CAS 83-67-0|Theobromine
Introduction：Basic information about CAS 83-67-0|Theobromine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Theobromine | ||
|---|---|---|---|
| CAS Number | 83-67-0 | Molecular Weight | 180.164 |
| Density | 1.6±0.1 g/cm3 | Boiling Point | 495.5±37.0 °C at 760 mmHg |
| Molecular Formula | C7H8N4O2 | Melting Point | 345-350 °C |
| MSDS | ChineseUSA | Flash Point | 253.5±26.5 °C |
| Symbol | GHS02, GHS06, GHS08 | Signal Word | Danger |
Names
| Name | theobromine |
|---|---|
| Synonym | More Synonyms |
Theobromine BiologicalActivity
| Description | Theobromine is a methylxanthine found in cacao beans which can inhibit adenosine receptor A1 (AR1) signaling. |
|---|---|
| Related Catalog | Signaling Pathways >>GPCR/G Protein >>Adenosine ReceptorNatural Products >>AlkaloidResearch Areas >>Neurological Disease |
| Target | Human Endogenous Metabolite |
| In Vitro | Theobromine, at concentrations above 25 μM, decreases lipid accumulation in these cells. Cell viability is not affected by Theobromine. Theobromine, at concentrations above 25 μM, suppresses protein expression of PPARγ, C/EBPα and adipogenic genes. The mRNA levels of these genes are also decreased by Theobromine[1]. |
| In Vivo | Body weights are lower in the Theobromine group than in the vehicle group. In addition, Theobromine suppresses gains in weight of epididymal and perirenal adipose tissues. The mean adipocyte area is smaller in the Theobromine group than in the vehicle group[1]. Theobromine group shows lower counts than the other groups when considering the number of bacteria per fecal weight (p=0.021 and p=0.055 compare to the reference (RF) and the cocoa (CC) groups, respectively). The Theobromine diet leads to higher pH values than those found after the RF and CC diets. Fecal concentrations of lactic acid are not significantly affected by the experimental diets (4.26±1.54 mM in RF group; 1.96±0.41 mM in CC group; 2.69±0.73 mM in Theobromine group)[2]. |
| Kinase Assay | 3T3-L1 preadipocytes are pre-incubated with MG132 (10 μM) for 30 min, followed by incubation with IBMX in the presence or absence of Theobromine (25 μM) for 8 h. The cells are lysed in denaturing cell extraction buffer (50 mM Tris-HCl, pH 7.5, containing 70 mM β-mercaptoethanol and 2% SDS) at 95°C for 10 min. The cell lysates are diluted 20 fold with dilution buffer (20 mM Tris-HCl, pH 7.5, containing 150 mM NaCl, 1 mM EDTA, 1mM EGTA, 1% TritonX-100, 2.5 mM sodium pyrophosphate and protease inhibitor cocktail) and centrifuged at 20,000 g for 30 s. The supernatant is incubated with rabbit polyclonal anti-C/EBPβ IgG, anti-FLAG IgG or control IgG at 4°C overnight, followed by incubation with 30 μL protein G-Sepharose resin at 4°C for 1 h. The resin is washed with lysis buffer three times and proteins bound to the resin are separated by SDS-PAGE and analyzed by western blotting[1]. |
| Animal Admin | Lewis rats (3 week old) are used in this study. The rats are randomly distributed into three dietary groups (n=7 per group): the reference (RF) group ingested standard diet AIN-93M, the cocoa (CC) group ingested a standard diet with 10% of natural Forastero cocoa containing 0.25% Theobromine, and the Theobromine (TB) group ingested a standard diet including 0.25% of Theobromine, i.e. the content of Theobromine presents in the CC diet[2]. |
| References | [1]. Mitani T, et al. Theobromine suppresses adipogenesis through enhancement of CCAAT-enhancer-binding protein β degradation by adenosine receptor A1. [2]. Martín-Peláez S, et al. Effect of cocoa's theobromine on intestinal microbiota of rats. Mol Nutr Food Res. 2017 Oct;61(10). |
Chemical & Physical Properties
| Density | 1.6±0.1 g/cm3 |
|---|---|
| Boiling Point | 495.5±37.0 °C at 760 mmHg |
| Melting Point | 345-350 °C |
| Molecular Formula | C7H8N4O2 |
| Molecular Weight | 180.164 |
| Flash Point | 253.5±26.5 °C |
| Exact Mass | 180.064728 |
| PSA | 72.68000 |
| LogP | -2.08 |
| Vapour Pressure | 0.0±1.3 mmHg at 25°C |
| Index of Refraction | 1.737 |
| InChIKey | YAPQBXQYLJRXSA-UHFFFAOYSA-N |
| SMILES | Cn1cnc2c1c(=O)[nH]c(=O)n2C |
| Storage condition | Refrigerator |
| Water Solubility | slightly soluble, |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human
- DOSE/DURATION :
- 26 mg/kg
- TOXIC EFFECTS :
- Behavioral - changes in motor activity (specific assay) Gastrointestinal - nausea or vomiting
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 1265 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 837 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 552 mg/kg
- TOXIC EFFECTS :
- Behavioral - convulsions or effect on seizure threshold
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 530 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Mammal - dog
- DOSE/DURATION :
