CAS 58-08-2|1,3,7-三甲基黄嘌呤|caffeine|咖啡因|Caffeine|1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione|Caffeine|CAFFEINE ANHYDROUS|1,3,7-Trimethylxanthine|咖啡因溶液|2,6-Dioxo-2,3,6,7-tetra...

General Information

Structure

Molecular Formula

C₈H₁₀N₄O₂

Molecular Mass

194.1906

Exact Mass

194.08037558

Charge

InChI

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

InChIKey

RYYVLZVUVIJVGH-UHFFFAOYSA-N

Canonic Smiles

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

Isomeric Smiles

O=c1n(c(=O)n(c2ncn(c12)C)C)C

Calculated Properties

JChem

LogD (pH = 7.4)

-0.55

LogD (pH = 5.5)

-0.55

Log P

-0.55

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

-1.16

Polar Surface Area

58.44

Polarizability

18.96

Molar Refractivity

49.83

LOG S

-0.44

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

1,3,7-三甲基黄嘌呤咖啡因CaffeineCaffeineCAFFEINE ANHYDROUS1,3,7-Trimethylxanthine咖啡因溶液2,6-Dioxo-2,3,6,7-tetrahydro-1,3,7-trimethyl-1H-purineCaffeine 99%1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dioneCaffeine solution3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dioneMethyltheobromideCaffeine PureCompound 65CafeinaTheobromine METheophylline MECFFMonomethyl Derivative of TheophyllineCaffeine, AnhydrousMethyltheobromineCaffeine, MonohydrateCaffeinCaffeine, Synthetic咖啡因Mettler-Toledo® 校准物质 ME 18872，咖啡因CaffeineStay AlertCafipelCafalgineCaffedrineKoffeinStimSK 65 CompoundDiurexDasinNew CetamolHycominePhensalShape PlusWigrainePalergot-CTheinGuaranine7-MethyltheophyllineTri-AquaAlert-PepMiudolSynalgosDHCplusNo-DozMateinaTheineDurvitanNSC 5036Refresh'nMettler-Toledo® Calibration substance ME 18872, Caffeine1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dioneCoffeine熔点标准品 235-237°CMelting point standard 235-237°CCoffeinummateinacafeinaCoffeinteina1,3,7-trimethylpurine-2,6-dioneguaranineanhydrous caffeinecafeineCaffeinetheine1-methyltheobromineCAFFEINEcaffeinecaffeineKoffein1,3,7-TrimethylxanthineThein1,3,7-trimethylxanthine3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dion1,3,7-trimethyl-2,6-dioxopurine7-methyltheophyllinemethyltheobromine

IUPAC Traditional name

caffeine 1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

IUPAC name

1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

Brand Name

EnerjetsKofeinCafeconWake-UpNorgesicRefresh'nSK 65 CompoundDasinAlert-PepCoffeinInvagesic ForteTheineCafamilCaffedrine CapletsFiorinalHycomineDarvon Compound-65CaffedrineFemcetTriadEsgic-PlusKeep AlertEldiatric CPhensalWigraineNorgesic ForteGuaranineNix NapCafipelOrganexAnoquanUltra Pep-BackNatural CaffeinumCafcitPropoxyphene Compound 65DurvitanErcatabCaffineQuick PepLanorinalFioricetDhc PlusEsgicDiurexOrphengesic ForteKoffeinDexitac Stay Alert StimulantMiudolCoffeineSynalgos-DcInvagesicMateinaMigergotPep-BackVivarinNodacaMaximum Strength Snapback Stimulant PowdersMedigesic PlusOrphengesicNodoz Maximum Strength CapletsTheinNo-DozPropoxyphene Compound-65Darvon CompoundStimDexitac

API Name

Caffeine

Names and Identifiers

Registration numbers

Beilstein Number

17705

PubChem SID

4650640824892436160963549248566872427768224886771248928292489298424900939248931178144467

MDL Number

EC Number

CAS Number

PubChem CID

KEGG ID

CHEBI ID

27732CHEBI:27732CHEBI:41472CHEBI:3295CHEBI:22982

Unique Ingredient Identifier

CHEMBL

IUPHAR ligand ID

DrugBank ID

Wikipedia Title

ATC CODE

Chemspider ID

Merck Index

Flavis Number

Council of Europe Number

11741

FEMA ID

2224

Protein Data Bank

6jiy6tv45tat6jrr6icp7m6a1l7x6icn5tas6qtl4y4d6jrs5tal5tam3rfm5taq7d7l1gfz5t9v3dd17d7k5mzp1l5q3dds3g6m5ta36jii6ji06ug47pbb3ddw7m6l5tap5tav6sf91c8l5tan6jhn6jiu6m2w2a3b5tau

