Cannabis Ruderalis

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{{Short description|Chemical compound}}
{{Use dmy dates|date=October 2013}}
{{Use dmy dates|date=October 2013}}
{{Drugbox
{{Drugbox
| IUPAC_name = (4-ethyl-1-naphthalenyl)[1-(5-fluoropentyl)-1''H''-indol-3-yl]-methanone
| IUPAC_name = (4-Ethyl-1-naphthalenyl)[1-(5-fluoropentyl)-1''H''-indol-3-yl]-methanone
| image = EAM-2201_structure.png
| image = EAM-2201_structure.png
| width = 150


<!--Clinical data-->
<!--Clinical data-->
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| pregnancy_category =
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_BR = F2
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-07-25}}</ref>
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_CA = Schedule II
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_UK = PSA
⚫
| legal_status = Temporary Class Drug (NZ)
| legal_US = Schedule I
| legal_DE = Anlage II
⚫
| legal_NZ = Temporary Class
| legal_status =
| routes_of_administration =
| routes_of_administration =


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| CAS_number = 1364933-60-7
| CAS_number = 1364933-60-7
| ATC_prefix =
| ATC_prefix =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = OO52S1U9ET
| ATC_suffix =
| ATC_suffix =
| PubChem = 71308187
| PubChem = 71308187
| ChemSpiderID = 29341514
⚫
| smiles = CCC1=CC=C(C(C2=CN(CCCCCF)C3=C2C=CC=C3)=O)C4=C1C=CC=C4
⚫
| StdInChI = 1S/C26H26FNO/c1-2-19-14-15-23(21-11-5-4-10-20(19)21)26(29)24-18-28(17-9-3-8-16-27)25-13-7-6-12-22(24)25/h4-7,10-15,18H,2-3,8-9,16-17H2,1H3
⚫
| StdInChIKey = NSCXPXDWLZORPX-UHFFFAOYSA-N


<!--Chemical data-->
<!--Chemical data-->
| C=26 | H=26 | F=1 | N=1 | O=1
| C=26 | H=26 | F=1 | N=1 | O=1
⚫
| smiles = CCC1=CC=C(C(C2=CN(CCCCCF)C3=C2C=CC=C3)=O)C4=C1C=CC=C4
| molecular_weight = 387.488 g/mol
⚫
| StdInChI = 1S/C26H26FNO/c1-2-19-14-15-23(21-11-5-4-10-20(19)21)26(29)24-18-28(17-9-3-8-16-27)25-13-7-6-12-22(24)25/h4-7,10-15,18H,2-3,8-9,16-17H2,1H3
⚫
| StdInChIKey = NSCXPXDWLZORPX-UHFFFAOYSA-N
}}
}}


