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| | (-)-ANABASINE Basic information |
| Product Name: | (-)-ANABASINE | | Synonyms: | (±)-Anabasine, tech. 85%;3-(2-Piperidinyl)pyridine, Neonicotine;2-(3-Pyridyl)piperidine, Neonicotine;3-piperidin-2-ylpyridine hydrochloride;(±)-Anabasine,3-(2-Piperidinyl)pyridine, Neonicotine;Anabasine,2-(3-Pyridyl)piperidine, Neonicotine;Anabasine, Neonicotine, 2-(Pyridin-3-yl)piperidine;Nicotine EP Impurity G (Anabasine ) | | CAS: | 13078-04-1 | | MF: | C10H14N2 | | MW: | 162.23 | | EINECS: | 621-972-8 | | Product Categories: | Aromatics Compounds;Alkaloids;Pyrans, Piperidines &Piperazines;Neuroscience;Neurotransmission;Neurotransmitters;Aromatics;Heterocycles;Nicotinic Acetylcholine Receptor Modulators;Agonists;Analytical Standards;Pesticides &;Pesticides Standards;Pyridines;Nicotine Derivatives;Pyrans, Piperidines & Piperazines;Analytical/Chromatography;AN-AZ;Bioactive Small Molecules;Botanicals;Building Blocks;C10;Cell Biology;Cell Signaling and Neuroscience;Chemical Synthesis;Cholinergics;Chromatography;Environmental Standards;Heterocyclic Building Blocks;Insecticides;Ion Channels;Ligand-Gated Ion Channels;Metabolites | | Mol File: | 13078-04-1.mol |  |
| | (-)-ANABASINE Chemical Properties |
| Melting point | 9 °C | | Boiling point | 270 °C | | density | 1.05 g/mL at 25 °C(lit.) | | refractive index | 1.5440 | | Fp | 93 °C | | storage temp. | Keep in dark place,Inert atmosphere,2-8°C | | solubility | H2O: 10 mg/mL | | pka | 8.98±0.10(Predicted) | | form | liquid | | color | colorless to yellow | | Merck | 14,619 | | BRN | 82639 | | InChIKey | MTXSIJUGVMTTMU-UHFFFAOYSA-N | | LogP | 0.852 (est) |
| | (-)-ANABASINE Usage And Synthesis |
| Description | Anatabine is an alkaloid found in the root, fibrous roots, or bark of Alangium chinense (Lour) Harms. The herb was recorded in “Jianyi Bencao,” “Bencao Gangmu
Shiyi,” and “Zhi Wu Ming Shi Tu Kao.” Alangium chinense is widely distributed in
the east and south of China. It is also called “Bailongxu” in Shaanxi, Yunnan, and
Guizhou provinces, “Baijintiao” in Guangxi province, and “Bajiaowutong,”
“Bajiaojinpan,” or “Laolongxu” in Jiangxi and Hubei provinces. This plant is commonly used as a traditional Chinese medicine. The Alangium species includes more
than 30 plants which are distributed in Asia, Oceania, and Africa. Nine of these plants
are distributed in China. The root and the stem parts of Alangium plants are toxic. | | Chemical Properties | Colourless Oil | | Physical properties | Appearance: Colorless to yellow liquid. Solubility: Soluble in water and common
organic solvents. Boiling point: 110?°C. Refractive index: 1.5418. Density: 1.0516?g
cm?3. | | History | Alangium chinense contains alkaloids, sugars, saponins, steroids, triterpenes,
anthraquinones and their glycosides, and other ingredients. In 1974, dl-anabasine
was isolated from the fibrous roots of Alangium chinense . Four isoquinoline
alkaloids including two new alkaloids (?)-10-O-dimethyl-eugenol base and
10-O-dimethyl-eugenol base were isolated. P-amyrin acetate, triacontanol, and
β-sitosterol were then found in its leaves . Seven glycosides were isolated from
the water-soluble fraction of dried leaves of Alangium chinense, and eight glycosides were also isolated from the n-butanol soluble part . Three new lignincompounds including 2-O-(β-apio-furanosyl)-β-glucoside, E ferulic acid ester, and
Z ferulic acid ester were extracted from Alangium chinense, and their structures
were determined. Nakamoto et?al. extracted 7-O-acetylmaleic acid from Alangium
chinense and determined the structure. There are also long-chain fatty acids and
short-chain alkanes in Alangium chinense leaves. The volatile oil was then analyzed, and 59 components are identified by GC-MS.?The total alkaloid content in
the Alangium chinense was found to be fibrous root > fine root > coarse root >
branch wood > leaf. | | Uses | Anabasine, a tobacco alkaloid, was used as a biomarker of active tobacco use. | | Uses | A nicotinic receptor agonist | | Uses | insecticide | | Definition | ChEBI: A pyridine alkaloid that is pyridine substituted by a piperidin-2-yl group at position 3. | | General Description | Anabasine inhibited androstenedione conversion to estrogen in a dose-dependent manner. | | Pharmacology | Alangium plants have wide pharmacological effects including muscle relaxation,
central inhibition, anticancer, antibacterial, and so on. The “Jisong-II” injection has
presynaptic and postsynaptic effects on the neuromuscular junction, and it acts as
noncompetitive muscular relaxant . In 1979, the respiratory suppression experiments showed that Alangium chinense is a central nervous system depressant .
The extract of Alangium chinense significantly inhibits the growth of P388 lymphoblastic leukemia and Gardner lymphosarcoma in mice, but it has no effect on Gross
virus-induced leukemia, Warner myelomonocytic leukemia, and B16 melanoma .
Another study reported that the anabasine could excite respiratory similar to nicotine
and lobeline. Anabasine also induces high blood pressure and bradycardia. The components in the Alangium chinense extract can bind to the M, 5-HT and dopamine
receptors indicating that Alangium chinense affects the central nervous system. | | Clinical Use | The Alangium chinense was used for treating rheumatoid arthritis. |
| | (-)-ANABASINE Preparation Products And Raw materials |
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