2-ピリジン-3-イルピペリジン
2-ピリジン-3-イルピペリジン · 2‐ピリジン‐3‐イルピペリジン · (R,S)-アナバシン · アナバシン, DL-(NEONネオニコチン · DL-アナバシン · rac-3-[(R*)-2-ピペリジニル]ピリジン · (±)-アナバシン · ANABASINE
識別子と物理属性
| CAS No. | 13078-04-1 |
|---|---|
| 分子式 | C10H14N2 |
| 平均分子量 | 162.23 g/mol |
| 単同位体質量 | 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 |
| 現地名 | 2-ピリジン-3-イルピペリジン |
化学・物理的性質
| XLogP | 1 |
|---|---|
| 極性表面積 | 24.9 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 1 |
| 重原子数 | 12 |
| 形式電荷 | 0 |
| 複雑度 | 136 |
| LogP（分配係数） | 0.97 |
| 溶解度 | 1000 mg/mL at 25 °CH2O: 10 mg/mL |
| 融点 | 9 °C |
| Physical Description | Liquid |
| Collision Cross Section | 138.32 Ų [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]140.18 Ų [M+H]+ [CCS Type: DTMethod: stepped-field]139.3 Ų [M+H]+ |
| 沸点 | 270 °C |
| 密度 | 1.05 g/mL at 25 °C(lit.) |
| 屈折率 | 1.5440 |
| 引火点 | 93 °C |
| 貯蔵条件 | Keep in dark place,Inert atmosphere,2-8°C |
| pKa（酸解離定数） | 8.98±0.10(Predicted) |
| 外観・状態 | 液体 |
| 色 | 無色～黄色 |
| Merck | 14,619 |
| BRN | 82639 |
| 主な用途 | 農業環境 |
| 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（分配係数） | 0.852 (est) |
化学的特性
Colourless Oil
安全性と法規制
| GHS 分類 | 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. |
| 健康影響 | 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. |
| 暴露経路 | Oral (ingestion) (L1817)dermal (L1817) |
| 毒性の概要 | Anabasine is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen. |
| Signs and Symptoms | Anabasine produces symptoms similar to nicotine poisoning, such as nausea, abdominal pain, vomiting, diarrhea, diaphoresis, flushing, dizziness, disturbed hearing and vision, confusion, weakness, palpitations, altered respiration and hypotension. (L327) |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| 水環境危害等級（WGK） | 3 |
| RTECS 番号 | BV4375000 |
| 輸送番号（UN） | UN 3140 6.1/PG 2 |
| 税関コード | 29339900 |
| 危険文句（R） | 23/24/25-36/37/38-25-20/21/22-51/53-27/28 |
| 消防法 | 危-4-3-III |
| 危険表示 | T,Xn |
| hazard_note | Toxic |
| 安全措置（S） | 36/37/39-45-26-36-57-27/28-23-20 |
| 危険等級 | 6.1Acute Tox. 3 Oral |
| 包装等級 | I |
| 毒劇物取締法 | III |
| 貯蔵分類 | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
用途
説明
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.
来歴
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.
使用
A nicotinic receptor agonist
一般的な説明
Anabasine inhibited androstenedione conversion to estrogen in a dose-dependent manner.