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83-67-0

Basic Information
CAS No.: 83-67-0
Name: 1H-Purine-2,6-dione,3,7-dihydro-3,7-dimethyl-
Molecular Structure:
Molecular Structure of 83-67-0 (1H-Purine-2,6-dione,3,7-dihydro-3,7-dimethyl-)
Formula: C7H8N4O2
Molecular Weight: 180.16 .
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;
EINECS: 201-494-2
Density: 1.608 g/cm3
Melting Point: 345-350 °C
Boiling Point: Sublimes 290-295oC
Flash Point: 290-295°C
Solubility: slightly soluble in water
Appearance: white to light yellow crystal powder
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 22-36/37/38
Safety: 22-24/25-36-26
Transport Information:
PSA: 72.68000
LogP: -1.03970
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%
14785-95-6

3-methyl-4-amino-5-formylamino-2,6-dioxypyrimidine

83-67-0

theobromine /

Conditions
ConditionsYield
With sodium hydroxide anschliessendes Behandeln mit Dimethylsulfat;
64-17-5

ethanol

519-41-5

3,7-dimethyl-3,7-dihydro-purine-2,6-dione, theobromine; salicylate

83-67-0

theobromine /

Conditions
ConditionsYield
Ausscheidung;

3-methyl-5-(N-methyl-ureido)-3H-imidazole-4-carboxylic acid methylamide

64-19-7

acetic acid

83-67-0

theobromine /

Conditions
ConditionsYield
Erhitzen ueber den Schmelzpunkt;
117882-90-3

3,7-dimethyl-8-trichloromethyl-3,7-dihydro-purine-2,6-dione

83-67-0

theobromine /

Conditions
ConditionsYield
With hydrogenchloride
80038-09-1

1-benzoyl-3,7-dimethyl-3,7-dihydro-purine-2,6-dione

furan-2,3,5(4H)-trione pyridine (1:1)

56-40-6

glycine

A

495-69-2

Hippuric Acid

B

83-67-0

theobromine /

Conditions
ConditionsYield
at 20℃;
77-78-1

dimethyl sulfate

69-89-6

xanthin

83-67-0

theobromine /

77-78-1

dimethyl sulfate

69-89-6

xanthin

A

83-67-0

theobromine /

B

58-08-2

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

Conditions
ConditionsYield
bei der Methylierung unter verschiedenen Bedingungen;
69-89-6

xanthin

74-88-4

methyl iodide

83-67-0

theobromine /

Conditions
ConditionsYield
at 100℃; Das Bleisalz liefert beim Erhitzen im Rohr;
541-41-3

chloroformic acid ethyl ester

115377-65-6

3-Methyl-5-methylamino-3H-imidazole-4-carboxylic acid amide; compound with perchloric acid

83-67-0

theobromine /

Conditions
ConditionsYield
With sodium hydroxide; triethylamine 1.) MeCN, r. t., 1.5 h, 2.) r. t., 10 min; Yield given. Multistep reaction;
86180-29-2

7,9-dimethylxanthinium iodide

A

83-67-0

theobromine /

B

552-62-5

7-methylxanthine

Conditions
ConditionsYield
at 230℃; for 0.75h; Title compound not separated from byproducts;

7,9-dimethylxanthinium hydrogensulfate

A

83-67-0

theobromine /

B

552-62-5

7-methylxanthine

Conditions
ConditionsYield
at 250℃; for 0.25h; Title compound not separated from byproducts;
5752-21-6

7,9-dimethylxanthinium betaine

83-67-0

theobromine /

Conditions
ConditionsYield
With iodine at 250℃; for 1h;
86180-34-9

3,7,9-trimethylxanthinium chloride

83-67-0

theobromine /

Conditions
ConditionsYield
at 260℃; for 0.75h; Yield given;
90198-42-8

3-methyl-4-methylamino-5-methylformylaminouracil

A

83-67-0

theobromine /

B

58-08-2

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

Conditions
ConditionsYield
fusion;
86180-33-8

1,7,9-trimethylxanthinium iodide

83-67-0

theobromine /

Conditions
ConditionsYield
at 230℃; for 0.25h; Yield given;

(5-Carbamoyl-1-methyl-1H-imidazol-4-yl)-methyl-carbamic acid ethyl ester

83-67-0

theobromine /

Conditions
ConditionsYield
With sodium hydroxide for 0.166667h; Heating; Yield given;
93079-86-8

3,7-dimethyl-6-(5-oxohexyloxy)-3,7-dihydro-2H-purin-2-one

A

83-67-0

theobromine /

B

21856-89-3

6-hydroxy-2-hexanone

Conditions
ConditionsYield
With hydrogenchloride
58-08-2

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

A

50-00-0

formaldehyd

B

83-67-0

theobromine /

Conditions
ConditionsYield
With Tris-HCl buffer; 1,4-dihydronicotinamide adenine dinucleotide; Pseudomonas putida No. 352 at 25℃; Product distribution; various substrates, enzyme activity;
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

