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Substance Name: Atropine [USP:BAN]
RN: 51-55-8
UNII: 7C0697DR9I
InChIKey: RKUNBYITZUJHSG-SPUOUPEWSA-N

Note

  • An alkaloid, originally from Atropa belladonna, but found in other plants, mainly SOLANACEAE. Hyoscyamine is the 3(S)-endo isomer of atropine.

Molecular Formula

  • C17-H23-N-O3

Molecular Weight

  • 289.3727
 

Classification Codes

  • Adjuvants, Anesthesia
  • Anti-Arrhythmia Agents
  • Anti-Asthmatic Agents
  • Anticholinergic
  • Autonomic Agents
  • Bronchodilator Agents
  • Cardiovascular Agents
  • Central Nervous System Agents
  • Cholinergic Agents
  • Cholinergic Antagonists
  • Drug / Therapeutic Agent
  • Human Data
  • Muscarinic Antagonists
  • Mutation Data
  • Mydriatics
  • Neurotransmitter Agents
  • Parasympatholytics
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Respiratory System Agents

Names and Synonyms

Name of Substance

  • Atropine
  • Atropine [USP:BAN]

MeSH Heading

  • Atropine

Synonyms

  • (+,-)-Tropyl tropate
  • 1alphaH,5alphaH-Tropan-3alpha-ol (+-)-tropate (ester)
  • 2-Phenylhydracrylic acid 3-alpha-tropanyl ester
  • AI3-60219
  • alpha-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester
  • Atropen
  • Atropin
  • Atropin [German]
  • Atropin-flexiolen
  • Atropina
  • Atropina [Italian]
  • Atropine
  • Atropinol
  • Benzeneacetic acid, alpha-(hydroxymethyl)-8-methyl-8-azabicyclo(3,2,1)oct-3-yl ester, endo-(+-)-
  • Benzeneacetic acid, alpha-(hydroxymethyl)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester, endo-(+-)-
  • beta-Phenyl-gamma-oxypropionsaeure-tropyl-ester
  • beta-Phenyl-gamma-oxypropionsaeure-tropyl-ester [German]
  • beta-Phenyl-gamma-oxypropionsaure-tropyl-ester
  • beta-Phenyl-gamma-oxypropionsaure-tropyl-ester [German]
  • CCRIS 3080
  • dl-Hyoscyamine
  • DL-Tropanyl 2-hydroxy-1-phenylpropionate
  • dl-Tropyltropate
  • EINECS 200-104-8
  • Eyesules
  • HSDB 2199
  • Isopto-atropine
  • Tropic acid, 3-alpha-tropanyl ester
  • Tropic acid, ester with tropine
  • Tropine tropate
  • Tropine, tropate (ester)
  • Troyl tropate
  • UNII-7C0697DR9I

Systematic Names

  • 1-alpha-H,5-alpha-H-Tropan-3-alpha-ol (+-)-tropate (ester) (8CI)
  • Atropine
  • Benzeneacetic acid, alpha-(hydroxymethyl)- (3-endo)-8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester
  • Benzeneacetic acid, alpha-(hydroxymethyl)-, 8-methyl-8-azabicyclo(3.2.1)oct-3-yl ester, endo-(+-)-

Superlist Name

  • Atropine

Mixture Names

  • ATNAA
  • Duodote

Registry Numbers

CAS Registry Number

  • 51-55-8

FDA UNII

  • 7C0697DR9I

Other Registry Numbers

  • 1445960-43-9
  • 78597-12-3

System Generated Number

  • 0000051558

Structure Descriptors

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?

