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

• ChemBase ID: 86
• Molecular Formular: C8H10N4O2
• Molecular Mass: 194.1906
• Monoisotopic Mass: 194.08037558
• SMILES: O=c1n(c(=O)n(c2ncn(c12)C)C)C
• Canonical SMILES: Cn1cnc2c1c(=O)n(C)c(=O)n2C
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• IUPAC Traditional name: caffeine; 1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• Brand Name: Esgic-Plus; Femcet; Fioricet; Fiorinal; Guaranine; Hycomine; Invagesic; Invagesic Forte; Keep Alert; Kofein; Koffein; Lanorinal; Mateina; Maximum Strength Snapback Stimulant Powders; Medigesic Plus; Migergot; Miudol; Natural Caffeinum; Nix Nap; No-Doz; Nodaca; Nodoz Maximum Strength Caplets; Norgesic; Norgesic Forte; Organex; Orphengesic; Orphengesic Forte; Pep-Back; Phensal; Propoxyphene Compound 65; Propoxyphene Compound-65; Quick Pep; Refresh'n; SK 65 Compound; Stim; Synalgos-Dc; Thein; Theine; Triad; Ultra Pep-Back; Vivarin; Wake-Up; Wigraine; Alert-Pep; Anoquan; Cafamil; Cafcit; Cafecon; Caffedrine; Caffedrine Caplets; Caffine; Cafipel; Coffein; Coffeine; Darvon Compound; Darvon Compound-65; Dasin; Dexitac; Dexitac Stay Alert Stimulant; Dhc Plus; Diurex; Durvitan; Eldiatric C; Enerjets; Ercatab; Esgic
• Synonyms: Caffeine solution; 1,3,7-Trimethylxanthine; CAFFEINE ANHYDROUS; Melting point standard 235-237°C; 7-Methyltheophylline; Alert-Pep; Cafalgine; Caffedrine; Cafipel; DHCplus; Dasin; Diurex; Durvitan; Guaranine; Hycomine; Koffein; Mateina; Miudol; NSC 5036; New Cetamol; No-Doz; Palergot-C; Phensal; Refresh'n; SK 65 Compound; Shape Plus; Stay Alert; Stim; Synalgos; Thein; Theine; Tri-Aqua; Wigraine; Caffeine, Anhydrous; Caffeine, Monohydrate; Caffeine, Synthetic; CFF; Cafeina; Caffein; Caffeine Pure; Compound 65; Methyltheobromide; Methyltheobromine; Monomethyl Derivative of Theophylline; Theobromine ME; Theophylline ME; Caffeine; 3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione; 2,6-Dioxo-2,3,6,7-tetrahydro-1,3,7-trimethyl-1H-purine; Caffeine 99%; Caffeine; 1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione; Caffeine; Mettler-Toledo® Calibration substance ME 18872, Caffeine; Coffeinum; Coffeine; 1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione; 咖啡因 溶液; 熔点标准品 235-237°C; 1,3,7-三甲基黄嘌呤; 咖啡因; 咖啡因; Mettler-Toledo® 校准物质 ME 18872，咖啡因

Database IDs

• CAS Number: 58-08-2
• EC Number: 200-362-1
• MDL Number: MFCD00005758
• Beilstein Number: 17705
• Merck Index: 141636
• PubChem SID: 46506408; 24277682; 24886771; 24892436; 160963549; 24900939; 24856687; 24892829; 24892984; 24893117
• PubChem CID: 2519
• CHEBI ID: 27732
• ATC CODE: N06BC01
• CHEMBL: 113
• Chemspider ID: 2424
• DrugBank ID: DB00201
• FEMA ID: 2224
• IUPHAR ligand ID: 407
• KEGG ID: D00528
• Unique Ingredient Identifier: 3G6A5W338E
• Wikipedia Title: Caffeine
• Council of Europe Number: 11741
• Flavis Number: 16.016

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -0.5456457
• LogD (pH = 7.4): -0.5456456
• Log P: -0.5456456
• Molar Refractivity: 49.8312 cm^3
• Polarizability: 17.868532 Å^3
• Polar Surface Area: 58.44 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.24
• LOG S: -1.25
• Solubility (Water): 1.10e+01 g/l

PROPERTIES

• Solubility: 2.17 g/100 mL (25 °C); 18.0 g/100 mL (80 °C); 67.0 g/100 mL (100 °C) in water; 22 mg/ml; chloroform: soluble0.5 M, clear, colorless; DMSO; H2O: soluble15 mg/mL; Hot Methanol; Soluble in pyrrole, THF-H2O mixture, ethyl acetate
• Apperance: Odorless, white needles or powder; Powder; white powder; White Solid
• Melting Point: 227–228 °C, 500-501 K (anhydrous); 234–235 °C, 507-508 K (monohydrate); 232-236°C; 233-238 °C; 234-236.5 °C(lit.); 234-236°C; 235-237 °C; 235-237 °C (±0.3°C); 235-237°C; 238
• Boiling Point: 178°C (subl.); 178°C subl.
• Flash Point: 11 °C; 51.8 °F
• Density: 1.23 g/cm^3, solid; 1.23 g/ml; 1.230
• Hydrophobicity(logP): -0.04; -0.5
• pKa: -0.13–1.22 protonated caffeine
• Dipole Moment: 3.64 D (calculated)

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• Storage Warning: Toxic/Harmful
• RTECS: EV6475000
• European Hazard Symbols: Flammable (F); Toxic (T); X; Harmful (Xn)
• UN Number: 1230; 1544; UN1544
• German water hazard class: 1
• Hazard Class: 3; 6.1
• Packing Group: 2; 3; III
• Australian Hazchem: 2X
• Risk Statements: 11-23/24/25-39/23/24/25; 22; R:22; R22
• Safety Statements: 16-36/37-45; 2; S2
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 151
• TSCA Listed: 是
• EU Index: 613-086-00-5
• GHS Pictograms: GHS02; GHS06; GHS07; GHS08
• GHS Signal Word: Danger; Warning
• NFPA704:
  

  2

  2

  0
• LD50: 192 mg/kg (rat, oral)
• GHS Hazard statements: H225-H301 + H311 + H331-H315-H319-H370; H302
• GHS Precautionary statements: P210-P260-P280-P301 + P310-P305 + P351 + P338-P311; P264-P270-P301+P312-P330-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1230 3/PG 2; UN 1544 6.1/PG 3
• Storage Temperature: 2-8°C
• Regulation Compliance: FCC; FDA 21 CFR (182.1180)

• Target: Others
• Admin Routes: Oral, insufflation, enema
• Bioavailability: 99%
• Dependency Liability: Moderate
• Excretion: urine (100%)
• Half Life: 5 hours
• Metabolism: demethylation by CYP1A2
• Protein Bound: 17% to 36%
• Legal Status: GSL (UK); OTC (US); unscheduled (Australia)
• Pregnancy Category: C (US)
• Gene Information: human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140), PDE4B(5142), PRKAR1A(5573), PRKAR1AP(5574), PRKAR1B(5575), PRKAR2A(5576), PRKAR2B(5577)mouse ... Adora2b(11541)rat ... Adora1(29290), Adora2a(25369); human ... ADORA1(134), ADORA2B(136), ADORA3(140), PDE4B(5142)mouse ... Adora2b(11541)rat ... Adora1(29290), Adora2a(25369)