CB-13

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C26H24O2
Molecular Weight	368.4676
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCOC1=CC=C(C(=O)C2=CC=CC3=C2C=CC=C3)C4=C1C=CC=C4

InChI

InChIKey=RSUMDJRTAFBISX-UHFFFAOYSA-N

InChI=1S/C26H24O2/c1-2-3-8-18-28-25-17-16-24(21-13-6-7-14-22(21)25)26(27)23-15-9-11-19-10-4-5-12-20(19)23/h4-7,9-17H,2-3,8,18H2,1H3

HIDE SMILES / InChI

Molecular Formula	C26H24O2
Molecular Weight	368.4676
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/24430917https://www.ncbi.nlm.nih.gov/pubmed/17630726
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23621668 | https://www.ncbi.nlm.nih.gov/pubmed/22954177 | https://www.ncbi.nlm.nih.gov/pubmed/24525548 | https://www.ncbi.nlm.nih.gov/pubmed/25777582 | https://www.ncbi.nlm.nih.gov/pubmed/23401746

CB-13 is a cannabinoid drug, which acts as a potent agonist at both the CB1 and CB2 receptors, but has poor blood-brain barrier penetration, and so produces only peripheral effects at low doses, with symptoms of central effects such as catalepsy only appearing at much higher dose ranges. CB-13 displays antihyperalgesic activity in a rat model of neuropathic pain with no CNS side effects.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cannabinoid CB1 receptor 85 Target ID: CHEMBL218 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17630726	Agonist 2678	6.1 nM [EC50]
Cannabinoid CB2 receptor 71 Target ID: CHEMBL253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17630726	Agonist 2678	27.9 nM [EC50]
Cytochrome P450 2C9 50 Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17630726	Inhibitor 8297	80800.0 nM [IC50]
Cannabinoid CB1 receptor 85 Target ID: CHEMBL218 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22284817	Agonist 2678	10.0 nM [Ki]
Cannabinoid CB2 receptor 71 Target ID: CHEMBL253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26000707	Agonist 2678	42.0 nM [Ki]
Vanilloid receptor 53 Target ID: CHEMBL4794 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25029033	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17630726	Primary	Phase I 428	Unknown Approved Use Unknown
Neuropathic pain 26 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23621668	Primary	Approved 8429	Sativex Approved Use Unknown
Spasticity 11 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22954177	Primary	Approved 8429	Sativex Approved Use Unknown
Cannabinoid dependence 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25777582	Primary	Phase III 656	Sativex Approved Use Unknown
Tourette's syndrome 20 Sources: https://clinicaltrials.gov/ct2/show/NCT03087201	Primary	Phase III 656	Sativex Approved Use Unknown

PubMed

Title	Date	PubMed
Naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone: a potent, orally bioavailable human CB1/CB2 dual agonist with antihyperalgesic properties and restricted central nervous system penetration.	2007 Aug 9	17630726
Characterization of the structural determinants required for potent mechanism-based inhibition of human cytochrome P450 1A1 by cannabidiol.	2014 May 25	24667653

Patents

Sample Use Guides

In Vivo Use Guide

2.7 mg delta-9-tetrahydrocannabinol (THC) and 2.5 mg cannabidiol (CBD), maximum dose (12 puffs): 32.4 mg THC/30 mg CBD

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:13:20 GMT 2023` Edited by `admin` on `Sat Dec 16 10:13:20 GMT 2023`
Record UNII	9XRJ6055XT
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CB-13

Common Name

English

METHANONE, 1-NAPHTHALENYL(4-(PENTYLOXY)-1-NAPHTHALENYL)-

Systematic Name

English

CB 13

Code

English

1-NAPHTHALENYL(4-(PENTYLOXY)-1-NAPHTHALENYL)METHANONE

Systematic Name

English

CRA-13

Code

English

Classification Tree Code System Code

WIKIPEDIA

Designer-drugs-CB-13