基本情報
- CAS
2552-55-8- 標準SMILES
NC(C(=O)O)c1cc(=O)[nH]o1- InChIKey
IRJCBFDCFXCWGO-UHFFFAOYSA-N- 分子式
- C5H6N2O4
- 平均分子量
- 158.11 g/mol
- 単同位体質量
- 158.03275668
概要
Ibotenic acid is a non-proteinogenic alpha-amino acid. It has a role as a neurotoxin.
名称と識別子
- 優先名称
- Ibotenic Acid
- IUPAC
- 2-amino-2-(3-oxo-1,2-oxazol-5-yl)acetic acid
- 現地名
- α-アミノ-3-ヒドロキシ-5-イソオキサゾール酢酸
- 英語名
- Ibotenic acid
- 分子式
- C5H6N2O4
- 分子量
- 158.11
名称と別名
Ibotenic acid2552-55-8DL-Ibotenic acid(RS)-Ibotenic acidAcid, Ibotenicalpha-Amino-2,3-dihydro-3-oxo-5-isoxazoleacetic acid2-amino-2-(3-oxo-1,2-oxazol-5-yl)acetic acid2-amino-2-(3-oxoisoxazol-5-yl)acetic acid44AS82FRSI5-Isoxazoleacetic acid, alpha-amino-2,3-dihydro-3-oxo-DTXSID408937714-Isoxazoline-5-acetic acid, alpha-amino-3-oxo-
名称をさらに表示
2-(3-ヒドロキシイソオキサゾール-5-イル)グリシンα-アミノ-3-ヒドロキシ-5-イソオキサゾール酢酸イボテン酸(±)-イボテン酸(±)‐イボテン酸2-アミノ-2-(3-ヒドロキシ-1,2-オキサゾール-5-イル)酢酸IBOTENIC ACID(RG)DL-Ibotenic acid.Ibotenic Acid (CRM)IBOTENIC ACID USP/EP/BPIbotenic acid in methanolIbotenic Acid [(RS)-Ibotenic acidIbotenic acid, excitotoxic agonist
NSC-2048502-Azaniumyl-2-(3-oxo-1,2-oxazol-5-yl)acetate(+-)-Ibotenic acidRefChem:789640DTXCID701323806637-415-7Ibotenate(+/-)-Ibotenic acid
物性
構造計算による物性
- XLogP
- -3.9
- 極性表面積
- 102 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 5
- 回転可能結合数
- 2
- 重原子数
- 11
- 形式電荷
- 0
- 複雑度
- 235
実験および物理化学的性質
DrugsDEA NFLIS-Drug Category -> Hallucinogens
物理化学的性質
- 融点
- 141 · 141-147 °C
- 比重(密度)
- 1.621 · 1.621±0.06 g/cm3 (20 ºC 760 Torr)
- 貯蔵温度
- Keep in dark place,Inert atmosphere,Room temperature
- 溶解性
- 2 O: · H2O: 可溶1mg/mL、透明、無色 (超音波処理あり)
- 外見
- 白い固体
- 酸解離定数(Pka)
- 2.16 · 2.16±0.10(Predicted)
- 色
- 白い
- 臭い (Odor)
- Practically odorless. Faint, meat-like, mild and sweet taste in aqueous dilutions.
- 水溶解度
- 10 mM · Soluble to 10 mM in water and to 100 mM in 1.1eq. NaOH
- 安定性
- -20 °C · その水溶液は、-20°C で最大 1 か月間保存できます。
- InChI
- 1S/C5H6N2O4/c6-4(5(9)10)2-1-3(8)7-11-2/h1,4H,6H2,(H,7,8)(H,9,10)
- InChIKey
- IRJCBFDCFXCWGO-UHFFFAOYSA-N
- SMILES
- NC(C(O)=O)C1=CC(=O)NO1
- LogP
- -1.07 · -1.070 (est)
- CAS データベース
- 2552 · 2552-55-8(CAS DataBase Reference)
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。
GHS分類
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 1 notifications to the ECHA C&L Inventory.
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
危険有害性情報
Hazard Classes and Categories
Acute Tox. 3 (100%)
Acute Tox. 3 (100%)
毒性情報
Health EffectsIbotenic acid is neurotoxic. (L1141)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary
A portion of ibotenic acid is metabolized to muscimol, a potent GABAA agonist, activating the receptor for the brain's major inhibitory neurotransmitter, GABA. Muscimol actually binds to the same binding site on the GABAA receptor complex as GABA itself, as opposed to other GABAergic drugs such as barbiturates and benzodiazepines which bind to separate regulatory sites. GABAA receptors are widely distributed in the brain, and so when muscimol is administered, it alters neuronal activity in multiple regions including the cerebral cortex, hippocampus, and cerebellum. However while muscimol is conventionally thought of as a selective GABAA agonist, it is also a potent partial agonist at the GABAC receptor, and so its effects profile results from a combined action at both targets. (L1142, L1672)
Signs and Symptoms
When ibotenic acid is ingested, a small portion is decarboxylated into muscimol. Ibotenic acid evokes entheogenic effects in human beings at doses in range of 50-100 mg. Peak intoxication is reached approximately 2-3 hours after oral ingestion, consisting of one or all of the following; visual distortions/hallucinations, loss of equilibrium, muscle twitching (commonly mislabeled as convulsions), and altered sensory perception. These effects generally last for 6-8 hours, varying with dose. (L1141)
化学と産業
薬理情報
MeSH Pharmacological ClassificationDrugs that bind to and activate excitatory amino acid receptors.
用途と製造
UsesIbotenic acid is used as a brain lesioning agent in the medical environment. When injected intracranially, ibotenic acid causes the development of lesions of the brain. (L1141)
応用分野
用途シグナル伝達研究用。
使用Ibotenic acid is a neuroexcitatory amino acid originally isolated from Amanita species that functions as a NMDA and metabotropic glutamate receptor agonist. As a neurotoxin, ibotenic acid is often used to induce brain lesions in animals that model cognitive dysfunctions resulting from neurodegenerative diseases, traumatic brain injury, and stroke.
調製方法
製造方法Isolated from the Japanese fly mushroom. The acid can be produced synthetically.
純化方法It has been converted to the ammonium salt (m 121-123o dec) dissolved in H2O, passed through an Amberlite IR 120 resin (H+ form) and eluted with H2O. The acidic fractions are collected, evaporated to dryness and the residue recrystallises from H2O as the monohydrate (m 144-146o). The anhydrous acid is obtained by making a slurry with MeOH, decanting and evaporating to dryness, and repeating the process twice more to give the anhydrous acid (m 151-152o). Recrystallisation from H2O gives the monohydrate. [Nakamura Chem Pharm Bull Jpn 19 46 1971.] The ethyl ester forms needles when crystallised from a small volume of Et2O and has m 78-79o and IR (CHCl3) with max 35002300 (OH), 1742 (ester C=O), 1628, 1528cm-1, and UV with λmax (EtOH) at 206nm (ε 7,080). The hydrazide has m 174-175o (from MeOH) with IR (KBr) 1656 (C=O)cm-1.
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