CAFFEINE

First marketed in 1921

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H10N4O2
Molecular Weight	194.1909
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=RYYVLZVUVIJVGH-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&code=C328
Curator's Comment:: description was created based on several sources, including http://www.webmd.com/vitamins-supplements/ingredientmono-979-caffeine.aspx?activeingredientid=979

Caffeine is a methylxanthine alkaloid found in the seeds, nuts, or leaves of a number of plants native to South America and East Asia that is structurally related to adenosine and acts primarily as an adenosine receptor antagonist with psychotropic and anti-inflammatory activities. Upon ingestion, caffeine binds to adenosine receptors in the central nervous system (CNS), which inhibits adenosine binding. This inhibits the adenosine-mediated downregulation of CNS activity; thus, stimulating the activity of the medullary, vagal, vasomotor, and respiratory centers in the brain. The anti-inflammatory effects of caffeine are due the nonselective competitive inhibition of phosphodiesterases. Caffeine is used by mouth or rectally in combination with painkillers (such as aspirin and acetaminophen) and a chemical called ergotamine for treating migraineheadaches. It is also used with painkillers for simple headaches and preventing and treating headaches after epidural anesthesia. Caffeine creams are applied to the skin to reduce redness and itching in dermatitis. Healthcare providers sometimes give caffeine intravenously (by IV) for headache after epidural anesthesia, breathing problems in newborns, and to increase urine flow. In foods, caffeine is used as an ingredient in soft drinks, energy drinks, and other beverages.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
Adenosine A2a receptor 25 Target ID: CHEMBL251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24164628	Antagonist 2575	23.4 µM [Ki]
Adenosine A2b receptor 18 Target ID: CHEMBL255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24164628	Antagonist 2575	20.5 µM [Ki]
Adenosine A1 receptor 42 Target ID: CHEMBL226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24164628	Antagonist 2575	44.9 µM [Ki]
Phosphodiesterase 1 11 Target ID: CHEMBL2111322 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2374150	Inhibitor 7687	70.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Migraine 98 Sources: https://www.drugs.com/pro/cafergot.html	Primary	Approved 7968	CAFERGOT Approved Use Ergotamine is an alpha adrenergic blocking agent with a direct stimulating effect on the smooth muscle of peripheral and cranial blood vessels and produces depression of central vasomotor centers. The compound also has the properties of serotonin antagonism. In comparison to hydrogenated ergotamine, the adrenergic blocking actions are less pronounced and vasoconstrictive actions are greater. Caffeine, also a cranial vasoconstrictor, is added to further enhance the vasoconstrictive effect without the necessity of increasing ergotamine dosage. Launch Date -6.6579838E11
Apnea of prematurity 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2000/20793s1lbl.pdf	Primary	Approved 7968	CAFCIT Approved Use Caffeine Citrate injection USP is indicated for the short-term treatment of apnea of prematurity in infants between 28 and <33 weeks gestational age. Launch Date 9.3778562E11
Atopic dermatitis 39 Sources: https://www.ncbi.nlm.nih.gov/pubmed/339846	Primary	Not Provided 523	Unknown Approved Use Unknown
Drowsiness 3 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4c561b00-c4cf-11df-851a-0800200c9a66	Primary	Approved 7968	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
3.35 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28561231	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		CAFFEINE unknown	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
65.64 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28561231	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		CAFFEINE unknown	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
43000 nM*h Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01361217	100 mg single, oral dose: 100 mg route of administration: oral experiment type: single co-administered:		CAFFEINE plasma	Homo sapiens population: healthy age: adults sex: food status:

