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58-08-2

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Basic Information
CAS No.: 58-08-2
Name: Caffeine
Article Data: 142
Molecular Structure:
Molecular Structure of 58-08-2 (Caffeine)
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: HarmfulXn, ToxicT
Risk Codes: 22-25
Safety: 16-36/37-45
Transport Information: UN 1544 6.1/PG 3
PSA: 61.82000
LogP: -1.02930
Synthetic route
74-83-9

methyl bromide

69-89-6

xanthin

58-08-2

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

Conditions
ConditionsYield
With solution aqueuse d'hydroxide de sodium; tetrabutylammomium bromide In dichloromethane 1)room temp. 12h 2)reflux 3h;100%

2,6-dimethoxy-7,9-dimethylpurinium iodide

58-08-2

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

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
In methanolA 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
ConditionsYield
With carbon monoxide at 140℃; under 37503 Torr; for 20h;A n/a
B 97%
58-55-9

theophylline

74-88-4

methyl iodide

58-08-2

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

Conditions
ConditionsYield
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
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
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
ConditionsYield
With tetramethyl ammoniumhydroxide; potassium carbonate In methanol; water at 65 - 70℃;92.5%
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
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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 cm
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: HarmfulXn,ToxicT
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.