6687. Norbormide

Nomenclature

CAS number: 991-42-4
3a,4,7,7a-Tetrahydro-5-(hydroxyphenyl-2-pyridinylmethyl)-8-(phenyl-2-pyridinylmethylene)-4,7-methano-1H-isoindole-1,3(2H)-dione; 5-(α-hydroxy-α-2-pyridylbenzyl)-7-(α-2-pyridylbenzylidene)-5-norbornene-2,3-dicarboximide; McN-1025; Raticate; Shoxin.
C33H25N3O3; mol wt 511.57.
C 77.48%, H 4.93%, N 8.21%, O 9.38%.

Description and references

Prepn: A. P. Roszkowski et al., Science 144, 412 (1964); R. J. Mohrbacher et al., BE 659610; eidem, US 3378566 (1965, 1968 both to McNeil). Stereoisomerism: idem et al., J. Org. Chem. 31, 2141 (1966); S. Abrahamsson, B. Nilsson, ibid. 3631. Structure-activity studies: G. I. Poos et al., J. Med. Chem. 9, 537 (1966). Toxicity data: A. P. Roszkowski, J. Pharmacol. Exp. Ther. 149, 288 (1965).

Chemical structure

Properties

Crystals from methylene chloride + ether, mp 190-198°. uv max (methanol): 250 nm (ε 17500). LD50 in rats (mg/kg): 5.3 orally; 0.65 i.v. (Roszkowski). Practically insol in water unless pH is below 4.

Use

Rodenticide.