Compound Selection

Formula: C17H23NO3

MW: 289.37

CAS: 51-55-8

MDL: MFCD00022622

TNP: TNP00272

ATROPINE; (+/-)-HYOSCYAMINE; HYOSCYAMINE; DL-HYOSCYAMINE; TIMTEC-BB SBB005985; (+,-)-Tropyl tropate; (+,-)-tropyltropate; 1alphaH,5alphaH-Tropan-3alpha-ol (

LogP: 3.07

LogS: -4.23

Acceptors: 3

Donors: 1

Rotation Bonds: 4

Chiral Centers: 3

N+O: 4

LIPINSKY: 4

IUPAC: (1S,5R)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 3-hydroxy-2-phenylpropanoate

Smiles: N1([C@@H]2C[C@@H](OC(C(c3ccccc3)CO)=O)C[C@H]1CC2)C

THERAPEUTIC CATEGORY: Antiholinergic; mydriatic.

VET THERAPEUTIC CATEGORY:Anticholinergic; mydriatic; antispasmodic

SOURCE: Parasympatholyc alkaloid isolated from Atropa beladonna L.,and other Solanaceae.

Biochem-Physiol Action: Competitive nonselective antagonist at central and peripheral muscarinic acetylcholine receptors.

Merck Reference:

Monograph Number:  0000879
Title:  Atropine
CAS Registry Number:  51-55-8
CAS Name:  a-(Hydroxymethyl)benzeneacetic acid (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester
Additional Names:  1aH,5aH-tropan-3a-ol (±)-tropate (ester);  dl-hyoscyamine;  tropic acid ester with tropine;  dl-tropyl tropate;  tropine tropate
Molecular Formula:  C17H23NO3
Molecular Weight:  289.37. 
Percent Composition:  C 70.56%, H 8.01%, N 4.84%, O 16.59%
Literature References:  Parasympatholytic alkaloid isolated from Atropa belladonna L., Datura stramonium L., and other Solanaceae.  Extraction procedure:  Chemnitius, J. Prakt. Chem. 116, 276 (1927).  During extraction, partial racemization of the l-hyoscyamine takes place which is completed by treatment with dil alkali on heating in chloroform soln:  Schneider, Arch. Pharm. 284, 306 (1951).  Structure and synthesis:  Ladenburg, Ann. 217, 75 (1883); Willstätter, Ber. 31, 1537 (1898); idem., Ann. 326, 23 (1903); Schwenker et al., Ber. 99, 2407 (1966).  Prepn of the sulfate:  DE 247455 (1912 to Hoffmann-La Roche), Frdl. 11, 1022.  Use as antidote to cholinesterase inhibitors:  R. V. Brown, Br. J. Pharmacol. 15, 170 (1960).  Effect on cardiac arrhythmias:  P. Schweitzer, H. Mark, Am. Heart J. 100, 119, 255 (1980).  Pharmacokinetics and pharmacodynamics:  P. H. Hinderling et al., J. Pharm. Sci. 74, 703, 711 (1985).  Toxicity:  R. L. Cahen, K. Tvede, J. Pharmacol. Exp. Ther. 105, 166 (1952); Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971).  Review of clinical use in anesthesia:  L. E. Shutt, J. B. Bowes, Anaesthesia 34, 476-490 (1979).  Comprehensive description:  A. A. Al-Badr, F. J. Muhtadi, Anal. Profiles Drug Subs. 14, 325-389 (1985).  Review of clinical toxicology:  J. D. Truwit, Crit. Care Clin. 7, 639-657 (1991).
Properties:  Long, orthorhombic prisms from acetone, mp 114-116°.  Sublimes in high vacuum at 93-110°.  pK 4.35; pH of 0.0015 molar soln 10.0.  Absorption spectra:  Dobbie, Fox, J. Chem. Soc. 103, 1194 (1913); Fischer, Arch. Exp. Pathol. Pharmakol. 170, 623 (1933).  One gram dissolves in 455 ml water, 90 ml water at 80°, 2 ml alc, 1.2 ml alc at 60°, 27 ml glycerol, 25 ml ether, 1 ml chloroform; also sol in benzene, dil acids.  LD50 orally in rats:  750 mg/kg (Cahen, Tvede).
Melting point:  mp 114-116°
pKa:  pK 4.35; pH of 0.0015 molar soln 10.0
Toxicity data:  LD50 orally in rats:  750 mg/kg (Cahen, Tvede)

Derivative Type:  Methylbromide
CAS Registry Number:  2870-71-5
Additional Names:  Methylatropine bromide
Trademarks:  Tropin (Takeda)
Molecular Formula:  C17H23NO3.CH3Br
Molecular Weight:  384.31. 
Percent Composition:  C 56.25%, H 6.82%, N 3.64%, O 12.49%, Br 20.79%
Properties:  Crystals, mp 222-223°.  Sol in 1 part water; slightly sol in alc.  Almost insol in chloroform, ether.
Melting point:  mp 222-223°

Derivative Type:  Methylnitrate
CAS Registry Number:  52-88-0
Additional Names:  Methylatropine nitrate
Trademarks:  Eumydrin (SKB)
Molecular Formula:  C17H23NO3.CH3NO3
Molecular Weight:  366.41. 
Percent Composition:  C 59.00%, H 7.15%, N 7.65%, O 26.20%
Properties:  Crystals, mp 163°.  Freely sol in water or alc, very slightly in chloroform, ether.
Melting point:  mp 163°

Derivative Type:  Sulfate monohydrate
CAS Registry Number:  5908-99-6;  55-48-1 (anhydrous)
Trademarks:  Atropisol (Novartis);  Atropt (Sigma)
Molecular Formula:  (C17H23NO3)2.H2SO4.H2O
Molecular Weight:  694.83. 
Percent Composition:  C 58.77%, H 7.25%, N 4.03%, O 25.33%, S 4.61%
Properties:  Granules or powder, mp 190-194°.  Almost inactive optically.  Very bitter.  pH ~5.4.  One gram dissolves in 0.4 ml water; 5 ml cold, 2.5 ml boil. alc; in 2.5 ml glycerol, 420 ml chloroform, 3000 ml ether.  Bitterness threshold 1:10,000.  Incompatible with alkalies, tannin, salts of mercury or gold, vegetable decoctions or infusions, borax, bromides, iodides, benzoates.  LD50 orally in rats:  622 mg/kg (Goldenthal).
Melting point:  mp 190-194°
Toxicity data:  LD50 orally in rats:  622 mg/kg (Goldenthal)

Derivative Type:  N-Oxide
CAS Registry Number:  4438-22-6
Additional Names:  Atropine aminoxide;  aminoxytropine tropate;  genatropine
Molecular Formula:  C17H23NO4
Molecular Weight:  305.37. 
Percent Composition:  C 66.86%, H 7.59%, N 4.59%, O 20.96%
Literature References:  Prepn:  Polonovski, Polonovski, Bull. Soc. Chim. Fr. 39, 1147 (1926).
Properties:  Crystalline powder, mp 127-128°, dec 135°.  Very hygroscopic.  Soluble in alc, chloroform.  Practically insol in ether.
Melting point:  mp 127-128°

CAUTION:  Causes blurred vision, suppressed salivation, vasodilation, hyperpyrexia, excitement, agitation, and delirium.  See:  Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th Ed., 1984) Section III, pp 47-50.
Therap-Cat:  Mydriatic; antispasmodic.  In preanesthetic medication.
Therap-Cat-Vet:  Mydriatic; antispasmodic.  Antidote to organophosphorus insecticides.

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