Compound Summary
Compound Information
caffeine
Compound Name: | caffeine |
Compound CID: | 2519 |
Synonyms: | caffeine 58-08-2 1,3,7-Trimethylxanthine Guaranine Thein More... |
Iupac Name: | 1,3,7-trimethylpurine-2,6-dione |
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 |
Canonical Smiles: | CN1C=NC2=C1C(=O)N(C(=O)N2C)C |
Isomeric Smiles: | CN1C=NC2=C1C(=O)N(C(=O)N2C)C |
Molecular Weight: | 194.19 |
Molecular Formula: | C8H10N4O2 |
Compound Structure
2D Structure:
3D Structure:
Computed Properties
caffeine
Molecular Weight: | 194.19 |
Molecular Formula: | C8H10N4O2 |
Hydrogen Bond Donor Count: | 0 |
Hydrogen Bond Acceptor Count: | 3 |
Rotatable Bond Count: | 0 |
Heavy Atom Count: | 14 |
Complexity: | 293 |
Synonyms
caffeine
| caffeine | caffeine |
|---|---|
caffeine |
58-08-2 |
1,3,7-Trimethylxanthine |
Guaranine |
Thein |
Methyltheobromine |
Cafeina |
Theine |
Koffein |
Mateina |
Alert-pep |
Caffein |
Cafipel |
Coffeine |
Refreshn |
Caffedrine |
Stim |
Cafamil |
Cafecon |
Caffine |
Dexitac |
Nodaca |
Anhydrous caffeine |
No-Doz |
Eldiatric C |
7-Methyltheophylline |
Hycomine |
Organex |
Vivarin |
Nix Nap |
Methyltheobromide |
Coffein |
Phensal |
3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione |
Caffeine, synthetic |
Quick-Pep |
Coffeinum |
Tirend |
1,3,7-Trimethyl-2,6-dioxopurine |
1,3,7-Trimethylpurine-2,6-dione |
Theophylline, 7-methyl |
DHCplus |
Tri-Aqua |
1H-Purine-2,6-dione, 3,7-dihydro-1,3,7-trimethyl- |
Kofein |
Miudol |
Caffeine, anhydrous |
Theobromine, 1-methyl- |
Propoxyphene Compound 65 |
1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dione |
Kofein Czech |
Coffein German |
Koffein German |
1-methyltheobromine |
Caffeine (natural) |
Xanthine, 1,3,7-trimethyl |
Caffeina Italian |
Theophylline Me |
Methylxanthine theophylline |
Theobromine Me |
NCI-C02733 |
SK-65 Compound |
Anacin |
Anacin Maximum Strength |
P-A-C Analgesic Tablets |
C8H10N4O2 |
HSDB 36 |
FEMA No. 2224 |
BRN 0017705 |
1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione |
NSC 5036 |
A.S.A. and Codeine Compound |
UNII-3G6A5W338E |
1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione |
AI3-20154 |
CHEMBL113 |
CFF |
CHEBI:27732 |
3G6A5W338E |
NSC-5036 |
MFCD00005758 |
caffenium |
SK 65 Compound |
Caffeina |
DSSTox_CID_232 |
Caffeine BAN:JAN |
CAFFEINE-D3 |
DSSTox_RID_75448 |
DSSTox_GSID_20232 |
1,3,7-trimethyl-1,3,7-trihydropurine-2,6-dione |
cafeine |
peyona |
teina |
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) |
Caffeine hydrous |
1gfz |
Caffeine, BioXtra |
TNP00310 |
Monohydrate Caffeine |
Respia (TN) |
1-methyl-Theobromine |
7-methyl Theophylline |
Cafergot (Salt/Mix) |
1,7-Trimethylxanthine |
Spectrum_001301 |
1l5q |
1l7x |
2a3b |
3g6m |
3,7-dihydro-1,3,7-trimethyl-1H-purine |
Xanthine,3,7-trimethyl |
Theine, methyltheobromine |
Spectrum2_001261 |
Spectrum3_000321 |
Spectrum4_001782 |
Spectrum5_000423 |
Lopac-C-0750 |
bmse000206 |
MolMap_000054 |
Probes1_000150 |
Probes2_000128 |
C 0750 |
EC 200-362-1 |
SCHEMBL5671 |
Anhydrous caffeine (JP17) |
NCIOpen2_008255 |
BIDD:PXR0172 |
Lopac0_000228 |
1, 3, 7-Trimethylxanthine |
BSPBio_001921 |
GTPL407 |
KBioGR_002325 |
KBioSS_001781 |
5-26-13-00558 (Beilstein Handbook Reference) |
MLS001055341 |
MLS001056714 |
MLS001066409 |
ARONIS25359 |
BIDD:ER0554 |
BIDD:GT0632 |
DivK1c_000730 |
SPECTRUM1500155 |
CU-01000012617-3 |
SPBio_001222 |
Caffeine melting point standard |
MEGxp0_001350 |
ZINC1084 |
1,3,7-trimethyl-2,6-dioxo-1,2,3,6-tetrahydropurine |
component of Dilone (Salt/Mix) |
DTXSID0020232 |
1,7-Trimethyl-2,6-dioxopurine |
ACon1_000085 |
BDBM10849 |
HMS502E12 |
KBio1_000730 |
KBio2_001781 |
KBio2_004349 |
KBio2_006917 |
KBio3_001141 |
Caffeine 1.0 mg/ml in Methanol |
NSC5036 |
Caffeine, powder, ReagentPlus(R) |
component of Percodan (Salt/Mix) |
NINDS_000730 |
Bio1_000473 |
Bio1_000962 |
Bio1_001451 |
HMS1920I09 |
HMS2091O11 |
HMS2232M13 |
HMS3260N17 |
HMS3372J18 |
HMS3435F10 |
HMS3715D13 |
Pharmakon1600-01500155 |
NoDoz Caplets and Chewable Tablets |
Caffeine 10 microg/mL in Methanol |
CS-M0795 |
Tox21_201685 |
Tox21_300010 |
Tox21_500228 |
BBL016491 |
caffeine (1,3,7-trimethylxanthine) |
Caffeine 100 microg/mL in Methanol |
CCG-38825 |
NSC755917 |
PDSP1_001016 |
PDSP1_001235 |
PDSP2_001000 |
PDSP2_001219 |
SBB006474 |
STK177283 |
Propoxyphene Compound 65 (Salt/Mix) |
AKOS000121334 |
5-26-13-00558 (Beilstein) |
ACN-034787 |
Bayer Select Headache Pain (Salt/Mix) |
Caffeine, anhydrous, 99%, FCC, FG |
DB00201 |
LP00228 |
MCULE-3362813910 |
NSC-755917 |
SDCCGMLS-0064595.P001 |
SDCCGMLS-0064595.P002 |
SDCCGSBI-0050216.P005 |
IDI1_000730 |
3,3,7-trimethyl-1H-purine-2,6-dione |
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 |
NCGC00015208-29 |
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 |
AC-12774 |
AS-15340 |
Caffeine, SAJ special grade, >=98.5% |
component of P-A-C Compound (Salt/Mix) |
O926 |
ST057528 |
component of A.S.A. Compound (Salt/Mix) |
SBI-0050216.P004 |
DB-023002 |
WLN: T56 BN DN FNVNVJ B1 F1 H1 |
EU-0100228 |
FT-0664195 |
N1379 |
N2379 |
3378-EP2269610A2 |
3378-EP2275420A1 |
3378-EP2277848A1 |
3378-EP2277867A2 |
3378-EP2280003A2 |
3378-EP2284160A1 |
3378-EP2289510A1 |
3378-EP2295409A1 |
3378-EP2295434A2 |
3378-EP2301937A1 |
3378-EP2305219A1 |
3378-EP2305662A1 |
3378-EP2305671A1 |
3378-EP2305677A1 |
3378-EP2305682A1 |
3378-EP2305695A2 |
3378-EP2305696A2 |
3378-EP2305697A2 |
3378-EP2305698A2 |
3378-EP2308562A2 |
3378-EP2308840A1 |
3378-EP2308867A2 |
3378-EP2308870A2 |
3378-EP2308879A1 |
3378-EP2311801A1 |
3378-EP2311802A1 |
3378-EP2311803A1 |
3378-EP2311806A2 |
3378-EP2311808A1 |
