AM-2201 Legal status
CA Schedule II DE Anlage II (Authorized trade only, not prescriptible) NZ Temporary Class UK :Class B US :Schedule I
show 1-[(5-Fluoropentyl)-1H -indol-3-yl]-(naphthalen-1-yl)methanone
CAS Number PubChem CID ChemSpider UNII CompTox Dashboard (EPA ) Formula C 24 H 22 F N O Molar mass −1 3D model (JSmol ) show O=C(C1=CN(CCCCCF)C2=C1C=CC=C2)C3=CC=CC4=C3C=CC=C4
show InChI=1S/C24H22FNO/c25-15-6-1-7-16-26-17-22(20-12-4-5-14-23(20)26)24(27)21-13-8-10-18-9-2-3-11-19(18)21/h2-5,8-14,17H,1,6-7,15-16H2
Y Key:ALQFAGFPQCBPED-UHFFFAOYSA-N
Y N Y (what is this?)
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 .[1] AM series of cannabinoids discovered by Alexandros Makriyannis at Northeastern University .
Hazards [ ] Convulsions have been reported[2] [3]
Pharmacology [ ] AM-2201 is a full agonist for cannabinoid receptors . Affinities are: with a K i CB1 and 2.6 nM at CB2 .[4] 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.[5] 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.[5]
Pharmacokinetics [ ] See also: JWH-018 § 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.[6]
Legal status [ ] In the United States, AM-2201 is a Schedule I controlled substance .[7]
See also [ ] AM-694 AM-1235 AM-2232 AM-2233 JWH-018 SDB-005 THJ-018 THJ-2201 MEPIRAPIM NM-2201 References [ ]
^ 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 . ^ 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 ^ Jump up to: 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" (PDF) . 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 show Cannabinoids
Phytocannabinoids
Cannabichromenes Cannabicyclols Cannabidiols Cannabielsoins Cannabigerols Cannabinols and cannabinodiols Cannabitriols Delta-8-tetrahydrocannabinols Delta-9-tetrahydrocannabinols
Delta-9-THC (THC)
THCP
THCV
Miscellaneous cannabinoids
Caryophyllene Alkylamides Epigallocatechin gallate Gallocatechol Perrottetinene Serinolamide A Yangonin Active metabolites
Endocannabinoids
Arachidonoyl ethanolamide (AEA; anandamide) 2-Arachidonoylglycerol (2-AG) 2-Arachidonyl glyceryl ether (2-AGE; noladin ether) 2-Oleoylglycerol (2-OG) N-Arachidonoyl dopamine (NADA) N-Arachidonylglycine (NAGly) N-Arachidonoyl serotonin (AA-5-HT) Docosatetraenoylethanolamide (DEA) Lysophosphatidylinositol (LPI) Oleamide Oleoylethanolamide (OEA) Palmitoylethanolamide (PEA) RVD-Hpα Stearoylethanolamide (SEA) O-Arachidonoyl ethanolamine (O-AEA; virodhamine) Synthetic
Classical cannabinoids Non-classical Adamantoylindoles Benzimidazoles Benzoylindoles Cyclohexylphenols Eicosanoids Hydrocarbons Indazole carboxamides Indazole-3- Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Pyrrolobenzoxazines Quinolinyl esters Tetramethylcyclo- Tetramethylcyclo-
A-796,260 A-834,735 FUB-144 UR-144 XLR-11 XLR-12 Tetramethylcyclo- Others
Allosteric CBR ligands Endocannabinoid (inactivation inhibitors) Anticannabinoids (antagonists/inverse
See also: Cannabinoid receptor modulators (cannabinoids by pharmacology)List of: AM cannabinoids JWH cannabinoids Designer drugs § Synthetic cannabimimetics
show Receptor (ligands )
CB1
Agonists (abridged; see here for more) : 2-AG 2-AGE (noladin ether) 11-Hydroxy-THC α-Amyrin · β-Amyrin AB-CHMINACA AM-1220 AM-1221 AM-1235 AM-2201 AM-2232 Anandamide AZ-11713908 Cannabinol CB-13 CP 47,497 CP 55,940 Dimethylheptylpyran DEA ECG EGCG Epicatechin Gallocatechol (gallocatechin) Honokiol HU-210 JWH-007 JWH-015 JWH-018 JWH-073 Kavain L-759,633 Levonantradol Menabitan Nabilone Nabitan NADA O-1812 Oleamide Pravadoline Serinolamide A THC (dronabinol) UR-144 WIN 55,212-2 Yangonin CB2
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-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-133 L-759,633 L-759,656 Magnolol MDA-19 Nabitan NADA Olorinab (APD-371) PF-03550096 S-444,823 SER-601 Serinolamide A UR-144 Tedalinab THC (dronabinol) THCV Virodhamine NAGly GPR18 )
Agonists: Abnormal cannabidiol ACPA AM251 Anandamide Cannabidiol NADGly THC (dronabinol) O-1602 GPR55
Agonists: 2-AGE (noladin ether) Abnormal cannabidiol AM-251 CP 55,940 Lysophosphatidylinositol O-1602 Oleoylethanolamide Palmitoylethanolamide THC (dronabinol) GPR119 Unsorted
Transporter (modulators )
eCBTs
Inhibitors: AM-404 Arachidonoyl serotonin Cannabidiol Guineensine LY-2183240 Paracetamol (acetaminophen) URB-597 VDM-11
Enzyme (modulators )
FAAH MAGL
Inhibitors: IDFP JZL-184 JZL-195 MAFP URB-602 ABHD6 ABHD12
Inhibitors: Betulinic acid Maslinic acid MAFP Oleanolic acid Orlistat (tetrahydrolipstatin) Ursolic acid
Others
Precursors: Phosphatidylethanolamine NAPE Diacylglycerol Others: (directly potentiates activity of 2-AG at CB1 receptor) (FAAH-like anandamide transporter inhibitor)
See also
Receptor/signaling modulators Cannabinoids (cannabinoids by structure)
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