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| CAS No.: | 58-08-2 |
|---|---|
| Name: | Caffeine |
| Article Data: | 142 |
| Molecular Structure: | |
|
|
|
| Formula: | C8H10N4O2 |
| Molecular Weight: | 194.193 |
| Synonyms: | 1H-Purine-2,6-dione,3,7-dihydro-1,3,7-trimethyl-;1,3,7-Trimethyl-2,6-dioxopurine;1,3,7-Trimethylxanthine;3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione;7-Methyltheophylline;Alert-Pep;Asia migrine;DHCplus;Durvitan;Guaranine;Koffein;Mateina;Methyltheobromine;Midron extra;Miudol;Phensal;Refresh'n;SK 65 Compound;Shape Plus;StayAlert;Theine; |
| EINECS: | 200-362-1 |
| Density: | 1.45 g/cm3 |
| Melting Point: | 234-236.5 °C(lit.) |
| Boiling Point: | 416.789 °C at 760 mmHg |
| Flash Point: | 205.867 °C |
| Solubility: | 20 g/L (20 °C) in water |
| Appearance: | white to light yellow crystal powder |
| Hazard Symbols: |
 Xn,  T
|
| Risk Codes: | 22-25 |
| Safety: | 16-36/37-45 |
| Transport Information: | UN 1544 6.1/PG 3 |
| PSA: | 61.82000 |
| LogP: | -1.02930 |
- 81281-59-67-Benzylideneaminotheophylline
- 82993-81-5D-threo-Ritalinic acid hydrochloride
- 73441-42-6METHYL-5-CHLORO-2,2-DIMETHYLVALERATE
- 68439-39-4Poly(oxy-1,2-ethanediyl), alpha-(2-ethylhexyl)-omega-hydroxy-,
- 852475-26-4MC1568
- 958254-66-51H-Imidazo[4,5-b]pyridine-2-carboxaldehyde, 1-methyl-, hydrochloride
- 99170-93-1N-Methyl-2-oxazolamine
- 717878-06-31-(4-fluorophenyl)-4-nitro-1H-imidazole
- 914458-26-7[5-(2-fluorophenyl)-1-pentyl-1H-pyrrol-3-yl]-1-naphthalenyl-Methanone
- 894852-01-87-BROMO-2,2-DIMETHYL-2H-PYRIDO[3,2-B][1,4]OXAZIN-3(4H)-ONE
| Conditions | Yield |
|---|---|
| With solution aqueuse d'hydroxide de sodium; tetrabutylammomium bromide In dichloromethane 1)room temp. 12h 2)reflux 3h; | 100% |
- 58-08-2
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
| Conditions | Yield |
|---|---|
| In xylene at 140℃; for 0.75h; Rearrangement; | 100% |
- 3485-82-3
theophylline sodium salt
- 616-38-6
carbonic acid dimethyl ester
- 58-08-2
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
| Conditions | Yield |
|---|---|
| With 1,8-diazabicyclo[5.4.0]undec-7-ene In water; ethylene glycol at 135℃; for 4h; Autoclave; Green chemistry; | 98.4% |
| With PEG 400 In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 12h; Solvent; Concentration; Temperature; Reagent/catalyst; | 94.9% |
| With NaY (Y-type sodium zeolite catalyst); turkey red oil In water for 5h; Reflux; |
- 74-83-9
methyl bromide
- 58-55-9
theophylline
A
- 58-08-2
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
B
- 7280-81-1
3-benzyladenine
| Conditions | Yield |
|---|---|
| With solution aqueuse d'hydroxide de sodium; tetrabutylammomium bromide In dichloromethane 1)20 deg C, 12h 2)40 deg C, 3h; | A 98% B n/a |
- 107-31-3
Methyl formate
- 57533-87-6
1,3-Dimethylxanthine potassium salt
A
- 58-55-9
theophylline
B
- 58-08-2
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
| Conditions | Yield |
|---|---|
| In methanol | A 97.5% B n/a |
- 67-56-1
methanol
- 57533-87-6
1,3-Dimethylxanthine potassium salt
A
- 107-31-3
Methyl formate
B
- 58-08-2
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
| Conditions | Yield |
|---|---|
| With carbon monoxide at 140℃; under 37503 Torr; for 20h; | A n/a B 97% |
| Conditions | Yield |
|---|---|
| With sodium hydride In dimethyl sulfoxide for 0.75h; | 95% |
| With sodium hydride In dimethyl sulfoxide at 20℃; for 24h; Reagent/catalyst; | 90% |
- 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 | Yield |
|---|---|
| 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 |
- 1076-22-8
3-methylxanthine
- 77-78-1
dimethyl sulfate
- 58-08-2
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
| Conditions | Yield |
|---|---|
| With tetramethyl ammoniumhydroxide; potassium carbonate In methanol; water at 65 - 70℃; | 92.5% |
| Conditions | Yield |
|---|---|
| potassium fluoride on basic alumina In acetonitrile for 24h; Ambient temperature; | 92% |
| With sodium hydroxide |
This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.
