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

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
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 16:17:16 GMT 2023
Edited
by admin
on Fri Dec 15 16:17:16 GMT 2023
Record UNII
CTT09X2F1M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NARCEINE
MART.   MI   WHO-DD  
Common Name English
NARCEINE [MART.]
Common Name English
6-((6-(2-(DIMETHYLAMINO)ETHYL)-4-METHOXY-1,3-BENZODIOXOL-5-YL)ACETYL)-2,3-DIMETHOXYBENZOIC ACID
Systematic Name English
NARCEINE [MI]
Common Name English
6-((6-(2-(DIMETHYLAMINO)ETHYL)-2-METHOXY-3,4-(METHYLENEDIOXY)PHENYL)ACETYL)-O-VERATRIC ACID
Common Name English
Narceine [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 16:17:16 GMT 2023 , Edited by admin on Fri Dec 15 16:17:16 GMT 2023
Code System Code Type Description
CAS
131-28-2
Created by admin on Fri Dec 15 16:17:16 GMT 2023 , Edited by admin on Fri Dec 15 16:17:16 GMT 2023
PRIMARY
EVMPD
SUB22705
Created by admin on Fri Dec 15 16:17:16 GMT 2023 , Edited by admin on Fri Dec 15 16:17:16 GMT 2023
PRIMARY
SMS_ID
100000088535
Created by admin on Fri Dec 15 16:17:16 GMT 2023 , Edited by admin on Fri Dec 15 16:17:16 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-021-0
Created by admin on Fri Dec 15 16:17:16 GMT 2023 , Edited by admin on Fri Dec 15 16:17:16 GMT 2023
PRIMARY
FDA UNII
CTT09X2F1M
Created by admin on Fri Dec 15 16:17:16 GMT 2023 , Edited by admin on Fri Dec 15 16:17:16 GMT 2023
PRIMARY
MERCK INDEX
m7774
Created by admin on Fri Dec 15 16:17:16 GMT 2023 , Edited by admin on Fri Dec 15 16:17:16 GMT 2023
PRIMARY Merck Index
PUBCHEM
8564
Created by admin on Fri Dec 15 16:17:16 GMT 2023 , Edited by admin on Fri Dec 15 16:17:16 GMT 2023
PRIMARY
EPA CompTox
DTXSID40156833
Created by admin on Fri Dec 15 16:17:16 GMT 2023 , Edited by admin on Fri Dec 15 16:17:16 GMT 2023
PRIMARY
WIKIPEDIA
NARCEINE
Created by admin on Fri Dec 15 16:17:16 GMT 2023 , Edited by admin on Fri Dec 15 16:17:16 GMT 2023
PRIMARY
NCI_THESAURUS
C91050
Created by admin on Fri Dec 15 16:17:16 GMT 2023 , Edited by admin on Fri Dec 15 16:17:16 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY