基本情報
- CAS
300-54-9- 標準SMILES
C[C@@H]1O[C@H](C[N+](C)(C)C)C[C@H]1O- InChIKey
UQOFGTXDASPNLL-XHNCKOQMSA-N- 分子式
- C9H20NO2+
- 平均分子量
- 174.26 g/mol
- 単同位体質量
- 174.14940388
概要
Muscarine is a monosaccharide.
名称と識別子
- 優先名称
- Muscarine
- IUPAC
- [(2S,4R,5S)-4-hydroxy-5-methyloxolan-2-yl]methyl-trimethylazanium
- 現地名
- ムスカリン
- 英語名
- (+/-)-MUSCARINE CHLORIDE
- 分子式
- C9H20NO2+
- 分子量
- 174.26
名称と別名
MUSCARINE300-54-9L-(+)-MuscarineMuscarinMuskarinMuscarine (alkaloid)Muscarine (the alkaloid)(+)-(2S,4R,5S)-Muscarine7T101UWZ5W2-Furanmethanaminium, tetrahydro-4-hydroxy-N,N,N,5-tetramethyl-, (2S-(2alpha,4beta,5alpha))-[(2S,4R,5S)-4-hydroxy-5-methyloxolan-2-yl]methyl-trimethylazanium{[(2S,4R,5S)-4-hydroxy-5-methyloxolan-2-yl]methyl}trimethylazanium
名称をさらに表示
[(2S)-4β-ヒドロキシ-5α-メチルオキソラン-2α-イル]メチルトリメチルアミニウムテトラヒドロ-4β-ヒドロキシ-N,N,N,5α-テトラメチル-2α-フランメタンアミニウム(+)-ムスカリン(2S)-テトラヒドロ-4β-ヒドロキシ-5α,N,N,N-テトラメチル-2α-フランメタンアミニウム(2S)-テトラヒドロ-4β-ヒドロキシ-N,N,N,5α-テトラメチル-2α-フランメタンアミニウムトリメチル[[(2S,4R,5S)-テトラヒドロ-4-ヒドロキシ-5-メチルフラン-2-イル]メチル]アミニウム(2S,4R,5S)-テトラヒドロ-4-ヒドロキシ-5,N,N,N-テトラメチル-2-フランメタンアミニウム(2S,4β,5α)-テトラヒドロ-4-ヒドロキシ-N,N,N,5-テトラメチル-2-フランメタンアミニウム(+)-L-ムスカリンムスカリン{[(2S,4R,5S)-4-ヒドロキシ-5-メチルオキソラン-2-イル]メチル}トリメチルアザニウムdl-muscarine(+)-L-Muscarinemuscarine(thealkaloid)(+)-MUSCARINE CHLORIDE
物性
構造計算による物性
- XLogP
- 0.1
- 極性表面積
- 29.5 Ų
- 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
- 2
- 重原子数
- 12
- 形式電荷
- 1
- 複雑度
- 153
物理化学的性質
- 沸点
- 305.25 °C · 305.25°C (rough estimate)
- 比重(密度)
- 1.0117 · 1.0117 (rough estimate)
- 屈折率
- 1.409 · 1.4090 (estimate)
- 溶解性
- 水(易)
化学的性質
化学的特性An unctuous, brownish, semiliquidwhen fresh; dried, in grains or lumps withcolor resembling dried blood. Strong characteris-tic odor. The odor-bearing constituent is muscone,CH3C15H27O, a 15-carbon ring with ketone oxygen.
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
毒性情報
TreatmentThe specific antidote is atropine. (L1011)
Health EffectsIntoxication generally subsides within 2 hours. Death is rare, but may result from cardiac or respiratory failure in severe cases. (L1011)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity SummaryMuscarine is a competitive inhibitor. It mimics the action of the neurotransmitter acetylcholine at acetylcholine receptors. (L1011)
Signs and Symptoms
Muscarine poisoning is characterized by increased salivation, sweating (perspiration), and tearflow (lacrimation) within 15 to 30 minutes after ingestion of the mushroom. With large doses, these symptoms may be followed by abdominal pain, severe nausea, diarrhea, blurred vision, and labored breathing. (L1011)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
安全データ
- wgk
- 3
- 毒性
- A toxic alkaloid of the mushroom Amanita muscaria and certain other fungi. Although useful as a pharmacological tool, muscarine has no clinical or pesticidal applications. The compound is a potent and selective mimic of acetylcholine at parasympathetic neuromuscular junctions and at central muscarinic acetylcholine receptors. Symptoms of poisoning are primarily those attributable to peripheral parasympathetic stimulation (i.e., miosis, vomiting, diarrhea, bradycardia, and cardiovascular collapse). The i.v. LD50 in mice is 0.23 mg/kg.
- risk_code
- 22-36
- hazard_code
- Xn
- safety_code
- 26-36
化学と産業
薬理情報
MeSH Pharmacological Classification
Drugs that mimic the effects of parasympathetic nervous system activity. Included here are drugs that directly stimulate muscarinic receptors and drugs that potentiate cholinergic activity, usually by slowing the breakdown of acetylcholine (CHOLINESTERASE INHIBITORS). Drugs that stimulate both sympathetic and parasympathetic postganglionic neurons (GANGLIONIC STIMULANTS) are not included here.
Drugs that bind to and activate muscarinic cholinergic receptors (RECEPTORS, MUSCARINIC). Muscarinic agonists are most commonly used when it is desirable to increase smooth muscle tone, especially in the GI tract, urinary bladder and the eye. They may also be used to reduce heart rate.
用途と製造
Uses
Muscarine is only a trace compound in the fly agaric Amanita muscaria; the pharmacologically more relevant compound from this mushroom is muscimol. Mushrooms in the genera Entoloma and Mycena have also been found to contain levels of muscarine which can be dangerous if ingested. Muscarine has been found in harmless trace amounts in Boletus, Hygrocybe, Lactarius and Russula. (L1011)
応用分野
解説ムスカリン，ベニテングタケ，テングタケなどに含まれるアルカロイド。塩化物 C9H20O2N+Cl- は太い角柱状晶。融点 180～181℃。吸湿性が強い。水，エチルアルコールによく溶け，クロロホルム，エーテル，アセトンにわずかに溶ける。
使用Cosmetics and perfumery (fixative), fragrances,mothproofing agent.
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