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Name |
Theobromine |
EINECS | 201-494-2 |
CAS No. | 83-67-0 | Density | 1.608 g/cm3 |
PSA | 72.68000 | LogP | -1.03970 |
Solubility | slightly soluble in water | Melting Point |
345-350 °C |
Formula | C7H8N4O2 | Boiling Point | Sublimes 290-295oC |
Molecular Weight | 180.166 | Flash Point | 290-295°C |
Transport Information | N/A | Appearance | white to light yellow crystal powder |
Safety | 22-24/25-36-26 | Risk Codes | 22-36/37/38 |
Molecular Structure | Hazard Symbols | Xn, Xi | |
Synonyms |
Theobromine(8CI);3,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dione;3,7-Dimethylxanthine;Diurobromine;NSC 5039;SC 15090;Santheose;Teobromin;Theosalvose;Theostene;Thesal; |
Article Data | 57 |
1-amino-3,7-dimethylxanthine
theobromine /
Conditions | Yield |
---|---|
With sodium nitrite In acetic acid | 96% |
Conditions | Yield |
---|---|
Stage #1: 3-methylxanthine; dimethyl sulfate With sodium hydrogencarbonate In water; acetone at 55 - 60℃; for 4h; Stage #2: With hydrogenchloride In water at 80℃; pH=5 - 6; Product distribution / selectivity; | 87% |
Conditions | Yield |
---|---|
Stage #1: 3-methylxanthine disodium salt; dimethyl sulfate With sodium carbonate In acetone at 55 - 57℃; for 4h; Stage #2: With hydrogenchloride In water at 30℃; pH=6; Product distribution / selectivity; | 84.9% |
theobromine /
Conditions | Yield |
---|---|
at 260℃; for 1h; | 66% |
3-methylxanthine
methyl iodide
A
theobromine /
B
1,7,9-trimethylxanthinium iodide
Conditions | Yield |
---|---|
at 110℃; for 1.5h; closed Kjeldahl flask; | A 61% B 28% |
5-amino-3-methyl-3H-imidazole-4-carboxylic acid methylamide; hydrochloride
urea
theobromine /
Conditions | Yield |
---|---|
In melt 1) 140 deg C, 30 min 2) 170-175 deg C, 2h; | 55% |
theobromine /
Conditions | Yield |
---|---|
In pyridine at 115℃; for 3h; | 53% |
Conditions | Yield |
---|---|
With sodium thiophenolate at 250℃; for 1.5h; | A 37% B 21% |
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
A
theophylline
B
theobromine /
C
paraxanthine
Conditions | Yield |
---|---|
With hepatic cytochrome P450 Enzymatic reaction; | A 7% B 12% C n/a |
Conditions | Yield |
---|---|
With sodium thiophenolate at 280℃; for 1.5h; | 10% |
The Theobromine, also known as xantheose, is an organic compound with the formula C7H8N4O2. It belongs to the product categories of Heterocyclic Compounds; Alkaloids; Alkaloids (Others); Biochemistry; Heterocycles; Intermediates & Fine Chemicals; Metabolites & Impurities; Pharmaceuticals. Its EINECS registry number is 201-494-2. With the CAS registry number 83-67-0, its IUPAC name is 3,7-dimethylpurine-2,6-dione. What's more, this chemical is a white to light yellow crystal which can be used as a metabolite of caffeine.
Physical properties of Theobromine: (1)# of Rule of 5 Violations: 0; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 6.331; (5)ACD/KOC (pH 7.4): 6.312; (6)#H bond acceptors: 6; (7)#H bond donors: 1; (8)Index of Refraction: 1.737; (9)Molar Refractivity: 45.057 cm3; (10)Molar Volume: 112.05 cm3; (11)Surface Tension: 65.77 dyne/cm; (12)Density: 1.608 g/cm3.
Preparation of Theobromine: this chemical is the primary alkaloid found in cocoa and chocolate. Theobromine can also be found in small amounts in the kola nut (1.0-2.5%), the guarana berry, ilex guayusa, and the tea plant.
Uses: In modern medicine, theobromine is used as a vasodilator (a blood vessel widener), a diuretic (urination aid), and heart stimulant. In addition, possible future uses of theobromine in such fields as cancer prevention have been patented. Theobromine has also been used in birth defect experiments involving mice and rabbits. A decreased fetal weight was noted in rabbits following forced feeding, but not after other administration of theobromine. Birth defects were not seen in rats.
When you are using this chemical, please be cautious about it as the following:
This chemical may cause damage to health. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing. Finally, you must avoid contacting it with skin and eyes.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CN1C=NC2=C1C(=O)NC(=O)N2C
(2)InChI: 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)
(3)InChIKey: YAPQBXQYLJRXSA-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LD50 | oral | 200mg/kg (200mg/kg) | "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1372, 1986. | |
dog | LD50 | oral | 300mg/kg (300mg/kg) | Toxicology and Applied Pharmacology. Vol. 53, Pg. 481, 1980. | |
human | TDLo | oral | 26mg/kg (26mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) GASTROINTESTINAL: NAUSEA OR VOMITING | Journal of Pharmacology and Experimental Therapeutics. Vol. 86, Pg. 113, 1946. |
mouse | LD50 | intraperitoneal | 552mg/kg (552mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Acta Pharmaceutica Vol. 46, Pg. 93, 1996. |
mouse | LD50 | oral | 837mg/kg (837mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 26(3), Pg. 59, 1982. | |
mouse | LD50 | subcutaneous | 530mg/kg (530mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 6, Pg. 601, 1956. | |
rabbit | LDLo | subcutaneous | 1gm/kg (1000mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935. | |
rat | LD50 | oral | 1265mg/kg (1265mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 26(3), Pg. 59, 1982. |