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AP-238

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From Wikipedia, the free encyclopedia

Opioid designer drug

Pharmaceutical compound

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.^[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)
PubChemCID	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 anopioid designer drug related to drugs such asazaprocin andbucinnazine, with around the same potency asmorphine.^[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]

References

[edit]

^"2-Methyl-AP-237"(PDF).Office of Diversion Control. U.S Drug Enforcement Administration.
^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.Bibcode:2022ArTox..96.1701F.doi:10.1007/s00204-022-03257-7.PMID 35275255.S2CID 247383361.
^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.
^{{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 }}
^"AP-238"(PDF).NPS Discovery at CFSRE. Center for Forensic Science Research and Education (CFSRE). 11 November 2020.

Opioid receptor modulators

μ-opioid
(MOR)

Agonists
(abridged;
full list)

Antagonists

δ-opioid
(DOR)

Agonists

Antagonists

κ-opioid
(KOR)

Agonists

Antagonists

Nociceptin
(NOP)

Agonists

Antagonists

Others

Propeptides:β-Lipotropin (proendorphin)
Prodynorphin
Proenkephalin
Pronociceptin
Proopiomelanocortin (POMC)

Others:Kyotorphin (met-enkephalin releaser/degradation stabilizer)

v t e Arylpiperazines
Phenylpiperazines	1-Phenylpiperazine (1-PP; PP) 3,4-CFP 2C-B-PP Acaprazine Antrafenine Aripiprazole Batoprazine Bifeprunox BRL-15,572 Ciprofloxacin Dapiprazole DCPP DMPP Diphenylpiperazine Dropropizine EGIS-7625 EGIS-12,233 Elopiprazole Eltoprazine Enpiprazole Ensaculin Etoperidone Flesinoxan Fluanisone Flibanserin Fluprazine Itraconazole Ketoconazole Levodropropizine Lorpiprazole mCPP Mefway MeOPP Mepiprazole Naftopidil Naluzotan Nefazodone Niaprazine Oxypertine Pardoprunox pCPP pFPP Posaconazole S-14,506 S-14,671 S-15,535 SB-258,585 SB-271,046 SB-357,134 SB-399,885 Sonepiprazole TFMPP Tolpiprazole Trazodone Urapidil Vesnarinone Vilazodone Vortioxetine WAY-100,135 WAY-100,635
Benzylpiperazines	2C-B-BZP 3-Methylbenzylpiperazine Befuraline Bifeprunox Buclizine BZP Chlorbenzoxamine DBZP EGIS-7625 Fipexide Imatinib MBZP MDBZP Meclozine Methoxypiperamide NSI-189 Piberaline Piribedil RN-1747 Sunifiram Trimetazidine Vesnarinone
Naphthylpiperazines	1-Naphthylpiperazine (1-NP) 2-Naphthylpiperazine (2-NP) CSP-2503 F-11,461 S-14,506 S-14671
Quinolinylpiperazines	FPPQ 6-Nitroquipazine Isoquipazine Quipazine
Diphenylalkylpiperazines	AD-1211 Almitrine Amperozide BRL-15,572 Buclizine BW373U86 Cetirizine Chlorbenzoxamine Chlorcyclizine Cinnarizine Clocinizine Cyclizine DBL-583 Diphenpipenol Diphenylmethylpiperazine Dotarizine DPI-221 DPI-287 DPI-3290 GBR-12,783 GBR-12,935 GBR-13,069 GBR-13,098 GBR-13,119 Hydroxyzine JJC8-088 Lidoflazine Manidipine Meclozine MT-45 Oxatomide SNC-80 Vanoxerine
Pyrimidinylpiperazines	Buspirone Dasatinib Eptapirone Gepirone Ipsapirone Piribedil Pyrimidinylpiperazine Revospirone Tandospirone Tirilazad Trimazosin Umespirone Zalospirone
Pyridinylpiperazines	Atevirdine Azaperone Delavirdine Mirtazapine ORG-12962 Pyridinylpiperazine
Benzo(iso)thiazolyl piperazines	Lurasidone Perospirone Revospirone Tiospirone Ziprasidone
Tricyclic-linked piperazines	Amoxapine Clopenthixol Clorotepine Clozapine Cyanothepin Doclothepin Docloxythepin Flupentixol Fluphenazine Isofloxythepin Loxapine Meperathiepin Metitepine Octomethothepin Olanzapine Opipramol Oxyclothepin Oxyprothepin Peradithiepin Perathiepin Perazine Perphenazine Pirenzepine Prochlorperazine Thiethylperazine Thiothixene Trifluoperazine Trifluthepin Zuclopenthixol
Others/uncategorized	AP-238 Azimilide Bucinnazine Cinepazet Cinepazic acid Cinepazide CPD-1 Cyclohexylpiperazine Hexocyclium Indinavir JNJ-7777120 Lodenafil MK-212 Mirodenafil PB-28 Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VUF-6002 WY-46824 Zipeprol