V-ASAnal_Skript_WS2324 (1) (verschoben) 2 PDF

– – –  + NH2 R NH2 R Cl + S S + Cl -...

– – –  + NH2 R NH2 R Cl + S S + Cl - NH2 NH2 OH O2 N NO2 - O + O 2N NO 2 R NH2 NO2 S - HCl NH2 NO 2  N Cl N N OH N OH + + 2 OH- R Cl R Cl R Cl R Cl - Cl - 2 Cl + N HO N HO N N + 2 OH- Cl - N O - O - 2 H2O N R - Cl- - O N N O R O 2N O 2N O O + R OH Cl - HCl O R O 2N O 2N O R N C O H N C + R OH O + NaOH R O + - + S C S R OH C S Na - H2O S NO 2 NO 2 O 2N F + R OH O 2N O - HF R – – –  1 1 R 1 R R - 2 + IO4- 2 O O 2 O R OH R R O O + - 3 I 3 I O R OH 3 OH R O R O OH - H2O O 4 4 R R 4 R ¹ OH 2 OH HO R O 2 O - O + H2O 2 + IO4- R O 2 R OH O R O + - 3 3 I 3 I O R OH R OH 3 OH R O R O OH - H2O O 4 4 4 R R R 4 R OH NO 2 OH NO 2 O + H H2O (H ) H NaIO4 Cl N - Cl2CHCOOH H2N H Cl OH OH ² H3C CH3 H OH HN O Cu2+ (OH-) Cu 2+ 2 O NH H3C NH H H3C CH3 CH3  ≈ ³ – – – – – ³ OH OH H COOH HO HO NH2 HO N CH3 H H2N HO HO HO Noradrenalin Adrenalin Levodopa OH HO NH2 H COOH HO HO N CH3 CH3 H2N HO CH3 HO HO Dopamin Isoprenalin Methyldopa O OH H3C O O OH O OH O O CH3 CH3 OH OH O Acetylsalicylsäure Salicylsäure Methylsalicylat O H NICHT! Vanillin  H3C NH2 H3C N O K3[Fe(CN)6] H3C N O + OH N N O H3C N C6H5 C6H5 Cl Cl OH Cl – + H2O HOCl O O O N O NH Cl - HOCl -2H Cl N Cl Cl  CHCl3 CH3 OH- - HCl Cl CH3 CH3 |CCl2 Cl Cl O - O - - Cl- O H3C CH3 H3C CH3 H3C CH3 CH3 CH3 H CH3 CH3 H CH3 - O H H3 C CH3 Cl - - O O - HCl O O H3C CH3 H3C CH3 H3C CH3 H3C CH3  - - N SO 3 + + - O N N SO 3 - O N x2 N OH + OH O + NO + Hg2+ O Hg + O O -H N O N HO O Ox. HO O – HO R HO R HO R O R HNO2 Ox. OH- - H2O - H2O O HO HO NO HO NO 2 HO N+ – O HO COOH HO COOH HO CH3 NH2 NH2 H2N HO HO HO Levodopa Dopamin Methyldopa  OH OH OH H H HO NH2 HO N HO N CH3 CH3 CH3 HO HO HO Noradrenalin Adrenalin Isoprenalin OH OH OH HO HO Ox. O HN HN HO N HO CH3 O H CH3 CH3 Adrenalin OH OH OH O O O Ox. Ox. O N O N O N CH3 CH3 I CH3 Adrenochrom Oxoadrenochrom 7-Iodadrenochrom ³  – – – – – ² 2- 3- + R S + NC N O -H NC N O NC Fe CN + HS R NC Fe CN NC CN + H+ NC CN  O S - HO O OH H2N NH2 O S O H2N NH2 H3C H3C NH2 + NH2 HO 3S R HO 3S R OH R HO 3S + O S O N N HO 3S R 2 RCHO, 2 HSO3-, 3H + H H N N - HSO3- H H - 2 H2O H3C H3C + HSO3- + NH3 + NH3 ® H R R NH2 NH2 RCHO HN NH O2 N N N HS NH N NH N N HS HS N N N N N N  - H H - O OC COO O O 2+ Cu - O O - O OC COO H H  HO 3S O SO 3H H H H H OH HO HO 3S OH HO SO 3H - 2 H2O (H2SO4) HO 3S H H SO 3H HO 3S H SO 3H [O] O O+ HO 3S OH HO SO 3H HO 3S OH HO SO 3H O O CH3 O O CH3 H3C CH3 H3C H3C + H2C O + CH3 H3C O O O O  C 6 H5 H 2N NH C 6H 5 H 2C O + C 6H 5 - H2 O N NH N N H 2C + - H+ H N N H2 N NH K3[Fe(CN) 6] N N+ C 6H 5 C6 H 5 C 6H 5 – ° C6H5 C6H5 NH N + H2C O NH - H2O N C6H5 C6H5 CH3 O CH3 CH3 CH3 CH3 CH3 CH2 H2C O O O O O O - 2 H2O - H2O H3C OH NH3 HO CH3 H3C NH2 O CH3 H3C N CH3 H  CH3 O O O H2N CH3 S S NH COOH O N CH3 H2N H Cl N H H3C N CH3 OH H2N Serin Hydrochlorothiazid Hexetidin CH3 N H3C H N O N + N N Na N N - N NH O3 S Methenamin (Urotropin) O H5C2 CH3 O Metamizol-Natrium Primidon  ° H O I O I O + 3 I2 OH- + - H I I H O R - 3 HI R R H I I R CH3 R R R R OH OH OH O O Cl CH3 Cl H3C (OH-) Cl CH3 Cl H + CH3 Cl OH Cl O – 1 R R O R R H3C O R CN NO 2 R H3C N 2 R O O O O O O  4- 3- (NC) 5Fe CH3 + H+ (NC) 5Fe CH3 N N – O O - H+ OH O rot violett  – – O O – – O N+ O N+ O 2N O O 1 – R CH 2 N+ Ox. N+ C R + NO 2 – O – O O H 2 1 C R R CH 2 C R 1 R C O O O O R H 3C HO O O N CH3 H3C H 3C O H H H CH3 O OH H N H N CH3 CH3 O O Hydromorphon Oxycodon Methadon F N O X OH X = Cl: Haloperidol X = Br: Bromperidol O O CH3 CH3 CH3 H H3C HO H3C O O O O OH H HO O HO O H OH Digitoxin  NO 2 H (OH-) H O H3C CH3 N O O N H O  – – N N + N N O OH - O (OH ) O O OH R R R H OH N N H N N OH O H5C6 C6H5 CH3 N N O OH + N N+ N N 2 Cl- CH3 H N N H5C6 H3CO OCH 3 C6H5 H H O Tetrazolblau Prednison  O O H3C H3C H H O H O H , HCl , 2 H2O H N H N CH3 CH3 HO HO Codein Codeinhydrochlorid-Dihydrat O O H3C H3C H H O H , H3PO4 , ½ H2O O H , H3PO4 , 1½ H2O H N H N CH3 CH3 HO HO Codeinphosphat-Hemihydrat Codeinphosphat-Sesquihydrat  H + + + + R NH2 N O R N N R N N O - H2O H H C H2 H2 N - H+ R CH2 C NH2 NaNO2 / HCl C N+ H2 R C R C C + - N2 R CH2 H2 H2 H2 + H2O C OH + R C -H H2 NH2 Amantadin  R NaNO2 / HCl R + N NH2 N N N NH2 N-(1-Naphthyl)ethylendiamin- 2-Naphthol NH dihydrochlorid ( -Naphthol) OH · 2 HCl (Bratton-Marshall-Reagenz)  O O O O O O H2N H2N Cl S S S S COOH N NH O O O N CH3 Cl N Cl N H H H Diazoxid Hydrochlorothiazid Furosemid NP: Essigsäure C6H5 H O H O N N CH3 N N N C6H5 O 2N N H9C4 N + H Cl O - O Phenylbutazon Benzidin-Umlagerung! Nitrazepam Chlordiazepoxid NP: Methylamin, Glycin-N-oxid Arzneistoff Verunreinigung CH3 H CH3 N N CH3 NH2 O CH3 CH3 CH3 Lidocain NO 2 OH O NO 2 N H H2N Cl Cl Niclosamid Cl N CH3 CH3 CH3 NH2 N H2N O COOH Methaqualon  – H CH3 2 2 N H CH3 R Zn / HOAc R 2 O CH3 R N N N N NH2 1 1 - H2O N N CH3 R O R 1 R 1 1 R HNO2 O R N N N 2 2 R R  1 R 2 N R N C O H 1 N C R + N R 2 O H H R N + + - S C