9-METHOXYELLIPTICINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H16N2O
Molecular Weight	276.3324
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC2=C(NC3=C2C(C)=C4C=NC=CC4=C3C)C=C1

InChI

InChIKey=BKRMCDAOAQWNTG-UHFFFAOYSA-N

InChI=1S/C18H16N2O/c1-10-15-9-19-7-6-13(15)11(2)18-17(10)14-8-12(21-3)4-5-16(14)20-18/h4-9,20H,1-3H3

HIDE SMILES / InChI

Molecular Formula	C18H16N2O
Molecular Weight	276.3324
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/5245921 | https://www.ncbi.nlm.nih.gov/pubmed/15497947

9-methoxyellipticine is an indole alkaloid from the roots of Ochrosia acuminata. Antitumor properties of 9-methoxyellipticine were demonstrated. 9-Methoxyellipticine possesses a relatively broad spectrum of antitumor activity, 10 of 17 mouse neoplasms tested having responded. Both intraperitoneal and oral activity have been noted. Significant activity was seen against both the ascites and solid forms of the Walker rat carcinosarcoma 256. 9-methoxyellipticine binds DNA through a single step mechanism, can be considered as a pure intercalator.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Stem cell growth factor receptor 57 Target ID: CHEMBL1936 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16190746	Inhibitor 8504		0.3 µM [IC50]
DNA 282 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1868167	Interacts 323

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/5245921 https://www.ncbi.nlm.nih.gov/pubmed/15497947 https://www.ncbi.nlm.nih.gov/pubmed/1151997 https://www.ncbi.nlm.nih.gov/pubmed/15078993	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
tert-Butyl 6-bromo-1,4-dimethyl-9H-carbazole-9-carboxyl-ate.	2010-07-10	21588291
Alkaloids from the Australian rainforest tree Ochrosia moorei.	2008-06	18412397
Preparation of polyfunctional aryl azides from aryl triazenes. A new synthesis of ellipticine, 9-methoxyellipticine, isoellipticine, and 7-carbethoxyisoellipticine.	2007-09-14	17705535
New indole alkaloids from the roots of Ochrosia acuminata.	2004-10	15497947
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991-01-01	1710653

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 9-methoxyellipticine was demonstrated to be active in certain cases by both the intraperitoneal and oral routes. The corresponding dose ranges were from 12-24 mg/kg and 24-36 mg/kg, respectively.

Route of Administration: Other

In Vitro Use Guide

MDA-MB-231 cells were treated with 5 uM 9-methoxyellipticine, which showed intermediate activity in the induction of apoptosis.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:19:53 GMT 2025` Edited by `admin` on `Mon Mar 31 19:19:53 GMT 2025`
Record UNII	U0924292N9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-69187

Preferred Name

English

9-METHOXYELLIPTICINE

Common Name

English

9-METHOXYELLIPTICIN

Systematic Name

English

METHOXYELLIPTICINE, 9-

Common Name

English

6H-PYRIDO(4,3-B)CARBAZOLE, 9-METHOXY-5,11-DIMETHYL-

Systematic Name

English

9-METHOXY-5,11-DIMETHYL-6H-PYRIDO(4,3-B)CARBAZOLE

Systematic Name

English

Code System Code Type Description

PUBCHEM

72512