Compound: caffeine
SMILES: O=c1n(c(=O)c2n(C)cnc2n1C)C
InChIKey: RYYVLZVUVIJVGH-UHFFFAOYSA-N
Synonyms: caffeine, 58-08-2, Guaranine, 1,3,7-Trimethylxanthine, Methyltheobromine, Theine, Thein, Cafeina, Caffein, Cafipel, Koffein, Mateina, Alert-pep, Coffeine, Anhydrous caffeine, Refresh'n, Caffedrine, Vivarin, Stim, No-Doz, Cafamil, Cafecon, Caffine, Dexitac, Nodaca, 7-Methyltheophylline, Eldiatric C, Durvitan, Hycomine, Organex, Nix Nap, Methyltheobromide, Coffeinum, Coffein, 3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione, Tirend, 1,3,7-Trimethylpurine-2,6-dione, 1,3,7-Trimethyl-2,6-dioxopurine, Tri-Aqua, Kofein, Caffeine, anhydrous, 1-methyltheobromine, 1H-Purine-2,6-dione, 3,7-dihydro-1,3,7-trimethyl-, Methylxanthine theophylline, teina, Caffeina, CAFFEINE ANHYDROUS, 1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dione, NCI-C02733, 1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione, FEMA No. 2224, cafeine, Caffeinum, DTXSID0020232, 1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione, NSC-5036, Caffeine melting point standard, 3G6A5W338E, DTXCID40232, TREZIX COMPONENT CAFFEINE, CHEBI:27732, NSC5036, NoDoz Caplets and Chewable Tablets, 5-26-13-00558 (Beilstein Handbook Reference), Quick Pep, 3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dion, QuickPep, NODOZ, Zanthine, Awake, NoSnooze, Allertness Aid, Diurex Ultimate, trimethylxanthine, Uplift Chewable, Alertness Aid, Diurex Ultra, Yeast-vite, Caffeine,, Conrx Alert, Pro-plus, Sprayable Energy, Stay Awake, Alert Aid, Hair Care, Nano Ppc, Caffeine 200mg, Diurex Water Pills, Topcare Stay Awake, Alert Alertness Aid, NoDoz Alertness Aid, Sohmed Alertness Aid, 357 Super Magnum, Caffeine 1508, Awake Maximum Strength, RefChem:6623, Diurex Water Pills XPL, Caffeine 200 mg Tablets, Jet Alert Double Strength, Jet Alert Regular Strength, Caffeine Tablets, 200 mg, Stay Awake Maximum Strength, Caffeine tablet, film-coated, CHEBI:27134, Topcare Stay Awake Maximum Strength, GROWTH Hair Serum Serum Capillaire, NoDoz Alertness Aid Maximum Strength, Valumeds Maximum Strength Stay Awake, FEELSHION 6% Caffeine 1% Retinol Eye Cream, 200-362-1, 619-173-4, BIOTIN; CITRUS AURANTIUM BERGAMIA (BERGAMOT) FRUIT OIL; CITRUS TANGERINA (TANGERINE) FRUIT; CURCUMA LONGA (TURMERIC) ROOT; LEMON; LYSYLTHREONYLTHREONYLLYSYLSERINE; NICOTIANA BENTHAMIANA WHOLE; TOBACCO LEAF; TRIFOLIUM PRATENSE LEAF, Phensal, Caffeine, synthetic, Quick-Pep, Synalgos, Theophylline, 7-methyl, DHCplus, Miudol, Theobromine, 1-methyl-, Propoxyphene Compound 65, Kofein [Czech], Coffein [German], Koffein [German], Caffeine (natural), Xanthine, 1,3,7-trimethyl, Caffeina [Italian], Theophylline Me, Theobromine Me, SK-65 Compound, Anacin, Anacin Maximum Strength, P-A-C Analgesic Tablets, HSDB 36, BRN 0017705, NSC 5036, MFCD00005758, A.S.A. and Codeine Compound, AI3-20154, CHEMBL113, CFF, caffenium, SK 65 Compound, Caffeine [BAN:JAN], 1,3,7-trimethyl-1,3,7-trihydropurine-2,6-dione, CAS-58-08-2, Caffeine (USP), SMR000326667, CCRIS 1314, SR-01000075187, Anhydrous caffeine (TN), EINECS 200-362-1, Monomethyl derivative of Theophylline, Caffeine [USP:BAN:JAN], Anhydrous caffeine (JP15), metilteobromina, Kafeina, trimetilksantina, UNII-3G6A5W338E, Guaranine;, Coffeine;, Caffeine RS, Theine;, Caffeine CRS, Methyltheobromine;, 1gfz, Caffeine, BioXtra, Caffeine for system suitability CRS, TNP00310, Monohydrate Caffeine, Respia (TN), 1-methyl-Theobromine, Caffeine M.P. RS, 7-methyl Theophylline, Cafergot (Salt/Mix), 1,7-Trimethylxanthine, Spectrum_001301, 1l5q, 1l7x, 2a3b, 3g6m, 3,7-dihydro-1,3,7-trimethyl-1H-purine, CAFFEINE [FHFI], CAFFEINE [HSDB], CAFFEINE [IARC], CAFFEINE [FCC], Xanthine,3,7-trimethyl, CAFFEINE [II], CAFFEINE [MI], 1 3 7-trimetilksantina, CAFFEINE [VANDF], CAFFEINUM [HPUS], 