Chemistry
IUPAC Name: 1,3,7-Trimethylpurine-2,6-dione
Molecular Formula: C8H10N4O2
Molecular Weight: 194.19 g/mol
EINECS: 200-362-1
Classification Code: Central Nervous System Agents; Central nervous system stimulants; Drug / Therapeutic Agent; Enzyme Inhibitors; Human Data; Mutation data; Natural Product; Phosphodiesterase inhibitors; Reproductive Effect; Stimulant [central]; Tumor data
Melting Point: 234-236.5 °C(lit.)
storage temp.: 2-8 °C
Water Solubility: 20 g/L (20 °C)
Sublimation: 178 °C
Stability: Stable. Incompatible with strong acids, strong bases, strong oxidizing agents, iodine, silver salts, tannins. Weakly light sensitive in solution.
Index of Refraction: 1.679
Molar Refractivity: 50.38 cm3
Molar Volume: 133.3 cm3
Surface Tension: 55.7 dyne/cm
Density: 1.45 g/cm3
Flash Point: 205.9 °C
Enthalpy of Vaporization: 67.01 kJ/mol
Boiling Point: 416.8 °C at 760 mmHg
Vapour Pressure of Caffeine (CAS NO.58-08-2): 3.72E-07 mmHg at 25 °C
Uses
Common sources of Caffeine are coffee, tea, and to a lesser extent chocolate derived from cocoa beans. Less commonly used sources of Caffeine include the yerba maté and guarana plants, which are sometimes used in the preparation of teas and energy drinks.
Production
Caffeine (CAS NO.58-08-2) has been isolated from waste tea and from the decaffeinization of coffee by extraction at 70 ℃, using rotating countercurrent drums and an organic solvent, frequently trichloroethylene. The solvent is drained off, and the beans steamed to remove residual solvent. The extraction solvent is evaporated, and the caffeine is hot-water-extracted from the wax, decolorized with carbon, and recrystallized.
Caffeine (CAS NO.58-08-2) is also manufactured synthetically by, for instance, the methylation of theobromine and also total synthesis by methylation and other reactions based upon urea.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| bird - wild | LD50 | oral | 316mg/kg (316mg/kg) | Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983. | |
| cat | LDLo | intraperitoneal | 180mg/kg (180mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1335, 1935. | |
| cat | LDLo | intravenous | 80mg/kg (80mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1335, 1935. | |
| cat | LDLo | oral | 100mg/kg (100mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1335, 1935. | |
| cat | LDLo | subcutaneous | 150mg/kg (150mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1335, 1935. | |
| child | LDLo | oral | 320mg/kg (320mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: CYANOSIS | Forensic Science. Vol. 3, Pg. 275, 1974. |
| child | TDLo | oral | 140mg/kg (140mg/kg) | BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP BLOOD: HEMORRHAGE | Pediatric Emergency Care. Vol. 10, Pg. 349, 1994. |
| dog | LD50 | oral | 140mg/kg (140mg/kg) | Drugs in Japan Vol. 6, Pg. 174, 1982. | |
| dog | LD50 | subcutaneous | 100mg/kg (100mg/kg) | Drugs in Japan Vol. 6, Pg. 174, 1982. | |
| dog | LDLo | intravenous | 4mg/kg (4mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1335, 1935. | |
| frog | LDLo | parenteral | 120mg/kg (120mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: STIFFNESS CARDIAC: OTHER CHANGES | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 166, Pg. 437, 1932. |
| frog | LDLo | subcutaneous | 120mg/kg (120mg/kg) | Acta Pharmacologica et Toxicologica. Vol. 15, Pg. 331, 1959. | |
| guinea pig | LD50 | oral | 230mg/kg (230mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Toxicology and Applied Pharmacology. Vol. 2, Pg. 23, 1960. |
| guinea pig | LDLo | intraperitoneal | 220mg/kg (220mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1335, 1935. | |
| guinea pig | LDLo | subcutaneous | 200mg/kg (200mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1335, 1935. | |
| hamster | LD50 | oral | 230mg/kg (230mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Toxicology and Applied Pharmacology. Vol. 44, Pg. 1, 1978. |
| human | LDLo | oral | 192mg/kg (192mg/kg) | Journal of New Drugs. Vol. 5, Pg. 252, 1965. | |
| human | TDLo | intravenous | 7mg/kg (7mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Acta Pharmacologica et Toxicologica. Vol. 15, Pg. 331, 1959. |
| infant | TDLo | intramuscular | 36mg/kg (36mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: ATAXIA | American Journal of Diseases of Children. Vol. 134, Pg. 495, 1980. |
| infant | TDLo | intravenous | 68mg/kg (68mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TREMOR BEHAVIORAL: ATAXIA | American Journal of Diseases of Children. Vol. 134, Pg. 495, 1980. |
