Cyclopentylfentanyl

Opioid analgesic

CA: Schedule I
DE: NpSG (Industrial and scientific use only)
UK: Class A
US: Schedule I
Illegal in Sweden

Identifiers

IUPAC name

N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]cyclopentanecarboxamide

CAS Number

2088918-01-6

PubChem CID

126682248

ChemSpider

81367208

UNII

79NY29L78C

Chemical and physical dataFormulaC₂₅H₃₂N₂OMolar mass376.544 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

C1CCC(C1)C(=O)N(C2CCN(CC2)CCC3=CC=CC=C3)C4=CC=CC=C4

InChI

InChI=1S/C25H32N2O/c28-25(22-11-7-8-12-22)27(23-13-5-2-6-14-23)24-16-19-26(20-17-24)18-15-21-9-3-1-4-10-21/h1-6,9-10,13-14,22,24H,7-8,11-12,15-20H2
Key:PEASFKSPITUZGT-UHFFFAOYSA-N

Cyclopentylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug, mainly in Sweden and other Scandinavian countries.^[1]^[2]

Side effects

Side effects of fentanyl analogs are similar to those of fentanyl itself, which include itching, nausea and potentially serious respiratory depression, which can be life-threatening. Fentanyl analogs have killed hundreds of people throughout Europe and the former Soviet republics since the most recent resurgence in use began in Estonia in the early 2000s, and novel derivatives continue to appear.^[3] A new wave of fentanyl analogues and associated deaths began in around 2014 in the US, and have continued to grow in prevalence; especially since 2016 these drugs have been responsible for hundreds of overdose deaths every week.^[4]

Legal status

Cyclopentylfentanyl was made illegal in Sweden in January 2017.^[5]

Cyclopentylfentanyl is a Schedule I controlled drug in the USA since 1 February 2018.^[6]

References

^ Helander A, Bäckberg M, Signell P, Beck O (July 2017). "Intoxications involving acrylfentanyl and other novel designer fentanyls - results from the Swedish STRIDA project". Clinical Toxicology. 55 (6): 589–599. doi:10.1080/15563650.2017.1303141. PMID 28349714. S2CID 11978059.
^ Zawilska JB (2017). "An Expanding World of Novel Psychoactive Substances: Opioids". Frontiers in Psychiatry. 8: 110. doi:10.3389/fpsyt.2017.00110. PMC 5492455. PMID 28713291.
^ Mounteney J, Giraudon I, Denissov G, Griffiths P (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". The International Journal on Drug Policy. 26 (7): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.
^ Armenian P, Vo KT, Barr-Walker J, Lynch KL (May 2018). "Fentanyl, fentanyl analogs and novel synthetic opioids: A comprehensive review". Neuropharmacology. 134 (Pt A): 121–132. doi:10.1016/j.neuropharm.2017.10.016. PMID 29042317. S2CID 21404877.
^ Fem nya ämnen klassas som narkotika. Publicerat 25 Januari 2017
^ "Schedules of Controlled Substances: Temporary Placement of Seven Fentanyl-Related Substances in Schedule I". Federal Register. 1 February 2018.

Opioid receptor modulators

μ-opioid
(MOR)

