A ferrochelatase inhibitor

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Product Type

Small Molecule Modulators

Small Molecule Inhibitors

Research Area

N-methyl Protoporphyrin IX

Name: N-methyl Protoporphyrin IX
Brand: -

Item No. 20846

N-methyl Protoporphyrin IX (NMPP, N-methyl PPIX, CAS Number: 79236-56-9)

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

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

λ_max

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

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

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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 (K_i = 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).

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