JWH-018

Details

Stereochemistry	ACHIRAL
Molecular Formula	C24H23NO
Molecular Weight	341.4455
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCN1C=C(C(=O)C2=CC=CC3=C2C=CC=C3)C4=C1C=CC=C4

InChI

InChIKey=JDNLPKCAXICMBW-UHFFFAOYSA-N

InChI=1S/C24H23NO/c1-2-3-8-16-25-17-22(20-13-6-7-15-23(20)25)24(26)21-14-9-11-18-10-4-5-12-19(18)21/h4-7,9-15,17H,2-3,8,16H2,1H3

HIDE SMILES / InChI

Molecular Formula	C24H23NO
Molecular Weight	341.4455
Charge	0
Count

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

Description
Sources: https://legal-high-inhaltsstoffe.de/sites/default/files/uploads/jwh-018.pdf
Curator's Comment: description was created based on several sources, including: https://psychonautwiki.org/wiki/JWH-018 | https://en.wikipedia.org/wiki/JWH-018

JWH-018 is a full agonist synthetic cannabinoid with a high binding affinity to CB1 and CB2 cannabinoid receptors. JWH-018 has not been used in therapy. Many of the risks linked to cannabis use are also present in the case of JWH-018, among them complications in patients suffering from cardiovascular diseases and triggering of acute psychosis. JWH-018 has not been used in therapy. Studies in mice showed anti-inflammatory and cancer chemopreventive properties of JWH-018.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cannabinoid CB1 receptor 85 Target ID: CHEMBL218 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10940540	Agonist 2678		9.0 nM [Ki]
Cannabinoid CB2 receptor 71 Target ID: CHEMBL253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10940540	Agonist 2678		2.94 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Inflammation 102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23837590	Primary		Preclinical	Unknown Approved Use Unknown
Skin cancer 23 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23837590	Preventing		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
		252160197
Discriminative stimulus functions of methanandamide and delta(9)-THC in rats: tests with aminoalkylindoles (WIN55,212-2 and AM678) and ethanol.	2010 Jan	19902182
Detection of JWH-018 metabolites in smoking mixture post-administration urine.	2010 Jul 15	20430547
A teenager with agitation: higher than she should have climbed.	2010 Jun	20531137
JWH018, a common constituent of 'Spice' herbal blends, is a potent and efficacious cannabinoid CB receptor agonist.	2010 Jun	20100276
Chemical analysis of synthetic cannabinoids as designer drugs in herbal products.	2010 May 20	20117892
In vitro phase I metabolism of the synthetic cannabimimetic JWH-018.	2010 Nov	20838779
Warning: legal synthetic cannabinoid-receptor agonists such as JWH-018 may precipitate psychosis in vulnerable individuals.	2010 Oct	20840203
Sensitive and rapid quantification of the cannabinoid receptor agonist naphthalen-1-yl-(1-pentylindol-3-yl)methanone (JWH-018) in human serum by liquid chromatography-tandem mass spectrometry.	2010 Oct 1	20378423
Toxicological profiles of selected synthetic cannabinoids showing high binding affinities to the cannabinoid receptor subtype CB₁.	2013 Jul	23494106
Human metabolites of synthetic cannabinoids JWH-018 and JWH-073 bind with high affinity and act as potent agonists at cannabinoid type-2 receptors.	2013 Jun 1	23537664
Cytotoxicity of synthetic cannabinoids on primary neuronal cells of the forebrain: the involvement of cannabinoid CB1 receptors and apoptotic cell death.	2014 Jan 1	24211273

Patents

Sample Use Guides

In Vivo Use Guide

2 to 5 mg when smoked/vaporized

Route of Administration: Other

In Vitro Use Guide

JWH-018 induces inhibition of forskolin-stimulated cAMP accumulation in CHO cell lines expressing CB1 receptors with an EC50 14.7 ± 3.9, maximum inhibition 79% and in Neuro2AWT cells with an EC50 of 5.31 ± 0.4 nM.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 06:18:26 GMT 2023` Edited by `admin` on `Sat Dec 16 06:18:26 GMT 2023`
Record UNII	G391998J57
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

JWH-018

Common Name

English

NAPHTHALEN-1-YL-(1-PENTYLINDOL-3-YL)METHANONE

Systematic Name

English

DEA NO. 7118

Code

English

J770.893I

Code

English

1-PENTYL-3-(1-NAPHTHOYL)INDOLE

Systematic Name

English

METHANONE, 1-NAPHTHALENYL(1-PENTYL-1H-INDOL-3-YL)-

Systematic Name

English

AM-678

Code

English

Classification Tree Code System Code

WIKIPEDIA

Designer-drugs-JWH-018