Agonists (abridged; full list)	3-HO-PCP 7-Acetoxymitragynine 7-Hydroxymitragynine ψ-Akuammigine α-Chlornaltrexamine α-Narcotine Acetyldihydrocodeine Acetylfentanyl Acrylfentanyl Adrenorphin (metorphamide) AH-7921 Akuammicine Akuammidine Alfentanil Anileridine Apparicine β-Endorphin BAM-12P BAM-18P BAM-22P Benzhydrocodone Benzylmorphine Bezitramide Biphalin BU08070 Buprenorphine Butorphan Butorphanol Butyrfentanyl BW373U86 Carfentanil Casokefamide Cebranopadol Chloroxymorphamine Codeine DADLE DAMGO (DAGO) Dermorphin Desmetramadol (desmethyltramadol) Desomorphine Dextromoramide Dextropropoxyphene (propoxyphene) Dezocine Dimenoxadol Dimethylaminopivalophenone Eluxadoline Diamorphine (heroin) Dihydrocodeine Dihydroetorphine Dihydromorphine Dinalbuphine sebacate Diphenoxylate Dipipanone Dynorphin A Embutramide Endomorphin-1 Endomorphin-2 Eseroline Ethylmorphine Etorphine Fentanyl Fluorophen Frakefamide Furanylfentanyl Hemorphin-4 Herkinorin Hodgkinsine Hydrocodone Hydromorphinol Hydromorphone IBNtxA Ketamine Ketobemidone Kratom Laudanosine Lefetamine Leu-enkephalin Levacetylmethadol Levomethorphan Levorphanol Lexanopadol Loperamide Loxicodegol LS-115509 Matrine Meptazinol Met-enkephalin (metenkefalin) Methadone Metkefamide Metopon Mitragynine Mitragynine pseudoindoxyl Morphiceptin Morphine Nalbuphine NalBzOH Nalmexone Naltalimide Neopine NFEPP Nicocodeine Nicodicodine Nicomorphine Norketamine Nufenoxole Octreotide Oliceridine Oxycodegol OM-3-MNZ Oripavine Oxycodone Oxymorphazone Oxymorphonazine Oxymorphone Oxymorphone phenylhydrazone OxyPNPH Papaver somniferum (opium) Pentazocine Pericine Pethidine (meperidine) Phenazocine Phencyclidine Piminodine Piritramide PL-017 Prodine Propiram PZM21 Racemethorphan Racemorphan Remifentanil Salsolinol SC-17599 Sinomenine Sufentanil Tapentadol Tetrahydropapaveroline TH-030418 Thebaine Thienorphine Tianeptine Tilidine Tramadol Trimebutine TRIMU 5 TRV734 Tubotaiwine U-47700 Valorphin Viminol Xorphanol
Antagonists	(3S,4S)-Picenadol 2-(S)-N,N-(R)-Viminol 3CS-nalmefene 4-Caffeoyl-1,5-quinide 4′-Hydroxyflavanone 4',7-Dihydroxyflavone 6β-Naltrexol 6β-Naltrexol-d4 18-MC α-Gliadin β-Chlornaltrexamine β-Funaltrexamine Akuammine Alvimopan AM-251 Apigenin AT-076 Axelopran Bevenopran Catechin Catechin gallate Clocinnamox CTAP CTOP Cyclofoxy Cyprodime Diacetylnalorphine Diprenorphine ECG EGC Epicatechin Eptazocine Gemazocine Ginsenoside R Hyperoside Ibogaine JDTic Levallorphan Lobeline LY-255582 LY-2196044 Methocinnamox Methylnaltrexone Methylsamidorphan chloride Naldemedine Nalmefene Nalodeine (N-allylnorcodeine) Nalorphine Nalorphine dinicotinate Naloxazone Naloxegol Naloxol Naloxonazine Naloxone Naltrexazone Naltrexonazine Naltrexone Naltrindole Naringenin Noribogaine Oxilorphan Pawhuskin A Rimonabant Quadazocine Samidorphan Taxifolin

Agonists
(abridged;
full list)

Antagonists

δ-opioid
(DOR)

Agonists	3CS-nalmefene 6'-GNTI 7-SIOM ADL-5747 (PF-04856881) ADL-5859 Alazocine (SKF-10047) Amoxapine AR-M100390 (ARM390) AZD2327 β-Endorphin BAM-18P Biphalin BU-48 Butorphan Butorphanol BW373U86 Casokefamide Cebranopadol Codeine Cyclazocine DADLE Deltorphin A Deltorphin I Deltorphin II Desmethylclozapine Desmetramadol (desmethyltramadol) Dezocine Diamorphine (heroin) Dihydroetorphine Dihydromorphine DPDPE DPI-221 DPI-3290 DSLET Ethylketazocine Etorphine Fentanyl FIT Fluorophen Hemorphin-4 Hydrocodone Hydromorphone Ibogaine Isomethadone JNJ-20788560 KNT-127 Kratom Laudanosine Leu-enkephalin Levomethorphan Levorphanol Lexanopadol Lofentanil Met-enkephalin (metenkefalin) Metazocine Metkefamide Mitragynine Mitragynine pseudoindoxyl Morphine N-Phenethyl-14-ethoxymetopon Norbuprenorphine NalBzOH Oripavine Oxycodone Oxymorphone Pethidine (meperidine) Proglumide Racemethorphan Racemorphan RWJ-394674 Samidorphan SB-235863 SNC-80 SNC-162 TAN-67 (SB-205,607) TH-030418 Thebaine Thiobromadol (C-8813) Tonazocine Tramadol TRV250 Xorphanol Zenazocine
Antagonists	4',7-Dihydroxyflavone 5'-NTII 6β-Naltrexol 6β-Naltrexol-d4 α-Santolol β-Chlornaltrexamine Apigenin AT-076 Axelopran Bevenopran BNTX Catechin Catechin gallate Clocinnamox Diacetylnalorphine Diprenorphine ECG EGC Eluxadoline Epicatechin ICI-154129 ICI-174864 LY-255582 LY-2196044 Methylnaltrexone Methylnaltrindole N-Benzylnaltrindole Nalmefene Nalorphine Naltrexone Naltriben Naltrindole Naloxone Naringenin Noribogaine Pawhuskin A Quadazocine SDM25N SoRI-9409 Taxifolin Thienorphine

