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| CAS No.: | 51-55-8 |
|---|---|
| Name: | Atropine |
| Molecular Structure: | |
|
|
|
| Formula: | C17H23NO3 |
| Molecular Weight: | 289.375 |
| Synonyms: | 1aH,5aH-Tropan-3a-ol (?à)-tropate (ester) (8CI);Tropine tropate;dl-Hyoscyamine; |
| EINECS: | 200-104-8 |
| Density: | 1.194 g/cm3 |
| Melting Point: | 115-118 °C |
| Boiling Point: | 429.804 °C at 760 mmHg |
| Flash Point: | 213.738 °C |
| Solubility: | 1.6g/L(18 oC) |
| Appearance: | white crystalline powder |
| Hazard Symbols: |
 T+, Xn
|
| Risk Codes: | 26/28-36/37/38-20/21/22 |
| Safety: | 25-45-36-26 |
| PSA: | 49.77000 |
| LogP: | 1.86880 |
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(1R,3r,5S)-3-tropoyloxytropanium sulfate
- 51-55-8
Atropine
| Conditions | Yield |
|---|---|
| With sodium hydroxide In water at 5℃; pH=12 - 13; Reagent/catalyst; | 90% |
| Conditions | Yield |
|---|---|
| Stage #1: atropine-N-oxide hydrochloride With ferrocene In isopropyl alcohol at 80℃; for 24h; Stage #2: With sodium hydroxide In chloroform; water; isopropyl alcohol | A 21% B 59% |
| Conditions | Yield |
|---|---|
| With iron(II) sulfate In methanol at 20℃; for 6h; | A 12% B 51% |
| Conditions | Yield |
|---|---|
| With sodium methylate In dimethyl sulfoxide at 20℃; | 50% |
| With sodium hydroxide In water at 100℃; under 5171.62 Torr; for 0.4h; Temperature; Flow reactor; |
| Conditions | Yield |
|---|---|
| With water und wiederholtes Eindampfen des entstandenen tropasauren Tropins mit verd.Salzsaeure; |
| Conditions | Yield |
|---|---|
| With methanol |
- 51-55-8
Atropine
| Conditions | Yield |
|---|---|
| aus Wurzeln; |
- 51-55-8
Atropine
| Conditions | Yield |
|---|---|
| Man laesst das entstandene salzsaure Acetylatropin in waessr.Loesung bei Zimmertemperatur stehen; | |
| Man laesst das entstandene salzsaure Acetylatropin in waessr.Loesung bei Zimmertemperatur stehen; |
- 51-55-8
Atropine
| Conditions | Yield |
|---|---|
| at 110 - 120℃; | |
| With sodium hydroxide; ethanol | |
| With sodium hydroxide; ethanol; carbon dioxide at 5℃; | |
| at 120 - 130℃; | |
| With methanol; phenol |
| Conditions | Yield |
|---|---|
| With isopropyl alcohol |
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History
Atropine (CAS NO.51-55-8) extracts from the Egyptian henbane were used by Cleopatra in the last century B.C. to dilate her pupils, in the hope that she would appear more alluring. The mydriatic effects of atropine were studied among others by the German chemist Friedrich Ferdinand Runge (1795–1867). In 1831, the pharmacist Mein succeeded the pure crystalline isolation of atropine. Its substance was first synthesized in 1901 by German chemist Richard Willstätter. The mydriatic effects of atropine were studied among others by the German chemist Friedrich Ferdinand Runge (1795–1867).
Consensus Reports
Reported in EPA TSCA Inventory.
Specification
The Atropine, with the CAS registry number 51-55-8, is also known as beta-Phenyl-gamma-oxypropionsaeure-tropyl-ester. It belongs to the product categories of Pharmaceutical; Alkaloids; Biochemistry; Tropane Alkaloids. Its EINECS registry number is 200-104-8. This chemical's molecular formula is C17H23NO3 and molecular weight is 289.37. Its IUPAC name is called [(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate. This chemical's classification codes are Adjuvants, anesthesia; Anti-Asthmatic Agents; Anti-arrhythmia 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.
Physical properties of Atropine: (1)ACD/LogP: 1.38; (2)ACD/LogD (pH 5.5): -2; (3)ACD/LogD (pH 7.4): -1; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 6; (11)Index of Refraction: 1.581; (12)Molar Refractivity: 80.788 cm3; (13)Molar Volume: 242.421 cm3; (14)Surface Tension: 50.459 dyne/cm; (15)Density: 1.194 g/cm3; (16)Flash Point: 213.738 °C; (17)Enthalpy of Vaporization: 72.224 kJ/mol; (18)Boiling Point: 429.804 °C at 760 mmHg; (19)Vapour Pressure: 0 mmHg at 25°C.
Preparation: Atropine is a tropane alkaloid extracted from deadly nightshade (Atropa belladonna), jimsonweed (Datura stramonium), mandrake (Mandragora officinarum) and other plants of the family Solanaceae. It is a secondary metabolite of these plants and serves as a drug with a wide variety of effects. Atropine can be synthesized by the reaction of tropine with tropic acid in the presence of hydrochloric acid.
Atropine increases 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. In general, atropine lowers the parasympathetic activity of all muscles and glands regulated by the parasympathetic nervous system. Topical atropine is used as a cycloplegic, to temporarily paralyze the accommodation reflex, and as a mydriatic, to dilate the pupils. Injections of atropine are used in the treatment of bradycardia (an extremely low heart rate), asystole and pulseless electrical activity (PEA) in cardiac arrest. 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.
When you are using this chemical, please be cautious about it as the following:
This chemical that at very low levels can cause damage to health. It may cause damage to health. It is harmful by inhalation, in contact with skin and if swallowed. In addition, it is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CN1C2CCC1CC(C2)OC(=O)C(CO)C3=CC=CC=C3
(2)Isomeric SMILES: CN1[C@@H]2CC[C@H]1CC(C2)OC(=O)C(CO)C3=CC=CC=C3
(3)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?
(4)InChIKey: RKUNBYITZUJHSG-PJPHBNEVSA-N
The toxicity data is as follows:
| 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) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: MUSCLE WEAKNESS GASTROINTESTINAL: NAUSEA OR VOMITING | 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 BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA | 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) | BEHAVIORAL: EXCITEMENT BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | 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: EXCITEMENT LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: ATAXIA | 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) | BEHAVIORAL: EXCITEMENT BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 59, Pg. 149, 1938. |
| rabbit | LD50 | intravenous | 50mg/kg (50mg/kg) | BEHAVIORAL: EXCITEMENT BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 59, Pg. 149, 1938. |
| rabbit | LD50 | oral | 600mg/kg (600mg/kg) | BEHAVIORAL: EXCITEMENT BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 59, Pg. 149, 1938. |
| rabbit | LDLo | intraperitoneal | 350ug/kg (0.35mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION CARDIAC: PULSE RATE | 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. |