(±)-毒藜碱 | 13078-04-1

• 物质功能分类: 天然产物 - 生物碱
• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 中文名称: (±)-毒藜碱
• 中文别名: DL-八角枫碱；2-吡啶-3-哌啶
• 英文名称: anabasine
• 英文别名: (±)-anabasine；3-(piperidin-2-yl)pyridine；2-(3'-pyridyl)-piperidine；3-(2-piperidyl)pyridine；Neonicotine；Pyridine, 3-(2-piperidinyl)-；3-piperidin-2-ylpyridine
• CAS: 13078-04-1
• 化学式: C₁₀H₁₄N₂
• 分子量: 162.235
• InChiKey: MTXSIJUGVMTTMU-UHFFFAOYSA-N

物化性质

• 熔点：
  9 °C
• 沸点：
  270 °C
• 密度：
  1.05 g/mL at 25 °C(lit.)
• 闪点：
  93 °C
• 溶解度：
  在水中的溶解度10 mg/mL
• LogP：
  0.852 (est)
• 物理描述：
  Liquid
• 颜色/状态：
  Colorless liquid, darkens on exposure to air
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与氧化物接触。
• 分解：
  When heated to decomposition it emits toxic fumes of /nitrogen oxides/.
• 折光率：
  Index of refraction: 1.5430 @ 20 °C/D; specific optical rotation: -83.1 deg @ 20 °C/D
• 解离常数：
  pKa= 11.0 (conjugate acid)
• 碰撞截面：
  140.18 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

ADMET

代谢

在体外，大鼠、兔和豚鼠对(-)-毒藜碱的代谢产生了(-)-毒藜碱，后者被代谢为1'-N-羟基毒藜碱和毒藜碱1'DELTA-亚硝基。加固的肺微粒体组分的代谢产物相似。

IN VITRO METABOLISM OF (-)-METHYLANABASINE BY RAT, RABBIT & GUINEA PIG GAVE (-)-ANABASINE WHICH WAS METABOLIZED TO 1'-N-HYDROXYANABASINE & ANABASINE 1'DELTA-NITRONE. METABOLIC PRODUCTS OF FORTIFIED LUNG MICROSOMAL FRACTIONS WERE SIMILAR.

来源:Hazardous Substances Data Bank (HSDB)

代谢

对氧磷酶（PON1）是有机磷代谢的关键酶。PON1可以通过水解使一些有机磷失活。PON1水解多种有机磷杀虫剂以及神经毒剂（如梭曼、沙林和VX）的活性代谢物。PON1的多态性导致不同个体具有不同的酶水平和催化效率，这表明不同个体可能对有机磷暴露的毒性效应更为敏感。

Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of OP exposure.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

尼古丁是一种胆碱酯酶或乙酰胆碱酯酶（AChE）抑制剂。胆碱酯酶抑制剂（或“抗胆碱酯酶”）抑制乙酰胆碱酯酶的作用。由于其基本功能，干扰乙酰胆碱酯酶作用的化学物质是强大的神经毒素，在低剂量时会导致过度流涎和眼泪，随后是肌肉痉挛，最终导致死亡。神经气体和许多用于杀虫剂的物质已被证明通过结合乙酰胆碱酯酶活性位点的丝氨酸，完全抑制该酶。乙酰胆碱酯酶分解神经递质乙酰胆碱，该递质在神经和肌肉接头处释放，以允许肌肉或器官放松。乙酰胆碱酯酶抑制的结果是乙酰胆碱积聚并继续发挥作用，使得任何神经冲动不断传递，肌肉收缩不会停止。最常见的乙酰胆碱酯酶抑制剂之一是基于磷的化合物，它们被设计用来结合到酶的活性位点上。结构要求是一个带有两个亲脂性基团的磷原子，一个离去基团（如卤素或硫氰酸盐），以及一个末端的氧。

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.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

