U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of CAFFEINE

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
Molecular Formula C8H10N4O2
Molecular Weight 194.1909
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

1921
1413
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2575
 23.4 µM [Ki]
Antagonist
2575
 20.5 µM [Ki]
Antagonist
2575
 44.9 µM [Ki]
Inhibitor
7728
 70.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8043
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
Primary
Approved
8043
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
Primary
Not Provided
492
Unknown

Approved Use

Unknown
Primary
Approved
8043
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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:
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1475

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1383
CYP1A2
972

CYP2E1
606

CYP3A
172

CYP2C11
7

CYP1A1
325

CYP1B1
88
P-gp
248

CYP1A2
637
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1532
 no
weak (co-administration study)
Comment: When caffeine was coadministered the Cmax of melatonin was increased on average by 137% and AUC by 120%
CYP1A2
1532
 yes
P-gp
1514
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
972
 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)
Page: 7.0
CYP1A1
325
 yes
CYP1B1
88
 yes
CYP2C11
7
 yes
CYP2E1
606
 yes
CYP3A
172
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1507
Sourcing

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
Methadone, ciprofloxacin, and adverse drug reactions.
2000 Dec 16
Effect of caffeine on the genotoxic effects of gamma radiation and 4-NQO in diploid yeast.
2001
Contribution of ryanodine receptor subtype 3 to ca2+ responses in Ca2+-overloaded cultured rat portal vein myocytes.
2001 Apr 6
An apoplastic Ca2+ sensor regulates internal Ca2+ release in aequorin-transformed tobacco cells.
2001 Apr 6
Caffeine and intraocular pressure in a Nigerian population.
2001 Feb
Age, fatigue, and excitation-contraction coupling in masseter muscles of rats.
2001 Feb
Caffeine stores and dopamine differentially require Ca(2+) channels in goldfish somatotropes.
2001 Feb
BK channel activation by NS-1619 is partially mediated by intracellular Ca2+ release in smooth muscle cells of porcine coronary artery.
2001 Feb
Calcium homeostasis and cell death in Sol8 dystrophin-deficient cell line in culture.
2001 Feb
Intravenous nicotine and caffeine: subjective and physiological effects in cocaine abusers.
2001 Feb
Selected contribution: effect of the aldehyde acrolein on acetylcholine-induced membrane current in airway smooth muscle cells.
2001 Feb
Regional differences in mechanisms of cerebral circulatory response to neuronal activation.
2001 Feb
Uric acid inhibits liver phosphorylase a activity under simulated in vivo conditions.
2001 Feb
Predetermined recruitment of calcium release sites underlies excitation-contraction coupling in rat atrial myocytes.
2001 Feb 1
The effects of intracellular pH changes on resting cytosolic calcium in voltage-clamped snail neurones.
2001 Feb 1
Determination of urinary methylated purine pattern by high-performance liquid chromatography.
2001 Feb 10
Evidence for glutamate receptor mediated transmission at mechanoreceptors in the skin.
2001 Feb 12
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
