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Details

Stereochemistry ACHIRAL
Molecular Formula C23H27NO8
Molecular Weight 445.4624
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NARCEINE

SMILES

COC1=CC=C(C(=O)CC2=C(CCN(C)C)C=C3OCOC3=C2OC)C(C(O)=O)=C1OC

InChI

InChIKey=DEXMFYZAHXMZNM-UHFFFAOYSA-N
InChI=1S/C23H27NO8/c1-24(2)9-8-13-10-18-22(32-12-31-18)20(29-4)15(13)11-16(25)14-6-7-17(28-3)21(30-5)19(14)23(26)27/h6-7,10H,8-9,11-12H2,1-5H3,(H,26,27)

HIDE SMILES / InChI

Molecular Formula C23H27NO8
Molecular Weight 445.4624
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Narceine methyl ester and narceine are potent alkaloids which were isolated from Corydalis longipes were found effective in vitro at very low concentration, i.e., 100~500 ppm against spore germination of some test plant pathogenic fungi (Alternaria solani, A. tagetica, Cercospora abelmoschi, Curvularia maculans, Erysiphe cichoracearum, E. pisi, Fusarium udum, Helminthosporium oryzae, H. penniseti, Ustilago cynodontis). George Bell Frankforter was the first person to isolate narceine (in 1893) during his Ph.D. research for August Hofmann at the University of Berlin. Narceine has a weak morphine-like action, but is not much used in medicine. It may be administered in a pill, as a mild hypnotic and to allay cough; it is less depressant than morphine and does not constipate. Ethylnarceine is a narcotic, analgesic, and antitussive.

CNS Activity

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Single dose is 3 to 6 centigrams (½ to 1 grain).
Route of Administration: Oral
In Vitro Use Guide
Narceine did not show any toxic effect on HT29,T47D, HT1080 and NIH-3 T3 cell lines in the dose range 0.1-1000 uM.
Substance Class Chemical
Record UNII
CTT09X2F1M
Record Status Validated (UNII)
Record Version