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Theobromine

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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 Molecular Structure of 83-67-0 (Theobromine) Hazard Symbols HarmfulXn, IrritantXi
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

Theobromine Synthetic route

81281-47-2

1-amino-3,7-dimethylxanthine

83-67-0

theobromine /

Conditions
ConditionsYield
With sodium nitrite In acetic acid96%
1076-22-8

3-methylxanthine

77-78-1

dimethyl sulfate

83-67-0

theobromine /

Conditions
ConditionsYield
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%

3-methylxanthine disodium salt

77-78-1

dimethyl sulfate

83-67-0

theobromine /

Conditions
ConditionsYield
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%

3,7,9-trimethylxanthinium hydrogensulfate

83-67-0

theobromine /

Conditions
ConditionsYield
at 260℃; for 1h;66%
1076-22-8

3-methylxanthine

74-88-4

methyl iodide

A

83-67-0

theobromine /

B

86180-33-8

1,7,9-trimethylxanthinium iodide

Conditions
ConditionsYield
at 110℃; for 1.5h; closed Kjeldahl flask;A 61%
B 28%
94453-49-3

5-amino-3-methyl-3H-imidazole-4-carboxylic acid methylamide; hydrochloride

83-67-0

theobromine /

Conditions
ConditionsYield
In melt 1) 140 deg C, 30 min 2) 170-175 deg C, 2h;55%

3,7,9-trimethylxanthinium perchlorate

83-67-0

theobromine /

Conditions
ConditionsYield
In pyridine at 115℃; for 3h;53%
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

A

58-55-9

theophylline

B

83-67-0

theobromine /

Conditions
ConditionsYield
With sodium thiophenolate at 250℃; for 1.5h;A 37%
B 21%
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

A

58-55-9

theophylline

B

83-67-0

theobromine /

C

611-59-6

paraxanthine

Conditions
ConditionsYield
With hepatic cytochrome P450 Enzymatic reaction;A 7%
B 12%
C n/a
58-55-9

theophylline

83-67-0

theobromine /

Conditions
ConditionsYield
With sodium thiophenolate at 280℃; for 1.5h;10%

Theobromine Specification

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.

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