バルビタール

Barbital

HCID 2294CAS 57-44-3

基本情報

標準SMILES: CCC1(CC)C(=O)NC(=O)NC1=O
InChIKey: FTOAOBMCPZCFFF-UHFFFAOYSA-N
分子式: C8H12N2O3
平均分子量: 184.19 g/mol
単同位体質量: 184.08479224

概要

5,5-diethylbarbituric acid is a member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by two ethyl groups. Formerly used as a hypnotic (sleeping aid). It has a role as a drug allergen.

名称と識別子

優先名称: Barbital
IUPAC: 5,5-diethyl-1,3-diazinane-2,4,6-trione
現地名: バルビタール
英語名: BARBITAL
分子式: C8H12N2O3
分子量: 184.19

名称と別名

barbitalBarbitone5,5-Diethylbarbituric acid57-44-3DiethylmalonylureaEthylbarbitalDiemalDEBADTXSID50226435,5-diethylpyrimidine-2,4,6(1H,3H,5H)-trione5WZ53ENE2PNSC-31352

名称をさらに表示

5,5-ジエチルヘキサヒドロピリミジン-2,4,6-トリオン5,5-ジエチルバルビツル酸バルビトン5,5-ジエチル-ピリミジン-2,4,6(1H,3H,5H)-トリオン5,5-ジエチルピリミジン-2,4,6(1H,3H,5H)-トリオンジエチルマロニル尿素ベロナール5,5-ジエチル-2,4,6(1H,3H,5H)-ピリミジントリオンべロナール(バルビタール)バルビタール (JP17)バルビタール5,5-ジエチル-1,3-ジアジナン-2,4,6-トリオンジエチルバルビツル酸5,5-ジエチルバルビツール酸Barbitone acidDIETHYLBARBITURIC ACID5,5-diethyl-1,3-diazinane-2,4,6-trioneMalona

CHEBI:31252DTXCID802643RefChem:388818200-331-2VeronalVesperalMalonalUronal

データベース識別子

CAS: 57-44-3
PubChem CID: 2294
DTXSID: DTXSID5022643
ChEMBL: CHEMBL444
ChEBI: CHEBI:31252
UNII: 5WZ53ENE2P
EC Number: 200-331-2
Nikkaji: J2.326D

物性

構造計算による物性

XLogP: 0.6
極性表面積: 75.3 Å²
水素結合供与体数: 2
水素結合受容体数: 3
回転可能結合数: 2
重原子数: 13
形式電荷: 0
複雑度: 247

実験および物理化学的性質

Drugs · 5 件

DEA NFLIS-Drug Category -> Depressants and Tranquilizers

DEA Schedule IV Controlled Substance -> Depressants

Pharmaceuticals -> Barbiturates

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

SpringerMaterials PropertiesCrystal structure

LogP0.71

Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan

Dissociation Constants8.14 (at 15 °C)

Collision Cross Section145.28 Å² [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点: 188 · 188-192°C
沸点: 318.14 °C · 318.14°C (rough estimate)
比重(密度): 1.22 · 1.2200
屈折率: 1.42 · 1.4200 (estimate)
闪点: 11 °C · 11 °C
貯蔵温度: 2 · 2-8°C
溶解性: DMSO (Slightly), Methanol (Slightly)
外見: Solid
酸解離定数(Pka): 7.43 · 7.43(at 25℃)
色: 2 O · H2O からのわずかに苦い結晶。多形体;三方晶、単斜プリズム、単斜晶針、三斜晶
水溶解度: 7.149 g/L · 7.149g/L(25℃)
Merck: 13 · 13,965
主な用途: 法医学と毒物学医薬品（低分子化合物）獣医
InChI: 1S/C8H12N2O3/c1-3-8(4-2)5(11)9-7(13)10-6(8)12/h3-4H2,1-2H3,(H2,9,10,11,12,13)
InChIKey: FTOAOBMCPZCFFF-UHFFFAOYSA-N
SMILES: CCC1(CC)C(=O)NC(=O)NC1=O
EPAの化学物質情報: 5 · 5,5-Diethylbarbituric acid (57-44-3)

化学的性質

化学的特性White crystals or powder; bitter taste; odorless. Stable in air. Soluble in hot water, alcohol, ether, acetone, and ethyl acetate.

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, 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.

危険有害性情報

Regulatory Information · 3 件

DEA schedule IV controlled substance

Status: Active Update: 26-05-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/17765

Barbitone: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5,5-diethyl-: Human health tier I assessment

Hazard Classes and CategoriesAcute Tox. 4 (100%)

安全データ

wgk: 3
rtecs: CQ3500000
ridadr: UN 1230 3/PG 2
毒性: LDLo orl-cat: 280 mg/kg PHREA7 19,472,39
risk_code: 22-39/23/24/25-23/24/25-11-63-40-20
hazard_code: Xn,T,F
safety_code: 36-45-36/37-16-7
Hazard Classifications: Acute Tox. 4 Oral
ストレージクラス: 11 - Combustible Solids
DEA Controlled Substances: CSCN: 2145CSA SCH: Schedule IVNARC: No

化学と産業

薬理情報

ATC Code · 2 件

N - Nervous system

QN - Nervous system

MeSH Pharmacological Classification · 2 件

Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.

Substances that do not act as agonists or antagonists but do affect the GAMMA-AMINOBUTYRIC ACID receptor-ionophore complex. GABA-A receptors (RECEPTORS, GABA-A) appear to have at least three allosteric sites at which modulators act: a site at which BENZODIAZEPINES act by increasing the opening frequency of GAMMA-AMINOBUTYRIC ACID-activated chloride channels; a site at which BARBITURATES act to prolong the duration of channel opening; and a site at which some steroids may act. GENERAL ANESTHETICS probably act at least partly by potentiating GABAergic responses, but they are not included here.

用途と製造

Use ClassificationPharmaceuticals -> Animal Drugs -> Approved in Taiwan

応用分野 · 5 件

解説バルビタール白色の針状晶．無臭で，わずかに苦味を呈す．融点188～192 ℃．水，熱水，エタノールに溶解する．バルビツル酸誘導体の長時間作用型睡眠薬で，中枢神経系に対する抑制作用がある．習慣性を有し，0.8～1.0 g を2～3か月連続使用すると禁断症状を伴う慢性中毒となる．そのほか，吐き気，頭痛，無気力感などの副作用もある．ベロナール，バルビトーン，マロナールなどの商品名で市販されている．エチル基がフェニル基に置き換わったフェノバルビタールは，バルビタールに比べて4倍の催眠作用をもつ．

用途バルビツール酸誘導体です。中枢神経系に作用し、特に脳幹網様体賦活系に対する抑制作用を示します。作用時間は長時間です。

説明Barbital is an analytical reference material that is categorized as a barbiturate. It acts as an agonist at GABAA receptors to induce central nervous system depression. Formulations containing barbital have been used as a sedative to treat insomnia and seizures in human and veterinary medicine. Barbital is regulated as a Schedule IV compound in the United States. This product is intended for research and forensic applications.

使用Prototype of the barbiturate hypnotics.

調製方法

純化方法Crystallise barbital from water or EtOH and dry it in a vacuum over P2O5. [Beilstein 24 III/IV 1901.]

上流・下流製品情報

上流原料

マロン酸ジエチル

補足説明

定義ChEBI: A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by two ethyl groups. Formerly used as a hypnotic (sleeping aid).