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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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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 Antagonists
- Purinergic P1 Receptor Antagonists
- Reproductive Effect
- Stimulant (Central)
- Tumor Data
Superlist Classification Code
- Overall Carcinogenic Evaluation: Group 3
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Links to Resources
NLM Resources (File Locators)
Regulatory Agencies (Superlist Locators)
Other Resources (Internet Locators)
Search for this InChIKey on the Web
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
InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3InChIKey
RYYVLZVUVIJVGH-UHFFFAOYSA-NSmiles
CN1C(=O)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: ATAXIA BEHAVIORAL: TREMOR BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | 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) | MUSCULOSKELETAL: TUMORS KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" CARDIAC: CHANGE IN RATE | Annals of Emergency Medicine. Vol. 18, Pg. 94, 1989. |
mouse | LD50 | intraperitoneal | 168mg/kg (168mg/kg) | KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED BEHAVIORAL: AGGRESSION BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) | 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) | KIDNEY, URETER, AND BLADDER: STRUCTURAL OR FUNCTIONAL CHANGES IN URETER LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA | Journal of Pharmacology and Experimental Therapeutics. Vol. 82, Pg. 89, 1944. |
rat | LD50 | oral | 192mg/kg (192mg/kg) | KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS BEHAVIORAL: WITHDRAWAL BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES | 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) | 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: TOXIC PSYCHOSIS BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | 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.