ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /化合物

Tetramethylenedisulfotetramine

HCID 64148
ノートを作成反応を作成見積依頼を出す
印刷プレビュー
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
80-12-6
標準SMILES
O=S1(=O)N2CN3CN1CN(C2)S3(=O)=O
InChIKey
AGGKEGLBGGJEBZ-UHFFFAOYSA-N
分子式
C4H8N4O4S2
平均分子量
240.3 g/mol
単同位体質量
239.9986971

概要

Tetramethylenedisulfotetramine is a neurotoxic synthetic polyhedral organic compound and type A gamma-aminobutyric acid receptor (GABAAR) antagonist that was banned worldwide for use as a pesticide in 1991. It is characterized as a colorless and odorless solid, and exposure occurs by inhalation, ingestion, or contact.

名称と識別子

優先名称
Tetramethylenedisulfotetramine
IUPAC
2λ6,6λ6-dithia-1,3,5,7-tetrazatricyclo[3.3.1.13,7]decane 2,2,6,6-tetraoxide
英語名
2,6-Dithia-1,3,5,7-tetraazatricyclo3.3.1.13,7decane, 2,2,6,6-tetraoxide
分子式
C4H8N4O4S2
分子量
240.26

名称と別名

TetramethylenedisulfotetramineTETS80-12-6TetramethylenedisulphotetramineDSTAF6TS3WME05DTXSID8040307NSC-1728242,6-Dithia-1,3,5,7-tetraazatricyclo(3.3.1.13,7)decane, 2,2,6,6-tetraoxide2,6-Dithia-1,3,5,7-tetraazatricyclo[3.3.1.13,7]decane, 2,2,6,6-tetraoxideRefChem:188783DTXCID6020307
名称をさらに表示
Tretamine in methanolTetramethylenedisulfotetramine solution2,6-Dithia-1,3,5,7-tetraazatricyclo3.3.1.13,7decane, 2,2,6,6-tetraoxide
CHEBI:391662,6-dithia-1,3,5,7-tetraazatricyclo(3.3.1.1(3,7)-decane 2,2,6,6-tetraoxide)disulfotetraazaadamantaneTetramineTetramine (adamantane derivative)199488-98-72lambda6,6lambda6-dithia-1,3,5,7-tetrazatricyclo[3.3.1.13,7]decane 2,2,6,6-tetraoxideUNII-F6TS3WME05

データベース識別子

CAS
80-12-6
PubChem CID
64148
DTXSID
DTXSID8040307
UNII
F6TS3WME05

物性

構造計算による物性

XLogP
-1.7
極性表面積
98 Ų
水素結合供与体数
0
水素結合受容体数
8
回転可能結合数
0
重原子数
14
形式電荷
0
複雑度
378

実験および物理化学的性質

OdorReported as being odorless.
TasteReported as being tasteless.
Color/FormReported as being colorless.

物理化学的性質

融点
242.5 °C · 242.5°C (rough estimate)
沸点
498.1 · 498.1±45.0 °C(Predicted)
比重(密度)
1.574 · 1.574 (estimate)
屈折率
1.6 · 1.6000 (estimate)
闪点
2 °C · 2°C
貯蔵温度
-20 °C · -20°C
酸解離定数(Pka)
-11.52 · -11.52±0.20(Predicted)
外見
個体
主な用途
農業環境
InChI
1S/C4H8N4O4S2/c9-13(10)5-1-6-3-8(13)4-7(2-5)14(6,11)12/h1-4H2
InChIKey
AGGKEGLBGGJEBZ-UHFFFAOYSA-N
SMILES
O=S1(=O)N2CN3CN1CN(C2)S3(=O)=O
EPAの化学物質情報
2 · 2,6-Dithia-1,3,5,7-tetraazatricyclo[3.3.1.13,7]decane, 2,2,6,6-tetraoxide (80-12-6)

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 · 4 件

Danger

H300 (100%): Fatal 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 39 reports by companies from 1 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory Information · 1 件

2,6-Dithia-1,3,5,7-tetraazatricyclo3.3.1.13,7decane, 2,2,6,6-tetraoxide: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

History and Incidents · 1 件

A 2020 publication details the serendipitous discovery of the neurotoxicity of TETS through the investigation of a mysterious occupational exposure in 1949 at a German uphostery factory. Also, it provides a what have we learned in the past 70 years discussion about the neurotoxicity of TETS, e.g., after being promoted as a rodenticide, it was banned worldwide due to its danger to human health. However, despite the ban, the clandestine manufacture of TETS has continued and there have been large numbers of inadvertent, intentional, and mass poisonings with no known antidote or targeted treatment. A 2017 publication about TETS states that over 14,000 accidental and intentional poisonings have occurred worldwide, with the vast majority of TETS poisonings involving tainted food or drink.

