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

• ChemBase ID: 86
• Molecular Formular: C8H10N4O2
• Molecular Mass: 194.1906
• Monoisotopic Mass: 194.08037558
• SMILES: O=c1n(c(=O)n(c2ncn(c12)C)C)C
• Canonical SMILES: Cn1cnc2c1c(=O)n(C)c(=O)n2C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• IUPAC Traditional name: caffeine; 1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• Brand Name: Esgic-Plus; Femcet; Fioricet; Fiorinal; Guaranine; Hycomine; Invagesic; Invagesic Forte; Keep Alert; Kofein; Koffein; Lanorinal; Mateina; Maximum Strength Snapback Stimulant Powders; Medigesic Plus; Migergot; Miudol; Natural Caffeinum; Nix Nap; No-Doz; Nodaca; Nodoz Maximum Strength Caplets; Norgesic; Norgesic Forte; Organex; Orphengesic; Orphengesic Forte; Pep-Back; Phensal; Propoxyphene Compound 65; Propoxyphene Compound-65; Quick Pep; Refresh'n; SK 65 Compound; Stim; Synalgos-Dc; Thein; Theine; Triad; Ultra Pep-Back; Vivarin; Wake-Up; Wigraine; Alert-Pep; Anoquan; Cafamil; Cafcit; Cafecon; Caffedrine; Caffedrine Caplets; Caffine; Cafipel; Coffein; Coffeine; Darvon Compound; Darvon Compound-65; Dasin; Dexitac; Dexitac Stay Alert Stimulant; Dhc Plus; Diurex; Durvitan; Eldiatric C; Enerjets; Ercatab; Esgic
• Synonyms: Caffeine solution; 1,3,7-Trimethylxanthine; CAFFEINE ANHYDROUS; Melting point standard 235-237°C; 7-Methyltheophylline; Alert-Pep; Cafalgine; Caffedrine; Cafipel; DHCplus; Dasin; Diurex; Durvitan; Guaranine; Hycomine; Koffein; Mateina; Miudol; NSC 5036; New Cetamol; No-Doz; Palergot-C; Phensal; Refresh'n; SK 65 Compound; Shape Plus; Stay Alert; Stim; Synalgos; Thein; Theine; Tri-Aqua; Wigraine; Caffeine, Anhydrous; Caffeine, Monohydrate; Caffeine, Synthetic; CFF; Cafeina; Caffein; Caffeine Pure; Compound 65; Methyltheobromide; Methyltheobromine; Monomethyl Derivative of Theophylline; Theobromine ME; Theophylline ME; Caffeine; 3,7-Dihydro-1,3,7-trimethyl-1H-purine-2,6-dione; 2,6-Dioxo-2,3,6,7-tetrahydro-1,3,7-trimethyl-1H-purine; Caffeine 99%; Caffeine; 1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione; Caffeine; Mettler-Toledo® Calibration substance ME 18872, Caffeine; Coffeinum; Coffeine; 1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione; 咖啡因 溶液; 熔点标准品 235-237°C; 1,3,7-三甲基黄嘌呤; 咖啡因; 咖啡因; Mettler-Toledo® 校准物质 ME 18872，咖啡因

Database IDs

• CAS Number: 58-08-2
• EC Number: 200-362-1
• MDL Number: MFCD00005758
• Beilstein Number: 17705
• Merck Index: 141636
• PubChem SID: 24277682; 24886771; 24892436; 160963549; 24900939; 46506408; 24856687; 24892829; 24892984; 24893117
• PubChem CID: 2519
• CHEBI ID: 27732
• ATC CODE: N06BC01
• CHEMBL: 113
• Chemspider ID: 2424
• DrugBank ID: DB00201
• FEMA ID: 2224
• IUPHAR ligand ID: 407
• KEGG ID: D00528
• Unique Ingredient Identifier: 3G6A5W338E
• Wikipedia Title: Caffeine
• Council of Europe Number: 11741
• Flavis Number: 16.016

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -0.5456457
• LogD (pH = 7.4): -0.5456456
• Log P: -0.5456456
• Molar Refractivity: 49.8312 cm^3
• Polarizability: 17.868532 Å^3
• Polar Surface Area: 58.44 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.24
• LOG S: -1.25
• Solubility (Water): 1.10e+01 g/l

