13078-04-1 Usage
Description
(-)-Anabasine, also known as Anabasine, is a pyridine alkaloid that is pyridine substituted by a piperidin-2-yl group at position 3. It is a colorless to yellow liquid with a boiling point of 110°C, a refractive index of 1.5418, and a density of 1.0516 g/cm3. It is soluble in water and common organic solvents. Anabasine is found in the root, fibrous roots, or bark of Alangium chinense, a plant commonly used as a traditional Chinese medicine. It has been used as a biomarker of active tobacco use, a nicotinic receptor agonist, and an insecticide.
Uses
Used in Tobacco Industry:
(-)-Anabasine is used as a biomarker for active tobacco use, helping to identify and monitor tobacco consumption.
Used in Pharmaceutical Industry:
(-)-Anabasine is used as a nicotinic receptor agonist, playing a role in the development of medications targeting the nervous system.
Used in Agriculture:
(-)-Anabasine is used as an insecticide, providing a natural method for pest control in the agricultural industry.
Used in Research:
(-)-Anabasine is used in research for its ability to inhibit androstenedione conversion to estrogen in a dose-dependent manner, which may have implications in the study of hormone-related conditions and diseases.
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 13078-04-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,0,7 and 8 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 13078-04:
(7*1)+(6*3)+(5*0)+(4*7)+(3*8)+(2*0)+(1*4)=81
81 % 10 = 1
So 13078-04-1 is a valid CAS Registry Number.
InChI:InChI=1/C10H14N2/c1-2-7-12-10(5-1)9-4-3-6-11-8-9/h3-4,6,8,10,12H,1-2,5,7H2
13078-04-1Relevant articles and documents
SYNTHESIS OF TOBACCO ALKALOIDS VIA TERTIARY AZIDES
Alberici, Gilles F.,Andrieux, Jean,Adam, Gerard,Plat, Michel M.
, p. 1937 - 1940 (1983)
A convenient new synthesis of different tobacco alkaloids, such as nicotine and anabasine is described, using as key step the SCHMIDT reaction applied to tertiary alcohols.
From building block to natural products: A short synthesis and complete NMR spectroscopic characterization of (±)-anatabine and (±)-anabasine
Saloranta, Tiina,Leino, Reko
, p. 4619 - 4621 (2011)
A short and straightforward synthesis of the racemic tobacco alkaloids anatabine and anabasine in five and six steps, respectively, from 3-pyridinecarboxaldehyde utilizing Barbier-type Zn-mediated allylation and ring-closing olefin metathesis, as the key steps, is reported. Additionally, a complete NMR spectroscopic analysis of the final products is carried out and full assignment of the NMR spectra of anatabine and anabasine with accurate coupling constants is accomplished and reported here for the first time.
Direct α-C-H bond functionalization of unprotected cyclic amines
Chen, Weijie,Ma, Longle,Paul, Anirudra,Seidel, Daniel
, p. 165 - 169 (2018/02/06)
Cyclic amines are ubiquitous core structures of bioactive natural products and pharmaceutical drugs. Although the site-selective abstraction of C-H bonds is an attractive strategy for preparing valuable functionalized amines from their readily available parent heterocycles, this approach has largely been limited to substrates that require protection of the amine nitrogen atom. In addition, most methods rely on transition metals and are incompatible with the presence of amine N-H bonds. Here we introduce a protecting-group-free approach for the α-functionalization of cyclic secondary amines. An operationally simple one-pot procedure generates products via a process that involves intermolecular hydride transfer to generate an imine intermediate that is subsequently captured by a nucleophile, such as an alkyl or aryl lithium compound. Reactions are regioselective and stereospecific and enable the rapid preparation of bioactive amines, as exemplified by the facile synthesis of anabasine and (-)-solenopsin A.
One-pot formation of piperidine- and pyrrolidine-substituted pyridinium salts via addition of 5-alkylaminopenta-2,4-dienals to N-acyliminium ions: Application to the synthesis of (±)-nicotine and analogs
Peixoto, Sabrina,Nguyen, Tuan Minh,Crich, David,Delpech, Bernard,Marazano, Christian
supporting information; body text, p. 4760 - 4763 (2010/12/25)
Addition of 5-alkylaminopenta-2,4-dienals onto N-acyliminium ions, generated in situ from α-hydroxycarbamates derived from pyrrolidine or piperidine, in the presence of zinc triflate, followed by dehydrative cyclization, allowed the formation of pyridinium salts substituted at their 3-position by a five- or six-membered nitrogen heterocycle. Subsequent N-dealkylation of the pyridinium moiety and deprotection of the secondary amine or reduction of the carbamate function led to (±)-nicotine and analogs.