5415-44-1

1,3,7-trimethyl-7,9-dihydro-3H-purine-2,6,8-trione

Conditions
ConditionsYield
With dihydrogen peroxide In water Product distribution; Mechanism; Irradiation; other reagent;
83-67-0

theobromine /

872-17-3

11-chloroundec-1-ene

156918-64-8

1-(10-undecenyl)-3,7-dimethylxanthine

Conditions
ConditionsYield
With potassium carbonate In water; dimethyl sulfoxide100%
83-67-0

theobromine /

6280-87-1

δ-chlorovaleronitrile

5-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanenitrile

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 130℃; for 3h;100%
83-67-0

theobromine /

89359-54-6

9-bromo-1-nonene

156918-55-7

1-(8-nonenyl)-3,7-dimethylxanthine

Conditions
ConditionsYield
In dimethyl sulfoxide99%
In dimethyl sulfoxide99%
In dimethyl sulfoxide99%
In dichloromethane; dimethyl sulfoxide99%
83-67-0

theobromine /

2695-47-8

6-Bromo-1-hexene

58999-18-1

1-(hex-5-enyl)-3,7-dimethylxanthine

Conditions
ConditionsYield
In water; dimethyl sulfoxide98%
In water; dimethyl sulfoxide95.5%
83-67-0

theobromine /

13154-13-7

(E)-1-bromohex-1-ene

58999-18-1

1-(hex-5-enyl)-3,7-dimethylxanthine

Conditions
ConditionsYield
In water; dimethyl sulfoxide98%
In water; dimethyl sulfoxide98%
In water; dimethyl sulfoxide
In water; dimethyl sulfoxide
83-67-0

theobromine /

13154-13-7

(E)-1-bromohex-1-ene

A

58999-18-1

1-(hex-5-enyl)-3,7-dimethylxanthine

B

154719-57-0

1-(5,6-oxidohexyl)-3,7-dimethylxanthine

Conditions
ConditionsYield
In water; dimethyl sulfoxideA 98%
B n/a
In water; dimethyl sulfoxideA 98%
B n/a
83-67-0

theobromine /

86444-90-8

8-iodotheobromine

Conditions
ConditionsYield
With iodine In acetonitrile for 1.5h; Heating;97%
83-67-0

theobromine /

2695-48-9

8-Bromo-1-octene

1-(7-octenyl)-3,7-dimethylxanthine

Conditions
ConditionsYield
In dimethyl sulfoxide97%
In dimethyl sulfoxide97%
83-67-0

theobromine /

111-83-1

1-bromo-octane

103976-48-3

3,7-dimethyl-1-octyl-3,7-dihydro-1H-purine-2,6-dione

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; Inert atmosphere;96%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; Inert atmosphere; Schlenk technique;88%
With potassium hydroxide; Aliquat 336 1.) 80 deg C, 2 h, 2.) 1 h; Yield given. Multistep reaction;
83-67-0

theobromine /

142-28-9

1,3-Dichloropropane

74409-52-2

1-(3-chloropropyl)-3,7-dimethyl-2,3,6,7-tetrahydro-1H-2,6-purinedione

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride for 2h; Heating;96%
83-67-0

theobromine /

100-39-0

benzyl bromide

1243688-83-6

3,7-dimethyl-9-benzylxanthinium bromide

Conditions
ConditionsYield
With potassium iodide for 24h; Reflux; Inert atmosphere;96%
83-67-0

theobromine /

2273-93-0

2,6-dichloro-7-methylpurine

Conditions
ConditionsYield
With trichlorophosphate; phosphorus trichloride Substitution;95%
With trichlorophosphate at 140℃;
With N,N-diethylaniline; trichlorophosphate at 130℃; for 18h; Inert atmosphere;
With trichlorophosphate at 140℃;
83-67-0

theobromine /

100-39-0

benzyl bromide

55247-90-0

1-benzyl-3,7-dimethylxanthine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Schlenk technique;95%
Stage #1: theobromine / With potassium carbonate In N,N-dimethyl-formamide for 0.5h;
Stage #2: benzyl bromide In N,N-dimethyl-formamide
89%
With caesium carbonate In toluene; acetonitrile for 18h;80%
83-67-0

theobromine /

106-95-6

allyl bromide

2530-99-6

N-allyltheobromine

Conditions
ConditionsYield
Stage #1: theobromine /; allyl bromide With sodium t-butanolate In N,N-dimethyl-formamide at 150℃; for 12h;
Stage #2: In N,N-dimethyl-formamide at 100℃; for 12h;
95%
With potassium carbonate In N,N-dimethyl-formamide80%
With hydrogenchloride In dimethyl sulfoxide42%
83-67-0