PROPERTIES

Physical Property

• Solubility: 2.17 g/100 mL (25 °C); 18.0 g/100 mL (80 °C); 67.0 g/100 mL (100 °C) in water; 22 mg/ml; chloroform: soluble0.5 M, clear, colorless; DMSO; H2O: soluble15 mg/mL; Hot Methanol; Soluble in pyrrole, THF-H2O mixture, ethyl acetate
• Apperance: Odorless, white needles or powder; Powder; white powder; White Solid
• Melting Point: 227–228 °C, 500-501 K (anhydrous); 234–235 °C, 507-508 K (monohydrate); 232-236°C; 233-238 °C; 234-236.5 °C(lit.); 234-236°C; 235-237 °C; 235-237 °C (±0.3°C); 235-237°C; 238
• Boiling Point: 178°C (subl.); 178°C subl.
• Flash Point: 11 °C; 51.8 °F
• Density: 1.23 g/cm^3, solid; 1.23 g/ml; 1.230
• Hydrophobicity(logP): -0.04; -0.5
• pKa: -0.13–1.22 protonated caffeine
• Dipole Moment: 3.64 D (calculated)

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• Storage Warning: Toxic/Harmful
• RTECS: EV6475000
• European Hazard Symbols: Flammable (F); Toxic (T); X; Harmful (Xn)
• UN Number: 1230; 1544; UN1544
• German water hazard class: 1
• Hazard Class: 3; 6.1
• Packing Group: 2; 3; III
• Australian Hazchem: 2X
• Risk Statements: 11-23/24/25-39/23/24/25; 22; R:22; R22
• Safety Statements: 16-36/37-45; 2; S2
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 151
• TSCA Listed: 是
• EU Index: 613-086-00-5
• GHS Pictograms: GHS02; GHS06; GHS07; GHS08
• GHS Signal Word: Danger; Warning
• NFPA704:
  

  2

  2

  0
• LD50: 192 mg/kg (rat, oral)
• GHS Hazard statements: H225-H301 + H311 + H331-H315-H319-H370; H302
• GHS Precautionary statements: P210-P260-P280-P301 + P310-P305 + P351 + P338-P311; P264-P270-P301+P312-P330-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1230 3/PG 2; UN 1544 6.1/PG 3
• Storage Temperature: 2-8°C
• Regulation Compliance: FCC; FDA 21 CFR (182.1180)

Pharmacology Properties

• Target: Others
• Admin Routes: Oral, insufflation, enema
• Bioavailability: 99%
• Dependency Liability: Moderate
• Excretion: urine (100%)
• Half Life: 5 hours
• Metabolism: demethylation by CYP1A2
• Protein Bound: 17% to 36%
• Legal Status: GSL (UK); OTC (US); unscheduled (Australia)
• Pregnancy Category: C (US)
• Gene Information: human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140), PDE4B(5142), PRKAR1A(5573), PRKAR1AP(5574), PRKAR1B(5575), PRKAR2A(5576), PRKAR2B(5577)mouse ... Adora2b(11541)rat ... Adora1(29290), Adora2a(25369); human ... ADORA1(134), ADORA2B(136), ADORA3(140), PDE4B(5142)mouse ... Adora2b(11541)rat ... Adora1(29290), Adora2a(25369); human ... ADORA1(134), PDE4B(5142); human ... ADORA2B(136), ADORA3(140)mouse ... Adora2b(11541)rat ... Adora1(29290), Adora2a(25369)
• Allergens: no known allergens
• Mechanism of Action: Antagonist of adenosine receptors; Inhibitor of cyclic nucleotide phosphodiesterases; Modulator of intracellular calcium handling