3378-EP2311829A1 |
3378-EP2311842A2 |
3378-EP2314588A1 |
3378-EP2314590A1 |
3378-EP2314593A1 |
3378-EP2316457A1 |
3378-EP2316458A1 |
3378-EP2316825A1 |
3378-EP2316826A1 |
3378-EP2316827A1 |
3378-EP2316828A1 |
3378-EP2371814A1 |
BIM-0050216.0001 |
C07481 |
D00528 |
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 |
3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dion |
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 |
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 |
Z112207564 |
Caffeine 2000 microg/mL in Water:Methanol (81:19 g/g) |
07E4FB58-FD79-4175-8E3D-05BF96954522 |
3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dion (coffein) |
Caffeine solution, analytical standard, 1.0 mg/mL in methanol |
Caffeine, United States Pharmacopeia (USP) Reference 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 |
Caffeine solution, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material |
114303-55-8 |
Caffeine Melting Point Standard, Pharmaceutical Secondary Standard; Certified Reference Material |
Caffeine, PharmaGrade, EP, Manufactured under appropriate GMP controls for pharma or biopharmaceutical production |
Mettler-Toledo Calibration substance ME 18872, Caffeine, analytical standard, for the calibration of the thermosystem 900, traceable to primary standards (LGC) |
Experimental Data
caffeine
| Species | Dosage | Unit | CG Lifespan(AVG/MED days) | TG Lifespan(AVG/MED days) | Lifespan Change(AVG/MED%) | CG Lifespan(MAX days) | TG Lifespan(MAX days) | Lifespan Change(MAX%) | Significant | Strain | Gender | PubMed | Active Label |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Caenorhabditis elegans | 400 | umol/L | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 200 | umol/L | Unclear | N2 | 33683565 | ||||||||
| Saccharomyces cerevisiae | 0.4 | mM | Unclear | 18513215 | |||||||||
| Caenorhabditis elegans | 5 | mM | 20 | 20 | 0 | NS | N2 | 26696878 | Inactive | ||||
| Drosophila melanogaster | 0.1 | mg/mL | 1.7 | Unclear | Oregon-R | MALES | 8326745 | ||||||
| Caenorhabditis elegans | 200 | umol/L | 25.9 | S | N2 | 33683565 | Active | ||||||
| Apis mellifera | 2500 | ppm | 20 | 18 | -0.1 | NS | 30626025 | Inactive | |||||
| Drosophila melanogaster | 1 | mg/mL | -3.3 | Unclear | Oregon-R | MALES | 8326745 | Inactive | |||||
| Caenorhabditis elegans | 60 | mM | 15 | 1 | -0.93 | S | N2 | 26696878 | Inactive | ||||
| Caenorhabditis elegans | 30 | mM | 15 | 10 | -0.33 | S | N2 | 26696878 | Inactive | ||||
| Apis mellifera | 250 | ppm | 20 | 30 | 0.5 | S | 30626025 | Active | |||||
| Drosophila melanogaster | 0.01 | mg/mL | -10.1 | Unclear | Oregon-R | MALES | 8326745 | Inactive | |||||
| Caenorhabditis elegans | 5 | mM | 15 | 27 | 0.8 | S | N2 | 26696878 | Active | ||||