Patent number

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

IntEnz Database

EC 2.1.1.160EC 1.17.5.2EC 1.14.13.178

MassBank Database

EA030309EA030308EA030302EA030313EA030303EA030304EA030305EA030306EA030312EA030311EA030314EA030301EA030310EA030307

BRENDA Ligand Database

20763520763451266

Golm Database

f85610e2-69ef-43d3-9066-ff421eff38c80184b419-0e0b-4dda-abab-b6e8d564e4c8fa0e6f19-72de-43ac-8aa8-cf23d44c8d1743595824-4fd6-4b29-afc2-2771e487f6f3

HMDB Database

BKMS React Database

LINCS Database

SABIO-RK Database

MetaCyc Database

1-3-7-TRIMETHYLXANTHINE

ACToR Database

58-08-2

GeneOntology Database

GO:0071313GO:0031000

BioModels Database

BIOMD0000000241BIOMD0000000601

Rhea Database

RHEA:47148RHEA:20944RHEA:10280RHEA:36267RHEA:27902RHEA:36271

CompTox Database

DTXSID0020232

Reactom Database

R-HSA-9728748R-HSA-380073R-HSA-76426R-HSA-9728747R-HSA-3296233R-HSA-749456R-HSA-749454R-HSA-9728752

EnzymePortal Database

Q68CM3Q8H0D3Q9JKK8Q55F68A4GE70H9N289Q9FZN8Q96Q15Q13535D7REY3D7REY5D7REY4Q8BKX6Q8H0D2

BindingDB Database

Gmelin ID

Reaxys Registry

SureChEMBL Database

Drug Central Database

KNApSAcK Database

PDBeChem Database

KEGG DRUG Database

NMRShiftDB Database

Registration numbers

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00201

Drug Groups

approved

Description

A methylxanthine naturally occurring in some beverages and also used as a pharmacological agent. Caffeine's most notable pharmacological effect is as a central nervous system stimulant, increasing alertness and producing agitation. It also relaxes smooth muscle, stimulates cardiac muscle, stimulates diuresis, and appears to be useful in the treatment of some types of headache. Several cellular actions of caffeine have been observed, but it is not entirely clear how each contributes to its pharmacological profile. Among the most important are inhibition of cyclic nucleotide phosphodiesterases, antagonism of adenosine receptors, and modulation of intracellular calcium handling. [PubChem]

Indication

For management of fatigue, orthostatic hypotension, and for the short term treatment of apnea of prematurity in infants.

Pharmacology

Caffeine, a naturally occurring xanthine derivative like theobromine and the bronchodilator theophylline, is used as a CNS stimulant, mild diuretic, and respiratory stimulant (in neonates with apnea of prematurity). Often combined with analgesics or with ergot alkaloids, caffeine is used to treat migraine and other headache types. Over the counter, caffeine is available to treat drowsiness or mild water-weight gain.

Toxicity

LD₅₀=127 mg/kg (orally in mice)

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic cytochrome P450 1A2 (CYP 1A2) is involved in caffeine biotransformation. About 80% of a dose of caffeine is metabolized to paraxanthine (1,7-dimethylxanthine), 10% to theobromine (3,7-dimethylxanthine), and 4% to theophylline (1,3-dimethylxanthine).

Absorption

Readily absorbed after oral or parenteral administration. The peak plasma level for caffeine range from 6-10mg/L and the mean time to reach peak concentration ranged from 30 minutes to 2 hours.

Half Life

3 to 7 hours in adults, 65 to 130 hours in neonates

Protein Binding

Low (25 to 36%).

Elimination

In young infants, the elimination of caffeine is much slower than that in adults due to immature hepatic and/or renal function.

Distribution

* 0.8 to 0.9 L/kg [infants]
* 0.6 L/kg [adults]

References

• Nathanson JA: Caffeine and related methylxanthines: possible naturally occurring pesticides. Science. 1984 Oct 12;226(4671):184-7. [Pubmed]

• Haskell CF, Kennedy DO, Wesnes KA, Milne AL, Scholey AB: A double-blind, placebo-controlled, multi-dose evaluation of the acute behavioural effects of guarana in humans. J Psychopharmacol. 2007 Jan;21(1):65-70. Epub 2006 Mar 13. [Pubmed]

• Smit HJ, Gaffan EA, Rogers PJ: Methylxanthines are the psycho-pharmacologically active constituents of chocolate. Psychopharmacology (Berl). 2004 Nov;176(3-4):412-9. Epub 2004 May 5. [Pubmed]

• Benjamin LT Jr, Rogers AM, Rosenbaum A: Coca-Cola, caffeine, and mental deficiency: Harry Hollingworth and the Chattanooga trial of 1911. J Hist Behav Sci. 1991 Jan;27(1):42-55. [Pubmed]

• Nehlig A, Daval JL, Debry G: Caffeine and the central nervous system: mechanisms of action, biochemical, metabolic and psychostimulant effects. Brain Res Brain Res Rev. 1992 May-Aug;17(2):139-70. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

MP Biomedicals

02150114

Anhydrous

Sigma Aldrich

C8960

Biochem/physiol Actions
一种据信是通过腺苷受体和单胺类神经递质发挥作用的中枢神经系统兴奋剂。它为腺苷受体拮抗剂和腺苷3′，5′-环单磷酸 (cAMP) 磷酸二酯酶抑制剂。因此，在用咖啡因处理后，细胞内 cAMP 的水平将升高。据报道，它会影响细胞的钙水平，从而使细胞内的钙离子外流。它会使多种化学物质(例如蛋白酶抑制剂)的细胞周期效应无效，从而防止细胞凋亡;同时，还发现它可以抑制细胞的 DNA 修复机制。

C1778

包装
棕色螺旋盖样品瓶包装
Biochem/physiol Actions
一种据信是通过腺苷受体和单胺类神经递质发挥作用的中枢神经系统兴奋剂。它为腺苷受体拮抗剂和腺苷3′，5′-环单磷酸 (cAMP) 磷酸二酯酶抑制剂。因此，在用咖啡因处理后，细胞内 cAMP 的水平将升高。据报道，它会影响细胞的钙水平，从而使细胞内的钙离子外流。它会使多种化学物质(例如蛋白酶抑制剂)的细胞周期效应无效，从而防止细胞凋亡;同时，还发现它可以抑制细胞的 DNA 修复机制。
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C1778.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

C0750

Caution
保持密封。
包装
1 kg in poly bottle
5, 100 g in poly bottle
Biochem/physiol Actions
一种据信是通过腺苷受体和单胺类神经递质发挥作用的中枢神经系统兴奋剂。它为腺苷受体拮抗剂和腺苷3′，5′-环单磷酸 (cAMP) 磷酸二酯酶抑制剂。因此，在用咖啡因处理后，细胞内 cAMP 的水平将升高。据报道，它会影响细胞的钙水平，从而使细胞内的钙离子外流。它会使多种化学物质(例如蛋白酶抑制剂)的细胞周期效应无效，从而防止细胞凋亡;同时，还发现它可以抑制细胞的 DNA 修复机制。
法律信息
ReagentPlus 注册商标 Sigma-Aldrich Co. LLC

C7731

56396

General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Biochem/physiol Actions
A central nervous system stimulant believed to act through adenosine receptors and monoamine neurotransmitters. It is an adenosine receptor antagonist and adenosine 3′,5′-cyclic monophosphate (cAMP) phosphodiesterase inhibitor. Thus, levels of cAMP increase in cells following treatment with caffeine. It has been reported to affect cellular calcium levels, releasing calcium from intracellular stores. It overrides the cell cycle effects of various chemicals such as protease inhibitors, preventing apoptosis; and it has been shown to inhibit cellular DNA repair mechanisms.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

Wikipedia

Caffeine

TRC

C080100

Caffeine is a bitter, white crystalline xanthine alkaloid that acts as a stimulant drug and a reversible acetylcholinesterase inhibitor. Caffeine is found in varying quantities in the seeds, leaves, and fruit of some plants, where it acts as a natural pes

ChEBI

CHEBI:27732

A trimethylxanthine in which the three methyl groups are located at positions 1, 3, and 7. A purine alkaloid that occurs naturally in tea and coffee.

