Potency and safety analysis of hemp-derived delta-9 products: The hemp vs. cannabis demarcation problem

Dimethylallyl pyrophosphate
Skeletal formula
Ball-and-stick model
IUPAC name
3-Methyl-2-buten-1-yl trihydrogen diphosphate
Other names
Dimethylallyl diphosphate; isoprenyl pyrophosphate; isoprenyl diphosphate
3D model (JSmol)
MeSH 3,3-dimethylallyl+pyrophosphate
  • InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h3H,4H2,1-2H3,(H,9,10)(H2,6,7,8)
  • CC(=CCOP(=O)(O)OP(=O)(O)O)C
Molar mass 246.092 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dimethylallyl pyrophosphate (DMAPP; or alternatively, dimethylallyl diphosphate (DMADP); also isoprenyl pyrophosphate) is an isoprenoid precursor. It is a product of both the mevalonate pathway and the MEP pathway of isoprenoid precursor biosynthesis. It is an isomer of isopentenyl pyrophosphate (IPP) and exists in virtually all life forms. The enzyme isopentenyl pyrophosphate isomerase catalyzes isomerization between DMAPP and IPP.[1]

In the mevalonate pathway DMAPP is synthesised from mevalonic acid. In contrast, DMAPP is synthesised from HMBPP in the MEP pathway.

At present, it is believed that there is crossover between the two pathways in organisms that use both pathways to create terpenes and terpenoids, such as in plants, and that DMAPP is the crossover product.

Mevalonate pathway
Simplified version of the steroid synthesis pathway with the intermediates isopentenyl pyrophosphate (IPP), dimethylallyl pyrophosphate (DMAPP), geranyl pyrophosphate (GPP) and squalene shown. Some intermediates are omitted.


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