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Substance Name: Caffeine [USP:BAN:JAN]
RN: 58-08-2
UNII: 3G6A5W338E
InChIKey: RYYVLZVUVIJVGH-UHFFFAOYSA-N

Note

  • A methylxanthine naturally occurring in some beverages and also used as a pharmacological agent. Caffeine's most notable pharmacological effect is as a central nervous system stimulant, increasing alertness and producing agitation. It also relaxes smooth muscle, stimulates cardiac muscle, stimulates diuresis, and appears to be useful in the treatment of some types of headache. Several cellular actions of caffeine have been observed, but it is not entirely clear how each contributes to its pharmacological profile. Among the most important are inhibition of cyclic nucleotide phosphodiesterases, antagonism of adenosine receptors, and modulation of intracellular calcium handling.

Molecular Formula

  • C8-H10-N4-O2

Molecular Weight

  • 194.193
 

Classification Codes

Classification Codes

  • Central Nervous System Agents
  • Central Nervous System Stimulants
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Mutation Data
  • Natural Product
  • Neurotransmitter Agents
  • Phosphodiesterase Inhibitors
  • Purinergic Agents
  • Purinergic Antagonists
  • Purinergic P1 Receptor Antagonists
  • Reproductive Effect
  • Stimulant (Central)
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3

Names and Synonyms

Name of Substance

  • 1H-Purine-2,6-dione, 3,7-dihydro-1,3,7-trimethyl-
  • 3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
  • Caffeine
  • Caffeine [USP:BAN:JAN]

MeSH Heading

  • Caffeine

Synonyms

  • 1,3,7-Trimethyl-2,6-dioxopurine
  • 1,3,7-Trimethylxanthine
  • 1H-Purine-2,6-dione, 3,7-dihydro-1,3,7-trimethyl-
  • 3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
  • 5-26-13-00558 (Beilstein Handbook Reference)
  • AI3-20154
  • Alert-pep
  • Anhydrous caffeine
  • BRN 0017705
  • Cafamil
  • Cafecon
  • Cafeina
  • Caffedrine
  • Caffein
  • Caffeina
  • Caffeina [Italian]
  • Caffeine
  • Caffeine (natural)
  • Caffeine, anhydrous
  • Caffeine, synthetic
  • Caffine
  • Cafipel
  • CCRIS 1314
  • Coffein
  • Coffein [German]
  • Coffeine
  • Coffeinum
  • Dexitac
  • EC 200-362-1
  • EINECS 200-362-1
  • Eldiatric C
  • FEMA No. 2224
  • Guaranine
  • HSDB 36
  • Hycomine
  • Kofein
  • Kofein [Czech]
  • Koffein
  • Koffein [German]
  • Mateina
  • Methyltheobromine
  • Methylxanthine theophylline
  • Miudol
  • NCI-C02733
  • Nix Nap
  • NO-Doz
  • Nodaca
  • NoDoz Caplets and Chewable Tablets
  • NSC 5036
  • Organex
  • Quick-Pep
  • Refresh'N
  • Stim
  • Synalgos
  • Thein
  • Theine
  • Theobromine, 1-methyl-
  • Theophylline, 7-methyl
  • Tirend
  • Tri-Aqua
  • UNII-3G6A5W338E
  • Vivarin
  • Wigraine
  • Xanthine, 1,3,7-trimethyl

Systematic Names

  • 1H-Purine-2,6-dione, 3,7-dihydro-1,3,7-trimethyl-
  • Caffeine

Superlist Name

  • Caffeine

Mixture Names

  • A.S.A. and Codeine Compound
  • Anacin
  • Anacin Maximum Strength
  • Bayer Select Headache Pain
  • Cafergot
  • Dasin
  • DHCplus
  • Fiorinal
  • Hycomine Compound
  • Midol Maximum Strength
  • Norgesic
  • P-A-C Analgesic Tablets
  • Phensal
  • Propoxyphene Compound 65
  • SK-65 Compound
  • Synalgos-DC
  • Vanquish

Registry Numbers

CAS Registry Number

  • 58-08-2

FDA UNII

  • 3G6A5W338E

Other Registry Numbers

  • 71701-02-5
  • 95789-13-2

System Generated Number

  • 0000058082

Structure Descriptors

InChI

1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3

InChIKey

RYYVLZVUVIJVGH-UHFFFAOYSA-N

Smiles

c12c(n(c(=O)n(c1=O)C)C)ncn2C

Toxicity

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) BLOOD: HEMORRHAGE

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP		 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: STIFFNESS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

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: TREMOR

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

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

MUSCULOSKELETAL: TUMORS

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"		 Annals of Emergency Medicine. Vol. 18, Pg. 94, 1989.
mouse LD50 intraperitoneal 168mg/kg (168mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED

BEHAVIORAL: AGGRESSION		 Chemical and Pharmaceutical Bulletin. Vol. 22, Pg. 1459, 1974.
mouse LD50 intravenous 62mg/kg (62mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 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) BEHAVIORAL: WITHDRAWAL

BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES

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) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Acta Pharmacologica et Toxicologica. Vol. 15, Pg. 331, 1959.
women LDLo oral 400mg/kg (400mg/kg) SKIN AND APPENDAGES (SKIN): SWEATING: OTHER

CARDIAC: OTHER CHANGES

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 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"

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: TOXIC PSYCHOSIS		 Journal of Pediatrics. Vol. 105, Pg. 493, 1984.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 238 deg C   EXP
pKa Dissociation Constant 10.4 (none) 40 EXP
log P (octanol-water) -0.07 (none)   EXP
Water Solubility 2.16E+04 mg/L 25 EXP
Vapor Pressure 15 mm Hg 89 EXP
Henry's Law Constant 1.90E-19 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.52E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.