An herbicide
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Amiprofos-methyl

Item No. 23379

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(1-methylethyl)-phosphoramidothioic acid, O-methyl O-(4-methyl-2-nitrophenyl) ester
CAS Number
36001-88-4
Synonyms
  • APM
  • NSC 313446
Molecular Formula
C11H17N2O4PS
Formula Weight
304.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 10 mg/mlPBS (pH 7.2): 0.2 mg/ml
λmax
206, 245, 254 nm
SMILES
CC1=CC([N+]([O-])=O)=C(OP(NC(C)C)(OC)=S)C=C1
InChi Code
InChI=1S/C11H17N2O4PS/c1-8(2)12-18(19,16-4)17-11-6-5-9(3)7-10(11)13(14)15/h5-8H,1-4H3,(H,12,19)
InChi Key
VHEWQRWLIDWRMR-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Amiprofos-methyl (APM) is a phosphoric amide herbicide.1 It reversibly decreases H. vulgare root and shoot length and inhibits in vitro polymerization of Rosa tubulin induced by paclitaxel (Item No. 10461) in a dose-dependent manner.1,2 APM completely inhibits tubulin polymerization in Hemanthus endosperm cells at a concentration of 0.1 μM.1 The antitubulin effects of APM are specific to plants as it has no effect on bovine brain tubulin polymerization at concentrations up to 100 μM. APM inhibits calcium accumulation in corn mitochondria (ID50 = 140 nM) and induces a 3-fold increase in the rate of calcium efflux from rat liver mitochondria at a concentration of 100 nM.3 APM inhibits the growth of P. falciparum (IC50 = 3.5 μM) and completely inhibits microtubule polymerization in P. falciparum trophozoites at a concentration of 20 μM.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Morejohn, L.C., and Fosket, D.E. Inhibition of plant microtubule polymerization in vitro by the phosphoric amide herbicide amiprophos-methyl. Science 224(4651), 874-876 (1984).

    2. Temel, A., and Gozukirmizi, N. Cytotoxic effects of metaphase-arresting methods in barley. Tsitol. Genet. 49(6), 43-49 (2015).

    3. Hertel, C., Quader, H., Robinson, D.G., et al. Herbicides and fungicides stimulate Ca2+ efflux from rat liver mitochondria. FEBS Lett. 127(1), 37-39 (1981).

    4. Fennell, B.J., Naughton, J.A., Dempsey, E., et al. Cellular and molecular actions of dinitroaniline and phosphorothioamidate herbicides on Plasmodium falciparum: Tubulin as a specific antimalarial target. Mol. Biochem. Parasitol. 145(2), 226-238 (2006).