(+)-Corlumidine - CAS 25344-54-1
Category:
Main Product
Product Name:
(+)-Corlumidine
Catalog Number:
25344-54-1
Synonyms:
(6R)-6-[(1S)-7-hydroxy-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one; (+)-Corlumidine; 25344-54-1; SCHEMBL12363726
CAS Number:
25344-54-1
Molecular Weight:
369.37
Molecular Formula:
C2OH19NO6
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
CN1CCC2=CC(=C(C=C2C1C3C4=C(C5=C(C=C4)OCO5)C(=O)O3)O)OC
InChI:
InChI=1S/C20H19NO6/c1-21-6-5-10-7-15(24-2)13(22)8-12(10)17(21)18-11-3-4-14-19(26-9-25-14)16(11)20(23)27-18/h3-4,7-8,17-18,22H,5-6,9H2,1-2H3/t17-,18+/m0/s1
InChIKey:
IORPHWDBRHOADK-ZWKOTPCHSA-N
Chemical Structure
CAS 25344-54-1 (+)-Corlumidine

Reference Reading


1.The alkaloids of Corydalis meifolia.
Bhakuni DS, Chaturvedi R. J Nat Prod. 1983 May-Jun;46(3):320-4.
Six tetrahydroprotoberberines, (+)-sinactine, apocavidine, stylopine, (+)-cavidine, cheilanthifoline, and dehydrocavidine; two spirobenzylisoquinolines, yenhusomine and yenhusomidine; one phthalideisoquinoline, corlumine; one benzophenanthridine, dihydrosanguinarine and protopine, have been isolated from the leaves and stems of Corydalis meifolia Wall. Of these alkaloids, dehydrocavidine was a new base. The remaining alkaloids, although known, were isolated for the first time for this plant. (+)-Cavidine, protopine, corlumine, yenhusomine, and dehydrocavidine exhibited spasmolytic activity.
2.1-Magnesiotetrahydroisoquinolyloxazolines as Chiral Nucleophiles in Stereoselective Additions to Aldehydes: Auxiliary Optimization, Asymmetric Synthesis of (+)-Corlumine, (+)-Bicuculline, (+)-Egenine, and (+)-Corytensine, and Preliminary (13)C NMR Studies of 1-Lithio- and 1-Magnesiotetrahydroisoquinolyloxazolines.
Gawley RE1, Zhang P. J Org Chem. 1996 Nov 15;61(23):8103-8112.
Transmetalation of 1-lithiotetrahydroisoquinolyloxazolines with magnesium halides affords Grignard reagents that add to aldehydes with up to 80% selectivity for one of the four possible diastereomeric products. An oxazoline chiral auxiliary derived from camphor provides an optimal blend of diastereoselectivity and isomer separability. Synthetic applications of the optimal auxiliary, patterned after a literature approach in the racemic series, comprise an improved (formal) synthesis of bicuculline, egenine, and corytensine, as well as an efficient synthesis of corlumine. Preliminary NMR studies show that both 1-lithio- and 1-magnesiotetrahydroisoquinolyloxazolines are dynamic mixtures in THF solution at low temperatures. The barrier to pyramidal inversion of the secondary Grignard reagent is in the 9.8-10.1 kcal/mol range, while an upper limit of about 8.2 kcal/mol can be assigned to the barrier to the organolithium inversion.
3.1H and 13C NMR signal assignment of benzylisoquinoline alkaloids from Fumaria officinalis L. (Papaveraceae).
Seger C1, Sturm S, Strasser EM, Ellmerer E, Stuppner H. Magn Reson Chem. 2004 Oct;42(10):882-6.
The NMR signal assignments of a series of structurally divergent benzylisoquinolines isolated from Fumaria officinalis L. (Fumariaceae, Papaverales), namely adlumine, corlumine, corydamine, cryptopine, fumarophycine, O-methylfumarophycine, hydrastine, parfumine, protopine and sinactine, are presented.
4.Suicide with cisatracurium and thiopental: forensic and analytical aspects.
Castaing N1, Benali L, Ducint D, Molimard M, Gromb S, Titier K. J Anal Toxicol. 2011 Jul;35(6):375-80.
The suicide of a 43-year-old male by intravenous injection of cisatracurium, a non-depolarizing neuromuscular blocking agent, and thiopental, an ultra-short-acting barbiturate, is presented. Systematic toxicological screening by gas chromatography-mass spectrometry (GC-MS), liquid chromatography (LC)-diode-array detection, and LC-MS-MS confirmed the presence of thiopental. A large peak in the GC-MS chromatogram was matched by the Pfleger-Maurer library as corlumine, but neither atracurium neither its metabolite, laudanosine, were detected. To confirm the absence or the presence of laudanosine in the blood sample, an ultra-performance liquid chromatography-MS-MS method for cisatracurium and laudanosine quantification was developed. The calibration range was 2.5-500 ng/mL for laudanosine and 10-500 ng/mL for cisatracurium. The biases were lower than 12.3%. Intraday and interday precisions, expressed as coefficient of variation, were lower than 13.