- 300 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Mammal - cat
- DOSE/DURATION :
- 200 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - rabbit
- DOSE/DURATION :
- 1 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 11596 mg/kg/28D-C
- TOXIC EFFECTS :
- Endocrine - changes in thymus weight Related to Chronic Data - changes in testicular weight
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 4172 gm/kg/49D-C
- TOXIC EFFECTS :
- Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - changes in testicular weight
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 23520 mg/kg/7W-C
- TOXIC EFFECTS :
- Behavioral - food intake (animal) Endocrine - changes in thymus weight Related to Chronic Data - changes in testicular weight
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 39900 mg/kg/19W-C
- TOXIC EFFECTS :
- Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - changes in testicular weight
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 40320 mg/kg/28D-C
- TOXIC EFFECTS :
- Endocrine - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Mammal - dog
- DOSE/DURATION :
- 4 gm/kg/28D-C
- TOXIC EFFECTS :
- Cardiac - other changes
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Mammal - dog
- DOSE/DURATION :
- 30400 mg/kg/43W-C
- TOXIC EFFECTS :
- Cardiac - other changes
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - hamster
- DOSE/DURATION :
- 33600 mg/kg/28D-C
- TOXIC EFFECTS :
- Behavioral - food intake (animal) Endocrine - changes in thymus weight
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 7500 mg/kg
- SEX/DURATION :
- male 49 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Paternal Effects - testes, epididymis, sperm duct
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 17640 mg/kg
- SEX/DURATION :
- male 49 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 6300 mg/kg
- SEX/DURATION :
- female 1-21 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 500 mg/kg
- SEX/DURATION :
- female 13 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 500 mg/kg
- SEX/DURATION :
- female 13 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 3 gm/kg
- SEX/DURATION :
- female 6-29 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
MUTATION DATA - TEST SYSTEM :
- Rodent - hamster
- DOSE/DURATION :
- 300 mg/kg
- REFERENCE :
- EXPEAM Experientia. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1945- Volume(issue)/page/year: 38,600,1982 *** REVIEWS *** IARC Cancer Review:Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 51,421,1991 IARC Cancer Review:Animal No Available Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 51,421,1991 IARC Cancer Review:Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 51,421,1991 TOXICOLOGY REVIEW JRPMAP Journal of Reproductive Medicine. (2 Jacklynn Ct., St. Louis, MO 63132) V.3- 1969- Volume(issue)/page/year: 12,27,1974 TOXICOLOGY REVIEW FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 13,747,1989
- TEST SYSTEM :
- Rodent - hamster
- DOSE/DURATION :
- 300 mg/kg
- REFERENCE :
- EXPEAM Experientia. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1945- Volume(issue)/page/year: 38,600,1982 *** REVIEWS *** IARC Cancer Review:Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 51,421,1991 IARC Cancer Review:Animal No Available Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 51,421,1991 IARC Cancer Review:Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 51,421,1991 TOXICOLOGY REVIEW JRPMAP Journal of Reproductive Medicine. (2 Jacklynn Ct., St. Louis, MO 63132) V.3- 1969- Volume(issue)/page/year: 12,27,1974 TOXICOLOGY REVIEW FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 13,747,1989
Safety Information
| Symbol | GHS02, GHS06, GHS08 |
|---|---|
| Signal Word | Danger |
| Hazard Statements | H225-H301 + H311 + H331-H370 |
| Precautionary Statements | P210-P260-P280-P301 + P310-P311 |
| Personal Protective Equipment | dust mask type N95 (US);Eyeshields;Gloves |
| Hazard Codes | Xn:Harmful; |
| Risk Phrases | R22 |
| Safety Phrases | S22-S24/25 |
| RIDADR | 2811.0 |
| WGK Germany | 1 |
| RTECS | XH2275000 |
| Hazard Class | 6.1 |
| HS Code | 2933990090 |
Customs
| HS Code | 2933990090 |
|---|---|
| Summary | 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
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Synonyms
| 3,7-Dimethyl-xanthine |
| Diurobromine |
| 1H-Purine-2,6-dione, 3,7-dihydro-3,7-dimethyl- |
| EINECS 201-494-2 |
| Teobromin |
| Theostene |
| 2,6-Dihydroxy-3,7-dimethyl-purine |
| Theobromine |
| Diuretin |
| Thesal |
| 3,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dione |
| 3,7-dimethylpurine-2,6-dione |
| Theosalvose |
| Theobromin |
| 3,7-dimethyl xanthine |
| Thesodate |
| 5-26-13-00553 (Beilstein Handbook Reference) |
| Santheose |
| 3,7-dihydro-3,7-dimethyl-1H-purine-2,6-dione |
| MFCD00022830 |