| Caenorhabditis elegans | 0.1 | % | 21.31 | 27.58 | 0.29 | 27 | 41 | 0.52 | S | N2 | 22114686 | Active | |
| Caenorhabditis elegans | 7.5 | mM | 17 | 15 | -11.6 | S | N2 | 24764514 | Inactive | ||||
| Apis mellifera | 25 | ppm | 20 | 41 | 1.05 | S | 30626025 | Active | |||||
| Caenorhabditis elegans | 5 | mM | 20 | 27 | 0.35 | S | N2 | 26696878 | Active | ||||
| Caenorhabditis elegans | 5 | mM | 17 | 28 | 0.65 | S | N2 | 26696878 | Active | ||||
| Caenorhabditis elegans | 5 | mM | 17 | 14 | -13.6 | S | N2 | 24764514 | Inactive | ||||
| Caenorhabditis elegans | 15 | mM | 15 | 31 | 1.07 | S | N2 | 26696878 | Active | ||||
| Caenorhabditis elegans | 0.5 | mM | 23 | 26 | 7.7 | S | N2 | 24764514 | Active | ||||
| Caenorhabditis elegans | 400 | umol/L | 31.2 | S | N2 | 33683565 | Active | ||||||
| Caenorhabditis elegans | 30 | mM | 23 | 19 | -24.4 | S | N2 | 24764514 | Inactive | ||||
| Caenorhabditis elegans | 50 | mM | 27 | 17 | -40.9 | S | N2 | 24764514 | Inactive | ||||
| Caenorhabditis elegans | 33 | umol/L | -2 | NS | N2 | 24134630 | Inactive | ||||||
| Caenorhabditis elegans | 50 | ug/mL | 17.41 | 20.09 | 0.15 | S | N2 | 30061824 | Active | ||||
| Drosophila melanogaster | 0.0125 | % | 32 | 30 | -0.06 | NS | N2 | 29093334 | Inactive | ||||
| Caenorhabditis elegans | 7.5 | mM | 23 | 28 | 8.7 | S | N2 | 24764514 | Active | ||||
| Caenorhabditis elegans | 2.5 | mM | 23 | 28 | 17.2 | S | N2 | 24764514 | Active | ||||
| Caenorhabditis elegans | 45 | mM | 15 | 2 | -0.87 | S | N2 | 26696878 | Inactive | ||||
| Caenorhabditis elegans | 20 | mM | 27 | 34 | 21.6 | S | N2 | 24764514 | Active | ||||
| Caenorhabditis elegans | 75 | mM | 27 | 3 | -82.8 | S | N2 | 24764514 | Inactive | ||||
| Caenorhabditis elegans | 100 | mM | 27 | 3 | -89.5 | S | N2 | 24764514 | Inactive | ||||
| Caenorhabditis elegans | 10 | mM | 27 | 39 | 36.7 | S | N2 | 24764514 | Active | ||||
| Drosophila melanogaster | 0.05 | % | 32 | 28 | -0.12 | S | N2 | 29093334 | Inactive | ||||
| Caenorhabditis elegans | 5 | mM | 23 | 26 | 10.8 | S | N2 | 24764514 | Active | ||||
| Caenorhabditis elegans | 10 | mM | 23 | 28 | 16.9 | S | N2 | 24764514 | Active | ||||
| Caenorhabditis elegans | 7.5 | mM | 27 | 34 | 19.6 | S | N2 | 24764514 | Active | ||||
| Drosophila melanogaster | 0.025 | % | 32 | 28 | -0.12 | S | N2 | 29093334 | Inactive | ||||
| Caenorhabditis elegans | 5 | mM | 27 | 35 | 28.5 | S | N2 | 24764514 | Active |
Experimental Data Visualization
caffeine
Statistics Data
caffeine
| Species | Lifespan Change(AVG/MED%) | Lifespan Change(MAX%) | Count Reference | Count Data point |
|---|---|---|---|---|
| Apis mellifera | 1.05 | 1 | 3 | |
| Caenorhabditis elegans | 36.7 | 0.52 | 6 | 30 |
| Drosophila melanogaster | 1.7 | 2 | 6 | |
| Saccharomyces cerevisiae | 1 | 1 |
Statistics Data Visualization
caffeine
