Anisodamine
Synonym(s):α-(Hydroxymethyl)-benzeneacetic acid 6-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester;6β-Hydroxyhyoscyamine;6-Hydroxyhyoscyamine
- CAS NO.:17659-49-3
- Empirical Formula: C17H23NO4
- Molecular Weight: 305.37
- MDL number: MFCD03764601
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-21 18:03:03
What is Anisodamine?
Description
Amisodamine 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.
Description
Anisodamine 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 properties
Appearance: 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°.
History
It 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”.
The Uses of Anisodamine
anticholinergic, antispasmodic
The Uses of Anisodamine
Tropic Acid 6-Hydroxy-3-tropanyl Ester is a Hycosamine (H674300) derivative, which is a natural compound with inhibitory activity against cholinesterases.
Indications
Anisodamine 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.
Pharmacology
1. 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 Use
Anisodamine 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.
Properties of Anisodamine
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) |
form | Solid |
pka | 14.12±0.10(Predicted) |
color | White |
Safety information for Anisodamine
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H227:Flammable liquids H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation |
Precautionary Statement Codes |
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P332+P313:IF SKIN irritation occurs: Get medical advice/attention. P337+P313:IF eye irritation persists: Get medical advice/attention. P370+P378:In case of fire: Use … for extinction. P403+P235:Store in a well-ventilated place. Keep cool. |
Computed Descriptors for Anisodamine
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