A methylxanthine alkaloid with diverse biological activities
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Theobromine

Item No. 21745

Technical Information
Formal Name
3,7-dihydro-3,7-dimethyl-1H-purine-2,6-dione
CAS Number
83-67-0
Synonyms
  • Diurobromine
  • NSC 5039
  • SC-15090
Molecular Formula
C7H8N4O2
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 20 mg/mlDMSO: 30 mg/mlDMSO:PBS(pH 7.2) (1:3): 0.25 mg/mlEthanol: 0.5 mg/ml
λmax
273 nm
SMILES
O=C(C(N(C)C=N1)=C1N2C)NC2=O
InChi Code
InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2/h3H,1-2H3,(H,9,12,13)
InChi Key
YAPQBXQYLJRXSA-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Theobromine is a methylxanthine alkaloid and derivative of caffeine (Item No. 14118) that has been found in cocoa beans and has diverse biological activities.1,2,3 It is an adenosine A1 receptor antagonist (IC50s = 200-280 μM in radioligand binding assays using rat brain membranes).2 Theobromine (150 μg/ml) increases AMPK phosphorylation and inhibits adipocyte differentiation, ERK and JNK phosphorylation, and IL-6 and TNF-α production in 3T3-L1 preadipocytes cultured in differentiation medium.1 It inhibits decreases in renal cortex SIRT1 activity and increases in NADPH oxidase-dependent reactive oxygen species (ROS) production, as well as reduces kidney hypertrophy and albuminuria in a spontaneously hypertensive rat model of streptozotocin-induced diabetes when administered at a dose of 5 mg/kg per day.3 Theobromine is toxic to dogs with an LD50 value of 250 to 500 mg/kg.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jang, Y.J., Koo, H.J., Sohn, E.-H., et alTheobromine inhibits differentiation of 3T3-L1 cells during the early stage of adipogenesis via AMPK and MAPK signaling pathways. Food Funct. 6(7), 2365-2374 (2015).

    2. Daly, J.W., Butts-Lamb, P., and Padgett, W. Subclasses of adenosine receptors in the central nervous system: Interaction with caffeine and related methylxanthines. Cell. Mol. Neurobiol. 3(1), 69-80 (1983).

    3. Papadimitriou, A., Silva, K.C., Peixoto, E.B.M.I., et alTheobromine increases NAD⁺/Sirt-1 activity and protects the kidney under diabetic conditions. Am. J. Physiol. Renal Physiol. 308(3), F209-F225 (2015).

    4. Lawrence, L.P. Chocolate toxicosis. The 5-minute veterinary consult: Canine and feline (2004).