'''EAM-2201''' ('''4'-ethyl-AM-2201''', '''5"-fluoro-JWH-210''') is a drug that presumably acts as a potent [[agonist]] for the [[cannabinoid receptor]]s. It had never previously been reported in the scientific or patent literature, and was first identified by laboratories in Japan in July 2012 as an ingredient in [[synthetic cannabis]] smoking blends.<ref>{{Cite journal | last1 = Uchiyama | first1 = N. | last2 = Kawamura | first2 = M. | last3 = Kikura-Hanajiri | first3 = R. | last4 = Goda | first4 = Y. | title = URB-754: A new class of designer drug and 12 synthetic cannabinoids detected in illegal products | doi = 10.1016/j.forsciint.2012.08.047 | journal = Forensic Science International | volume = 227 | issue = 1–3 | pages = 21–32 | year = 2012 | pmid = 23063179| pmc = }}</ref> Like the closely related [[MAM-2201]] which had been first reported around a year earlier, EAM-2201 thus appears to be another novel compound invented by [[designer drug]] suppliers specifically for [[recreational drug use|recreational use]]. Structurally, EAM-2201 is a hybrid of two known cannabinoid compounds [[JWH-210]] and [[AM-2201]], both of which had previously been used as active ingredients in synthetic cannabis blends before being banned in many countries.
'''EAM-2201''' ('''4'-ethyl-AM-2201''', '''5"-fluoro-JWH-210''', '''SGT-14''') is a drug that presumably acts as a potent [[agonist]] for the [[cannabinoid receptor]]s.<ref>{{cite journal | vauthors = Kim JH, Kim HS, Kong TY, Lee JY, Kim JY, In MK, Lee HS | title = In vitro metabolism of a novel synthetic cannabinoid, EAM-2201, in human liver microsomes and human recombinant cytochrome P450s | journal = Journal of Pharmaceutical and Biomedical Analysis | volume = 119 | issue = 5 | pages = 50–8 | date = February 2016 | pmid = 26641707 | doi = 10.1016/j.jpba.2015.11.023 }}</ref> It had never previously been reported in the scientific or patent literature, and was first identified by laboratories in Japan in July 2012 as an ingredient in [[synthetic cannabis]] smoking blends<ref>{{cite journal | vauthors = Uchiyama N, Kawamura M, Kikura-Hanajiri R, Goda Y | title = URB-754: a new class of designer drug and 12 synthetic cannabinoids detected in illegal products | journal = Forensic Science International | volume = 227 | issue = 1–3 | pages = 21–32 | date = April 2013 | pmid = 23063179 | doi = 10.1016/j.forsciint.2012.08.047 | url = http://www.fsijournal.org/article/S0379-0738%2812%2900434-3/abstract }}</ref> Like the closely related [[MAM-2201]] which had been first reported around a year earlier, EAM-2201 thus appears to be another novel compound invented by [[designer drug]] suppliers specifically for [[recreational drug use|recreational use]]. Structurally, EAM-2201 is a hybrid of two known cannabinoid compounds [[JWH-210]] and [[AM-2201]], both of which had previously been used as active ingredients in synthetic cannabis blends before being banned in many countries.


==Pharmacology==
==Pharmacology==
Nothing has been published on the pharmacology of EAM-2201, though it presumably has similar properties to the closely related AM-2201 and JWH-210, which are both [[full agonist]]s and [[Binding selectivity|unselectively]] bind to [[Cannabinoid receptor type 1|CB<sub>1</sub>]] and [[Cannabinoid receptor type 2|CB<sub>2</sub>]] [[cannabinoid]] receptors with low nanomolar [[Affinity (pharmacology)#Protein-ligand binding|affinity]].
EAM-2201 acts as a [[full agonist]] with a [[Affinity (pharmacology)#Protein-ligand binding|binding affinity]] of 0.380&nbsp;nM at [[Cannabinoid receptor type 1|CB<sub>1</sub>]] and 0.371&nbsp;nM at [[Cannabinoid receptor type 2|CB<sub>2</sub>]] [[cannabinoid]] receptors.<ref>{{cite journal | vauthors = Hess C, Schoeder CT, Pillaiyar T, Madea B, Müller CE | title = Pharmacological evaluation of synthetic cannabinoids identified as constituents of spice | journal = Forensic Toxicology | volume = 34 | issue = 2 | pages = 329–343 | date = 1 July 2016 | pmid = 27429655 | pmc = 4929166 | doi = 10.1007/s11419-016-0320-2 }}</ref>


==Legal status==
==Legal status==
In the United States, all CB<sub>1</sub> receptor agonists of the 3-(1-naphthoyl)indole class such as EAM-2201 are [[Schedule I Controlled Substance]]s.<ref>{{UnitedStatesCode2|21|812|Schedules of controlled substances}}</ref>
⚫
EAM-2201 was banned in New Zealand as a [[temporary class drug]] from 6 December 2012, after reports of addiction and psychosis associated with use of products containing EAM-2201 as an active ingredient, however this has been protested by some users who claim to have found medical benefits in the treatment of conditions such as [[phantom limb pain]], since medicinal marijuana is not available in New Zealand and [[synthetic cannabis]] products are used as a legal alternative.<ref>[http://www.nzherald.co.nz/nz/news/article.cfm?c_id=1&objectid=10837617 I was possessed by a demon, says ex-legal high user. New Zealand Herald, Monday 1 Oct 2012]</ref><ref>[http://www.nzherald.co.nz/nz/news/article.cfm?c_id=1&objectid=10850580 Amputee: K2 'takes away my pain'. New Zealand Herald, Wednesday 28 Nov 2012]</ref>