T_1/2

Value	Dose	Co-administered	Analyte	Population
10.19 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28561231	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:		CAFFEINE unknown	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
12.4 g single, oral Overdose Dose: 12.4 g Route: oral Route: single Dose: 12.4 g Sources: https://pubmed.ncbi.nlm.nih.gov/30734410	unknown, 14 years n = 1 Health Status: unknown Age Group: 14 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/30734410	Other AEs: Nausea, Vomiting... Other AEs: Nausea (1 patient) Vomiting (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/30734410
50 g single, oral Overdose Dose: 50 g Route: oral Route: single Dose: 50 g Sources: https://pubmed.ncbi.nlm.nih.gov/23396922	unknown, 27 years n = 1 Health Status: unknown Age Group: 27 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/23396922	Other AEs: Tachycardia, Seizure... Other AEs: Tachycardia (1 patient) Seizure (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/23396922
5000 mg single, oral (total) Overdose Dose: 5000 mg Route: oral Route: single Dose: 5000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/29884665	healthy, 32 years n = 1 Health Status: healthy Age Group: 32 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/29884665	Other AEs: Malaise, Anxiety... Other AEs: Malaise (1 patient) Anxiety (1 patient) Dizziness (1 patient) Nausea (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/29884665
4000 mg single, oral Overdose Dose: 4000 mg Route: oral Route: single Dose: 4000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/32021978	pregnant, 33 years n = 1 Health Status: pregnant Age Group: 33 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/32021978	Other AEs: Nausea, Vomiting... Other AEs: Nausea (1 patient) Vomiting (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/32021978
1.6 g single, oral Overdose Dose: 1.6 g Route: oral Route: single Dose: 1.6 g Sources: https://pubmed.ncbi.nlm.nih.gov/25632790	healthy, 44 years n = 1 Health Status: healthy Age Group: 44 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/25632790	Other AEs: Atrial fibrillation... Other AEs: Atrial fibrillation (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/25632790
800 mg multiple, oral (total) Highest studied dose Dose: 800 mg Route: oral Route: multiple Dose: 800 mg Sources: https://pubmed.ncbi.nlm.nih.gov/33852164	healthy, adult n = 12 Health Status: healthy Age Group: adult Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/33852164	Sources: https://pubmed.ncbi.nlm.nih.gov/33852164
24 g single, oral Overdose Dose: 24 g Route: oral Route: single Dose: 24 g Sources: https://pubmed.ncbi.nlm.nih.gov/24079989	unknown, adult n = 1 Health Status: unknown Age Group: adult Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/24079989	Other AEs: Rhabdomyolysis, Acute renal failure... Other AEs: Rhabdomyolysis (1 patient) Acute renal failure (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/24079989

AEs

AE	Significance	Dose	Population
Nausea	1 patient	12.4 g single, oral Overdose Dose: 12.4 g Route: oral Route: single Dose: 12.4 g Sources: https://pubmed.ncbi.nlm.nih.gov/30734410	unknown, 14 years n = 1 Health Status: unknown Age Group: 14 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/30734410
Vomiting	1 patient	12.4 g single, oral Overdose Dose: 12.4 g Route: oral Route: single Dose: 12.4 g Sources: https://pubmed.ncbi.nlm.nih.gov/30734410	unknown, 14 years n = 1 Health Status: unknown Age Group: 14 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/30734410
Seizure	1 patient	50 g single, oral Overdose Dose: 50 g Route: oral Route: single Dose: 50 g Sources: https://pubmed.ncbi.nlm.nih.gov/23396922	unknown, 27 years n = 1 Health Status: unknown Age Group: 27 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/23396922
Tachycardia	1 patient	50 g single, oral Overdose Dose: 50 g Route: oral Route: single Dose: 50 g Sources: https://pubmed.ncbi.nlm.nih.gov/23396922	unknown, 27 years n = 1 Health Status: unknown Age Group: 27 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/23396922
Anxiety	1 patient	5000 mg single, oral (total) Overdose Dose: 5000 mg Route: oral Route: single Dose: 5000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/29884665	healthy, 32 years n = 1 Health Status: healthy Age Group: 32 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/29884665
Dizziness	1 patient	5000 mg single, oral (total) Overdose Dose: 5000 mg Route: oral Route: single Dose: 5000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/29884665	healthy, 32 years n = 1 Health Status: healthy Age Group: 32 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/29884665
Malaise	1 patient	5000 mg single, oral (total) Overdose Dose: 5000 mg Route: oral Route: single Dose: 5000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/29884665	healthy, 32 years n = 1 Health Status: healthy Age Group: 32 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/29884665
Nausea	1 patient	5000 mg single, oral (total) Overdose Dose: 5000 mg Route: oral Route: single Dose: 5000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/29884665	healthy, 32 years n = 1 Health Status: healthy Age Group: 32 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/29884665
Nausea	1 patient	4000 mg single, oral Overdose Dose: 4000 mg Route: oral Route: single Dose: 4000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/32021978	pregnant, 33 years n = 1 Health Status: pregnant Age Group: 33 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/32021978
Vomiting	1 patient	4000 mg single, oral Overdose Dose: 4000 mg Route: oral Route: single Dose: 4000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/32021978	pregnant, 33 years n = 1 Health Status: pregnant Age Group: 33 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/32021978
Atrial fibrillation	1 patient	1.6 g single, oral Overdose Dose: 1.6 g Route: oral Route: single Dose: 1.6 g Sources: https://pubmed.ncbi.nlm.nih.gov/25632790	healthy, 44 years n = 1 Health Status: healthy Age Group: 44 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/25632790
Acute renal failure	1 patient	24 g single, oral Overdose Dose: 24 g Route: oral Route: single Dose: 24 g Sources: https://pubmed.ncbi.nlm.nih.gov/24079989	unknown, adult n = 1 Health Status: unknown Age Group: adult Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/24079989
Rhabdomyolysis	1 patient	24 g single, oral Overdose Dose: 24 g Route: oral Route: single Dose: 24 g Sources: https://pubmed.ncbi.nlm.nih.gov/24079989	unknown, adult n = 1 Health Status: unknown Age Group: adult Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/24079989

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 1359

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1268	CYP1A2 892 CYP2E1 567 CYP3A 154 CYP2C11 7 CYP1A1 302 CYP1B1 82	P-gp 225 CYP1A2 618

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 1406	inhibitor 2612 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1884289/	no	weak (co-administration study) Comment: When caffeine was coadministered the Cmax of melatonin was increased on average by 137% and AUC by 120% Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1884289/
CYP1A2 1406	inducer 1333 Sources: https://pubmed.ncbi.nlm.nih.gov/8723732/	yes
P-gp 1253	inducer 1333 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3163078/	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP1A2 892	substrate 2751 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020793s019lbl.pdf#page=7 Page: 7.0	major	likely (co-administration study) Comment: lower doses of caffeine may be needed following coadministration of drugs which are reported to decrease caffeine elimination (e.g., cimetidine and ketoconazole) and higher caffeine doses may be needed following coadministration of drugs that increase caffeine elimination (e.g., phenobarbital and phenytoin) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020793s019lbl.pdf#page=7 Page: 7.0
CYP1A1 302	substrate 2751 Sources: https://pubmed.ncbi.nlm.nih.gov/8857078/	yes
CYP1B1 82	substrate 2751 Sources: https://pubmed.ncbi.nlm.nih.gov/9152602/	yes
CYP2C11 7	substrate 2751 Sources: http://if-pan.krakow.pl/pjp/pdf/2007/3_296.pdf	yes
CYP2E1 567	substrate 2751 Sources: https://pubmed.ncbi.nlm.nih.gov/8204093/ Page: 9.0	yes
CYP3A 154	substrate 2751 Sources: http://if-pan.krakow.pl/pjp/pdf/2007/3_296.pdf	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1391	inhibitor 1373 Sources: https://www.sciencedirect.com/science/article/abs/pii/S0014299917300833