急性接触胆碱酯酶抑制剂可能会导致胆碱能危象，表现为严重的恶心/呕吐、流涎、出汗、心动过缓、低血压、晕厥和抽搐。肌肉无力可能性增加，如果呼吸肌受累，可能会导致死亡。在运动神经积累的乙酰胆碱会导致神经肌肉接头处烟碱受体的过度刺激。当这种情况发生时，可能会看到肌肉无力、疲劳、肌肉痉挛、肌束震颤和麻痹的症状。当自主神经节积累乙酰胆碱时，这会导致交感系统中烟碱受体的过度刺激。与此相关的症状是高血压和低血糖。由于乙酰胆碱积累而在中枢神经系统中过度刺激烟碱乙酰胆碱受体，会导致焦虑、头痛、抽搐、共济失调、呼吸和循环抑制、震颤、全身无力，甚至可能昏迷。当由于副交感乙酰胆碱受体上乙酰胆碱过多而导致毒蕈碱过度刺激时，可能会出现视力障碍、胸痛、由于支气管收缩引起的喘息、支气管分泌物增加、唾液分泌增加、流泪、出汗、肠蠕动和排尿的症状。与有机磷农药暴露特别相关的生育效应，包括男性和女性的生育力、生长和发育。关于生育效应的大多数研究都是在农村地区使用农药和杀虫剂的农民中进行的。在女性中，月经周期紊乱、怀孕时间延长、自然流产、死产以及后代的一些发育效应都与有机磷农药暴露有关。产前暴露与胎儿生长和发育受损有关。神经毒性效应也与人因有机磷农药中毒导致的四种神经毒性效应有关：胆碱能综合症、中间综合症、有机磷诱导的迟发性多发性神经病（OPIDP）和慢性有机磷诱导的精神神经障碍（COPIND）。这些综合症在急性暴露和慢性暴露于有机磷农药后出现。

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.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服（摄入）（L1817）；皮肤（L1817）

Oral (ingestion) (L1817) ; dermal (L1817)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

Anabasine会产生类似于尼古丁中毒的症状，如恶心、腹痛、呕吐、腹泻、出汗、潮红、眩晕、听力视力障碍、混乱、虚弱、心悸、呼吸改变和低血压。

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)

来源:Toxin and Toxin Target Database (T3DB)

吸收、分配和排泄

尼古丁很容易通过皮肤和粘膜被吸收。

Anabasine is readily absorbed from the skin and from mucous membranes.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  6.1
• 危险品标志：
  T
• 安全说明：
  S28,S36/37/39,S45
• 危险类别码：
  R23/24/25
• WGK Germany：
  3
• 海关编码：
  2933990090
• 危险类别：
  6.1
• 危险品运输编号：
  UN 3140 6.1/PG 2
• 包装等级：
  III
• 危险性防范说明：
  P261,P264,P301+P310+P330,P305+P351+P338
• 危险性描述：
  H300,H315,H319,H335

SDS

Name:	2-Pyridin-3-ylpiperidine tech Material Safety Data Sheet
Synonym:	AnabasineNeonicotin
CAS:	13078-04-1

Section 1 - Chemical Product MSDS Name:2-Pyridin-3-ylpiperidine tech Material Safety Data Sheet
Synonym:AnabasineNeonicotin

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
13078-04-1	2-Pyridin-3-ylpiperidine		unlisted

Hazard Symbols: T
Risk Phrases: 23/24/25

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Toxic by inhalation, in contact with skin and if swallowed.Hygroscopic (absorbs moisture from the air).Light sensitive.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. Toxic in contact with skin.
Ingestion:
May cause irritation of the digestive tract. Toxic if swallowed.
Inhalation:
May cause respiratory tract irritation. Toxic if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid immediately. Wash mouth out with water.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container.

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Section 7 - HANDLING and STORAGE
Handling:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Keep away from sources of ignition. Store in a cool, dry place. Do not store in direct sunlight. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 13078-04-1: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: colorless - yellow - orange
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 270 - 272 deg C
Freezing/Melting Point: 9 deg C
Autoignition Temperature: Not available.
Flash Point: 93 deg C ( 199.40 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water:
Specific Gravity/Density: 1.046
Molecular Formula: C10H14N2
Molecular Weight: 162

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials, light, exposure to moist air or water.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, acrid smoke and fumes.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 13078-04-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Pyridin-3-ylpiperidine - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: ALKALOIDS, LIQUID, N.O.S.*
Hazard Class: 6.1
UN Number: 3140
Packing Group: II
IMO
Shipping Name: ALKALOIDS, LIQUID, N.O.S.
Hazard Class: 6.1
UN Number: 3140
Packing Group: II
RID/ADR
Shipping Name: ALKALOIDS, LIQUID, N.O.S.
Hazard Class: 6.1
UN Number: 3140
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T
Risk Phrases:
R 23/24/25 Toxic by inhalation, in contact with skin
and if swallowed.
Safety Phrases:
S 28A After contact with skin, wash immediately with
plenty of water.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 13078-04-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 13078-04-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 13078-04-1 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性的(±)安巴辛是一种肌肉松弛剂，可用于外科手术中的肌肉松弛。其作用靶点为人内源性代谢物。