⚫
EAM-2201 was banned in New Zealand as a [[temporary class drug]] from 6 December 2012, after reports of addiction and psychosis associated with use of products containing EAM-2201 as an active ingredient, however this has been protested by some users who claim to have found medical benefits in the treatment of conditions such as [[phantom limb pain]], since medicinal marijuana was not available in New Zealand and [[synthetic cannabis]] products were used as a legal alternative.<ref>{{cite web | url=http://www.nzherald.co.nz/nz/news/article.cfm?c_id=1&objectid=10837617 | title=I was possessed by a demon, says ex-legal high user | publisher=New Zealand Herald | date=1 October 2012 | first = Hamish | last = McNeilly | name-list-style = vanc }}</ref><ref>{{cite web | url=http://www.nzherald.co.nz/nz/news/article.cfm?c_id=1&objectid=10850580 | title=Amputee: K2 'takes away my pain' | publisher=New Zealand Herald | date=28 November 2012 | work = Bay of Plenty Times}}</ref>
⚫
EAM-2201 is listed in [[Drugs controlled by the German Betäubungsmittelgesetz|Anlage II]] and therefore illegal in Germany.


⚫
EAM-2201 is an [[Drugs controlled by the German Betäubungsmittelgesetz|Anlage II]] controlled drug in Germany.
⚫
As of October 2015 EAM-2201 is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=Chinese | accessdate=1 October 2015}}</ref>

⚫
As of October 2015 EAM-2201 is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=Chinese | access-date=1 October 2015 | archive-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | url-status=dead }}</ref>


==Detection==
==Detection==
A forensic standard of EAM-2201 is available and commonly used in [[mass spectrometry]].<ref>{{cite web | url=https://www.caymanchem.com/app/template/Product.vm/catalog/ISO00127 | title=EAM-2201 | publisher=Cayman Chemical | accessdate=21 July 2015}}</ref>
A forensic standard of EAM-2201 is available and commonly used in [[mass spectrometry]].<ref>{{cite web | url=https://www.caymanchem.com/app/template/Product.vm/catalog/ISO00127 | title=EAM-2201 | publisher=Cayman Chemical | access-date=21 July 2015}}</ref>


==See also==
== See also ==
* [[AM-694]]
* [[AM-694]]
* [[AM-1235]]
* [[AM-1235]]
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* [[NM-2201]]
* [[NM-2201]]


==References==
== References ==
{{reflist}}
<references/>


{{Cannabinoids}}
{{Cannabinoids}}


[[Category:Cannabinoids]]
[[Category:Naphthoylindoles]]
[[Category:Naphthoylindoles]]
[[Category:Organofluorides]]
[[Category:Organofluorides]]
[[Category:Designer drugs]]
[[Category:Designer drugs]]
[[Category:CB1 receptor agonists]]

[[Category:CB2 receptor agonists]]
{{cannabinoid-stub}}

Latest revision as of 05:10, 19 February 2024

EAM-2201
Legal status
Legal status
Identifiers
  • (4-Ethyl-1-naphthalenyl)[1-(5-fluoropentyl)-1H-indol-3-yl]-methanone
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H26FNO
Molar mass387.498 g·mol−1
3D model (JSmol)
  • CCC1=CC=C(C(C2=CN(CCCCCF)C3=C2C=CC=C3)=O)C4=C1C=CC=C4
  • InChI=1S/C26H26FNO/c1-2-19-14-15-23(21-11-5-4-10-20(19)21)26(29)24-18-28(17-9-3-8-16-27)25-13-7-6-12-22(24)25/h4-7,10-15,18H,2-3,8-9,16-17H2,1H3
  • Key:NSCXPXDWLZORPX-UHFFFAOYSA-N

