AP-238

AP-238
Legal status
Legal status	UK: Under Psychoactive Substances Act; US: The DEA is not of the opinion that AP-237 and derivatives are Controlled Substances, or analogues thereof. ;
Identifiers
	IUPAC name 1-[(2R,6S)-2,6-dimethyl-4-[(E)-3-phenylprop-2-enyl]piperazin-1-yl]propan-1-one;
CAS Number	(racemic) 4204-01-7 (racemic) ; 140924-11-4 (2R,6S enantiomer);
PubChem CID	124389619;
ChemSpider	4941886;
UNII	N26WML8AR7;
Chemical and physical data
Formula	C18H26N2O
Molar mass	286.419 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC(=O)N1[C@@H](CN(C[C@@H]1C)C/C=C/C2=CC=CC=C2)C;
	InChI InChI=1S/C18H26N2O/c1-4-18(21)20-15(2)13-19(14-16(20)3)12-8-11-17-9-6-5-7-10-17/h5-11,15-16H,4,12-14H2,1-3H3/b11-8+/t15-,16+; Key:JELNWDOXWGBBLO-QJBCGIKSSA-N;

AP-238 is an opioid designer drug related to drugs such as azaprocin and bucinnazine, with around the same potency as morphine.^[2] It was first discovered in Italy in the 1960s but was never marketed,^[3] subsequently appearing on the illicit market around 2020 and being detected in both Slovenia and the USA.^[4]^[5]

Quick Facts Legal status, Identifiers ...

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[1]
"2-Methyl-AP-237" (PDF). Office of Diversion Control. U.S Drug Enforcement Administration.
[2]
Fogarty MF, Vandeputte MM, Krotulski AJ, Papsun D, Walton SE, Stove CP, Logan BK (June 2022). "Toxicological and pharmacological characterization of novel cinnamylpiperazine synthetic opioids in humans and in vitro including 2-methyl AP-237 and AP-238". Archives of Toxicology. 96 (6): 1701–1710. doi:10.1007/s00204-022-03257-7. PMID 35275255. S2CID 247383361.
[3]
Cignarella G, Testa E (May 1968). "2,6-Dialkylpiperazines. IV. 1-Propionyl-4-substituted cis-2,6-dimethylpiperazines structurally related to the analgetic 8-acyl-3,8-diazabicyclo[3.2.1]octanes". Journal of Medicinal Chemistry. 11 (3): 592–594. doi:10.1021/jm00309a039. PMID 5656502.
[4]
{{cite web | url = https://www.policija.si/apps/nfl_response_web/0_Analytical_Reports_final/AP-238-ID-2185-20_report.pdf | title = Analytical Report. AP-238. 1-{2,6‐dimethyl‐4‐[(2E)‐3‐phenylprop‐2‐en‐1‐yl]piperazin‐1‐yl}propan-1-one. | work =Nacionalni Forenzični Laboratorij | date = 20 October 2020 }}
[5]
"AP-238" (PDF). NPS Discovery at CFSRE. Center for Forensic Science Research and Education (CFSRE). 11 November 2020.

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[1] [1]
"2-Methyl-AP-237" (PDF). Office of Diversion Control. U.S Drug Enforcement Administration.

[2] [2]
Fogarty MF, Vandeputte MM, Krotulski AJ, Papsun D, Walton SE, Stove CP, Logan BK (June 2022). "Toxicological and pharmacological characterization of novel cinnamylpiperazine synthetic opioids in humans and in vitro including 2-methyl AP-237 and AP-238". Archives of Toxicology. 96 (6): 1701–1710. doi:10.1007/s00204-022-03257-7. PMID 35275255. S2CID 247383361.

[3] [3]
Cignarella G, Testa E (May 1968). "2,6-Dialkylpiperazines. IV. 1-Propionyl-4-substituted cis-2,6-dimethylpiperazines structurally related to the analgetic 8-acyl-3,8-diazabicyclo[3.2.1]octanes". Journal of Medicinal Chemistry. 11 (3): 592–594. doi:10.1021/jm00309a039. PMID 5656502.

[4] [4]
{{cite web | url = https://www.policija.si/apps/nfl_response_web/0_Analytical_Reports_final/AP-238-ID-2185-20_report.pdf | title = Analytical Report. AP-238. 1-{2,6‐dimethyl‐4‐[(2E)‐3‐phenylprop‐2‐en‐1‐yl]piperazin‐1‐yl}propan-1-one. | work =Nacionalni Forenzični Laboratorij | date = 20 October 2020 }}

[5] [5]
"AP-238" (PDF). NPS Discovery at CFSRE. Center for Forensic Science Research and Education (CFSRE). 11 November 2020.

[2]

[3]

[4]

[5]

[1]

AP-238

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References

Legal status

Legal status	UK: Under Psychoactive Substances Act US: The DEA is not of the opinion that AP-237 and derivatives are Controlled Substances, or analogues thereof. ^[1]
Identifiers
IUPAC name 1-[(2R,6S)-2,6-dimethyl-4-[(E)-3-phenylprop-2-enyl]piperazin-1-yl]propan-1-one
CAS Number	(racemic) 4204-01-7 (racemic) 140924-11-4 (2R,6S enantiomer)
PubChem CID	124389619
ChemSpider	4941886
UNII	N26WML8AR7
Chemical and physical data
Formula	C₁₈H₂₆N₂O
Molar mass	286.419 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCC(=O)N1[C@@H](CN(C[C@@H]1C)C/C=C/C2=CC=CC=C2)C
InChI InChI=1S/C18H26N2O/c1-4-18(21)20-15(2)13-19(14-16(20)3)12-8-11-17-9-6-5-7-10-17/h5-11,15-16H,4,12-14H2,1-3H3/b11-8+/t15-,16+ Key:JELNWDOXWGBBLO-QJBCGIKSSA-N