NONABINE

Details

Stereochemistry	UNKNOWN
Molecular Formula	C25H33NO2
Molecular Weight	379.535
Optical Activity	UNSPECIFIED
Defined Stereocenters	0 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCC(C)C(C)C1=CC2=C(C(O)=C1)C(=CC(C)(C)O2)C3=CC=NC=C3

InChI

InChIKey=YHUDSHIRWOVVCV-UHFFFAOYSA-N

InChI=1S/C25H33NO2/c1-6-7-8-9-17(2)18(3)20-14-22(27)24-21(19-10-12-26-13-11-19)16-25(4,5)28-23(24)15-20/h10-18,27H,6-9H2,1-5H3

HIDE SMILES / InChI

Molecular Formula	C25H33NO2
Molecular Weight	379.535
Charge	0
Count

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	0 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2860687 | https://www.ncbi.nlm.nih.gov/pubmed/6402096

Nonabine is a chromenol structurally related to the cannabinoids which has shown antiemetic efficacy in clinical trials. Nonabine also produced sedative clinical effects, but with an EEG profile which resembled that reportedly caused by cannabinoids. In contrast to cannabinoids, nonabine did not cause changes of mood or perception, suggesting that nonabine lacks the potential for social abuse at antiemetic doses. Nonabine was studied in the 1980s for the prevention of nausea and vomiting associated with cancer chemotherapy.

Approval Year

PubMed

Title	Date	PubMed
Pilot investigation of the quantitative EEG and clinical effects of ketazolam and the novel antiemetic nonabine in normal subjects.	1985	2860687
Antiemetic effect of nonabine in cancer chemotherapy: a double blind study comparing nonabine and chlorpromazine.	1983-01-29	6402096
Clinical studies with a THC analog (BRL-4664) in the prevention of cisplatin-induced vomiting.	1981-08-01	7197692

Patents

Sample Use Guides

In Vivo Use Guide

Oral doses of 5, 10, and 15 mg were given to healthy volunteers

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:42:20 GMT 2025` Edited by `admin` on `Wed Apr 02 09:42:20 GMT 2025`
Record UNII	77DUK856J7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NONABINE

Official Name

English

BRL 4664

Preferred Name

English

7-(1,2-DIMETHYLHEPTYL)-2,2-DIMETHYL-4-(4-PYRIDYL)-2H-1-BENZOPYRAN-5-OL

Systematic Name

English

nonabine [INN]

Common Name

English

BRL-4664

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C267