Anisodamine

Anisodamine Basic information
Product Name:Anisodamine
Synonyms:ANISODAMINE;α-(Hydroxymethyl)benzeneacetic acid 6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl ester;Tropic acid 6-hydroxy-3-tropanyl ester;LAnisodaMine;6-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate;Racanisodamine, 98%, from Anisodus tanguticus;[(3S,5S,6S)-6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2S)-3-hydroxy-2-phenylpropanoate;Anisodamine Intermediate
CAS:17659-49-3
MF:C17H23NO4
MW:305.37
EINECS:
Product Categories:
Mol File:17659-49-3.mol
Anisodamine Structure
Anisodamine Chemical Properties
Melting point 106-109°C
Boiling point 474.6±45.0 °C(Predicted)
density 1.27
storage temp. Sealed in dry,Room Temperature
solubility Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
pka14.12±0.10(Predicted)
form Solid
color White
Safety Information
HS Code 29399990
MSDS Information
Anisodamine Usage And Synthesis
DescriptionAmisodamine is a kind of alkaloid which is mainly living in anisodus tanguticus, which is a M receptor just like Atropine. It is a kind of traditional Chinese medicine which comes from the “National assembly of Chinese Herbal medicine”, and it is the alias of zangjia registered in “Chines herbal medicine summary of shan gan ning qing”. It is a perennial root herb that lives in the bottom slope in the eastern Tibet, Qinghai Province, the Southern GanSu Province, the western SiChuan Province, the northwestward YunNan Province. Since the sources is scare, racemic form of raceanisodamine is the main drug in clinic.
DescriptionAnisodamine is a natural tropane alkaloid shown to be a weak antagonist of α1-adrenoceptors, blocking WB-4101 and clonidine binding in brain membrane preparations with pKi values of 2.63 and 1.61, respectively. Anisodamine also has antioxidant effects that may protect against free radical-induced cellular damage. Anisodamine is predominantly found in the roots of A. tanguticus, which is used in traditional Chinese medicine for topical applications.
Physical propertiesAppearance: raceanisodamine is a kind of white crystal and crystalline powder. It is odorless and bitter to the taste. Solubility: it is easy dissolubility in hydrochloric acid and ethyl alcohol and is soluble in water. Melting point: it’s melting point is from 103 to 113?°C.?The weld spacing is within 6°. Specific optical rotation: ?9° to +11°.
HistoryIt is the traditional Chinese medicine and the rich folk herbs that create favorable conditions to look for and develop good medicine. Dated from ancient times, anisodus tanguticus used to the treatment of pain. Unfortunately, it can lead to atropine poisoning resulted from large dosage. When found the adverse effects, research made analysis and finally discovered six kinds of ramifications. Besides, they found two types alkaloid anisodamine and anisodine. Compared with atropine, anisodamen has one more hydroxy in tropic ring and named “654”.
Usesanticholinergic, antispasmodic
UsesTropic Acid 6-Hydroxy-3-tropanyl Ester is a Hycosamine (H674300) derivative, which is a natural compound with inhibitory activity against cholinesterases.
IndicationsAnisodamine is a kind of anticholinergic agent. The tablet and injection form are mainly used to relieve smooth muscle spasm, biliary spasm and AOIP in clinical practice. The eye drop is used to treat teenage pseudomyopia; raceanisodamine concomitant with other drugs to treat cluster headache syndrome, renal colic, infantile diarrhea, infantile jaundice hepatitis, infantile purpura, bronchopneumonia, etc.
Pharmacology1. Cholinolytic effect. Anisodamine can block acetylcholine receptors. We always take it as a merely blocker of M receptor. In recent years, it turns out that anisodamine is also a blocker of N receptor.
2. Calcium antagonist effect. Anisodamine will put up Clacium antagonist effect when ischemia, oxygen deficit or other reasons result in irreversible damage and apoptosis. 3. Reduce the level of NO. 50 mg/L anisodamine can restrain lipopolysaccharide combined with vascular endothelial cells and promote the production of NO and over-dosage of NO is the pivotal pathologic mechanism of the toxic shock . Pretreatment with anisodamine can reduce the level of NO obviously when cells are damaged and remit toxicity resulted from over-dosage of NO. 4. Anti-oxygenation. anisodamine can restrain myocardial function damage resulted from pyrogallol obviously and can adjust the function of cardioid damaged by ROS .
Clinical UseAnisodamine is a new drug developed by Chinese scientists. It has been widely put into use in clinical practice such as slow reflow phenomenon of ST-elevation acute myocardial infarction patients with percutaneous coronary intervention, infusion leakage , neonatal sclerosis. At present, it is mainly used to dilate vessels, remove vasospasm, improve blood circulation, increase tolerance of ischemia hypoxia and reduce the probability of the surrounding tissue necrosis
references[1] varma d r, yue t l. adrenoceptor blocking properties of atropine‐like agents anisodamine and anisodine on brain and cardiovascular tissues of rats[j]. british journal of pharmacology, 1986, 87(3): 587-594.
[2] piascik m t, perez d m. α1-adrenergic receptors: new insights and directions[j]. journal of pharmacology and experimental therapeutics, 2001, 298(2): 403-410.
[3] poupko j m, baskin s i, moore e. the pharmacological properties of anisodamine[j]. journal of applied toxicology, 2007, 27(2): 116-121.
Anisodamine Preparation Products And Raw materials
Phloroglucinol Tannic acid berberine Atropine D(+)-Glucose 6-hydroxy-8-methyl-8-aza-bicyclo(3.2.1)octan-3-y1 2-phenylacrylate Sodium chloride Raceanisodamine impurity 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-methoxybenzamide Metronidazole Omeprazole Magnesium sulfate Scopolamine butylbromide ANISODAMINE D-Glucurone Scopolamine Racanisodamine Anisodamine HYOSCINE HYDROCHLORIDE

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