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Apholate

Apholate structure

CAS No:
52-46-0
Formula:
C12H24N9P3
Chemical Name:
Apholate
Synonyms:
2λ5,4λ5,6λ5-1,3,5,2,4,6-Triazatriphosphorine,2,2,4,4,6,6-hexakis(1-aziridinyl)-;1,3,5,2,4,6-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)-2λ5,4λ5,6λ5-1,3,5,2,4,6-triazatriphosphorine;Apholate;APN;2,2,4,4,6,6-Hexahydro-2,2,4,4,6,6-hexakis(1-aziridinyl)-1,3,5,2,4,6-triazatriphosphorine;2,2,4,4,6,6-Hexakis(1-aziridinyl)cyclotriphosphaza-1,3,5-triene;2,2,4,4,6,6-Hexakis(1-aziridinyl)-2,2,4,4,6,6-hexahydro-1,3,5,2,4,6-triazatriphosphorine;ENT 26316;Hexakis(aziridinyl)phosphotriazine;Hexa(1-aziridinyl)triphosphatriazine;Myko 63;NSC 26812
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Prevents reproduction in certain insects by inhibiting formation of DNA in eggs.

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 insect sterilant and an alkylating agent. It is a member of aziridines and a ring assembly. It derives from a 1,3,5,2,4,6-triazatriphosphinine.

Apholate Basic Attributes

Molecular Weight：

387.30100

Exact Mass：

387.30

UNII：

MN3Q1B846W

NSC Number：

26812

DSSTox ID：

DTXSID7073149

Color/Form：

CRYSTALS FROM HEPTANE

Characteristics

PSA：

84.57000

XLogP3：

0.6

Density：

2.32g/cm3

Melting Point：

147.5 °C

Refractive Index：

2.201

Water Solubility：

100g/L(temperature not stated)

Toxicity：

LD50 in male, female rats (mg/kg): 98, 113 orally (Gaines)

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

UN 2811

Drug Information

Reported Fatal Dose：

6. 6= SUPER TOXIC; PROBABLE ORAL LETHAL DOSE (HUMAN) LESS THAN 5 MG/KG, A TASTE (LESS THAN 7 DROPS) FOR 70 KG PERSON (150 LB).

Mechanism of Action：

/IT/ PREVENTS REPRODUCTION OF CERTAIN INSECTS BY INHIBITING FORMATION OF DNA IN EGGS.

Human Toxicity Excerpts：

TREATMENT OF CULTURED HUMAN LYMPHOCYTES FOR 8 HR WITH APHOLATE PRODUCED 89% ABNORMAL CELLS WITH 2.6 GAPS OR BREAKS/CELL.

MeSH Entry Terms：

apholate

Apholate Use and Manufacturing

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).

Uses

Insect chemosterilant.

Manufacturing Info：

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.

Analytic Methods：

ANALYTICAL METHODS FOR ESTIMATION OF APHOLATE INCL TITRIMETRY, COLORIMETRY & TLC (BEROZA M, BORKOVEC AB; J MED CHEM 7: 44 (1964)). FOLLOWING ITS EXTRACTION FROM BIOLOGICAL MATERIAL, 0.1 NG APHOLATE CAN BE DETECTED BY GAS CHROMATOGRAPHY (BOWMAN MC, BEROZA M; J ASSOC OFFIC ANALYT CHEM 49: 1046 (1966)).

Use Classification：

INSECTICIDES

Computed Properties

Molecular Weight:387.30
XLogP3:0.6
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:6
Exact Mass:387.13675280
Monoisotopic Mass:387.13675280
Topological Polar Surface Area:55.1
Heavy Atom Count:24
Complexity:592
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes