NICOTREDOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H15N3O
Molecular Weight	265.3098
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C(NCCC1=CNC2=C1C=CC=C2)C3=CC=CN=C3

InChI

InChIKey=ZDAZUJBASMCUAK-UHFFFAOYSA-N

InChI=1S/C16H15N3O/c20-16(13-4-3-8-17-10-13)18-9-7-12-11-19-15-6-2-1-5-14(12)15/h1-6,8,10-11,19H,7,9H2,(H,18,20)

HIDE SMILES / InChI

Molecular Formula	C16H15N3O
Molecular Weight	265.3098
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/2973002 | https://www.ncbi.nlm.nih.gov/pubmed/2972998

Nicotredole (Tryptamide), similarly to ibuprofen and piroxicam, shows anti-inflammatory and analgesic properties. Tryptamide reversed pyrogen-induced hyperthermia in rats, elicited analgesic effects in rats, but not in mice, prolonged the time of hexobarbital sleep in rats and inhibited locomotor activity in rats and mice. Tryptamide has not elicited side effects on the circulatory system of rats and cats.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase 89 Target ID: CHEMBL2095157 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2972998	Modulator 828

Conditions

Condition	Modality	Targets	Highest Phase	Product
Inflammation 102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2973002 https://www.ncbi.nlm.nih.gov/pubmed/2972998	Primary		Preclinical	Unknown Approved Use Unknown
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2973002 https://www.ncbi.nlm.nih.gov/pubmed/2972998	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Influence of N-3-pyridoyltryptamine (tryptamide) on fetal development in rats and mice.	1987 Nov-Dec	2973004
Pharmacokinetics of tryptamide following oral and intraperitoneal administration in rats.	1990	12959253
Pharmacokinetics of tryptamide following intravenous administration in rats.	1991 Jan-Feb	1837608
Development of a gas-liquid chromatographic method for the analysis of fatty acid tryptamides in cocoa products.	2006 May 3	16637672
Characterization of the binding properties of SIRT2 inhibitors with a N-(3-phenylpropenoyl)-glycine tryptamide backbone.	2008 Sep 1	18701307

Patents

Sample Use Guides

In Vivo Use Guide

Rats: Plasma and tissue levels of N-3-pyridoyl-tryptamine (Nicotredole) vs. time were determined in rats following iv administration of various doses: 6.25, 12.5, 25.0 and 37.5 mg/kg.

Route of Administration: Intravenous

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:16:07 GMT 2023` Edited by `admin` on `Fri Dec 15 16:16:07 GMT 2023`
Record UNII	0F1T12OCLX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NICOTREDOLE

Official Name

English

NSC-138472

Code

English

nicotredole [INN]

Common Name

English

N-(2-INDOL-3-YLETHYL)NICOTINAMIDE

Systematic Name

English

Nicotredole [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C257