Molecule Details

References

PubChem Literature

From Data Sources

• Benjamin LT Jr, Rogers AM, Rosenbaum A: Coca-Cola, caffeine, and mental deficiency: Harry Hollingworth and the Chattanooga trial of 1911. J Hist Behav Sci. 1991 Jan;27(1):42-55. Pubmed

• Nathanson JA: Caffeine and related methylxanthines: possible naturally occurring pesticides. Science. 1984 Oct 12;226(4671):184-7. Pubmed

• Smit HJ, Gaffan EA, Rogers PJ: Methylxanthines are the psycho-pharmacologically active constituents of chocolate. Psychopharmacology (Berl). 2004 Nov;176(3-4):412-9. Epub 2004 May 5. Pubmed

• Zubair, U.M., et al.: Anal. Profiles Drug Subs., 15, 71 (1986)

• Cherrah, Y., et al.: Biochem. Pharmacol., 37, 1311 (1986)

• Nicolau, C. et al., Z. Naturforsch., C, 1974, 29, 475, (cmr)

• Benowitz, N.L. et al., Annu. Rev. Med., 1990, 41, 277, (rev, pharmacol)

• Parliment, T.H. et al., ACS Symp. Ser., 2000, 754

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 921

• Fischer, E. et al., Ber., 1895, 28, 2473; 3135, (synth)

• Bredereck, H. et al., Chem. Ber., 1950, 83, 201; 1962, 95, 1902, (synth)

• Twanmoh, L.-M. et al., J. Het. Chem., 1973, 10, 187, (pmr)

• Zubair, M.U. et al., Anal. Profiles Drug Subst., 1986, 15, 71, (rev, ir, uv, pmr, cmr, ms, occur, anal)

• IARC Monog., 1991, 51, 291, (rev, tox)

• Sitkowski, J. et al., Spectrochim. Acta A, 1995, 51, 839, (pmr, cmr, N-15 nmr)

• Aldrich Library of NMR Spectra, 2nd edn., 1983, 2, 586A, (nmr)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 710B, (ir)

• Caffeine, (ed. Spiller, G.A.), CRC Press, 1998, (book)

• Encyclopedia of Food and Color Additives, (ed. Burdock, G.A.), CRC Press, 1997, 363

• Bogo, A. et al., Phytochemistry, 2000, 54, 937-939, (isol, ms)

• Blout, E.R. et al., J.A.C.S., 1950, 72, 479, (ir)

• Spiteller, G. et al., Monatsh. Chem., 1962, 93, 632, (ms)

• Somani, S.M. et al., Int. J. Clin. Pharmacol., Ther. Toxicol., 1988, 26, 521, (rev)

• Bott, K., Chem. Ber., 1993, 126, 1955, (synth)

• Sutor, D.J., Acta Cryst., 1958, 11, 453, (cryst struct)

• Suzuki, T. et al., Phytochemistry, 1976, 15, 1235, (biosynth)

• Lewis, R.J., Food Additives Handbook, Van Nostrand Reinhold International, New York, 1989, CAK500

• Arnaud, M.J., Prog. Drug Res., 1987, 31, 273, (rev, chem, pharmacol, toxicity)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CAK500

References

Bioactivity

PubChem BioAssay

Bioactivity

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Molecule Details

DrugBank

DB00201

Drug Groups

approved

Description

Indication

For management of fatigue, orthostatic hypotension, and for the short term treatment of apnea of prematurity in infants.

Pharmacology

Toxicity

LD₅₀=127 mg/kg (orally in mice)

Affected Organisms

Humans and other mammals

Biotransformation

Absorption

Readily absorbed after oral or parenteral administration. The peak plasma level for caffeine range from 6-10mg/L and the mean time to reach peak concentration ranged from 30 minutes to 2 hours.

Half Life

3 to 7 hours in adults, 65 to 130 hours in neonates

Protein Binding

Low (25 to 36%).

Elimination

In young infants, the elimination of caffeine is much slower than that in adults due to immature hepatic and/or renal function.

Distribution

* 0.8 to 0.9 L/kg [infants]
* 0.6 L/kg [adults]

References

• Nathanson JA: Caffeine and related methylxanthines: possible naturally occurring pesticides. Science. 1984 Oct 12;226(4671):184-7. [Pubmed]

• Smit HJ, Gaffan EA, Rogers PJ: Methylxanthines are the psycho-pharmacologically active constituents of chocolate. Psychopharmacology (Berl). 2004 Nov;176(3-4):412-9. Epub 2004 May 5. [Pubmed]

• Benjamin LT Jr, Rogers AM, Rosenbaum A: Coca-Cola, caffeine, and mental deficiency: Harry Hollingworth and the Chattanooga trial of 1911. J Hist Behav Sci. 1991 Jan;27(1):42-55. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

MP Biomedicals

02150114

Anhydrous

Sigma Aldrich

C8960

C1778

C0750

C7731