Mechanisms of hydrogen peroxide-induced relaxation in rabbit mesenteric small artery.
2001 Feb 2
Coordinated control of cell Ca(2+) loading and triggered release from the sarcoplasmic reticulum underlies the rapid inotropic response to increased L-type Ca(2+) current.
2001 Feb 2
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
[Cerebral infarction in a patient consuming MaHuang extract and guarana].
2001 Feb 3
Is the combination of ibuprofen and caffeine effective for the treatment of a tension-type headache?
2001 Jan
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
A preferred amplitude of calcium sparks in skeletal muscle.
2001 Jan
Risk factors for sleep bruxism in the general population.
2001 Jan
Calculation of the dimensions of dosage forms with release controlled by diffusion for in vivo use.
2001 Jan
Number of K(Ca) channels underlying spontaneous miniature outward currents (SMOCs) in mudpuppy cardiac neurons.
2001 Jan
Is decaf tea healthy?
2001 Jan
The associations of maternal caffeine consumption and nausea with spontaneous abortion.
2001 Jan
Relationships between use of television during meals and children's food consumption patterns.
2001 Jan
Neurotransmitter release from bovine adrenal chromaffin cells is modulated by capacitative Ca(2+)entry driven by depleted internal Ca(2+)stores.
2001 Jan
Hypothesized treatment for migraines using low doses of tryptophan, niacin, calcium, caffeine, and acetylsalicylic acid.
2001 Jan
PROP (6-n-Propylthiouracil) tasting and sensory responses to caffeine,sucrose, neohesperidin dihydrochalcone and chocolate.
2001 Jan
[Ca(2+)](i) signaling in renal arterial smooth muscle cells of pregnant rat is enhanced during inhibition of NOS.
2001 Jan
cADP-ribose activates reconstituted ryanodine receptors from coronary arterial smooth muscle.
2001 Jan
Heterogeneity of calcium stores and elementary release events in canine pulmonary arterial smooth muscle cells.
2001 Jan
G2-phase delays after irradiation and/or heat treatment as assessed by two-parameter flow cytometry.
2001 Jan
Ryanodine-sensitive Ca2+ release mechanism in non-excitable cells (Review).
2001 Jan
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
Characterization of adriamycin-induced G2 arrest and its abrogation by caffeine in FL-amnion cells with or without p53.
2001 Jan 1
Sorption and desorption studies on chitin gels.
2001 Jan 10
The effects of phosphodiesterase inhibition on cyclic GMP and cyclic AMP accumulation in the hippocampus of the rat.
2001 Jan 12
Origin and propagation of spontaneous excitation in smooth muscle of the guinea-pig urinary bladder.
2001 Jan 15
Ras reduces L-type calcium channel current in cardiac myocytes. Corrective effects of L-channels and SERCA2 on [Ca(2+)](i) regulation and cell morphology.
2001 Jan 19
Functional analysis of the Neurospora crassa PZL-1 protein phosphatase by expression in budding and fission yeast.
2001 Jan 30
Acute but not chronic caffeine impairs functional responses to ischaemia-reperfusion in rat isolated perfused heart.
2001 Jan-Feb
Signalling mechanisms underlying the myogenic response in human subcutaneous resistance arteries.
2001 Mar
Multiple effects of caffeine on Ca2+ release and influx in human B lymphocytes.
2001 Mar
Ca2+-induced Ca2+ release from the endoplasmic reticulum amplifies the Ca2+ signal mediated by activation of voltage-gated L-type Ca2+ channels in pancreatic beta-cells.
2001 Mar 30
Patents

