کافئین

Key facts

Drug.image

Caffeine structure.svg

Drug.image_class

skin-invert-image

Drug.width

187

Drug.alt

2D structure of caffeine

Drug.image_class2

bg-transparent

Drug.alt2

3D structure of caffeine

Drug.imageL

Caffeine molecule ball from xtal (1).png

Drug.image_classL

bg-transparent

Drug.imageR

Caffeine molecule spacefill from xtal (1).png

Drug.image_classR

bg-transparent

Drug.DailyMedID

Caffeine

Drug.pregnancy_AU

A

Drug.dependency_liability

Physical: Low–moderate (9–30%) Psychological: Low–moderate

Drug.addiction_liability

Low (9%)

Drug.routes_of_administration

Common: By mouth Medical: Intravenous Uncommon: Insufflation, rectal, transdermal, topical, buccal, sublingual

Drug.class

Stimulant;Adenosinergic; Eugeroic;Nootropic;Anxiogenic; Analeptic; PDE inhibitor;Diuretic

Drug.ATC_prefix

N06B

Drug.ATC_suffix

C01

via Wikipedia infobox

Chemical data

Formula

C8H10N4O2

Molecular weight

194.19 g/mol

IUPAC name

1,3,7-trimethylpurine-2,6-dione

SMILES

CN1C=NC2=C1C(=O)N(C(=O)N2C)C

InChIKey

RYYVLZVUVIJVGH-UHFFFAOYSA-N

XLogP

-0.1

Polar surface area

58.4 Ų

H-bond donors

0

H-bond acceptors

3

Formal charge

0

via PubChem

• Caffeine: cognitive and physical performance enhancer or psychoactive drug?ReviewCurrent neuropharmacology · 2015Cappelletti S, Piacentino D, Sani G et al.DOI: 10.2174/1570159X13666141210215655
• Common questions and misconceptions about caffeine supplementation: what does the scientific evidence really show?ReviewJournal of the International Society of Sports Nutrition · 2024Antonio J, Newmire DE, Stout JR et al.DOI: 10.1080/15502783.2024.2323919
• A review of caffeine's effects on cognitive, physical and occupational performance.ReviewNeuroscience and biobehavioral reviews · 2016McLellan TM, Caldwell JA, Lieberman HRDOI: 10.1016/j.neubiorev.2016.09.001
• Caffeine, coffee, and appetite control: a review.ReviewInternational journal of food sciences and nutrition · 2017Schubert MM, Irwin C, Seay RF et al.DOI: 10.1080/09637486.2017.1320537
• Caffeine's mechanisms of action and its cosmetic use.ReviewSkin pharmacology and physiology · 2013Herman A, Herman APDOI: 10.1159/000343174
• Coffee and mental disorders: How caffeine affects anxiety and depression.ReviewProgress in brain research · 2024Meamar M, Raise-Abdullahi P, Rashidy-Pour A et al.DOI: 10.1016/bs.pbr.2024.06.015
• Caffeine and Exercise: What Next?ReviewSports medicine (Auckland, N.Z.) · 2019Pickering C, Grgic JDOI: 10.1007/s40279-019-01101-0
• Impacts of Caffeine during Pregnancy.ReviewTrends in endocrinology and metabolism: TEM · 2020Qian J, Chen Q, Ward SM et al.DOI: 10.1016/j.tem.2019.11.004

via PubMed

Wikidata facts

Subclass of

methylxanthine

Has part

hydrogen

Named after

coffee

Mass

194.08037556

Image

Sublimated caffeine.jpg

Has use

drug

via Wikidata · CC0