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Details

Stereochemistry ACHIRAL
Molecular Formula C8H10N4O2.I.Na
Molecular Weight 344.0848
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of caffeine sodium iodide

SMILES

[Na+].[I-].CN1C=NC2=C1C(=O)N(C)C(=O)N2C

InChI

InChIKey=JPEVTJYUOIQUFC-UHFFFAOYSA-M
InChI=1S/C8H10N4O2.HI.Na/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2;;/h4H,1-3H3;1H;/q;;+1/p-1

HIDE SMILES / InChI

Description

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 TargetPharmacologyConditionPotency
23.4 µM [Ki]
20.5 µM [Ki]
44.9 µM [Ki]
70.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CAFERGOT
Primary
CAFCIT
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
3.35 μg/mL
200 mg single, oral
CAFFEINE unknown
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
65.64 μg × h/mL
200 mg single, oral
CAFFEINE unknown
Homo sapiens
43000 nM*h
100 mg single, oral
CAFFEINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
10.19 h
200 mg single, oral
CAFFEINE unknown
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

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.