| 词条 | AM-2201 |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 451565418 | IUPAC_name = 1-[(5-Fluoropentyl)-1H-indol-3-yl]-(naphthalen-1-yl)methanone | image = AM-2201.svg | tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = Schedule II | legal_DE = Anlage II | legal_UK = | legal_US = Schedule I | legal_NZ = Temporary Class | legal_status = | routes_of_administration = | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 335161-24-5 | ATC_prefix = | ATC_suffix = | PubChem = 53393997 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 24751884 | UNII_Ref = {{fdacite|changed|FDA}} | UNII = TBJ0966F1O | C=24 | H=22 | F=1 | N=1 | O=1 | molecular_weight = 359.44 g/mol | smiles = O=C(C1=CN(CCCCCF)C2=C1C=CC=C2)C3=CC=CC4=C3C=CC=C4 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = ALQFAGFPQCBPED-UHFFFAOYSA-N }} 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] It is part of the AM series of cannabinoids discovered by Alexandros Makriyannis at Northeastern University. HazardsConvulsions have been reported[2] including at doses as low as 10 mg.[3]Recreational use of AM-2201 in the United States has led to it being specifically listed in a proposed 2011 amendment to the Controlled Substances Act, aiming to add a number of synthetic drugs into Schedule I.[4] PharmacologyAM-2201 is a full agonist for cannabinoid receptors. Affinities are: with a Ki of 1.0 nM at CB1 and 2.6 nM at CB2.[5] The 4-methyl functional analog MAM-2201 probably has similar affinities.{{or|date=June 2015}} AM-2201 has an EC50 of 38 nM for human CB1 receptors, and 58 nM for human CB2 receptors.[6] 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.[6] Pharmacokinetics{{Refimprove section|date=July 2012}}{{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|date=February 2014}} DetectionA forensic standard of AM-2201 is available, and the compound has been posted on the Forendex website of potential drugs of abuse.[7] See also
References1. ^{{cite journal | title=Bioisosteric Fluorine in the Clandestine Design of Synthetic Cannabinoids | journal=Australian Journal of Chemistry | year=2015 | volume=68 | pages=4–8 | doi=10.1071/CH14198 | vauthors = Wilkinson SM, Banister, Kassiou M | url=http://www.publish.csiro.au/?paper=CH14198 | issue=1}} {{Cannabinoids}}{{Cannabinoidergics}}2. ^{{cite journal | vauthors = McQuade D, Hudson S, Dargan PI, Wood DM | title = First European case of convulsions related to analytically confirmed use of the synthetic cannabinoid receptor agonist AM-2201 | journal = European Journal of Clinical Pharmacology | volume = 69 | issue = 3 | pages = 373–6 | date = March 2013 | pmid = 22936123 | doi = 10.1007/s00228-012-1379-2 }} 3. ^{{cite web | url=https://erowid.org/experiences/exp.php?ID=89294 | title=The Night I Killed My Friends | work=Erowid.org | date=20 February 2011 | access-date=11 June 2012 | author=ekaJ}} 4. ^[https://www.gpo.gov/fdsys/pkg/BILLS-112hr1254ih/pdf/BILLS-112hr1254ih.pdf Synthetic Drug Control Act of 2011]. H.R. 1254, 112th Congress, 1st Session (2011). 5. ^{{Ref patent2 | country = WO | number = 0128557 | status = granted | title = Cannabimimetic indole derivatives | pubdate = 2001-04-26 | gdate = 2001-06-07 | pridate= 1999-10-18 | inventor = Makriyannis A, Deng H | assign1= }} 6. ^1 {{cite journal | vauthors = 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 | title = 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 | journal = ACS Chemical Neuroscience | volume = 6 | issue = 8 | pages = 1445–58 | date = August 2015 | pmid = 25921407 | doi = 10.1021/acschemneuro.5b00107 }} 7. ^Southern Association of Forensic Scientists 7 : Cannabinoids|Naphthoylindoles|Organofluorides|AM cannabinoids|Designer drugs|CB1 receptor agonists|CB2 receptor agonists |
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