Hazard Classes and CategoriesAcute Tox. 1 (100%)

安全と保護具

Acute Exposure Guideline Levels (AEGLs)The compound is currently at the Holding Status AEGLs which have been reviewed by the NAC/AEGL Committee and are on hold due to insufficient data to develop AEGL values.

化学と産業

薬理情報

Mechanism of ActionNoncompetitive blocker of the GABA type A receptor (GABAAR).

用途と製造

Use ClassificationRODENTICIDES
応用分野 · 2 件

説明Tetramethylenedisulfotetramine (2,6-dithia-1,3,5,7-tetraazadamantane, 2,2,6,6-tetraoxide, TETS) is a highly toxic heteroadamantane rodenticide. It is an odorless, tasteless, white crystalline powder that is slightly soluble in water (0.25 mg ml-1), dimethyl sulfoxide and acetone. It was originally synthesized in 1933 as a resinous condensation product of sulfamide and formaldehyde and used commercially in pillows and upholstery as an impregnating stiffening and antimold agent. However, in 1950, a massive poisoning of German workers in the furniture manufacturing industry was linked to ‘Crinex’ wool, which contained TETS as a byproduct of processing. Early experimental studies in rodents revealed that TETS was an extremely toxic convulsant agent. It was also discovered at this time that TETS is a highly effective rodent repellent, which resulted in its use during reforestation projects to prevent seed predation by rodents. However, because of its high toxicity in mammals, including humans, and its persistence in the environment, many countries banned its production and use in 1984. This ban became worldwide when China issued similar restrictions in 1991. However, due to its relative ease of synthesis and low cost, TETS remains available on the black market, particularly in many rural areas of China and in regions outside of China that have large Asian populations.

使用Despite the worldwide ban on its production and use, TETS continues to be used illicitly as a rodenticide in various regions of the world. In China, TETS is known as ‘Dushuqiang’, ‘Meishuming,’ or ‘Shanbudao.’ In 2000, the National Poison Control Center of China revealed that 74% of commercial rodenticides contained illegal chemicals, with TETS found in nearly 50% of these pesticides. From 1977 to 2002, it was estimated that there were thousands of cases of TETS poisoning in China, resulting in hundreds of deaths. A more recent analysis indicates that between 1991 and 2010, there were over 14 000 cases of TETS intoxication in China, of which 932 resulted in death. In 2003, the first case of TETS intoxication in the United States was reported: a healthy 15-month-old girl was poisoned following accidental ingestion of a rodenticide imported from China that contained TETS. While many cases are thought to be due to accidental poisonings, there have been numerous reports of TETS being used to intentionally poison humans.

関連反応

1 件
反応記録を作成
HRID 21850 の反応式
HRID 21850反応物としてuspto-grants-1995_06

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す
EC Number
804-552-0
AEGLs NotesAEGLs Status: Holding

毒性情報

Toxicity Summary · 1 件

Acute intoxication with TETS or picrotoxin can cause seizures that rapidly progress to status epilepticus and death. Both inhibit γ-aminobutyric acid type-A (GABAA) receptors with similar potency; however, TETS is approximately 100-fold more lethal than picrotoxin. TETS is also 100 times more toxic than potassium cyanide.

Acute Toxicity LinkChemical: TETRAMINE
Human Toxicity Excerpts · 2 件

A 2011 publication includes a case report of a 28-year-old female who died of multi-organ failure after exposure to TETS. The authors also performed a retrospective study of 40 cases of poisoning from the 1996 to 2010 literature. They summarized the pathological changes related to TETS poisoning in all cases as includng signs of asphyxia, along with edema and congestion of organs (in particular,the brain). Also, subarachnoid and cerebral hemorrhaging were common. They concluded that TETS poisoning should be considered when there are signs of abnormal excitation of the central nervous system, convulsions, hyperspasmia, and cerebral hemorrhage.

A 2016 publication includes two case reports , one for TETS and one for fluoroacetamide (FAA). Both patients were initially misdiagnosed and they died. The authors suggest that physicians should consider TETS and FAA poisoning when seeing patients with generalized seizures, especially for cases without a clear cause and diagnosis of disease.

Non-Human Toxicity ExcerptsA female mixed-breed dog ingested TETS in rat bait. There was a rapid onset of tremors, ataxia and hyperthermia. Prolonged anorexia, weight loss, behavioral changes and ataxia were noted at the 49-day follow-up examination.
Human Toxicity ValuesThe lethal dose of TETS in adult humans is reported to be 7 to 10 mg, based on an 1991 accidental oral exposure of 78 people in a factory in Hebei Province, China. There is no established antidote.

安全データ

wgk
2
ridadr
UN 1648 3 / PGII
毒性
LD in mice (mg/kg): 0.20 orally or s.c. (Hagen)
risk_code
11-20/21/22-36
hazard_code
F,Xn
safety_code
16-36/37
Hazard Classifications
Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
ストレージクラス
3 - Flammable liquids