous nerve agents having anti-cholinesterase activity (cholinesterase inhibitors) as well as organophosphorous or carbamate insecticides.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Atropine, a naturally occurring belladonna alkaloid, is a racemic mixture of equal parts of d- and l-hyoscyamine, whose activity is due almost entirely to the levo isomer of the drug. Atropine is commonly classified as an anticholinergic or antiparasympathetic (parasympatholytic) drug. More precisely, however, it is termed an antimuscarinic agent since it antagonizes the muscarine-like actions of acetylcholine and other choline esters. Adequate doses of atropine abolish various types of reflex vagal cardiac slowing or asystole. The drug also prevents or abolishes bradycardia or asystole produced by injection of choline esters, anticholinesterase agents or other parasympathomimetic drugs, and cardiac arrest produced by stimulation of the vagus. Atropine may also lessen the degree of partial heart block when vagal activity is an etiologic factor. Atropine in clinical doses counteracts the peripheral dilatation and abrupt decrease in blood pressure produced by choline esters. However, when given by itself, atropine does not exert a striking or uniform effect on blood vessels or blood pressure.


5.2 MeSH Pharmacological Classification

Adjuvants, Anesthesia

Agents that are administered in association with anesthetics to increase effectiveness, improve delivery, or decrease required dosage. (See all compounds classified as Adjuvants, Anesthesia.)


Anti-Arrhythmia Agents

Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)


Muscarinic Antagonists

Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system. (See all compounds classified as Muscarinic Antagonists.)


Bronchodilator Agents

Agents that cause an increase in the expansion of a bronchus or bronchial tubes. (See all compounds classified as Bronchodilator Agents.)


Mydriatics

Agents that dilate the pupil. They may be either sympathomimetics or parasympatholytics. (See all compounds classified as Mydriatics.)


Parasympatholytics

Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS. (See all compounds classified as Parasympatholytics.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
ATROPINE
5.3.2 FDA UNII
7C0697DR9I
5.3.3 Pharmacological Classes
Cholinergic Antagonists [MoA]; Cholinergic Muscarinic Antagonist [EPC]; Cholinergic Muscarinic Antagonists [MoA]; Anticholinergic [EPC]
5.4 ATC Code

A03BA01

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


A - Alimentary tract and metabolism

A03 - Drugs for functional gastrointestinal disorders

A03B - Belladonna and derivatives, plain

A03BA - Belladonna alkaloids, tertiary amines

A03BA01 - Atropine


A - Alimentary tract and metabolism

A03 - Drugs for functional gastrointestinal disorders

A03B - Belladonna and derivatives, plain

A03BA - Belladonna alkaloids, tertiary amines

A03BA03 - Hyoscyamine


S - Sensory organs

S01 - Ophthalmologicals

S01F - Mydriatics and cycloplegics

S01FA - Anticholinergics

S01FA01 - Atropine


5.5 Absorption, Distribution and Excretion

Absorption

Atropine is rapidly and well absorbed after intramuscular administration. Atropine disappears rapidly from the blood and is distributed throughout the various body tissues and fluids.


Route of Elimination

Much of the drug is destroyed by enzymatic hydrolysis, particularly in the liver; from 13 to 50% is excreted unchanged in the urine.


BELLADONNA ALKALOIDS...ARE ABSORBED RAPIDLY FROM THE GI TRACT. THEY ALSO ENTER CIRCULATION WHEN APPLIED...TO MUCOSAL SURFACES OF THE BODY. ABSORPTION FROM INTACT SKIN IS LIMITED, ALTHOUGH EFFICIENT ABSORPTION DOES OCCUR IN THE POSTAURICULAR REGION. ... ATROPINE HAS A HALF-LIFE OF APPROX 4 HR; HEPATIC METAB ACCOUNTS FOR THE ELIMINATION OF ABOUT HALF OF A DOSE, & THE REMAINDER IS EXCRETED UNCHANGED IN THE URINE.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 167


...WHEN ADMIN TO MOTHER PASS RAPIDLY INTO FETAL BLOOD.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 634


IN DOG, 27% OF SC DOSE OF (3)H-ATROPINE WAS EXCRETED IN 2-HR URINE MOSTLY UNCHANGED. 50%...WAS EXCRETED WITHIN 6-HR, & RENAL EXCRETION OF ATROPINE OCCURRED BY GLOMERULAR FILTRATION & TUBULAR SECRETION.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 69


