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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
- All
- Classifications
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- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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
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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
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-NSmiles
CN1[C@@H]2CC[C@H]1C[C@H](C2)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.