InChIKey

RKUNBYITZUJHSG-SPUOUPEWSA-N

Smiles

CN1[C@@H]2CC[C@H]1C[C@H](C2)OC(=O)C(CO)c3ccccc3

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 70mg/kg (70mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 483, 1948.
cat LDLo subcutaneous 130mg/kg (130mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 60, Pg. 1, 1937.
dog LDLo intravenous 50mg/kg (50mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Proceedings of the Society for Experimental Biology and Medicine. Vol. 40, Pg. 244, 1939.
dog LDLo unreported 60mg/kg (60mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 513, 1948.
frog LDLo intramuscular 750mg/kg (750mg/kg) BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Proceedings of the Society for Experimental Biology and Medicine. Vol. 40, Pg. 244, 1939.
frog LDLo subcutaneous 1gm/kg (1000mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1311, 1935.
guinea pig LD50 intraperitoneal 400mg/kg (400mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 105, Pg. 166, 1952.
guinea pig LD50 oral 1100mg/kg (1100mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 105, Pg. 166, 1952.
human TDLo intramuscular 1ug/kg (0.001mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE "Possible Long-Term Health Effects of Short-Term Exposure to Chemical Agents," National Research Council, 3 vols., Washington, DC, National Academy Press, 1982-85Vol. 1, Pg. L1, 1982.
human TDLo oral 33ug/kg (0.033mg/kg) SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE

BEHAVIORAL: MUSCLE WEAKNESS
Journal of Toxicology, Clinical Toxicology. Vol. 22, Pg. 581, 1984/1985.
man LDLo unreported 143ug/kg (0.143mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 482, 1948.
man TDLo intramuscular 175ug/kg (0.175mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 32, Pg. 250, 1973.
man TDLo intravenous 14ug/kg (0.014mg/kg) BEHAVIORAL: HEADACHE

VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION
Annals of Internal Medicine. Vol. 101, Pg. 720, 1984.
mouse LD50 intradermal 550mg/kg (550mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA

BEHAVIORAL: EXCITEMENT
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 59, Pg. 149, 1938.
mouse LD50 intraperitoneal 30mg/kg (30mg/kg)   Journal of Medicinal Chemistry. Vol. 31, Pg. 683, 1988.
mouse LD50 intravenous 30mg/kg (30mg/kg)   Journal of Medicinal Chemistry. Vol. 28, Pg. 1760, 1985.
mouse LD50 oral 75mg/kg (75mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: EXCITEMENT
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 59, Pg. 149, 1938.
mouse LD50 subcutaneous 428mg/kg (428mg/kg)   Zhongcaoyao. Chinese Traditional and Herbal Medicine. Vol. 11, Pg. 457, 1980.
rabbit LD50 intradermal 500mg/kg (500mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA

BEHAVIORAL: EXCITEMENT
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 59, Pg. 149, 1938.
rabbit LD50 intravenous 50mg/kg (50mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: ATAXIA
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 59, Pg. 149, 1938.
rabbit LD50 oral 600mg/kg (600mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: ATAXIA
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 59, Pg. 149, 1938.
rabbit LDLo intraperitoneal 350ug/kg (0.35mg/kg) CARDIAC: PULSE RATE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Journal of Pharmacology and Experimental Therapeutics. Vol. 60, Pg. 14, 1937.
rabbit LDLo subcutaneous 500mg/kg (500mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1311, 1935.
rat LD50 intramuscular 920mg/kg (920mg/kg)   Drug and Chemical Toxicology. Vol. 1, Pg. 355, 1978.
rat LD50 intraperitoneal 280mg/kg (280mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 105, Pg. 166, 1952.
rat LD50 intravenous 73mg/kg (73mg/kg)   Schweizerische Medizinische Wochenschrift. Vol. 76, Pg. 1282, 1946.
rat LD50 oral 500mg/kg (500mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 155, Pg. 393, 1965.
rat LD50 subcutaneous 250mg/kg (250mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 68, Pg. 339, 1942.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 118.5 deg C   EXP
pKa Dissociation Constant 9.43 (none)   EXP
log P (octanol-water) 1.83 (none)   EXP
Water Solubility 2200 mg/L 25 EXP
Vapor Pressure 1.95E-08 mm Hg 25 EST
Henry's Law Constant 2.73E-13 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 6.11E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.