1,3,7-Trimethylxantine, Spectrum2_001261, Spectrum3_000321, Spectrum4_001782, Spectrum5_000423, Lopac-C-0750, 1 3 7-Trimethylxanthine, CAFFEINE [MART.], bmse000206, CAFFEINE [USP-RS], CAFFEINE [WHO-DD], CAFFEINE [WHO-IP], MolMap_000054, Probes1_000150, Probes2_000128, C 0750, EC 200-362-1, SCHEMBL5671, Anhydrous caffeine (JP18), NCIOpen2_008255, BIDD:PXR0172, Lopac0_000228, BSPBio_001921, GTPL407, KBioGR_002325, KBioSS_001781, MLS001055341, MLS001056714, MLS001066409, orb422048, BIDD:ER0554, BIDD:GT0632, Caffeine, 1mg/ml in methanol, DivK1c_000730, SPECTRUM1500155, CU-01000012617-3, SPBio_001222, CAFFEINE [ORANGE BOOK], ESGIC COMPONENT CAFFEINE, TRIAD COMPONENT CAFFEINE, 829 - Tea quality parameters, MEGxp0_001350, SCHEMBL1341011, SCHEMBL6362289, CAFFEINE [EP MONOGRAPH], DIMENHYDRINATE IMPURITY C, FEMCET COMPONENT CAFFEINE, 1,3,7-trimethyl-2,6-dioxo-1,2,3,6-tetrahydropurine, ANHYDROUS CAFFEINE [JAN], CAFFEINE [USP MONOGRAPH], component of Dilone (Salt/Mix), 1,7-Trimethyl-2,6-dioxopurine, ACon1_000085, ANOQUAN COMPONENT CAFFEINE, BDBM10849, HMS502E12, KBio1_000730, KBio2_001781, KBio2_004349, KBio2_006917, KBio3_001141, Caffeine 1.0 mg/ml in Methanol, COFFEINUM [WHO-IP LATIN], CAFERGOT COMPONENT CAFFEINE, Caffeine, powder, ReagentPlus(R), component of Percodan (Salt/Mix), EXCEDRIN COMPONENT CAFFEINE, FIORICET COMPONENT CAFFEINE, FIORINAL COMPONENT CAFFEINE, MIGERGOT COMPONENT CAFFEINE, NINDS_000730, NORGESIC COMPONENT CAFFEINE, WIGRAINE COMPONENT CAFFEINE, Bio1_000473, Bio1_000962, Bio1_001451, DHC PLUS COMPONENT CAFFEINE, HMS1920I09, HMS2091O11, HMS2232M13, HMS3260N17, HMS3372J18, HMS3435F10, HMS3715D13, HMS5091J20, Pharmakon1600-01500155, INVAGESIC COMPONENT CAFFEINE, LANORINAL COMPONENT CAFFEINE, Caffeine 10 microg/mL in Methanol, CAFFEINE ANHYDROUS [WHO-IP], CIA28298, CS-M0795, DDA07266, XCA23885, Tox21_201685, Tox21_300010, Tox21_500228, caffeine (1,3,7-trimethylxanthine), Caffeine 100 microg/mL in Methanol, CCG-38825, EBC-03517, HB2846, NSC755917, ORPHENGESIC COMPONENT CAFFEINE, PDSP1_001016, PDSP1_001235, PDSP2_001000, PDSP2_001219, SBB006474, STK177283, Propoxyphene Compound 65 (Salt/Mix), SYNALGOS-DC COMPONENT CAFFEINE, AKOS000121334, 5-26-13-00558 (Beilstein), Bayer Select Headache Pain (Salt/Mix), Caffeine, anhydrous, 99%, FCC, FG, DB00201, FT05891, LP00228, NSC-755917, SDCCGMLS-0064595.P001, SDCCGMLS-0064595.P002, SDCCGSBI-0050216.P005, IDI1_000730, MEDIGESIC PLUS COMPONENT CAFFEINE, SYNALGOS-DC-A COMPONENT CAFFEINE, 3,3,7-trimethyl-1H-purine-2,6-dione, DARVON COMPOUND COMPONENT CAFFEINE, INVAGESIC FORTE COMPONENT CAFFEINE, NCGC00015208-01, NCGC00015208-02, NCGC00015208-03, NCGC00015208-04, NCGC00015208-05, NCGC00015208-06, NCGC00015208-07, NCGC00015208-08, NCGC00015208-10, NCGC00015208-11, NCGC00015208-12, NCGC00015208-13, NCGC00015208-14, NCGC00015208-15, NCGC00015208-16, NCGC00015208-17, NCGC00015208-18, NCGC00015208-20, NCGC00015208-27, NCGC00015208-29, NCGC00090699-01, NCGC00090699-02, NCGC00090699-03, NCGC00090699-04, NCGC00090699-05, NCGC00090699-06, NCGC00090699-07, NCGC00090699-08, NCGC00090699-09, NCGC00168808-01, NCGC00168808-02, NCGC00254057-01, NCGC00259234-01, NCGC00260913-01, 95789-13-2, AC-12774, AS-15340, Caffeine, SAJ special grade, >=98.5%, component of P-A-C Compound (Salt/Mix), ST057528, component of A.S.A. Compound (Salt/Mix), ORPHENGESIC FORTE COMPONENT CAFFEINE, SBI-0050216.P004, DB-023002, WLN: T56 BN DN FNVNVJ B1 F1 H1, C2042, EU-0100228, NS00000273, THEOPHYLLINE IMPURITY A [EP IMPURITY], 526 - Nutritional Analysis of Energy Drinks, EN300-21663, BIM-0050216.0001, C07481, D00528, DIMENHYDRINATE IMPURITY C [EP IMPURITY], PENTOXIFYLLINE IMPURITY F [EP IMPURITY], Q60235, 1,3,7-trimethyl-3,7-dihydropurine-2,6-dione, 1H-Purine-2, 3,7-dihydro-1,3,7-trimethyl-, AB00051930-09, AB00051930_10, Caffeine, purum, anhydrous, >=99.0% (HPLC), 