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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.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:09:16 UTC 2021
Edited
by admin
on Fri Jun 25 21:09:16 UTC 2021
Record UNII
3G6A5W338E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CAFFEINE
EP   FCC   FHFI   HSDB   II   INCI   MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD   WHO-IP  
INCI  
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
JAN  
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
HPUS  
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
EP  
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
USP-RS  
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
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
NDF-RT N0000175729
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
CFR 21 CFR 340.10
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
NDF-RT N0000175790
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
WHO-VATC QN06BC01
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
NCI_THESAURUS C54060
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
NCI_THESAURUS C47795
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
NDF-RT N0000175739
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
IARC Caffeine
NDF-RT N0000008118
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
NDF-RT N0000008118
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
DSLD 367 (Number of products:3156)
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
FDA ORPHAN DRUG 367512
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
EPA PESTICIDE CODE 660
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
WHO-ATC V04CG30
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
FDA ORPHAN DRUG 31288
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
WHO-ATC N06BC01
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
LIVERTOX 137
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
CFR 21 CFR 340.50
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
Code System Code Type Description
LACTMED
Caffeine
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
PRIMARY
MESH
D002110
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
PRIMARY
RXCUI
1886
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
PRIMARY RxNorm
IUPHAR
407
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CAFFEINE
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
PRIMARY Description: Silky, colourless crystals or a white, crystalline powder; odourless. Solubility: Soluble in 60 parts of water and in 100 parts of ethanol (~750 g/l) TS; slightly soluble in ether R. Category: Central nervous stimulant. Storage: Caffeine should be kept in a well-closed container. Labelling: The designation on the container of Caffeine should state whether the substance is the monohydrate or is in the anhydrous form. Additional information: Caffeine monohydrate is efflorescent in air. Definition: Caffeine contains not less than 98.5% and not more than 101.0% of C8H10N4O2, calculated with reference to the dried substance.
DRUG CENTRAL
463
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
PRIMARY
DRUG BANK
DB00201
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
PRIMARY
ChEMBL
CHEMBL113
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
PRIMARY
HSDB
35
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
PRIMARY
USP_CATALOG
1085003
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
PRIMARY USP-RS
PUBCHEM
2519
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
PRIMARY
WIKIPEDIA
CAFFEINE
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
PRIMARY
NCI_THESAURUS
C328
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
PRIMARY
USP_CATALOG
1086006
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
PRIMARY USP-RS
EPA CompTox
58-08-2
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
PRIMARY
EVMPD
SUB26077
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-362-1
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
PRIMARY
EVMPD
SUB13146MIG
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
PRIMARY
CAS
58-08-2
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
PRIMARY
MERCK INDEX
M2909
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
PRIMARY Merck Index
FDA UNII
3G6A5W338E
Created by admin on Fri Jun 25 21:09:16 UTC 2021 , Edited by admin on Fri Jun 25 21:09:16 UTC 2021
PRIMARY
Related Record Type Details
Structure of CAFFEINE CITRATE
SALT/SOLVATE -> PARENT
CYTOCHROME P450 1A2
METABOLIC ENZYME -> SUBSTRATE
Structure of CAFFEINE BENZOATE
SALT/SOLVATE -> PARENT
COCOA
PARENT -> CONSTITUENT ALWAYS PRESENT
Secondary metabolite detected in developing cacao seeds.
Structure of CAFFEINE MONOHYDRATE
SALT/SOLVATE -> PARENT
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
COFFEA ARABICA SEED, ROASTED
PARENT -> ACTIVE CONSTITUENT ALWAYS PRESENT
ADENOSINE RECEPTOR A2A
TARGET -> INHIBITOR
CYTOCHROME P450 2E1
METABOLIC ENZYME -> SUBSTRATE
PAULLINIA CUPANA SEED
PARENT -> CONSTITUENT ALWAYS PRESENT
COLA NUT
PARENT -> CONSTITUENT ALWAYS PRESENT
Structure of CAFFEINE SALICYLATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of THEOBROMINE
METABOLITE ACTIVE -> PARENT
MINOR
PLASMA
Structure of 5-ACETYLAMINO-6-AMINO-3-METHYLURACIL
METABOLITE -> PARENT
Structure of TRIMETHYLURIC ACID, 1,3,7-
METABOLITE -> PARENT
IN-VIVO
URINE
Structure of THEOPHYLLINE ANHYDROUS
PARENT -> METABOLITE ACTIVE
Structure of 1,7-DIMETHYLURIC ACID
METABOLITE -> PARENT
URINE
Structure of 1-METHYLXANTHINE
METABOLITE -> PARENT
URINE
Structure of 1,3,7-TRIMETHYL-5,9-DIHYDRO-4H-PURINE-2,6,8-TRIONE
METABOLITE -> PARENT
Structure of PARAXANTHINE
METABOLITE ACTIVE -> PARENT
MAIN PRIMARY METABOLITE; METABOLISM OCCURS IN LIVER
MAJOR
PLASMA; URINE
Structure of 1-METHYLURIC ACID
METABOLITE -> PARENT
Hepatic biotransformation prior to excretion results in about equal amounts of 1-methylxanthine and 1-methyluric acid.
Structure of 1,3,7-TRIMETHYLDIHYDROURIC ACID
METABOLITE -> PARENT
Human, oral
IN-VITRO
URINE
Related Record Type Details
Structure of ISOCAFFEINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of THEOBROMINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of AMINOPHYLLINE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of THEOPHYLLINE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of THEOPHYLLINE ANHYDROUS
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of PARAXANTHINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of CAFFEIDINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 6-AMINO-5-FORMAMIDO-1,3-DIMETHYLURACIL
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of THEOPHYLLINE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of THEOPHYLLINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of PENTOXIFYLLINE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of AMINOPHYLLINE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
Structure of CAFFEINE
ACTIVE MOIETY
http://apps.who.int/phint/pdf/b/Jb.6.1.66.pdf
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
NIH
NCATS
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ACCESSIBILITY
DISCLAIMER
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