S 2 R NH2 C S R NH3 S – – – – – – ≡ H2O (H+), + R-NH2, H5C2O OC 2H5 O O N O - 2 C2H5OH - H2O R H CH3 N (H+) O CH3 + H+ N CH3 N CH3 R R N+ N - H2O HO CH3 CH3  H R O O O N R + NH2 O R H H - H2O N SO 3Na SO 3Na - NaHSO3 HN SO 3Na H R O OH HO N NH2 H2O - RCHO SO 3Na SO 3Na O O O H O O O + R NH2 - NaHSO3 SO 3Na N N R H R O O O O 1 + R NH 2 R - NaHSO3 SO 3Na 1 N 2 R R – – O H C6H11 H O O + H2N-OH N C6H11 R N C6H11 R R + N C N O C N OH + O C OH H11C6 N C6H11 N C6H11 H H O O H R N C6H11 R O C N C6H11 N C6H11 O C N C6H11 H  ³ ² O O (Ni2+) R R + H2N OH N OH OH - H2O H – ≡ –  Cl COOH O N CH3 O O CH3 N S N H3C H H CH3 O Benzylpenicillin HOOC Indometacin OH H + H + C - H2O O O – O H + C O R NH + R NH2 - H+ O O – – – – – ³ 1 R H x3 N Fe3+ O O O O H2N-OH (HCl) O 2 OH 3+ R 1 O Fe NH R 1 O - R2OH R N H 1 R O O N 1 H R –  O O OH O CH3 O O H2N CH3 Benzocain Acetylsalicylsäure ³ –  I HO COOH COOH I O HO H CH3 NH2 NH2 H2N HO HO I HO COOH I Levodopa Methyldopa Levothyroxin  R O O O O COOH OH - H2O H2N N R O N OH + H2O - H2O - CO2 R O O O O O OH H O O O O O H2O NH2 - RCHO - H2O - H+ N N O O OH – OH O O N+ O Mit Prolin: – O O O ² R O H2N Cu NH2 O R O  – – R H2N COOH O 2N F + COOH - HF O 2N NH R NO 2 NO 2 HO H R O H2N H N N O 2N O 2N + COOH - HCl O 2N O O R Cl R O HO O R O - R N N + O 2N H N - H2O O - H+ O O O - O COOH COOH HO HO H CH3 H2N H2N HO HO Levodopa Methyldopa  – H2N HN H2O O O Ox. COOH COOH COOH H R R - NH3 R - CO2 R ²  – – – – – ³ R O O x3 N OH OH Fe3+ O HN O + Cl - HCl N O Fe 3+ O N R R R O O N R OH NO 2 O H Cl N H Cl OH Chloramphenicol  O CH3 N N O O N H2N S N H2N S N H H O O Sulfamethoxazol Sulfadiazin O O O O H2N H2N S S S COOH NH O O O Cl N Cl N H H Furosemid Hydrochlorothiazid O H H N N S O O O Cl N H Glibenclamid O CH3  ² ² ² O O OH S O (H+) R NH + R S NH2 - H2O O O O  O H2N S NH2 O Sulfanilamid Br O O H 2 Br2 H H2N S N H2N S N O R - 2 HBr O R Br – N N O N N H2N S N H H2N O  + H2N + H+ H2N H2N H2N + NH NH2 NH2 NH2 + H2N -H H2N H2N+ H2N  – – H2N N H2N OCl- Cl NH OH- Cl N C NH2 NH2 NH2 - OH- N R N R N - H2O R N - Cl- R OH O O H2N H2O NH OCl- OH- R N O N - H2O N H NH N R R – N O N O H H Br NH NH - NH N OBr R R R R N N N - OH - N N N - HBr H H H H H H N N N N R R OBr- R R N N N N N N H H H H  CH3 OH HN NH2 OH HN NH NH H2N N O CH3 O OH N H2N N N HO O OH N NH2 H H CH3 O CHO Guanethidin Metformin N OH CH3 OH H2N NH2 Streptomycin Cl NH2 NH2 H H N N N CH3 N N N N N N H NH2 NH2 CH3 NH2 NH2 Cl Cl Chlorhexidin Proguanil