反应信息

• 作为反应物：
  描述：

  (±)-毒藜碱 在 ammonia borane 、 6-hydroxy-D-nicotine oxidase E₃₅₀L/E₃₅₂D mutant 作用下， 反应 72.0h， 以55%的产率得到新烟碱
  参考文献：
  名称：

  具有宽底物特异性和高对映选择性的R选择性胺氧化酶的开发

  摘要：

  胺氧化酶是用于合成对映体纯的1°，2°和3°手性胺的有用生物催化剂。先前报道的此类酶（例如，来自黑曲霉的MAO-N ）已显示出高度的S选择性。在此，我们报道了基于6-羟基-D-烟碱氧化酶（6-HDNO）的对映体互补R-选择性胺氧化酶的开发，该酶具有扩大的底物范围和高对映选择性。工程化的6-HDNO酶已应用于一系列外消旋胺的制备脱硝反应，以产生具有S构型的产物，例如高ee的（S）-烟碱。

  DOI：

  10.1002/cctc.201301008
• 作为产物：
  描述：

  新烟碱 在 硫酸 作用下， 生成 (±)-毒藜碱
  参考文献：
  名称：

  Orechoff; Norkina, Chemische Berichte, 1932, vol. 65, p. 1126,1128

  摘要：

  DOI：

文献信息

• [EN] MICROBIOCIDAL OXADIAZOLE DERIVATIVES<br/>[FR] DÉRIVÉS D'OXADIAZOLE MICROBIOCIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2017157962A1

  公开（公告）日：2017-09-21

  Compounds of the formula (I) wherein the substituents are as defined in claim 1, useful as a pesticides, especially fungicides.

  式(I)的化合物，其中取代基如权利要求1所定义，作为杀虫剂特别是杀菌剂有用。
• Thieno-pyrimidine compounds having fungicidal activity
  申请人：Brewster Kirkland William

  公开号：US20070093498A1

  公开（公告）日：2007-04-26

  The present invention relates to thieno[2,3-d]-pyrimidine compounds having fungicidal activity.

  本发明涉及具有杀真菌活性的噻吩[2,3-d]-嘧啶化合物。
• [EN] INSECTICIDAL TRIAZINONE DERIVATIVES<br/>[FR] DÉRIVÉS DE TRIAZINONE INSECTICIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2013079350A1

  公开（公告）日：2013-06-06

  Compounds of the formula (I) or (I'), wherein the substituents are as defined in claim 1, are useful as pesticides.

  式(I)或(I')的化合物，其中取代基如权利要求1所定义的那样，可用作杀虫剂。
• PREPARATION METHOD AND USE OF COMPOUNDS HAVING HIGH INSECTICIDAL ACTIVITIES
  申请人：Li Zhong

  公开号：US20090111847A1

  公开（公告）日：2009-04-30

  The present invention discloses a kind of nitromethylene derivatives as well as their preparation method and their uses. The insecticidal activity tests show that the nitromethylene derivatives of the present invention not only show high insecticidal activities against insects with piercing-sucking type or scratching type mouthparts, such as aphid, leafhopper, plant hopper, thrips and white fly and their resistant strains, but also show high insecticidal activities against Lissorhoptrus oryzophilus , carmine spider mite, and they can also be used to prevent sanitary pest, and white ant.

  本发明公开了一种亚硝基甲烯衍生物，以及它们的制备方法和用途。杀虫活性测试表明，本发明的亚硝基甲烯衍生物不仅对具有刺吸型或擦伤型口器的昆虫（如蚜虫、叶蝉、植食蝗、蓟马和烟粉虱及其抗性品系）表现出高杀虫活性，而且对水稻纵卷叶象、胭脂蜘蛛螨等也表现出高杀虫活性，它们还可用于预防卫生害虫和白蚁。
• Novel insecticides
  申请人：Syngenta Participations AG

  公开号：EP2540718A1

  公开（公告）日：2013-01-02

  Compounds of formula I wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts and all stereoisomers and tautomeric forms of the compounds of formula I can be used as insecticides and can be prepared in a manner known per se.

  式I的化合物 其中取代基如权利要求1所定义，并且式I化合物的农药可接受盐以及所有立体异构体和互变异构形式可用作杀虫剂，并且可以按照已知的方法制备。

表征谱图