CHEBI:4947 - thiocyclam

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ChEBI Name thiocyclam
ChEBI ID CHEBI:4947
Definition An organosulfur heterocyclic compound that is 1,2,3-trithiane in which one of the hydrogens at position 5 has been replaced by a dimethylamino group. A nicotinic acetylcholine receptor agonist, it was used (particularly as its hydrogen oxalate salt, known as thyocyclam oxalate) as a broad-spectrum insecticide, but it is also toxic to bees, fish and other aquatic organisms. It is not approved for use within the European Union.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C5H11NS3
Net Charge 0
Average Mass 181.346
Monoisotopic Mass 181.00536
InChI InChI=1S/C5H11NS3/c1-6(2)5-3-7-9-8-4-5/h5H,3-4H2,1-2H3
InChIKey DNVLJEWNNDHELH-UHFFFAOYSA-N
SMILES S1SSCC(C1)N(C)C
Roles Classification
Biological Role(s): nicotinic acetylcholine receptor agonist
An agonist that selectively binds to and activates a nicotinic acetylcholine receptor.
Application(s): agrochemical
An agrochemical is a substance that is used in agriculture or horticulture.
nicotinic acetylcholine receptor agonist
An agonist that selectively binds to and activates a nicotinic acetylcholine receptor.
insecticide
Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.
(via organosulfur insecticide )
pesticide
Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.
(via organosulfur pesticide )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing thiocyclam (CHEBI:4947) has parent hydride 1,2,3-trithiane (CHEBI:39194)
thiocyclam (CHEBI:4947) has role agrochemical (CHEBI:33286)
thiocyclam (CHEBI:4947) has role nicotinic acetylcholine receptor agonist (CHEBI:47958)
thiocyclam (CHEBI:4947) is a nereistoxin analogue insecticide (CHEBI:39191)
thiocyclam (CHEBI:4947) is a organosulfur heterocyclic compound (CHEBI:38106)
thiocyclam (CHEBI:4947) is conjugate base of thiocyclam(1+) (CHEBI:133552)
Incoming thiocyclam(1+) (CHEBI:133552) is conjugate acid of thiocyclam (CHEBI:4947)
IUPAC Name
N,N-dimethyl-1,2,3-trithian-5-amine
Synonyms Sources
5-(dimethylamino)-1,2,3-trithiane ChemIDplus
N,N-dimethyl-1,2,3-trithian-5-ylamine ChemIDplus
Thiocyclam KEGG COMPOUND
thiocyclame ChEBI
Manual Xrefs Databases
1065 PPDB
C11473 KEGG COMPOUND
thiocyclam Alan Wood's Pesticides
View more database links
Registry Numbers Types Sources
31895-21-3 CAS Registry Number KEGG COMPOUND
31895-21-3 CAS Registry Number NIST Chemistry WebBook
31895-21-3 CAS Registry Number ChemIDplus
31895-21-3 CAS Registry Number Alan Wood's Pesticides
4738857 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
20725716 PubMed citation Europe PMC
23961080 PubMed citation Europe PMC
Last Modified
30 September 2016