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Anisodine is a naturally occurring alkaloid that is isolated from the roots of the plant Solanaceae Anisodus tanguticus (Maxim.) Pasch. (Scopolia tangutica Maxim.), commonly known as Zhang-Liu-Shen. This plant is typically found growing at high altitudes of 1700–4300 meters and is widely distributed in various provinces in China, including Tibet, Sichuan, Qinghai, and Gansu.

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  • 52646-92-1 Structure
  • Basic information

    1. Product Name: Anisodine
    2. Synonyms: (αS)-α-Hydroxy-α-(hydroxymethyl)benzeneacetic acid (1R,2R,4S,5S,7α)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nona-7-yl ester
    3. CAS NO:52646-92-1
    4. Molecular Formula: C17H21NO5
    5. Molecular Weight: 319.355
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 52646-92-1.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 495°Cat760mmHg
    3. Flash Point: 253.2°C
    4. Appearance: /
    5. Density: 1.39g/cm3
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: Anisodine(CAS DataBase Reference)
    10. NIST Chemistry Reference: Anisodine(52646-92-1)
    11. EPA Substance Registry System: Anisodine(52646-92-1)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 52646-92-1(Hazardous Substances Data)

52646-92-1 Usage

Uses

1. Used in Pharmaceutical Industry:
Anisodine is used as a pharmaceutical agent for its various therapeutic properties. It is known for its antispasmodic, sedative, and analgesic effects, making it useful in the treatment of conditions such as asthma, bronchitis, and other respiratory disorders.
2. Used in Traditional Chinese Medicine:
In Traditional Chinese Medicine, Anisodine is used as a component in various herbal formulations to treat a range of ailments, including pain relief, inflammation, and respiratory issues.
3. Used in Research and Development:
Anisodine is also utilized in research and development for its potential applications in the development of new drugs and therapies, particularly in the areas of neuroscience and respiratory medicine.
Physical properties of Anisodine:
Appearance: White crystals or crystalline powder
Flash point: 253.2°C
Melting point: 126–128°C (acetone-H2O), 190–192°C (95% ethanol), and 197–200°C (absolute ethanol)
MS m/e (%): 319(51), 154(14), 138(100), 96(5), 95(5), 94(36), 97(15), 96(5), 42(15), 137(25), and 119(23)

History

Anisodine hydrobromide was an originally created new drug in China. It was separated from the herbal medicine Anisodus tanguticus from Qinghai province. In the early 1960s, Anisodus tanguticus was given the common name of Zhang-Liu-Shenin Qinghai province, similar to the common name Zhang Liu of Radix Phytolaccae. As a result, the root was misused as Radix Phytolaccae until the occurrence of atropine poisoning symptoms. Histological identification found that it is Anisodus tanguticus (Maxim.) Pasch, not Radix Phytolaccae. In order to make full use of the wild plant’s resources and develop the products of henbane drugs in China, the Chinese Academy of Medical Sciences carried out the systemic research on the plant .

Indications

Anisodine hydrobromide is recorded in the second volume of national standards for chemical drugs of the People’s Republic of China. The formulation consists of injection and tablet. It is used clinically for treatment of migraine, retinal vascular spasm, ischemic lesions, shrinking of the optic nerve, retina, and choroid, etc. It could improve the functional recovery after acute paralysis induced by inflammation of the nervous system and cerebrovascular disease, paralysis agitants, and carbon monoxideinduced toxic encephalopathy. It was also used for intravenous combined anesthesia, organophosphorus poisoning, bronchitis, asthma, and prevention and treatment of seasickness.

Pharmacology

Central anticholinergic effects: anisodine competes with acetylcholine in the M cholinergic receptor to prevent acetylcholine binding M cholinergic receptor, thus blocking the nerve impulse transmission and interfering with the physiological function based on the cholinergic neurotransmission. It has similar or slightly weaker effects than that of atropine on electrical activity of the brain, on pain caused by tremorine, and on tremor caused by arecoline in mice. Its effect is 19 times weaker than those of scopolamine . Peripheral anticholinergic effects: anisodine possesses antispasmodic and antiasthma effects and inhibits saliva secretion and mydriasis, which are weaker than those of atropine. It acts against organic phosphate pesticide poisoning. Anti-shock effect: anisodine prolonged significantly the survival time of animals or reduced mortality in patients with clinical shock through directly relieving vasospasm of vascular smooth muscle, antagonizing adrenaline-induced vasoconstriction, and improving microcirculation . Anti-cerebral ischemic disease: the effect of anisodine on cerebral blood circulation is mainly to regulate vasomotor, decrease cerebral vascular resistance, and increase cerebral blood flow, thereby improving the symptoms of cerebral ischemia.

Clinical Use

In the past, anisodine was mainly used in the treatment of various diseases of the central nervous system. It had a certain therapeutic effect on patients with very low vision and deservesclinical application . When used for ischemic optic neuropathy treatment, anisodine significantly promoted the recovery of the visual field, with the effective rate as high as 82.14% compared with conventional therapeutic regimen using corticosteroids combined with vasodilators, thrombolytic agents, vitamins, and antibiotics.

Check Digit Verification of cas no

The CAS Registry Mumber 52646-92-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,2,6,4 and 6 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 52646-92:
(7*5)+(6*2)+(5*6)+(4*4)+(3*6)+(2*9)+(1*2)=131
131 % 10 = 1
So 52646-92-1 is a valid CAS Registry Number.

52646-92-1Downstream Products

52646-92-1Relevant articles and documents

An efficient approach to?the?asymmetric total synthesis of?(-)-anisodine

Chang, Junbiao,Xie, Weilin,Wang, Limin,Ma, Nianchun,Cheng, Senxiang,Xie, Jingxi

, p. 397 - 400 (2007/10/03)

-Anisodine (l-6,7-epoxy-3-tropyl-α-hydroxytropate), which was isolated from the medicinal plant Scopolia tanguticus Maxim, was the first efficiently prepared using 6-β-acetyltropine as the starting material via a key step of the Sharpless asymmetric dihydroxylation (AD). The intermediate compounds 10 and 11 showed promising cholinergic activity.

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