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Identification Of Photoproducts Of Hexahydroquinoline Derivatives By GC-EI-MS And HPLC-ESI-MS

J. Mielcarek, A. Matłoka, Paweł Grobelny
Published 2005 · Chemistry, Medicine

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Photoproducts of hexahydroquinoline derivatives have been analyzed with gas chromatography electro ionization-mass spectrometry (GC-EI-MS) and high performance chromatography electrospray ionization-mass spectrometry (HPLC-ESI-MS). The study was performed on four HHQ derivatives: 2,6,6-trimethyl-3-carbomethoxy-5-oxo-4-(R-phenyl)-1,4,5,6,7,8-hexahydroquinoline; R=2′-Me, 3′-Me, 2′-MeO, and 3′-MeO. The photochemical degradation of each of the HHQ derivatives led to the appearance of one product. The photoproducts were identified as the corresponding tetrahydroquinoline analogues, which were formed by dehydrogenation of dihydropyridine moiety. In GC-mass spectra, the most frequent way of fragmentation was elimination of CH3* or CH3O* radical of the ester group. In the photoproducts substituted at 2′-position of the phenyl ring, elimination of isobutene (C4H8) was observed. In the photoproducts with 3′-position substituents, elimination of COOCH3* radical was noted.
This paper references
10.1007/s005350050008
Effect of nifedipine administration (10 mg) on esophageal acid exposure time
H. Ishikawa (2000)
10.1055/S-0031-1300509
Studies on calcium modulatory activities of 2,6,6-trimethyl-3-acetyl-4-aryl-5-oxo-1,4,5,6,7,8-hexahydroquinoline derivatives.
Y. Altaş (1999)
10.1097/00000446-196503000-00036
DRUGS IN PREGNANCY.
V. Apgar (1964)
10.1002/CHIN.199745313
Medicinal Photochemistry: Phototoxic and Phototherapeutic Aspect of Drugs
G. M. J. B. Henegouwen (1997)
10.1016/S0014-827X(00)00004-5
UV derivative spectrophotometric study of the photochemical degradation of nisoldipine.
V. Marinkovic (2000)
Hypertensive diseas and pregnacy
J. U. Hibbard (2002)
10.1056/NEJM199804163381607
Drugs in pregnancy.
G. Koren (1998)
Drugs, photochemistry and photostability
A. Albini (1998)
10.1016/S0731-7085(01)00556-8
Photodegradation monitoring of amlodipine by derivative spectrophotometry.
G. Ragno (2002)
10.1016/S0065-2490(97)80014-7
Medicinal Photochemistry: Phototoxic and Phototherapeutic Aspects of Drugs
G. M. J. B. Henegouwen (1997)
10.1016/S0014-827X(00)00086-0
Synthesis and calcium antagonistic activity of 2,6,6-trimethyl-3-carbomethoxy(ethoxy)-4-aryl-1,4,5,6,7,8-hexahydroquinoline derivatives.
R. Şimşek (2000)
10.1002/CHIN.200005153
Studies on Calcium Modulatory Activities of 2,6,6‐Trimethyl‐3‐acetyl‐4‐aryl‐5‐oxo‐1,4,5,6,7,8‐hexahydroquinoline Derivatives.
Y. Altaş (2000)
10.1016/S0731-7085(00)00375-7
Identification of photodegradation products of nilvadipine using GC-MS.
J. Mielcarek (2000)
10.1016/S0378-4347(98)00126-1
Determination of nifedipine in human plasma by flow-injection tandem mass spectrometry.
J. Dankers (1998)
10.1002/JPS.2600830412
Photodecomposition of a new 1,4-dihydropyridine: furnidipine.
L. Núñez-Vergara (1994)
10.1002/CHIN.199612166
3-Acetyl-4-aryl-5-oxo-2,7,7-trimethyl-1,4,5,6,7,8-hexahydro-quinoline derivatives and their calcium antagonistic activities.
C. Şafak (1995)
10.1053/BEOG.2001.0232
Drugs in pregnancy. Antihypertensives.
L. Magee (2001)
10.1067/MOB.2002.126294
Efficacy and safety of nifedipine tablets for the acute treatment of severe hypertension in pregnancy.
M. Brown (2002)
Studies on calcium modulatory activities of 2,6,6-trimethyl-3-acethyl-4-aryl-5-oxo-1,4,5,6,7,8-hexahydroquinoline derivatives. Arzneimittel-Forschung
Y Altas (1999)
FIGURE 7 Scheme of Photodegradation 2,6,6-Trimethyl-3-Carbomethoxy-4-(R-Phenyl)-5-Oxo-5
10.1016/S0731-7085(00)00489-1
Oxidative degradation study of nitrendipine using stability indicating, HPLC, HPTLC and spectrophotometric method.
D. N. Tipre (2001)
10.1002/JPS.2600810917
Polarographic study of the photodecomposition of nimodipine.
A. Zanocco (1992)
Meta-3'-Me or 3'-MeO
10.1002/CHIN.199101214
Synthesis of some 1,4-dihydropyridine derivatives and their calcium antagonistic activity.
C. Şafak (1990)
10.1097/01.ogx.0000079642.69018.34
A comparison of magnesium sulfate and nimodipine for the prevention of eclampsia.
M. Belfort (2003)
10.1002/CHIN.199507151
Synthesis of some 1,4,5,6,7,8-hexahydroquinoline derivatives and their calcium antagonistic activity.
C. Şafak (1993)
10.1007/BF01666964
The structure of ethyl allyl 1,4-dihydro-2,6-dimethyl-4-[4-(4H-4-oxo-1-benzopyran-2-yl)phenyl]-3,5-pyridine dicarboxylate
E. Kendi (1994)
Synthesis and calcium antagonistic activity
R. Simsek (2000)
10.1039/9781847550712-00227
Photostability of drug substances and drug products: A validated reference method for implementing the ICH photstability study guidelines
A. Albini (1998)
10.1016/S0016-5107(02)70178-8
Nifedipine for prevention of post-ERCP pancreatitis: a prospective, double-blind randomized study.
F. Prat (2002)
10.1055/S-0031-1300145
Studies on calcium antagonist activities of 2-ethyl-3-carbmethoxy-4-aryl- 5-oxo-6,6-dimethyl-1,4,5,6,7,8-hexahydroquinoline derivatives.
R. Şimşek (2001)
10.1007/BF01212612
Amputation and dexniguldipine as treatment for canine appendicular osteosarcoma
K. Hahn (2005)
10.1046/j.0004-8666.2003.00074.x
Calcium channel blockers for inhibiting preterm labour; a systematic review of the evidence and a protocol for administration of nifedipine
J. King (2003)
10.1016/S0165-1838(00)00128-4
In search of selective P2 receptor ligands: interaction of dihydropyridine derivatives at recombinant rat P2X(2) receptors.
K. Jacobson (2000)
10.1016/S0301-2115(00)00548-0
Calcium channel blockers in the management of preterm labor and hypertension in pregnancy.
D. Papatsonis (2001)
10.3109/00498259109039452
Pharmacokinetics of the enantiomers of felodipine in the dog after oral and intravenous administration of a pseudoracemic mixture.
U. Eriksson (1991)
Calcium channel blockers and progression of renal disease: clinical studies put into perspective
G. L. Bakris (1996)



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