Chemical Data :

IUPAC: (1-(5-fluoropentyl)-1H-indol-3-yl)(4-methyl-1-naphthalenyl)-methanone

CAS: 1354631-24-5

ChemSpider: 28289977

Molecular Weight: C25H24FNO

Molecular Formula: 373.462

MAM-2201, otherwise known as 4′-methyl-AM-2201 and 5″-fluoro-JWH-122, is a potent synthetic cannabinoid.

It was first identified in 2011 as an ingredient in synthetic cannabis blends in Germany and the Netherlands. Previous to this it has no history of use, and does not appear in the scientific literature.

MAM-2201 has been invented solely for the purpose of supply as a “research chemical” or “designer drug”.  In chemical structure it combines elements of JWH-122 and AM-2201, two cannabinoids that have been a popular commercial success within this market. This is most likely an attempt to circumvent drug laws that have prohibited these previous cannabinoids.

MAM-2201 has the systematic IUPAC name (1-(5-fluoropentyl)-1H-indol-3-yl)(4-methyl-1-naphthalenyl)-methanone. It has a molar mass of 373.462 grams and empirical formula C25H24FNO.

It is a fluorinated cannabinoid. Fluorine is often added to the structure as it is known to increase potency and binding at the CB1 receptor site. However, it is likely that the fluorinated cannabinoids present additional health risks. Owing to the electronegativity of the fluorine containing cannabinoids, they have a high melting point around 500 OC. When heat is applied either through combustion or heat vaporisation, these compounds will decompose thermally before their boiling point.

A proportion of the cannabinoid will break down, producing reactive fluorinated decomposition products that are then inhaled. These by-products are likely to have a noxious effect on mucous membranes and may contribute to respiratory illness and disease. Furthermore it is unknown what effect they may have if absorbed systemically. Therefore it is advisable if fluorinated cannabinoids such as MAM-2201 are to be taken, it should be done via a cold method. This would include oral ingestion or ultrasonic vaporisation. The majority of “E-cigarette” vaporisers on the market today use a heating element to produce vapour from their propylene glycol substrate.

Even discounting this health risk, the effects of short term or long term recreational use of MAM-2201 are unknown.

The synthetic cannabinoids have been associated with seizures, hospitalisations and deaths around the world in the last decade. This is largely as a result of their pharmacological action. They act as full agonists at CB1, as opposed to the partial agonist action of THC. This means that, unlike with THC containing herbal cannabis, it is possible to overdose on synthetic cannabinoids. The fluorinated indoles and indazoles to which MAM-2201 belongs is noted to be extremely potent. MAM-2201 has been reported online to be active at 0.5 mg. Therefore it is readily apparent why these compounds are lethal in the wrong hands.

MAM-2201 is not fit for animal or human consumption.

Tentative online reports give us some indication as to the action of this compound.

MAM-2201 is reported as being heavily sedating at sub 1 mg doses. It produces a heavy and overwhelming “body high” with attendant loss of motor control. Users additionally report pain relief and dehydration as common physical side effects.

Cognitive effects range from euphoria to extreme paranoia and anxiety.

Long term use will increase the risk of adverse effects.

These compounds are known to be addictive.

Other names and synonyms for MAM-2201:

[1-(5-Fluoropentyl)-1H-indol-3-yl](4-methyl-1-naphthyl)methanone [ACD/IUPAC Name]
[1-(5-Fluoropentyl)-1H-indol-3-yl](4-méthyl-1-naphtyl)méthanone [French] [ACD/IUPAC Name]
[1-(5-Fluorpentyl)-1H-indol-3-yl](4-methyl-1-naphthyl)methanon [German] [ACD/IUPAC Name]
1354631-24-5 [RN]
MAM-2201 [Wiki]
Methanone, [1-(5-fluoropentyl)-1H-indol-3-yl](4-methyl-1-naphthalenyl)- [ACD/Index Name]
4-Methyl AM-2201
MFCD22421647 [MDL number]