(+-)-Anabasine

ANABASINE · NEONICOTINE · (-)-ANABASINE · (n)-anabasine · Anabasine >=97% · L(-)-NEONICOTINE · Anabasine, Neonicotine · 2-(3-PYRIDYL)PIPERIDINE

https://huagongshe.com/de/chemical/2181

Identifikatoren & physikalische Daten

CAS No.	13078-04-1
Summenformel	C10H14N2
Durchschnittliche Molmasse	162,23 g/mol
Monoisotopische Masse	162,11569845 g/mol
SMILES	c1cncc(C2CCCCN2)c1
InChIKey	MTXSIJUGVMTTMU-UHFFFAOYSA-N
PubChem CID	2181
ChEMBL	CHEMBL280963
ChEBI	CHEBI:28986
EC No.	621-972-8
DTXSID	DTXSID50859409

Chemische & physikalische Eigenschaften

XLogP	1
Polarare Oberfläche (TPSA)	24,9
H-Brücken-Donoren	1
H-Brücken-Akzeptoren	2
Frei drehbare Bindungen	1
Schwere Atome	12
Formalladung	0
Komplexität	136
LogP (Verteilungskoeffizient)	0.97
Löslichkeit	1000 mg/mL at 25 °CH2O: 10 mg/mL
Schmelzpunkt	9 °C
Physical Description	Liquid
Collision Cross Section	138.32 Å² [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]140.18 Å² [M+H]+ [CCS Type: DTMethod: stepped-field]139.3 Å² [M+H]+
Siedepunkt	270 °C
Dichte	1.05 g/mL at 25 °C(lit.)
Brechungsindex	1.5440
Flammpunkt	93 °C
Lagerbedingungen	Keep in dark place,Inert atmosphere,2-8°C
pKa (Säurekonstante)	8.98±0.10(Predicted)
Aggregatzustand	liquid
Farbe	colorless to yellow
Merck	14,619
BRN	82639
Hauptanwendungen	agricultureenvironmental
InChI	InChI=1S/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
InChIKey	MTXSIJUGVMTTMU-UHFFFAOYSA-N
SMILES	C1(C2NCCCC2)=CN=CC=C1
LogP (Verteilungskoeffizient)	0.852 (est)

Sicherheit & Vorschriften

GHS-Einstufung	DangerH300 (97.3%): Fatal if swallowed [Danger Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 73 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard Classes and Categories	Acute Tox. 2 (97.3%)
Treatment	If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.
Gesundheitliche Auswirkungen	Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

Anwendungen & Verwendung

Beschreibung

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.

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 etal. 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.

Verwenden

A nicotinic receptor agonist