Basic information
- CAS
52-46-0- Standard SMILES
C1CN1P1(N2CC2)=NP(N2CC2)(N2CC2)=NP(N2CC2)(N2CC2)=N1- InChIKey
PXZAWHSJYIECNQ-UHFFFAOYSA-N- Molecular formula
- C12H24N9P3
- Average molar mass
- 387.3 g/mol
- Monoisotopic mass
- 387.1367528
Overview
Apholate is a member of the class of aziridines that is 1,3,5,2,4,6-triazatriphosphinine substituted by aziridin-1-yl groups at positions 2,2,4,4,6, and 6. It is an insect sterilant. It has a role as an alkylating agent and an insect sterilant. It is a member of aziridines and a ring assembly. It is functionally related to a 1,3,5,2,4,6-triazatriphosphinine.
Names & identifiers
- Preferred name
- Apholate
- IUPAC
- 2,2,4,4,6,6-hexakis(aziridin-1-yl)-1,3,5-triaza-2λ5,4λ5,6λ5-triphosphacyclohexa-1,3,5-triene
- English name
- 2,2,4,4,6,6-hexaaziridin-1-yl-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-tri phosphacyclohexa-1,3,5-triene
- Molecular formula
- C12H24N9P3
- Molecular weight
- 387.3
Names & synonyms
APHOLATE52-46-0Pholate1-Aziridinylphosphonitrile trimerAfolatHexakis(aziridinyl)phosphotriazineOlin MO. 2174Myko 63NSC-26812ENT 26,316CB 40068Hexa(1-aziridinyl)triphosphotriazine
Show more names
APNPEPNOM-2174Myko-63AI326316AI3 26316
Hexakis-(1-aziridinyl)phosphonitrileSQ 8388MN3Q1B846W1,3,5,2,4,6-Triazatriphosphorine, 2,2,4,4,6,6-hexakis(1-aziridinyl)-2,2,4,4,6,6-hexahydro-2,2,4,4,6,6-Hexakis(1-aziridinyl)-2,2,4,4,6,6-hexahydro-1,3,5,2,4,6-triazatriphosphorineAziridine, 1,3,5,2,4,6-triazatriphosphorine derivativeDTXSID7073149CHEBI:33111
Database identifiers
- CAS
52-46-0- PubChem CID
- 5845
- DTXSID
DTXSID7073149- ChEMBL
CHEMBL25805- ChEBI
CHEBI:33111- UNII
- MN3Q1B846W
Properties
Computed structural properties
- XLogP
- 0.6
- Topological polar surface area
- 55.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 6
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 592
Experimental & physicochemical properties
PesticidesPesticides -> Other Insecticides
Color/FormCRYSTALS FROM HEPTANE
Melting Point147.5 °C (CRYSTALLIZED FROM HEPTANE); 154-154.5 °C (CRYSTALLIZED FROM ETHYLACETATE)
Physical DescriptionSolid; [Merck Index]
Physicochemical properties
- Melting point
- 147.5 ° · 147.5°
- Density
- 2.32 · 2.32±0.1 g/cm3(Predicted)
- pka
- 1.31 · 1.31±0.50(Predicted)
- form
- solid
- color
- 2 · Orthorhombic needles from m-xylene;monoclinic crystals from CS2
- Water Solubility
- 100 g/L · 100g/L(temperature not stated)
- CAS DataBase Reference
- 52 · 52-46-0
- NCI Dictionary of Cancer Terms
- APN
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Hazards Summary
In high-dose animal studies, causes hepatitis and kidney injury; Causes ataxia and paralysis in birds; [RTECS] Mechanism appears to be as alkylating agent on genetic material; Causes marked leukopenia in mammals within 24 hours of injection; Mutagenic in Neurospora crassa; [HSDB]
Toxicology
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Acute Toxicity LinkChemical: APHOLATE
Human Toxicity ExcerptsTREATMENT OF CULTURED HUMAN LYMPHOCYTES FOR 8 HR WITH APHOLATE PRODUCED 89% ABNORMAL CELLS WITH 2.6 GAPS OR BREAKS/CELL.