Product Information

• Purity: ≥98.5%; ≥99.0% (HPLC); 95%; 99%; 99.7%
• Concentration: 1.0 mg/mL±5% in methanol
• Grade: analytical standard; analytical standard, for drug analysis; anhydrous; certified reference material; for the calibration of the thermosystem 900; Halal; Kosher; NI; Ph Eur; puriss.; purum; ReagentPlus®; SAJ special grade; Sigma Reference Standard; TraceCERT®
• Salt Data: Free Base
• Packaging: vial of 250 mg
• Suitability: meets USP testing specifications; suitable for 1694 per US EPA
• Ignition Residue: ≤0.1%
• Impurities: ≤0.0005% Phosphorus (P); ≤0.1% Insoluble matter
• Cation Traces: Al: ≤0.0005%; Ca: ≤0.001%; Cu: ≤0.0005%; Fe: ≤0.0005%; K: ≤0.005%; Mg: ≤0.001%; Na: ≤0.005%; NH4+: ≤0.05%; Pb: ≤0.001%; Zn: ≤0.0005%
• Antion Traces: chloride (Cl-): ≤0.05%; sulfate (SO42-): ≤0.05%
• Biological Source: Component of coffee beans ( Coffea arabica ), many other Coffea spp., chocolate ( Theobroma cacao ), tea ( Camellia thea ), kolanut ( Cola acuminata ) and several other Cola spp. and several other plants (Rubiaceae, Sterculiaceae, Theaceae). Also occurs as a fungal metab. of Claviceps sorghicola
• Shelf Life: (limited shelf life, expiry date on the certificate and label); (limited shelf life, expiry date on the label)
• Application(s): Analeptic; Chemosterilant against stored grain pests.; Diuretic; Flavouring ingredient; In the horse is used to treat colic, heat stroke, circulatory disturbance and fatigue, also for horse doping; Possesses virucidal props; Psychostimulant; Psychotonic; Used in many beverages; Widely used CNS, respiratory and cardiac stimulant, main effect on the cerebral cortex
• Quality: traceable to primary standards (LGC)
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Pharmacopeia Traceability: traceable to BP 766; traceable to PhEur C0100000; traceable to USP 1085003; traceable to USP 1086006
• Empirical Formula (Hill Notation): C8H10N4O2

DETAILS

MP Biomedicals - 02150114

Anhydrous

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

Sigma Aldrich - 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

Sigma Aldrich - W222402

Packaging
1 kg in poly bottle
1 sample in glass bottle
10, 25 kg in fiber drum
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.

Sigma Aldrich - C53

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.

Sigma Aldrich - 41019

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.

Sigma Aldrich - 01653

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.

Sigma Aldrich - 84677

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.

Sigma Aldrich - 27602

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.

Sigma Aldrich - 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

Sigma Aldrich - 75035

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
Mettler-Toledo is a registered trademark of Mettler-Toledo, Inc.

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。

Sigma Aldrich - 40776

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.

Sigma Aldrich - 05-0370

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.

Sigma Aldrich - 27600

Other Notes
Pharmacology and toxicology1
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.

Sigma Aldrich - 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.

Sigma Aldrich - 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

Sigma Aldrich - C7731

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。

Toronto Research Chemicals - 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

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
• Zubair, U.M., et al.: Anal. Profiles Drug Subs., 15, 71 (1986)
• Cherrah, Y., et al.: Biochem. Pharmacol., 37, 1311 (1986)
• Arnaud, M.J., Prog. Drug Res., 1987, 31, 273, (rev, chem, pharmacol, toxicity)
• Somani, S.M. et al., Int. J. Clin. Pharmacol., Ther. Toxicol., 1988, 26, 521, (rev)
• Lewis, R.J., Food Additives Handbook, Van Nostrand Reinhold International, New York, 1989, CAK500
• Benowitz, N.L. et al., Annu. Rev. Med., 1990, 41, 277, (rev, pharmacol)
• IARC Monog., 1991, 51, 291, (rev, tox)
• Bott, K., Chem. Ber., 1993, 126, 1955, (synth)
• Sitkowski, J. et al., Spectrochim. Acta A, 1995, 51, 839, (pmr, cmr, N-15 nmr)
• Encyclopedia of Food and Color Additives, (ed. Burdock, G.A.), CRC Press, 1997, 363
• Caffeine, (ed. Spiller, G.A.), CRC Press, 1998, (book)
• Parliment, T.H. et al., ACS Symp. Ser., 2000, 754
• Bogo, A. et al., Phytochemistry, 2000, 54, 937-939, (isol, ms)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CAK500
• Aldrich Library of NMR Spectra, 2nd edn., 1983, 2, 586A, (nmr)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 710B, (ir)
• Fischer, E. et al., Ber., 1895, 28, 2473; 3135, (synth)
• Bredereck, H. et al., Chem. Ber., 1950, 83, 201; 1962, 95, 1902, (synth)
• Blout, E.R. et al., J.A.C.S., 1950, 72, 479, (ir)
• Sutor, D.J., Acta Cryst., 1958, 11, 453, (cryst struct)
• Spiteller, G. et al., Monatsh. Chem., 1962, 93, 632, (ms)
• Twanmoh, L.-M. et al., J. Het. Chem., 1973, 10, 187, (pmr)
• Nicolau, C. et al., Z. Naturforsch., C, 1974, 29, 475, (cmr)
• Suzuki, T. et al., Phytochemistry, 1976, 15, 1235, (biosynth)
• Zubair, M.U. et al., Anal. Profiles Drug Subst., 1986, 15, 71, (rev, ir, uv, pmr, cmr, ms, occur, anal)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 921