| infant | TDLo | oral | 14700ug/kg (14.7mg/kg) | BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) | Clinical Biochemistry Vol. 10, Pg. 148, 1977. |
| man | TDLo | oral | 13mg/kg (13mg/kg) | BEHAVIORAL: TOXIC PSYCHOSIS | American Journal of Psychiatry. Vol. 143, Pg. 1320, 1986. |
| man | TDLo | oral | 51mg/kg (51mg/kg) | CARDIAC: CHANGE IN RATE KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" MUSCULOSKELETAL: TUMORS | Annals of Emergency Medicine. Vol. 18, Pg. 94, 1989. |
| mouse | LD50 | intraperitoneal | 168mg/kg (168mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: AGGRESSION KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED | Chemical and Pharmaceutical Bulletin. Vol. 22, Pg. 1459, 1974. |
| mouse | LD50 | intravenous | 62mg/kg (62mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Toxicology Letters. Vol. 29, Pg. 25, 1985. |
| mouse | LD50 | oral | 127mg/kg (127mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Toxicology and Applied Pharmacology. Vol. 44, Pg. 1, 1978. |
| mouse | LD50 | subcutaneous | 242mg/kg (242mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 6, Pg. 601, 1956. | |
| mouse | LD50 | unreported | 251mg/kg (251mg/kg) | Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 53, Pg. 2S, 1957. | |
| pigeon | LDLo | subcutaneous | 140mg/kg (140mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 1, Pg. 572, 1910. | |
| rabbit | LD50 | intravenous | 58mg/kg (58mg/kg) | Kiso to Rinsho. Clinical Report. Vol. 13, Pg. 791, 1979. | |
| rabbit | LD50 | oral | 224mg/kg (224mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Toxicology and Applied Pharmacology. Vol. 44, Pg. 1, 1978. |
| rabbit | LDLo | intramuscular | 200mg/kg (200mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 1, Pg. 572, 1910. | |
| rabbit | LDLo | intraperitoneal | 150mg/kg (150mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1335, 1935. | |
| rabbit | LDLo | subcutaneous | 275mg/kg (275mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 1, Pg. 572, 1910. | |
| rat | LD50 | intraperitoneal | 240mg/kg (240mg/kg) | Zeitschrift fuer Ernaehrungswissenschaft. Vol. 15, Pg. 64, 1976. | |
| rat | LD50 | intravenous | 105mg/kg (105mg/kg) | LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA KIDNEY, URETER, AND BLADDER: STRUCTURAL OR FUNCTIONAL CHANGES IN URETER | Journal of Pharmacology and Experimental Therapeutics. Vol. 82, Pg. 89, 1944. |
| rat | LD50 | oral | 192mg/kg (192mg/kg) | BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES BEHAVIORAL: WITHDRAWAL KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS | Journal of New Drugs. Vol. 5, Pg. 252, 1965. |
| rat | LD50 | rectal | 300mg/kg (300mg/kg) | Journal of Clinical Pharmacology and Journal of New Drugs. Vol. 7, Pg. 131, 1967. | |
| rat | LD50 | subcutaneous | 170mg/kg (170mg/kg) | Journal of Clinical Pharmacology and Journal of New Drugs. Vol. 7, Pg. 131, 1967. | |
| women | LDLo | intravenous | 57mg/kg (57mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION | Acta Pharmacologica et Toxicologica. Vol. 15, Pg. 331, 1959. |
| women | LDLo | oral | 400mg/kg (400mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD CARDIAC: OTHER CHANGES SKIN AND APPENDAGES (SKIN): SWEATING: OTHER | Veterinary and Human Toxicology. Vol. 39, Pg. 228, 1997. |
| women | LDLo | oral | 1gm/kg (1000mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING | Bulletin of the International Association of Forensic Toxicologists.Vol. -, Pg. 6, 1973. |
| women | TDLo | oral | 96mg/kg/1D-I (96mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: TOXIC PSYCHOSIS GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Journal of Pediatrics. Vol. 105, Pg. 493, 1984. |
Safety Profile
Hazard Codes: 
Xn,
T
Risk Statements : 22-25
R22: Harmful if swallowed
R25: Toxic if swallowed
Safety Statements : 16-36/37-45
S16: Keep away from sources of ignition - No smoking
S36/37: Wear suitable protective clothing and gloves
S45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
RIDADR : UN 1544 6.1/PG 3
WGK Germany : 1
F 10: Keep under argon.
HazardClass : 6.1
PackingGroup : III
RTECS : EV6475000
Specification
Caffeine (CAS NO.58-08-2), its Synonyms are 1H-Purine-2,6-dione, 3,7-dihydro-1,3,7-trimethyl- ; 3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione ; 1,3,7-Trimethyl-2,6-dioxopurine ; 1,3,7-Trimethylxanthine ; Alert-pep ; Anhydrous caffeine ; Vivarin ; Wigraine ; Xanthine, 1,3,7-trimethyl . It is white to light yellow crystal powder.