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA0039GH	http://www.aablocks.com/goods/Goods/detail?id=AA0039GH
AHH Chemical co.,ltd	NP-0568	http://www.ahhchemical.com/product/NP-0568.html
AK Scientific, Inc. (AKSCI)	O926	http://www.aksci.com/item_detail.php?cat=O926
AbMole Bioscience	M2485	http://www.abmole.com/products/caffeine.html
Achemtek	0102-020793	http://www.achemtek.com/58-08-2
Acorn PharmaTech	ACN-034787	http://www.acornpharmatech.com/
Acros Organics	AC393540010	https://www.fishersci.com/shop/products/caffeine-1mg-ml-methanol-acros-organics/AC393540010
Acros Organics	AC108160025	https://www.fishersci.com/shop/products/caffeine-98-5-usp-bp-acros-organics-1/AC108160025
Acros Organics	AC108160100	https://www.fishersci.com/shop/products/caffeine-98-5-usp-bp-acros-organics-1/AC108160100
Acros Organics	AC108165000	https://www.fishersci.com/shop/products/caffeine-98-5-usp-bp-acros-organics/AC108165000
Alfa Aesar	39214	https://www.alfa.com/en/catalog/039214/
Alfa Aesar	A10431	https://www.alfa.com/en/catalog/A10431/
Alfa Chemistry	58-08-2	https://www.alfa-chemistry.com/caffeine-cas-58-08-2-item-292760.htm
Alsachim	695	http://www.alsachim.com/product-C2705-glo.bal-view.html
Ambinter	Amb19079926	http://www.ambinter.com/reference/19079926
Angene	AGN-PC-00GTQE	http://www.angenechemical.com/productshow/AGN-PC-00GTQE.html
ApexBio Technology	N2379	http://www.apexbt.com/caffeine-15463.html
ApexBio Technology	N1379	http://www.apexbt.com/caffeine.html
Aronis	ARONIS25359	http://www.aronis.ru/store/index.php?main_page=product_info&cPath=1&products_id=18255
Aurora Fine Chemicals LLC	K00.331.541	http://online.aurorafinechemicals.com/info?ID=K00.331.541
Aurum Pharmatech LLC	H2815	http://www.Aurumpharmatech.com/Product/ProductDetails/H2815
Avantor Inc	75834-760	https://us.vwr.com/store/product/20514259/caffeine-restek
Avantor Inc	75834-762	https://us.vwr.com/store/product/20514259/caffeine-restek
Avantor Inc	75834-764	https://us.vwr.com/store/product/20514259/caffeine-restek
Avantor Inc	75835-320	https://us.vwr.com/store/product/21998648/exempted-drug-of-abuse-reference-standards-restek
Avantor Inc	101094-456	https://us.vwr.com/store/product/7889359/caffeine
BOC Sciences	78072-66-9	https://isotope.bocsci.com/product/caffeine-13c3-cas-78072-66-9-180910.html
BOC Sciences	72238-85-8	https://isotope.bocsci.com/product/caffeine-d9-cas-72238-85-8-467967.html
BOC Sciences	202282-98-2	https://www.bocsci.com/caffeine-cas-202282-98-2-item-349925.html
BOC Sciences	58-08-2	https://www.bocsci.com/product/caffeine-cas-58-08-2-456230.html
BioCrick	BCN5807	http://www.biocrick.com/Caffeine-BCN5807.html
Calbiochem	205548	http://www.emdbiosciences.com/product/205548
Capot Chemical	9436	http://www.capotchem.com/en/9436.htm
Capot Chemical	PubChem9436	http://www.capotchem.com/en/9436.htm
Chem Scene	CS-M0795	http://www.chemscene.com/58-08-2.html
ChemBridge	5122919	http://www.hit2lead.com/comp.asp?db=SC&id=5122919
ChemFaces	CFN99004	http://www.chemfaces.com/natural/Caffeine-CFN99004.html
ChemMol	1032194	http://www.chemmol.com/chemmol/1032194.html
ChemMol	30102481	http://www.chemmol.com/chemmol/30102481.html
ChemMol	49416400	http://www.chemmol.com/chemmol/49416400.html
ChemMol	99111257	http://www.chemmol.com/chemmol/99111257.html
ChemMol	99177113	http://www.chemmol.com/chemmol/99177113.html
ChemProbes	Met-D6-10mM	https://chemprobes.com/products/met-d6
ChemProbes	Met-D6-20mM	https://chemprobes.com/products/met-d6
ChemProbes	Met-D6-40mM	https://chemprobes.com/products/met-d6
Chemenu	CM110083	http://www.chemenu.com/products/CM110083
Chemspace	CSSB00000212252	https://chem-space.com/CSSB00000212252
Clearsynth	CS-EG-00234	https://www.clearsynth.com/en/CSEG00234.html
Clearsynth	CS-ER-02520	https://www.clearsynth.com/en/CSER02520.html
Clearsynth	CS-O-00486	https://www.clearsynth.com/en/CSO00486.html
Clearsynth	CS-T-50193	https://www.clearsynth.com/en/CST50193.html
DC Chemicals	DCK-013	http://www.dcchemicals.com//product_show-Caffeine.html
Debye Scientific	DB-023002	http://www.debyesci.com/DB-023002.html
EMD Millipore	205548	http://www.emdbiosciences.com/product/205548
Finetech	FT-0664195	https://www.finetechnology-ind.com/prod/detail/pub/72238-85-8.html
Fisher Chemical	O1728500	https://www.fishersci.com/shop/products/caffeine-powder-usp-fcc-fisher-chemical/O1728500
Glentham Life Sciences	GP3094	http://www.glentham.com/products/product/GP3094/
Hello Bio	HB2846	https://www.hellobio.com/caffeine.html
LGC Standards	DRE-A11693000ME-100	https://www.lgcstandards.com/US/en/p/DRE-A11693000ME-100
LGC Standards	DRE-C11693000	https://www.lgcstandards.com/US/en/p/DRE-C11693000
LGC Standards	DRE-CR11693000	https://www.lgcstandards.com/US/en/p/DRE-CR11693000
LGC Standards	DRE-GA09011177MW	https://www.lgcstandards.com/US/en/p/DRE-GA09011177MW
LGC Standards	DRE-L11693000ME	https://www.lgcstandards.com/US/en/p/DRE-L11693000ME
Matrix Scientific	133821	https://www.matrixscientific.com/133821.html
MuseChem	R009245	https://www.musechem.com/product/R009245.html
Oakwood	358299	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=196318&ExtHyperLink=1
Parchem	14	http://www.parchem.com/chemical-supplier-distributor/Caffeine-000049.aspx
Parchem	11774	http://www.parchem.com/chemical-supplier-distributor/Caffeine-Anhydrous-001774.aspx
Sigma-Aldrich	05-0370_SAJ	https://www.sigmaaldrich.com/catalog/product/saj/050370?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	27600_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/27600?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	27602_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/27602?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1085003_USP	https://www.sigmaaldrich.com/catalog/product/usp/1085003?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1086006_USP	https://www.sigmaaldrich.com/catalog/product/usp/1086006?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S522493	http://www.smolecule.com/products/s522493
TCI (Tokyo Chemical Industry)	C2042	http://www.tcichemicals.com/eshop/en/us/commodity/C2042/index.html
THE BioTek	bt-262466	https://www.thebiotek.com/product/inhibitors/bt-262466
Tocris	2793	https://www.tocris.com/products/caffeine_2793
Vitas-M Laboratory	BBL016491	http://www.request.vitasmlab.biz/index.php?option=com_search_stk&Itemid=22&stk=BBL016491&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
VladaChem	VL141059	https://www.vladachem.com/product.php?products=58-08-2
VladaChem	VL162027	https://www.vladachem.com/product.php?products=58-08-2
abcr GmbH	AB114457	http://www.abcr.com/shop/en/AB114457
abcr GmbH	AB208600	http://www.abcr.com/shop/en/AB208600
mcule	MCULE-3362813910	https://mcule.com/MCULE-3362813910/

