Caffeine, structure

The caffeine structure is shown below. It is classed as an alkaloid, meaning that with the nitrogen present, the molecule has base characteristics (alkali-like). In addition, the molecule has the purine ring system, a framework which plays an important role in living systems. 

Caffeine, structure, 55, 135 Calculations, see Theoretical calculations Carbaceph-2-em, 4/3-methyl-, synthesis via l-azetin-4-one, 58, 176 Carbanions... 

Complete the electron-dot structure of caffeine, showing all lone-pair electrons, and identify the hybridization of the indicated atoms. 

The Lewis structure of caffeine, C8H 0N4O2, a common stimulant, is shown below, (a) Give the hybridization of each atom other than hydrogen and predict the bond angles about that atom, (b) On the basis of your answers in part (a), estimate the bond angles around each carbon and nitrogen atom. 

Structural formula and line drawing of caffeine, and line drawing of cholesterol. 

Fig. 2.5.9 COSY spectra acquired at 600 MHz with an eight-coil probe along with the chemical structures of the compounds used. Each sample was a 10 mM solution in D20 loaded into the coil via the attached Teflon tubes, with the samples being (A) sucrose, (B) galactose, (C) arginine, (D) chloroquine, (E) cysteine, (F) caffeine, (G) fructose and (H)...

Foods derived from cocoa beans have been consumed by humans since at least 460 to 480 AD. The source of cocoa beans, the species Theobroma, contains a variety of biologically active components. These include the purine alkaloids theobromine, caffeine, and theophylline. Structurally, they are methylated xanthines and, thus, are often referred to as methylxanthines. Theobromine (3, 7-dimethylxanthine) is the predominant purine alkaloid in cocoa and chocolate. Caffeine (1, 3, 7-trimethylxanthine), the major purine alkaloid found in coffee and tea, is found in cocoa and chocolate at about one eighth the concentration of theobromine. Only trace amounts of theophylline (1, 3-dimethylxanthine) are detected in cocoa and chocolate products. 

This example will illustrate the quantitative analysis of aspirin (acetylsalicylic acid), phenacetin and caffeine in a mixture. The structures of these three are shown in Fig. 4.4a. 

Darenthin, molecular formula and structure, 5 96t Dark chocolate, 6 361 minerals content, 6 371t theobromine and caffeine content, 6 367t tocopherols, 6 370t typical formulation, 6 362t Dark conductivity ( D), of a-Si H, 22 ... 

FIGURE 4.7 Structures of the CYP1A2 substrates caffeine, phenacetin, their metabolites, and the CYP1A2 mechanism-based inhibitor, furafylline. 

Hepatic Effects. Hepatic changes were observed in one chronic human exposure to mirex, as well as in a number of workers exposed to chlordecone for intermediate or chronic durations. In the mirex study, human subjects (sex and number not specified) from a chronically exposed cohort from southeast Ohio (route of exposure not specified, assumed to be oral) were assessed for cytochrome P- 4501A2 induction using a breath test that measures caffeine metabolism. The subjects exposed to mirex had elevated caffeine metabolism as compared to negative control individuals (subjects with no known exposure to polyhalogenated biphenyls or other related chemicals) in which the metabolism did not increase (Lambert et al. 1992). In the chlordecone study, liver function and structure in 32 men exposed to high levels of chlordecone while employed for 1-22 months (5.6... 

In a further application of MI-SPE, theophylline could be separated from the structurally related caffeine by combining the specific extraction with pulsed elution, resulting in sharp baseline-separated peaks, which on the other hand was not possible when a theophylline imprinted polymer was used as stationary phase for HPLC. A detection limit of 120 ng mb1 was obtained, corresponding to a mass detection limit of only 2.4 ng [45]. This combination of techniques was also used for the determination of nicotine in tobacco. Nicotine is the main alkaloid in tobacco and is the focus of intensive HPLC or GC analyses due to its health risk to active and passive consumers. However, HPLC- and GC-techniques are time-consuming as well as expensive, due to the necessary pre-purification steps required because the sample matrices typically contain many other organic compounds besides nicotine. However, a simple pre-concentration step based on MI-SPE did allow faster determination of nicotine in tobacco samples. Mullett et al. obtained a detection limit of 1.8 jig ml 1 and a mass detection limit of 8.45 ng [95]. All these examples demonstrate the high potential of MI-SPE to become a broadly applicable sample pre-purification tool. 

Theophylline (Fig. 20) is structurally very similar to caffeine and present at a low concentration in tea. It is also known as dimethyl xanthine. It is used for the treatments of asthma and COPD, for more than 50 years despite its many side effects. The mechanism of beneficial effect of theophylline is through HD AC activation. 

After the nucleic acid purines adenine and guanine, the next most prominent purine in our everyday lives is probably caffeine. Caffeine, in the form of beverages such as tea, coffee, and cola, is one of the most widely consumed and socially accepted natural stimulants. Closely related structurally are theobromine and theophylline. Theobromine is a major constituent of cocoa, and related chocolate products. Caffeine is also used medicinally,... 

Lee, H., Yeom, H., Kim, Y. G., et al. (1998) Structure-related inhibition of human hepatic caffeine N3-demethylation by naturally occurring flavonoids. Biochem. Pharmacol. 55, 1369-1375. 

The chemical name of caffeine is 1,3,7-trimethylxanthine, and it is part of the purine family of derivatives of methylxanthines (Figure 4-2). Caffeine s basic chemical structure is similar to the purine structure found in DNA (see below). This similarity in structure generated speculation that caffeine may somehow cause... 

Ciprofloxacin (Cipro, Cipro XR, Proquin XR) [Antibiotic/ Fluoroquinolone] Uses Rx lower resp tract, sinuses, skin skin structure, bone/joints, urinary tract Infxns including prostatitis Action Quinolone antibiotic DNA gyrase Dose Adults. 250-750 mg PO ql2h XR 500-1000 mg PO q24h or 200-400 mg IV ql2h in renal impair Caution [C, /-] Children <18 y Contra Component sensitivity Disp Tabs, susp, inj SE Restlessness, N/V/D, rash, ruptured tendons, T LFTs Interactions T Effects Wf probenecid T effects OF diazepam, theophylline, caffeine, metoprolol, propranolol, phenytoin, warfarin effects W/ antacids, didanosine, Fe salts. Mg, sucralfate, Na bicarbonate,... 

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