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Details

Stereochemistry ACHIRAL
Molecular Formula C23H27NO8.3H2O
Molecular Weight 499.5082
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NARCEINE TRIHYDRATE

SMILES

O.O.O.COC1=C(OC)C(C(O)=O)=C(C=C1)C(=O)CC2=C(OC)C3=C(OCO3)C=C2CCN(C)C

InChI

InChIKey=MYBNKRVFDPXQSN-UHFFFAOYSA-N
InChI=1S/C23H27NO8.3H2O/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);3*1H2

HIDE SMILES / InChI

Molecular Formula C23H27NO8
Molecular Weight 445.4624
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
Patents

Patents

Sample Use Guides

Single dose is 3 to 6 centigrams (½ to 1 grain).
Route of Administration: Oral
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
Created
by admin
on Fri Dec 15 16:38:23 GMT 2023
Edited
by admin
on Fri Dec 15 16:38:23 GMT 2023
Record UNII
Y0YU07Y1WS
Record Status Validated (UNII)
Record Version
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Name Type Language
NARCEINE TRIHYDRATE
WHO-DD  
Common Name English
Narceine trihydrate [WHO-DD]
Common Name English
NARCEINUM
HPUS  
Common Name English
NARCEINUM [HPUS]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 16:38:23 GMT 2023 , Edited by admin on Fri Dec 15 16:38:23 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C91051
Created by admin on Fri Dec 15 16:38:23 GMT 2023 , Edited by admin on Fri Dec 15 16:38:23 GMT 2023
PRIMARY
FDA UNII
Y0YU07Y1WS
Created by admin on Fri Dec 15 16:38:23 GMT 2023 , Edited by admin on Fri Dec 15 16:38:23 GMT 2023
PRIMARY
PUBCHEM
53398768
Created by admin on Fri Dec 15 16:38:23 GMT 2023 , Edited by admin on Fri Dec 15 16:38:23 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE