Theacrine

Theacrine

Names
IUPAC name 1,3,7,9-Tetramethylpurine-2,6,8-trione
Other names 1,3,7,9-Tetramethyluric acid; Temurin; Temorine; Tetramethyluric acid; Tetramethyl uric acid
Identifiers
CAS Number	2309-49-1
ChemSpider	67862
Jmol 3D model	Interactive image
PubChem	75324
InChI InChI=1S/C9H12N4O3/c1-10-5-6(11(2)8(10)15)12(3)9(16)13(4)7(5)14/h1-4H3 Key: QGDOQULISIQFHQ-UHFFFAOYSA-N InChI=1/C9H12N4O3/c1-10-5-6(11(2)8(10)15)12(3)9(16)13(4)7(5)14/h1-4H3 Key: QGDOQULISIQFHQ-UHFFFAOYAN
SMILES CN1C2=C(N(C1=O)C)N(C(=O)N(C2=O)C)C
Properties
Chemical formula	C9H12N4O3
Molar mass	224.22 g·mol−1
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Theacrine, also known as 1,3,7,9-tetramethyluric acid, is a purine alkaloid found in Cupuaçu (Theobroma grandiflorum) and in a Chinese tea known as kudingcha (Camellia assamica var. kucha). It shows anti-inflammatory and analgesic effects and appears to affect adenosine signalling in a manner similar to caffeine. In kudingcha leaves, theacrine is synthesized from caffeine in what is thought to be a three-step pathway.

Similarity to caffeine

Theacrine is simply caffeine with an extra ketone and an additional methyl group on the free amine.

Safety

Theacrine has demonstrated clinical safety and non-habituating effects in healthy humans over 8 weeks of daily use at up to 300 mg/day. Moreover, there was no evidence of tachyphylaxis that is typical of neuroactive agents such as caffeine and other stimulants.

In animal studies, theacrine has an LD₅₀ of 810 mg/kg, compared to 265 mg/kg for caffeine.

See also

• Liberine
• Methylliberine
• Theobromine
• Theophylline