PubMed

Title	Date	PubMed
Rat ventral prostate xanthine oxidase bioactivation of ethanol to acetaldehyde and 1-hydroxyethyl free radicals: analysis of its potential role in heavy alcohol drinking tumor-promoting effects.	2001	11223889
Caffeine citrate: a review of its use in apnoea of prematurity.	2001	11220405
Effect of caffeine on the genotoxic effects of gamma radiation and 4-NQO in diploid yeast.	2001	11215705
Contribution of ryanodine receptor subtype 3 to ca2+ responses in Ca2+-overloaded cultured rat portal vein myocytes.	2001 Apr 6	11150292
Combined effects of red pepper and caffeine consumption on 24 h energy balance in subjects given free access to foods.	2001 Feb	11242488
Ionomycin and 2,5'-di(tertbutyl)-1,4,-benzohydroquinone elicit Ca2+-induced Ca2+ release from intracellular pools in Physarum polycephalum.	2001 Feb	11223389
Caffeine and intraocular pressure in a Nigerian population.	2001 Feb	11219635
Age, fatigue, and excitation-contraction coupling in masseter muscles of rats.	2001 Feb	11213268
Caffeine stores and dopamine differentially require Ca(2+) channels in goldfish somatotropes.	2001 Feb	11208580
BK channel activation by NS-1619 is partially mediated by intracellular Ca2+ release in smooth muscle cells of porcine coronary artery.	2001 Feb	11181423
Protection against cellular damage in the rat heart by iodoacetate.	2001 Feb	11170788
Uric acid inhibits liver phosphorylase a activity under simulated in vivo conditions.	2001 Feb	11158927
Adenoviral SERCA1a gene transfer to adult rat ventricular myocytes induces physiological changes in calcium handling.	2001 Feb 1	11164839
Predetermined recruitment of calcium release sites underlies excitation-contraction coupling in rat atrial myocytes.	2001 Feb 1	11158273
The effects of intracellular pH changes on resting cytosolic calcium in voltage-clamped snail neurones.	2001 Feb 1	11158272
Determination of urinary methylated purine pattern by high-performance liquid chromatography.	2001 Feb 10	11232859
Evidence for glutamate receptor mediated transmission at mechanoreceptors in the skin.	2001 Feb 12	11209947
The role of the D(2) dopamine receptor (D(2)R) in A(2A) adenosine receptor (A(2A)R)-mediated behavioral and cellular responses as revealed by A(2A) and D(2) receptor knockout mice.	2001 Feb 13	11172060
Comparison of the potency of adenosine as an agonist at human adenosine receptors expressed in Chinese hamster ovary cells.	2001 Feb 15	11226378
Mechanisms of hydrogen peroxide-induced relaxation in rabbit mesenteric small artery.	2001 Feb 2	11166293
Caffeine increases paragigantocellularis neuronal firing rate and induces withdrawal signs in morphine-dependent rats.	2001 Feb 2	11166287
Overexpression of FK506-binding protein FKBP12.6 in cardiomyocytes reduces ryanodine receptor-mediated Ca(2+) leak from the sarcoplasmic reticulum and increases contractility.	2001 Feb 2	11157671
[Cerebral infarction in a patient consuming MaHuang extract and guarana].	2001 Feb 3	11229306
Caffeine metabolism in a group of 67 patients with primary biliary cirrhosis.	2001 Jan	11204934
Health tips. Caffeine.	2001 Jan	11201528
Is the combination of ibuprofen and caffeine effective for the treatment of a tension-type headache?	2001 Jan	11195471
Clinical correlations in infants in the neonatal intensive care unit with varying severity of gastroesophageal reflux.	2001 Jan	11176324
Characterization of an intense bitter-tasting 1H,4H-quinolizinium-7-olate by application of the taste dilution analysis, a novel bioassay for the screening and identification of taste-active compounds in foods.	2001 Jan	11170582
Risk factors for sleep bruxism in the general population.	2001 Jan	11157584
Calculation of the dimensions of dosage forms with release controlled by diffusion for in vivo use.	2001 Jan	11154899
Number of K(Ca) channels underlying spontaneous miniature outward currents (SMOCs) in mudpuppy cardiac neurons.	2001 Jan	11152705
Is decaf tea healthy?	2001 Jan	11139300
The associations of maternal caffeine consumption and nausea with spontaneous abortion.	2001 Jan	11138817
Relationships between use of television during meals and children's food consumption patterns.	2001 Jan	11134471
Neurotransmitter release from bovine adrenal chromaffin cells is modulated by capacitative Ca(2+)entry driven by depleted internal Ca(2+)stores.	2001 Jan	11133355
Hypothesized treatment for migraines using low doses of tryptophan, niacin, calcium, caffeine, and acetylsalicylic acid.	2001 Jan	11133261
Ryanodine-sensitive Ca2+ release mechanism in non-excitable cells (Review).	2001 Jan	11115603
Caffeine dissociates complexes between DNA and intercalating dyes: application for bleaching fluorochrome-stained cells for their subsequent restaining and analysis by laser scanning cytometry.	2001 Jan 1	11122483
The effects of phosphodiesterase inhibition on cyclic GMP and cyclic AMP accumulation in the hippocampus of the rat.	2001 Jan 12	11150485
Characterization of the ryanodine receptor-Ca2+ release channel from the thoracic tissues of the lepidopteran insect Heliothis virescens.	2001 Jan 15	11220363
Origin and propagation of spontaneous excitation in smooth muscle of the guinea-pig urinary bladder.	2001 Jan 15	11208975
Suspected caffeine and ephedrine toxicosis resulting from ingestion of an herbal supplement containing guarana and ma huang in dogs: 47 cases (1997-1999).	2001 Jan 15	11195828
Functional analysis of the Neurospora crassa PZL-1 protein phosphatase by expression in budding and fission yeast.	2001 Jan 30	11169754
Acute but not chronic caffeine impairs functional responses to ischaemia-reperfusion in rat isolated perfused heart.	2001 Jan-Feb	11153532
Signalling mechanisms underlying the myogenic response in human subcutaneous resistance arteries.	2001 Mar	11230983
Adenosine induces initial hypoxic-ischemic depression of synaptic transmission in the rat hippocampus in vivo.	2001 Mar	11171640
Binding of urate and caffeine to haemocyanin analysed by isothermal titration calorimetry.	2001 Mar	11171426
Dopaminergic role in stimulant-induced wakefulness.	2001 Mar 1	11222668
Study of the cytolethal distending toxin (CDT)-activated cell cycle checkpoint. Involvement of the CHK2 kinase.	2001 Mar 2	11240139
Escape deficits induced by inescapable shock and metabolic stress are reversed by adenosine receptor antagonists.	2001 May	11182168

