| Identification | Back Directory | [Name]
ANISODAMINE | [CAS]
17659-49-3 | [Synonyms]
ANISODAMINE
LAnisodaMine
Tropic acid 6-hydroxy-3-tropanyl ester
α-(Hydroxymethyl)benzeneacetic acid 6-hydroxy-8-methyl-8-azabicyclo[3.2.1]octan-3-yl ester | [Molecular Formula]
C17H23NO4 | [MDL Number]
MFCD01732987 | [MOL File]
17659-49-3.mol | [Molecular Weight]
305.37 |
| Chemical Properties | Back Directory | [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 | [InChI]
InChI=1/C17H23NO4/c1-18-12-7-13(9-15(18)16(20)8-12)22-17(21)14(10-19)11-5-3-2-4-6-11/h2-6,12-16,19-20H,7-10H2,1H3/t12-,13+,14-,15+,16+/s3 | [InChIKey]
WTQYWNWRJNXDEG-FUSWRVNVNA-N | [SMILES]
[C@]12([H])C[C@H](C[C@]([H])(C[C@@H]1O)N2C)OC(=O)[C@H](CO)C1C=CC=CC=1 |&1:0,3,5,8,15,r| |
| Hazard Information | Back Directory | [Usage]
anticholinergic, antispasmodic | [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 (Item No. 15949) binding in brain membrane preparations with pKi values of 2.63 and 1.61, respectively.1 Anisodamine also has antioxidant effects that may protect against free radical-induced cellular damage.2 Anisodamine is predominantly found in the roots of A. tanguticus, which is used in traditional Chinese medicine for topical applications.3 | [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”. | [Uses]
anticholinergic, antispasmodic | [Uses]
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. |
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