From Wikipedia, the free encyclopedia
Chemical compound
AM-2201 (1-(5-fluoropentyl)-3-(1-naphthoyl)indole ) is a
recreational
designer drug that acts as a potent but nonselective
full agonist for the
cannabinoid receptor .
[3] It is part of the
AM series of cannabinoids discovered by
Alexandros Makriyannis at
Northeastern University .
Hazards
Convulsions have been reported
[4] including at doses as low as 10 mg.
[5]
Pharmacology
AM-2201 is a
full agonist for
cannabinoid receptors . Affinities are: with a
K i of 1.0 nM at
CB1 and 2.6 nM at
CB2 .
[6] The 4-methyl
functional analog
MAM-2201 probably has similar affinities.[
original research? ] AM-2201 has an EC50 of 38 nM for human CB1 receptors, and 58 nM for human CB2 receptors.
[7] AM-2201 produces
bradycardia and hypothermia in rats at doses of 0.3–3 mg/kg, comparable to the potency of
JWH-018 in rats, suggesting potent cannabinoid-like activity.
[7]
Pharmacokinetics
AM-2201
metabolism differs only slightly from that of
JWH-018 . AM-2201 N -
dealkylation produces fluoropentane instead of
pentane (or plain
alkanes in general).[
citation needed ]
Detection
A forensic standard of AM-2201 is available, and the compound has been posted on the Forendex website of potential drugs of abuse.
[8]
Legal status
In the United States, AM-2201 is a
Schedule I controlled substance .
[9]
See also
References
^
Anvisa (2023-07-24).
"RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).
Diário Oficial da União (published 2023-07-25).
Archived from the original on 2023-08-27. Retrieved 2023-08-27 .
^
"Substance Details AM-2201" . Retrieved 2024-01-22 .
^ Wilkinson SM, Banister, Kassiou M (2015).
"Bioisosteric Fluorine in the Clandestine Design of Synthetic Cannabinoids" . Australian Journal of Chemistry . 68 (1): 4–8.
doi :
10.1071/CH14198 .
^ McQuade D, Hudson S, Dargan PI, Wood DM (March 2013). "First European case of convulsions related to analytically confirmed use of the synthetic cannabinoid receptor agonist AM-2201". European Journal of Clinical Pharmacology . 69 (3): 373–6.
doi :
10.1007/s00228-012-1379-2 .
PMID
22936123 .
S2CID
23136932 .
^ ekaJ (20 February 2011).
"The Night I Killed My Friends" . Erowid.org . Retrieved 11 June 2012 .
^
WO patent 0128557 , Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07
^
a
b Banister SD, Stuart J, Kevin RC, Edington A, Longworth M, Wilkinson SM, Beinat C, Buchanan AS, Hibbs DE, Glass M, Connor M, McGregor IS, Kassiou M (August 2015).
"Effects of bioisosteric fluorine in synthetic cannabinoid designer drugs JWH-018, AM-2201, UR-144, XLR-11, PB-22, 5F-PB-22, APICA, and STS-135" . ACS Chemical Neuroscience . 6 (8): 1445–58.
doi :
10.1021/acschemneuro.5b00107 .
PMID
25921407 .
^
"Southern Association of Forensic Scientists" . Archived from
the original on 2014-09-10. Retrieved 2013-07-16 .
^
Controlled Substances listed by the DEA
Phytocannabinoids (
comparison )
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Hydrocarbons Indazole carboxamides Indazole-3- carboxamides Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles
Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Pyrrolobenzoxazines Quinolinyl esters Tetramethylcyclo- propanoylindazoles Tetramethylcyclo- propanoylindoles Tetramethylcyclo- propylindoles Others
Allosteric
CBR Tooltip Cannabinoid receptor
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Receptor (
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CB2 Tooltip Cannabinoid receptor type 2
Agonists
2-AG
2-AGE (noladin ether)
3,3'-Diindolylmethane
4-O-Methylhonokiol
α-Amyrin · β-Amyrin
A-796,260
A-834,735
A-836,339
AM-1172
AM-1221
AM-1235
AM-1241
AM-2232
Anandamide
AZ-11713908
Cannabinol
Caryophyllene
CB-13
CBS-0550
CP 55,940
GW-405,833 (L-768,242)
GW-842,166X
HU-308
JTE 7-31
JWH-007
JWH-015
JWH-018
JWH-73
JWH-133
L-759,633
L-759,656
Lenabasum (anabasum)
Magnolol
MDA-19
Nabitan
NADA
Olorinab (APD-371)
PF-03550096
S-444,823
SER-601
Serinolamide A
UR-144
Tedalinab
THC (dronabinol)
THCV
Tetrahydromagnolol
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Antagonists
NAGly (
GPR18 )
GPR55
GPR119
Transporter (
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eCBTs Tooltip Endocannabinoid transporter
Enzyme (
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Others
Others:
2-PG (directly potentiates activity of 2-AG at CB1 receptor)
ARN-272 (FAAH-like anandamide transporter inhibitor)