AM-1220

AM-1220
Legal status
Legal status	AU: S9 (Prohibited substance); CA: Schedule II; DE: Anlage II (Authorized trade only, not prescriptible); NZ: Temporary Class; UK: Class B; US: Schedule I;
Identifiers
	IUPAC name (R)-(1-((1-Methylpiperidin-2-yl)methyl)-1H-indol-3-yl)(naphthalen-1-yl)methanone;
JSmol)	Interactive image;
	SMILES O=C(C1=CC=CC2=C1C=CC=C2)C3=CN(C[C@@H]4N(C)CCCC4)C5=CC=CC=C53;
	InChI InChI=1S/C26H26N2O/c1-27-16-7-6-11-20(27)17-28-18-24(22-13-4-5-15-25(22)28)26(29)23-14-8-10-19-9-2-3-12-21(19)23/h2-5,8-10,12-15,18,20H,6-7,11,16-17H2,1H3/t20-/m1/s1 ; Key:URKVBEKZCMUTQC-HXUWFJFHSA-N ;
	(verify)

AM-1220 is a drug that acts as a potent and moderately selective

Sterling Winthrop,^[2] but has subsequently been researched by many others, most notably the team led by Alexandros Makriyannis at the University of Connecticut. The (piperidin-2-yl)methyl side chain of AM-1220 contains a stereocenter, so there are two enantiomers with quite different potency, the (R)-enantiomer having a K_i of 0.27 nM at CB₁ while the (S)-enantiomer has a much weaker K_i of 217 nM.^[3]

Related compounds

A number of related compounds are known with similar potent cannabinoid activity, with modifications such as substitution of the indole ring at the 2- or 6-positions, the naphthoyl ring substituted at the 4-position or replaced by substituted benzoyl rings or other groups, or the 1-(N-methylpiperidin-2-ylmethyl) group replaced by similar heterocyclic groups such as N-methylpyrrolidin-2-ylmethyl or N-methylmorpholin-3-ylmethyl.

synthetic cannabis smoking blends in 2010.^[7]

Related 1-(N-methylpyrrolidin-2-ylmethyl) and 1-(N-methylmorpholin-3-ylmethyl) derivatives

Legal status

United States

in the United States of America all CB₁ receptor agonists of the 3-(1-naphthoyl)indole class such as AM-1220 are Schedule I Controlled Substances under the Controlled Substances Act s.^[8]

United Kingdom

it's illegal to supply, smuggle, distribute, transport, sell or trade the pharmaceutical drug under the Psychoactive Substances Act 2016 which was enforced on May26th 2016.

China

As of October 2015, AM-1220 is a controlled substance in China.^[9]

References

^ WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07
^ US patent 5068234, D'Ambra TE, et al., "3-arylcarbonyl-1-(C-attached-N-heteryl)-1H-indoles", granted 1991-11-26
doi:10.1016/0960-894X(95)00560-G
.

ProQuest 304624325
.

PMID 16134948
.

^ US patent 7820144, Makriyannis A, et al., "Receptor selective cannabimimetic aminoalkylindoles", granted 2010-10-26

^ Head Shop ‘Legal Highs’ Active Constituents Identification Chart (July - August 2010)

^ 21 U.S.C. § 812: Schedules of controlled substances

^ "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.

Retrieved from "https://en.wikipedia.org/w/index.php?title=AM-1220&oldid=1090390113"

[WO_2001_28557_A1-1] WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07

[US_5068234-2] US patent 5068234, D'Ambra TE, et al., "3-arylcarbonyl-1-(C-attached-N-heteryl)-1H-indoles", granted 1991-11-26

[3] :10.1016/0960-894X(95)00560-G
.

[liganDesign-4] ProQuest 304624325
.

[5] PMID 16134948
.

[US_7820144-6] US patent 7820144, Makriyannis A, et al., "Receptor selective cannabimimetic aminoalkylindoles", granted 2010-10-26

[7] Head Shop ‘Legal Highs’ Active Constituents Identification Chart (July - August 2010)

[8] 21 U.S.C. § 812: Schedules of controlled substances

[9] "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.

[2]

[3]

[7]

[8]

[9]