A ferrochelatase inhibitor
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Product Type

Biochemicals
Small Molecule Modulators
Small Molecule Inhibitors

Research Area

N-methyl Protoporphyrin IX

Item No. 20846

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
7,12-diethenyl-3,8,13,17,23-pentamethyl-21H,23H-porphine-2,18-dipropanoic acid
CAS Number
79236-56-9
Synonyms
  • NMPP
  • N-methyl PPIX
Molecular Formula
C35H36N4O4
Formula Weight
576.7
Purity
≥95% (a mixture of isomers)
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMF:PBS (pH 7.2) (1:5): 0.17 mg/mlDMSO: 15 mg/ml
λmax
211, 303, 401, 573 nm
SMILES
CC1=C2[NH]C(/C=C(C(CCC(O)=O)=C3C)\[N]=C3/C=C4[N](C)/C(C(C=C)=C\4C)=C\C5=[N]/C(C(C=C)=C5C)=C\2)=C1CCC(O)=O
InChi Code
InChI=1S/C35H36N4O4/c1-8-22-18(3)28-17-33-23(9-2)21(6)32(39(33)7)16-27-20(5)25(11-13-35(42)43)31(38-27)15-30-24(10-12-34(40)41)19(4)26(36-30)14-29(22)37-28/h8-9,14-17,36H,1-2,10-13H2,3-7H3,(H,40,41)(H,42,43)/b26-14-,27-16-,28-17-,29-14-,30-15-,31-15-
InChi Key
UMUAJMDAFLPQGQ-YIYRCNGCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $49

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    1 mg

    $86

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    5 mg

    $213

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    Product Description

    N-methyl Protoporphyrin IX is a transition state analog that potently inhibits protoporphyrin IX ferrochelatase (Ki = 10 nM), blocking the terminal step of the heme biosynthetic pathway.1,2 It is used to study the effect of heme synthesis blockade in cell systems.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ortiz de Montellano, P.R., Beilan, H.S., and Kunze, K.L. N-Methylprotoporphyrin IX: Chemical synthesis and identification as the green pigment produced by 3,5-diethoxycarbonyl-1,4-dihydrocollidine treatment. Proc. Natl. Acad. Sci. USA 78(3), 1490-1494 (1981).

    2. Shi, Z., and Ferreira, G.C. Modulation of inhibition of ferrochelatase by N-methylprotoporphyrin. Biochem. J. 399(1), 21-28 (2006).

    3. Atamna, H., Brahmbhatt, M., Atamna, W., et al. ApoHRP-based assay to measure intracellular regulatory heme. Metallomics 7(2), 309-321 (2015).

    4. Lämsä, V., Levonen, A.-L., Sormunen, R., et al. Heme and heme biosynthesis intermediates induce heme oxygenase-1 and cytochrome P450 2A5, enzymes with putative sequential roles in heme and bilirubin metabolism: Different requirement for transcription factor nuclear factor erythroid- derived 2-like 2. Toxicol. Sci. 130(1), 132-144 (2012).