MAM-2201

Details

Stereochemistry	ACHIRAL
Molecular Formula	C25H24FNO
Molecular Weight	373.4626
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=C(C(=O)C2=CN(CCCCCF)C3=CC=CC=C23)C4=C1C=CC=C4

InChI

InChIKey=IGBHZHCGWLHBAE-UHFFFAOYSA-N

InChI=1S/C25H24FNO/c1-18-13-14-22(20-10-4-3-9-19(18)20)25(28)23-17-27(16-8-2-7-15-26)24-12-6-5-11-21(23)24/h3-6,9-14,17H,2,7-8,15-16H2,1H3

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25747605

MAM-2201 has been recently detected in herbal products and has psychoactive and intoxicating effects in humans, suggesting that MAM-2201 alters brain function. MAM-2201 acts as an agonist of human cannabinoid receptor type 1 (CB1R) and thus to suppress neurotransmitter release. The reduction of neurotransmitter release from CB1R-containing synapses could contribute to some of the symptoms of synthetic cannabinoid intoxication including impairments in cerebellum-dependent motor coordination and motor learning.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cannabinoid receptor 1 30 Target ID: P21554\|\|\|Q5UB37 Gene ID: 1268.0 Gene Symbol: CNR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25747605	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
URB-754: a new class of designer drug and 12 synthetic cannabinoids detected in illegal products.	2013 Apr 10	23063179
Inhibitory effect of synthetic cannabinoids on CYP1A activity in mouse liver microsomes.	2014	25374372

Patents

Sample Use Guides

In Vivo Use Guide

in rats: MAM-2201 was intraperitoneally administered to 6-week Wistar rats at 5 or 15mg/kg (n=5), and the cerebrum metabolome alteration was investigated using a gas chromatography/tandem mass spectrometry (GC/MS/MS)-based metabolomics technique.

Route of Administration: Intraperitoneal

In Vitro Use Guide

MAM-2201 inhibited neurotransmitter release with an inhibitory concentration 50% of 0.36 μM. MAM-2201 caused greater inhibition of neurotransmitter release than Δ(9)-tetrahydrocannabinol within the range of 0.1-30 μM and JWH-018, one of the most popular and potent synthetic cannabinoids detected in the herbal products, within the range of 0.03-3 μM. MAM-2201 caused a concentration-dependent suppression of GABA release onto Purkinje cells (PCs). Furthermore, MAM-2201 induced suppression of glutamate release at climbing fiber-PC synapses, leading to reduced dendritic Ca(2+) transients in (PCs)

Name

Type

Language

MAM-2201

Common Name

English

AM 2201-PME

Common Name

English

5-FLUORO-JWH-122

Common Name

English

J3.085.476D

Code

English

METHANONE, (1-(5-FLUOROPENTYL)-1H-INDOL-3-YL)(4-METHYL-1-NAPHTHALENYL)-

Systematic Name

English

4'-METHYL-AM-2201

Common Name

English

1-(5-FLUOROPENTYL)-3-(4-METHYLNAPHTHALENE-1-YLCARBONYL)-1H-INDOLE

Systematic Name

English

(1-(5-FLUOROPENTYL)-1H-INDOL-3-YL)(4-METHYL-1-NAPHTHALENYL)-METHANONE

Systematic Name

English

Classification Tree Code System Code

WIKIPEDIA

Designer-drugs-MAM-2201