EAM-2201 (4'-ethyl-AM-2201, 5"-fluoro-JWH-210, SGT-14) is a drug that presumably acts as a potent agonist for the cannabinoid receptors.[2] It had never previously been reported in the scientific or patent literature, and was first identified by laboratories in Japan in July 2012 as an ingredient in synthetic cannabis smoking blends[3] Like the closely related MAM-2201 which had been first reported around a year earlier, EAM-2201 thus appears to be another novel compound invented by designer drug suppliers specifically for recreational use. Structurally, EAM-2201 is a hybrid of two known cannabinoid compounds JWH-210 and AM-2201, both of which had previously been used as active ingredients in synthetic cannabis blends before being banned in many countries.

Pharmacology[edit]

EAM-2201 acts as a full agonist with a binding affinity of 0.380 nM at CB1 and 0.371 nM at CB2 cannabinoid receptors.[4]

Legal status[edit]

In the United States, all CB1 receptor agonists of the 3-(1-naphthoyl)indole class such as EAM-2201 are Schedule I Controlled Substances.[5]

EAM-2201 was banned in New Zealand as a temporary class drug from 6 December 2012, after reports of addiction and psychosis associated with use of products containing EAM-2201 as an active ingredient, however this has been protested by some users who claim to have found medical benefits in the treatment of conditions such as phantom limb pain, since medicinal marijuana was not available in New Zealand and synthetic cannabis products were used as a legal alternative.[6][7]

EAM-2201 is an Anlage II controlled drug in Germany.

As of October 2015 EAM-2201 is a controlled substance in China.[8]

Detection[edit]

A forensic standard of EAM-2201 is available and commonly used in mass spectrometry.[9]

See also[edit]

References[edit]

  1. ^ Anvisa (24 July 2023). "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 25 July 2023). Archived from the original on 27 August 2023. Retrieved 27 August 2023.
  2. ^ Kim JH, Kim HS, Kong TY, Lee JY, Kim JY, In MK, Lee HS (February 2016). "In vitro metabolism of a novel synthetic cannabinoid, EAM-2201, in human liver microsomes and human recombinant cytochrome P450s". Journal of Pharmaceutical and Biomedical Analysis. 119 (5): 50–8. doi:10.1016/j.jpba.2015.11.023. PMID 26641707.
  3. ^ Uchiyama N, Kawamura M, Kikura-Hanajiri R, Goda Y (April 2013). "URB-754: a new class of designer drug and 12 synthetic cannabinoids detected in illegal products". Forensic Science International. 227 (1–3): 21–32. doi:10.1016/j.forsciint.2012.08.047. PMID 23063179.
  4. ^ Hess C, Schoeder CT, Pillaiyar T, Madea B, Müller CE (1 July 2016). "Pharmacological evaluation of synthetic cannabinoids identified as constituents of spice". Forensic Toxicology. 34 (2): 329–343. doi:10.1007/s11419-016-0320-2. PMC 4929166. PMID 27429655.
  5. ^ 21 U.S.C. § 812: Schedules of controlled substances
  6. ^ McNeilly H (1 October 2012). "I was possessed by a demon, says ex-legal high user". New Zealand Herald.
  7. ^ "Amputee: K2 'takes away my pain'". Bay of Plenty Times. New Zealand Herald. 28 November 2012.
  8. ^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  9. ^ "EAM-2201". Cayman Chemical. Retrieved 21 July 2015.
source: https://en.wikipedia.org/w/index.php?title=EAM-2201&diff=1208845737&oldid=683539930

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