AFTER IM ADMIN OF RADIOACTIVELY LABELED ATROPINE TO MAN, DISAPPEARANCE OF RADIOACTIVITY FROM PLASMA WAS BIPHASIC, WITH...HALF-LIVES OF 2 HR & 13-28 HR... BETWEEN 77 & 94% OF TOTAL RADIOACTIVITY WAS EXCRETED IN URINE... CHROMATOGRAPHIC EVIDENCE SUGGESTED THAT RELATIVE PROPORTIONS OF METABOLITIES VARIED WITH TIME.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 455


For more Absorption, Distribution and Excretion (Complete) data for ATROPINE (6 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Much of the drug is destroyed by enzymatic hydrolysis, particularly in the liver. From 13 to 50% is excreted unchanged in the urine.


... HEPATIC METAB ACCOUNTS FOR THE ELIMINATION OF ABOUT HALF OF A DOSE, & THE REMAINDER IS EXCRETED UNCHANGED IN THE URINE.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 167


WITH (14)C RESTRICTED TO ALPHA-CARBON...ON TROPIC ACID PORTION...10 RADIOACTIVE...PRODUCTS...IN MOUSE & RAT URINE, PRINCIPAL METABOLITES WERE GLUCURONIDE CONJUGATES OF HYDROXYATROPINES FORMED IN VIVO BY METABOLIC HYDROXYLATION OF AROMATIC RING...GLUCURONIDES OF ATROPINE COULD NOT BE DETECTED IN HUMAN URINE...

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. III-44


5.7 Biological Half-Life

3.0 ± 0.9 hours in adults. The half-life of atropine is slightly shorter (approximately 20 minutes) in females than males.


AFTER IM ADMIN OF RADIOACTIVELY LABELED ATROPINE TO MAN, DISAPPEARANCE OF RADIOACTIVITY FROM PLASMA WAS BIPHASIC, WITH...HALF-LIVES OF 2 HR & 13-28 HR...

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 455


5.8 Mechanism of Action

Atropine binds to and inhibit muscarinic acetylcholine receptors, producing a wide range of anticholinergic effects.


Atropine... competes with ACh & other muscarinic agonists for a common binding site on the muscarinic receptor. The binding site for competitive antagonists & acetylcholine is in a cleft predicted to be formed by several of the receptor's 7 transmembrane helices, as shown recently for the position of retinol in the mammalian rhodopsin structure. An aspartic acid present in the N-terminal portion of the third transmembrane helix of all 5 muscarinic receptor subtypes is believed to form an ionic bond with the cationic quaternary nitrogen in acetylcholine & the tertiary or quaternary nitrogen of the antagonists.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 164


ATROPINE...(IS A) SELECTIVE ANTAGONIST OF MUSCARINIC AGENTS AT CORRESPONDING RECEPTORS OF SMOOTH & CARDIAC MUSCLE & EXOCRINE GLAND CELLS. THIS ANTAGONISM IS SO SELECTIVE THAT ATROPINE BLOCKADE OF ACTIONS OF NONCHOLINOMIMETIC DRUG... TAKEN AS EVIDENCE THAT DRUG ACTS INDIRECTLY THROUGH ACH RELEASE OR SOME OTHER CHOLINERGIC MECHANISM.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 516


...The site of action of atropine, a non-selective muscarinic receptor antagonist, in reducing increased muscle rigidity ...induced by the selective dopamine D2 receptor antagonist, raclopride /was investigated/. Atropine significantly reduced raclopride-induced EMG increases in rat hindlimb muscles, when injected into the ventral striatum, but not the dorsal striatum or the substantia nigra. Atropine's site of action was localized to a small area of muscarinic receptors within the ventral part of the striatum... These findings provide new information about the regulation of motor control by muscarinic receptor antagonists & additional evidence about the functional heterogeneity of the striatum.

PMID:11779574 Hemsley KM, Crocker AD; Eur J Pharmacol 434(3): 117-123 (2002)


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