Patents

Sample Use Guides

In Vivo Use Guide

Caffeine is used by mouth in combination with painkillers (such as aspirin and acetaminophen) for treating headaches. Maximum oral dose of excedrin is 2 tablets a day (each tablet of excedrin contains 65 mg of caffeine). Caffeine creams are applied to the skin to reduce redness and itching in dermatitis. Healthcare providers sometimes give caffeine intravenously (by IV) for headache after epidural anesthesia, breathing problems in newborns, and to increase urine flow. In foods, caffeine is used as an ingredient in soft drinks, energy drinks, and other beverages.

Route of Administration: Other

In Vitro Use Guide

Binding of caffeine to adrenergic receptors was measured using [3H]N6-Cyclohexyladenosine as a radioligand. Nonspecificbinding was less than 10% of total binding as defined with 10 uM 2-chloroadenosine. Membranes were incubated with 10-6 - 10-3 M caffeine.

Name

Type

Language

CAFFEINE

Official Name

English

FEMA NO. 2224

Code

English

CAFFEINE [II]

Common Name

English

TREZIX COMPONENT CAFFEINE

Brand Name

English

CAFFEINE [FCC]

Common Name

English

CAFFEINE COMPONENT OF CAFERGOT

Common Name

English

CAFFEINE [WHO-DD]

Common Name

English

CAFFEINE [HSDB]

Common Name

English

CAFFEINE COMPONENT OF NORGESIC

Common Name

English

THEOPHYLLINE MONOHYDRATE IMPURITY A [EP]

Common Name

English

CAFFEINE ANHYDROUS [WHO-IP]

Common Name

English

CAFFEINE COMPONENT OF FIORINAL

Common Name

English

FEMCET COMPONENT CAFFEINE

Common Name

English

THEOPHYLLINE IMPURITY A [EP]

Common Name

English

FIORINAL COMPONENT CAFFEINE

Common Name

English

1H-PURINE-2,6-DIONE, 3,7-DIHYDRO-1,3,7-TRIMETHYL-

Systematic Name

English

SYNALGOS

Common Name

English

INVAGESIC COMPONENT CAFFEINE

Common Name

English

DIMENHYDRINATE IMPURITY C [EP]

Common Name

English

CAFERGOT COMPONENT CAFFEINE

Common Name

English

CAFFEINE [ORANGE BOOK]

