Caffeine (data page)

{{chembox | container_only = yes

| Name =Caffeine

| ImageFileL1 = Caffeine_3d_structure.png

| ImageFileR1= Caffeine-3D-vdW.png

| ImageNameL1 = Hybrid skeletal structure of the caffeine molecule

| SystematicName =

| IUPACName = 1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dione
1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

| data page pagename = none

}}

{{chembox | container_only = yes

|Name=Caffeine

| data page pagename = none

|Section1={{Chembox Identifiers

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 3G6A5W338E

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D00528

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

| PubChem = 2519

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 27732

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 113

| IUPHAR_ligand = 407

| Beilstein = 17705

| Gmelin = 103040

| InChIKey = RYYVLZVUVIJVGH-UHFFFAOYAW

| SMILES1 = Cn1cnc2c1c(=O)n(c(=O)n2C)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = RYYVLZVUVIJVGH-UHFFFAOYSA-N

| CASNo = 58-08-2

| CASNo_Ref = {{cascite|correct|CAS}}

| EC_number = 200-362-1

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2424

| SMILES = O=C2N(c1ncn(c1C(=O)N2C)C)C

| RTECS = EV6475000

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00201 }}

}}

{{chembox | container_only = yes

|Name=Caffeine

| data page pagename = none

|Section2={{Chembox Properties

| C=8 | H=10 | N=4 | O=2

| Appearance = Odorless, white needles or powder

| Density = 1.23 g/cm³, solid[http://www.ilo.org/legacy/english/protection/safework/cis/products/icsc/dtasht/_icsc04/icsc0405.htm Caffeine] {{Webarchive|url=https://web.archive.org/web/20111231030423/http://www.ilo.org/legacy/english/protection/safework/cis/products/icsc/dtasht/_icsc04/icsc0405.htm |date=2011-12-31 }}, International Occupational Safety and Health Information Centre (CIS)

| Solubility = 2.17 g/100 mL (25 °C)
18.0 g/100 mL (80 °C)
67.0 g/100 mL (100 °C)

| MeltingPt = {{convert|227|to|228|C|F K}} (anhydrous)
{{convert|234|to|235|C|F K}} (monohydrate)

| BoilingPtC = 178

| BoilingPt_notes = (sublimation)

| pKa = −0.13–1.22This is the pK_a for protonated caffeine, given as a range of values included in {{cite book |title=Profiles of Drug Substances, Excipients and Related Methodology, volume 33: Critical Compilation of pK_a Values for Pharmaceutical Substances |author=Harry G. Brittain, Richard J. Prankerd |publisher=Academic Press |year=2007 |isbn=978-0-12-260833-9|url=https://books.google.com/books?id=D3vBu5Tx4XwC&pg=PT15}}

| Dipole = 3.64 D (calculated)

}}

}}

{{chembox | container_only = yes

|Name=Caffeine

| data page pagename = none

|Section7={{Chembox Hazards

| ExternalSDS = [http://www.ilo.org/legacy/english/protection/safework/cis/products/icsc/dtasht/_icsc04/icsc0405.htm ICSC 0405]

| GHS_ref = [https://www.merckmillipore.com/INTERSHOP/web/WFS/Merck-DE-Site/de_DE/-/EUR/ShowDocument-File?ProductSKU=MDA_CHEM-102584&DocumentId=102584_SDS_DE_DE.PDF&DocumentType=MSD Merck 102584]

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|H302}}

| PPhrases = {{P-phrases|P264|270|301+312|501}}

| NFPA-H = 2

| NFPA-F = 0

| NFPA-R = 0

| LD50 = 192 mg/kg (rat, oral){{cite journal|title = Factors Affecting Caffeine Toxicity: A Review of the Literature|last = Peters|first = Josef M.|journal = The Journal of Clinical Pharmacology and the Journal of New Drugs|volume = 7|year = 1967|issue = 3|pages = 131–141|url = http://jcp.sagepub.com/cgi/reprint/7/3/131|access-date = 2011-09-25|archive-url = https://web.archive.org/web/20080610131732/http://jcp.sagepub.com/cgi/reprint/7/3/131|archive-date = 2008-06-10|url-status = dead|doi = 10.1002/j.1552-4604.1967.tb00034.x}}

}}}}