Carcinogen Classification
Apholate
Group 3: Not classifiable as to its carcinogenicity to humans
Volume 9: (1975) Some Aziridines, N-, S- and O-Mustards and Selenium
1987
1987
Non-Human Toxicity Excerpts
SIXTY WEANLING MALE & FEMALE FISCHER RATS RECEIVED APHOLATE IN STEROID-SUSPENDING VEHICLE, BY GAVAGE, ON 5 DAYS/WK IN DAILY DOSES/ANIMAL OF 0.003-0.1 MG (12 MALES & 12 FEMALES), 0.3 MG (15 MALES & 15 FEMALES) OR 1 MG (MAX TOLERATED DOSE, GIVEN TO 3 MALES & 3 FEMALES) FOR UP TO 1 YR. AVG SURVIVAL TIMES RANGED FROM 340 DAYS IN MALES GIVEN THE HIGHEST DOSE TO 565 DAYS IN FEMALES GIVEN THE LOWEST DOSE. THE TUMOR INCIDENCE WAS REPORTED TO BE SIMILAR TO THAT IN CONTROLS; NO TUMORS WERE REPORTED TO HAVE OCCURRED IN ANIMALS GIVEN THE HIGHEST DOSE LEVEL. (THE SMALL NUMBER OF ANIMALS USED SHOULD BE NOTED).
THE LD50 BY SKIN APPLICATION WAS 400-800 MG/KG FOR RATS OF BOTH SEXES.
TREATMENT OF NEUROSPORA CONIDIA WITH APHOLATE INDUCED AN INCR IN THE FREQUENCY OF RECESSIVE LETHAL MUTATIONS. AFTER IP INJECTION OF 1.5 MG/KG BODY WT APHOLATE IN MICE, A PEAK OF CHROMOSOME & CHROMATID ABERRATIONS WAS FOUND IN THE BONE MARROW 24 HR LATER.
Chemistry & industry
Pharmacology
Mechanism of Action/IT/ PREVENTS REPRODUCTION OF CERTAIN INSECTS BY INHIBITING FORMATION OF DNA IN EGGS.
Uses & manufacturing
Uses
Used as an insect chemosterilant (prevents reproduction in certain insects); [HSDB]
Farming (Pesticides) [Category: Industry]
EXPTL INSECT CHEMOSTERILANT
Methods of Manufacturing
...BY ADDN OF AZIRIDINE TO 2,2,4,4,6,6-HEXACHLORO-2,2,4,4,5,5-HEXAHYDROTRIAZATRIPHOSPHORINE; HOWEVER, IT HAS BEEN PRODUCED FOR RESEARCH PURPOSES ONLY.
RATZ GRUNDMANN, US PATENT 2,858,306 (1958 TO OLIN MATHIESON).
Use ClassificationINSECTICIDES
General Manufacturing Information
WHEN A COLONY OF AEDES AEGYPTI WAS EXPOSED IN THE LARVAL STAGE TO THE CHEMOSTERILANT APHOLATE FOR GENERATION AFTER GENERATION, IT BECAME MORE TOLERANT TO THE STERILIZING EFFECT OF THE CHEMICAL.
APHOLATE HAS BEEN TESTED AS ANTINEOPLASTIC AGENT, BUT IT DOES NOT APPEAR TO HAVE BEEN USED FOR THIS PURPOSE IN HUMAN MEDICINE. IT HAS BEEN SHOWN TO BE AN EFFECTIVE CHEMOSTERILANT FOR VARIOUS INSECTS, BUT PROBLEMS ASSOC WITH ITS APPLICATION TO INSECTS, ITS TOXICITY & POSSIBLE ENVIRONMENTAL EFFECTS HAVE PREVENTED ITS USE IN THIS WAY ON A COMMERCIAL BASIS.
...EXPTL INSECT CHEMOSTERILANT ACTIVE AGAINST BOTH SEXES OF THE COMMON HOUSE FLY & OTHER ECONOMICALLY IMPORTANT SPECIES. ... HIGH TOXICITY LIMITS...PRESENT USE TO LAB IN WHICH STERILE POPULATIONS OF INSECTS ARE RAISED & RELEASED TO COMPETE FOR FERTILE MATES. SAID TO BE ALKYLATING AGENT WITH EFFECTS ON GENETIC MATERIAL SIMILAR TO IONIZING RADIATION.
Applications
UsesInsect chemosterilant.
Suppliers5 total
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…