3,7-dihydro-1,3,7-trimethyl-1H-purine (9CI), Caffeine, anhydrous, tested according to Ph.Eur., L000155, Caffeine, Sigma Reference Standard, vial of 250 mg, SR-01000075187-1, SR-01000075187-4, SR-01000075187-7, SR-01000075187-8, BRD-K02404261-001-02-7, BRD-K02404261-001-03-5, BRD-K02404261-001-07-6, BRD-K02404261-001-16-7, Caffeine, certified reference material, TraceCERT(R), Caffeine, meets USP testing specifications, anhydrous, Melting point standard 235-237C, analytical standard, 1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dione #, Caffeine, British Pharmacopoeia (BP) Reference Standard, Caffeine, European Pharmacopoeia (EP) Reference Standard, F3371-0262, THEOPHYLLINE MONOHYDRATE IMPURITY A [EP IMPURITY], Z104507896, 07E4FB58-FD79-4175-8E3D-05BF96954522, 3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dion (coffein), Caffeine, United States Pharmacopeia (USP) Reference Standard, Reagecon Melting Point Caffeine +235 to +237 degrees C Standard, Caffeine, Pharmaceutical Secondary Standard; Certified Reference Material, Caffeine for system suitability, European Pharmacopoeia (EP) Reference Standard, Caffeine melting point standard, United States Pharmacopeia (USP) Reference Standard, InChI=1/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H, 114303-55-8, Caffeine Melting Point Standard, Pharmaceutical Secondary Standard; Certified Reference Material, Mettler-Toledo Calibration substance ME 18872, Caffeine, analytical standard, for the calibration of the thermosystem 900, traceable to primary standards (LGC)
Theoretical properties:
molecular_formula: C8H10N4O2
molecular_weight: 194.19 g/mol
exact_mass: 194.08037557 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 0
heavy_atom_count: 14
topological_polar_surface_area: 58.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White, prismatic crystals
color: White, prismatic crystals
odor: Odorless
boiling_point: 352 °F at 760 mmHg (sublimes) (NTP, 1992)
melting_point: 460 °F (NTP, 1992)
density: 1.23 at 64 °F (NTP, 1992) - Denser than water; will sink
solubility: 10 to 50 mg/mL at 73 °F (NTP, 1992)
vapor_pressure: 0.00000001 [mmHg]
Descriptions:
{"pubchem": "Caffeine is a trimethylxanthine in which the three methyl groups are located at positions 1, 3, and 7. A purine alkaloid that occurs naturally in tea and coffee. It has a role as a geroprotector, a mutagen, a central nervous system stimulant, a psychotropic drug, a diuretic, a xenobiotic, an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor, an EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor, an adenosine A2A receptor antagonist, an adjuvant, a food additive, a ryanodine receptor agonist, an adenosine receptor antagonist, a mouse metabolite, a plant metabolite, a fungal metabolite, an environmental contaminant and a human blood serum metabolite. It is a purine alkaloid and a trimethylxanthine.", "chebi": "A trimethylxanthine in which the three methyl groups are located at positions 1, 3, and 7. A purine alkaloid that occurs naturally in tea and coffee.", "chembl": "CAFFEINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Caffeine is a central nervous system (CNS) stimulant of the methylxanthine class and is the most commonly consumed psychoactive substance globally. It is mainly used for its eugeroic (wakefulness promoting), ergogenic (physical performance-enhancing), or nootropic (cognitive-enhancing) properties; it is also used recreationally or in social settings. Caffeine acts by blocking the binding of adenosine at a number of adenosine receptor types, inhibiting the centrally depressant effects of adenosine and enhancing the release of acetylcholine. Caffeine has a three-dimensional structure similar to that of adenosine, which allows it to bind and block its receptors. Caffeine also increases cyclic AMP levels through nonselective inhibition of phosphodiesterase, increases calcium release from intracellular stores, and antagonizes GABA receptors, although these mechanisms typically occur at concentrations beyond usual human consumption.