Tetramethylenedisulfotetramine

HCID 64148CAS 80-12-6

Basic information

Standard SMILES
O=S1(=O)N2CN3CN1CN(C2)S3(=O)=O
InChIKey
AGGKEGLBGGJEBZ-UHFFFAOYSA-N
Molecular formula
C4H8N4O4S2
Average molar mass
240.3 g/mol
Monoisotopic mass
239.9986971

Names & identifiers

Preferred name
Tetramethylenedisulfotetramine
IUPAC
2lambda6,6lambda6-dithia-1,3,5,7-tetrazatricyclo[3.3.1.13,7]decane 2,2,6,6-tetraoxide
English name
2,6-Dithia-1,3,5,7-tetraazatricyclo3.3.1.13,7decane, 2,2,6,6-tetraoxide
Molecular formula
C4H8N4O4S2
Molecular weight
240.26

Names & synonyms

TetramethylenedisulfotetramineTetramineTETS80-12-6TetramethylenedisulphotetramineDSTAF6TS3WME05DTXSID8040307NSC-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:188783
Show more names
Tretamine in methanolTetramethylenedisulfotetramine solution2,6-Dithia-1,3,5,7-tetraazatricyclo3.3.1.13,7decane, 2,2,6,6-tetraoxide
DTXCID6020307CHEBI:391662,6-dithia-1,3,5,7-tetraazatricyclo(3.3.1.1(3,7)-decane 2,2,6,6-tetraoxide)disulfotetraazaadamantaneTetramine (adamantane derivative)199488-98-72lambda6,6lambda6-dithia-1,3,5,7-tetrazatricyclo[3.3.1.13,7]decane 2,2,6,6-tetraoxideUNII-F6TS3WME05

Database identifiers

CAS
80-12-6
PubChem CID
64148
DTXSID
DTXSID8040307
UNII
F6TS3WME05
EC Number
804-552-0

Properties

Computed structural properties

XLogP
-1.7
Topological polar surface area
98 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
8
Rotatable bonds
0
Heavy atoms
14

Physicochemical properties

Melting point
242.5 °C · 242.5°C (rough estimate)
Boiling point
498.1 · 498.1±45.0 °C(Predicted)
Density
1.574 · 1.574 (estimate)
refractive index
1.6 · 1.6000 (estimate)
Flash point
2 °C · 2°C
storage temp.
-20 °C · -20°C

Safety & regulation

GHS classification

GHS Classification · 5 items

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.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 1 item

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.

Hazard Classes and CategoriesAcute Tox. 1 (100%)

Safety & protection

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.
AEGLs NotesAEGLs Status: Holding

Toxicology

Acute Toxicity LinkChemical: TETRAMINE

Regulatory information

Regulatory Information · 1 item

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.

Safety data

wgk
2
ridadr
UN 1648 3 / PGII
Toxicity
LD in mice (mg/kg): 0.20 orally or s.c. (Hagen)
risk_code
11-20/21/22-36
Signal word
Danger
Symbol(GHS)
GHS02, GHS07

Chemistry & industry

Uses & manufacturing

Use ClassificationRODENTICIDES
Applications · 2 items

DescriptionTetramethylenedisulfotetramine (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.

UsesDespite 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.

Related reactions

1 records

Linked notes

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