Common Name

English

SYNALGOS-DC COMPONENT CAFFEINE

Common Name

English

CAFFEINUM [HPUS]

Common Name

English

VIVARIN

Common Name

English

ORPHENGESIC COMPONENT CAFFEINE

Common Name

English

CAFFEINE COMPONENT OF LANORINAL

Common Name

English

THEINE

Common Name

English

CAFFEINE COMPONENT OF ORPHENGESIC

Common Name

English

MIGERGOT COMPONENT CAFFEINE

Common Name

English

GUARANINE

Common Name

English

CAFFEINE COMPONENT OF SYNALGOS-DC-A

Common Name

English

DHC PLUS COMPONENT CAFFEINE

Common Name

English

PENTOXIFYLLINE IMPURITY F [EP]

Common Name

English

CAFFEINE COMPONENT OF FIORICET

Common Name

English

TRIAD COMPONENT CAFFEINE

Common Name

English

CAFFEINE [USP-RS]

Common Name

English

CAFFEINE COMPONENT OF INVAGESIC

Common Name

English

INVAGESIC FORTE COMPONENT CAFFEINE

Common Name

English

CAFFEINE [INCI]

Common Name

English

CAFFEINE [FHFI]

Common Name

English

ESGIC COMPONENT CAFFEINE

Common Name

English

CAFFEINE COMPONENT OF TRIAD

Common Name

English

NORGESIC COMPONENT CAFFEINE

Common Name

English

SYNALGOS-DC-A COMPONENT CAFFEINE

Common Name

English

COFFEINUM [WHO-IP LATIN]

Common Name

English

CAFFEINE COMPONENT OF DHC PLUS

Common Name

English

ANHYDROUS CAFFEINE

Common Name

English

CAFFEINE COMPONENT OF SYNALGOS-DC

Common Name

English

CAFFEINE [VANDF]

Common Name

English

CAFFEINE COMPONENT OF WIGRAINE

Common Name

English

CAFFEINE COMPONENT OF ESGIC

Common Name

English

DARVON COMPOUND COMPONENT CAFFEINE

Common Name

English

CAFFEINE COMPONENT OF ORPHENGESIC FORTE

Common Name

English

CAFFEINE [IARC]

Common Name

English

ORPHENGESIC FORTE COMPONENT CAFFEINE

Common Name

English

CAFFEINE COMPONENT OF EXCEDRIN

Common Name

English

CAFFEINE COMPONENT OF INVAGESIC FORTE

Common Name

English

CAFFEINE [EP MONOGRAPH]

Common Name

English

CAFFEINUM

Common Name

English

FIORICET COMPONENT CAFFEINE

Common Name

English

MEDIGESIC PLUS COMPONENT CAFFEINE

Common Name

English

METHYLTHEOBROMINE

Systematic Name

English

CAFFEINE COMPONENT OF FEMCET

Common Name

English

CAFFEINE COMPONENT OF DARVON COMPOUND

Common Name

English

EXCEDRIN COMPONENT CAFFEINE

Common Name

English

CAFFEINE COMPONENT OF MEDIGESIC PLUS

Common Name

English

CAFFEINE [WHO-IP]

Common Name

English

CAFFEINE COMPONENT OF MIGERGOT

Common Name

English

CAFFEINE [MI]

Common Name

English

NSC-5036

Code

English

DIMENHYDRINATE IMPURITY C

Common Name

English

ANHYDROUS CAFFEINE [JAN]

Common Name

English

WIGRAINE COMPONENT CAFFEINE

Common Name

English

CAFFEINE COMPONENT OF ANOQUAN

Common Name

English

LANORINAL COMPONENT CAFFEINE

Common Name

English

ANOQUAN COMPONENT CAFFEINE

Common Name

English

CAFFEINE MELTING POINT STANDARD

Common Name

English

CAFFEINE [MART.]

Common Name

English

1,3,7-TRIMETHYLXANTHINE

Systematic Name

English

CAFFEINE [USP]

Common Name

English

DURVITAN

Common Name

English

Classification Tree Code System Code

WHO-VATC

QV04CG30