\nCaffeine is a bitter, white crystalline purine, a methylxanthine alkaloid, and is chemically related to the adenine and guanine bases of deoxyribonucleic acid (DNA) and ribonucleic acid (RNA). It is found in the seeds, fruits, nuts, or leaves of a number of plants native to Africa, East Asia, and South America and helps to protect them against herbivores and from competition by preventing the germination of nearby seeds, as well as encouraging consumption by select animals such as honey bees. The most common sources of caffeine for human consumption are the tea leaves of the Camellia sinensis plant and the coffee bean, the seed of the Coffea plant. Some people drink beverages containing caffeine to relieve or prevent drowsiness and to improve cognitive performance. To make these drinks, caffeine is extracted by steeping the plant product in water, a process called infusion. Caffeine-containing drinks, such as tea, coffee, and cola, are consumed globally in high volumes. In 2020, almost 10 million tonnes of coffee beans were consumed globally. Caffeine is the world's most widely consumed psychoactive drug. Unlike most other psychoactive substances, caffeine remains largely unregulated and legal in nearly all parts of the world. Caffeine is seen as socially acceptable in most cultures and is encouraged in some.\nCaffeine has both positive and negative health effects. It can treat and prevent the premature infant breathing disorders bronchopulmonary dysplasia of prematurity and apnea of prematurity. Caffeine citrate is on the WHO Model List of Essential Medicines. It may confer a modest protective effect against some diseases, including Parkinson's disease. Caffeine can acutely improve reaction time and accuracy for cognitive tasks. Some people experience sleep disruption or anxiety if they consume caffeine, but others show little disturbance. Evidence of a risk during pregnancy is equivocal; some authorities recommend that pregnant women limit caffeine to the equivalent of two cups of coffee per day or less. Caffeine can produce a mild form of drug dependence \u2013 associated with withdrawal symptoms such as sleepiness, headache, and irritability \u2013 when an individual stops using caffeine after repeated daily intake. Tolerance develops to autonomic effects (blood pressure, heart rate, nervousness) and to alerting/vigilance benefits with regular use. Chronic exposure upregulates adenosine receptors, raising the effort threshold for allocating attention\u2014even to mundane or previously enjoyable tasks\u2014because habitual users operate from a lowered arousal baseline.\nCaffeine is classified by the US Food and Drug Administration (FDA) as generally recognized as safe. Lethal doses, over 10 grams per day for an adult, greatly exceed the typical dose of under 500 milligrams per day. The European Food Safety Authority reported that up to 400 mg of caffeine per day (around 5.7 mg/kg of body mass per day) does not raise safety concerns for non-pregnant adults, while intakes up to 200 mg per day for pregnant and lactating women do not raise safety concerns for the fetus or the breast-fed infants. A 6 ounce cup of coffee typically contains 50\u2013175 mg of caffeine, depending on what \"bean\" (seed) is used (and how much), how it is roasted, and how it is prepared (e.g., drip, percolation, or espresso). Thus roughly 50\u2013100 ordinary cups of coffee would be required to reach a lethal dose. However, pure powdered caffeine, which is available as a dietary supplement, can be lethal in tablespoon-sized amounts.\n\n"}