theobromine /

10297-06-0

1-chloro-5-hexyne

1-(hex-5-yn-1-yl)-3,7-dimethyl-1H-purine-2,6(3H,7H)-dione

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 100℃; for 2h;95%
83-67-0

theobromine /

12-phosphotungstic acid*29H2O

64-17-5

ethanol

O40PW12(3-)*3C7H9N4O2(1+)*1.5C2H6O

Conditions
ConditionsYield
Stage #1: theobromine /; 12-phosphotungstic acid*29H2O In water at 70 - 80℃;
Stage #2: ethanol
95%
74-83-9

methyl bromide

83-67-0

theobromine /

A

58-08-2

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

B

7280-81-1

3-benzyladenine

Conditions
ConditionsYield
With solution aqueuse d'hydroxide de sodium; tetrabutylammomium bromide In dichloromethane 1)20 deg C, 12h 2)40 deg C, 3h;A 94%
B n/a
624-76-0

Iodoethanol

83-67-0

theobromine /

1507-14-8

1-(2-hydroxyethyl)-3,7-dimethyl-3,7-dihydropurine-2,6-dione

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide for 4h;94%
Stage #1: theobromine / With potassium carbonate In N,N-dimethyl-formamide Reflux;
Stage #2: Iodoethanol for 18h; Reflux;
68%
83-67-0

theobromine /

1-propylhalide

1-propylhalide

63906-63-8

3,7-Dimethyl-1-propylxanthine

Conditions
ConditionsYield
Stage #1: theobromine / With sodium hydride In dimethyl sulfoxide at 60℃; for 0.333333h; Inert atmosphere;
Stage #2: 1-propylhalide In dimethyl sulfoxide at 60℃; Inert atmosphere;
94%
83-67-0

theobromine /

14267-92-6

1-chloro-4-pentyne

3,7-dimethyl-1-(pent-4-yn-1-yl)-1H-purine-2,6(3H,7H)-dione

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 100℃; for 2h;94%
83-67-0

theobromine /

5,8-dioxa-spiro[3,4]octane-2-ylmethyl methanesulfonate

1-(5,8-dioxa-spiro[3,4]octane-2-ylmethyl)-3,7-dimethyl-1H-purine-2,6(3H,7H)dione

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 130℃; for 3.5h;93%
83-67-0

theobromine /

77-78-1

dimethyl sulfate

58-08-2

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

Conditions
ConditionsYield
potassium fluoride on basic alumina In acetonitrile for 24h; Ambient temperature;92%
With sodium hydroxide
83-67-0

theobromine /

18904-08-0

2,6-dithiotheobromine

Conditions
ConditionsYield
With Lawessons reagent; aluminum oxide for 0.116667h; microwave irradiation;92%
With kerosine
83-67-0

theobromine /

1119-51-3

bromopentene

1-(Pent-4-enyl)-3,7-dimethyl-xanthine

Conditions
ConditionsYield
In water; dimethyl sulfoxide; Petroleum ether92%
83-67-0

theobromine /

(5-oxohexyl) mesylate

6493-05-6

pentoxyphylline

Conditions
ConditionsYield
With potassium carbonate In ethanol; water at 50℃; for 16h;91.1%
83-67-0

theobromine /

4286-55-9

1-bromo-6-hexanol

56395-71-2

1-(6-hydroxy-hexyl)-3,7-dimethyl-3,7-dihydro-purine-2,6-dione

Conditions
ConditionsYield
In water; dimethyl sulfoxide91%
In water; dimethyl sulfoxide91%
ethanol-dichloromethane

ethanol-dichloromethane

83-67-0

theobromine /

4286-55-9

1-bromo-6-hexanol

56395-71-2

1-(6-hydroxy-hexyl)-3,7-dimethyl-3,7-dihydro-purine-2,6-dione

Conditions
ConditionsYield
In water; dimethyl sulfoxide91%
In water; dimethyl sulfoxide91%
83-67-0

theobromine /

zirconyl chloride octahydrate

ZrO(C5H2N4(O)2(CH3)2)2(C5HN4(O)2(CH3)2)Cl(H2O)

Conditions
ConditionsYield
In ethanol Zr-compound refluxed in ethanol/triethyl orthoformate for 2 h; N-compound added and refluxed for 36 h; cooled to room temp.; filtered; washed with acetone; elem. anal.;91%
83-67-0

theobromine /

2417-72-3

Methyl 4-(bromomethyl)benzoate

4-((3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)methyl)benzoic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 25 - 110℃; for 3h; Inert atmosphere;91%
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    MSDS/COA Download

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    83-67-0

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    Address:No. 206 Zhen Hua Road, Hangzhou 310030, Zhejiang, China

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    83-67-0

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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.