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

HIDE SMILES / InChI

Molecular Formula	C25H24FNO
Molecular Weight	373.4626
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/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

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)

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:27:34 UTC 2023` Edited by `admin` on `Sat Dec 16 11:27:34 UTC 2023`
Record UNII	P4KP9PRG29
Record Status	`Validated (UNII)`
Record Version

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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