Agonists

Antagonists

κ-opioid
(KOR)

Agonists	3CS-nalmefene 6'-GNTI 8-CAC 18-MC 14-Methoxymetopon β-Chlornaltrexamine β-Funaltrexamine Adrenorphin (metorphamide) Akuammicine Alazocine (SKF-10047) Allomatrine Apadoline Asimadoline BAM-12P BAM-18P BAM-22P Big dynorphin Bremazocine BRL-52537 Butorphan Butorphanol BW373U86 Cebranopadol Ciprefadol CR665 Cyclazocine Cyclorphan Cyprenorphine Desmetramadol (desmethyltramadol) Diamorphine (heroin) Diacetylnalorphine Difelikefalin Dihydroetorphine Dihydromorphine Dinalbuphine sebacate Diprenorphine Dynorphin A Dynorphin B (rimorphin) Eluxadoline Enadoline Eptazocine Erinacine E Ethylketazocine Etorphine Fedotozine Fentanyl Gemazocine GR-89696 GR-103545 Hemorphin-4 Herkinorin HS665 Hydromorphone HZ-2 Ibogaine ICI-199,441 ICI-204,448 Ketamine Ketazocine Laudanosine Leumorphin (dynorphin B-29) Levallorphan Levomethorphan Levorphanol Lexanopadol Lofentanil LPK-26 Lufuradom Matrine MB-1C-OH Menthol Metazocine Metkefamide Mianserin Mirtazapine Morphine Moxazocine MR-2034 N-MPPP Nalbuphine NalBzOH Nalfurafine Nalmefene Nalodeine (N-allylnorcodeine) Nalorphine Naltriben Niravoline Norbuprenorphine Norbuprenorphine-3-glucuronide Noribogaine Norketamine Oripavine Oxilorphan Oxycodone Pentazocine Pethidine (meperidine) Phenazocine Proxorphan Racemethorphan Racemorphan RB-64 Salvinorin A (salvia) Salvinorin B ethoxymethyl ether Salvinorin B methoxymethyl ether Samidorphan Spiradoline (U-62,066) TH-030418 Thienorphine Tifluadom Tricyclic antidepressants (e.g., amitriptyline, desipramine, imipramine, nortriptyline) U-50488 U-54,494A U-69,593 Xorphanol
Antagonists	4′-Hydroxyflavanone 4',7-Dihydroxyflavone 5'-GNTI 6'-GNTI 6β-Naltrexol 6β-Naltrexol-d4 β-Chlornaltrexamine Buprenorphine/samidorphan Amentoflavone ANTI Apigenin Arodyne AT-076 Aticaprant Axelopran AZ-MTAB Binaltorphimine BU09059 Buprenorphine Catechin Catechin gallate CERC-501 (LY-2456302) Clocinnamox CVL-354 Cyclofoxy Dezocine DIPPA EGC ECG Epicatechin Hyperoside JDTic LY-255582 LY-2196044 LY-2444296 LY-2459989 LY-2795050 MeJDTic Methylnaltrexone ML190 ML350 MR-2266 N-Fluoropropyl-JDTic Naloxone Naltrexone Naltrindole Naringenin Navacaprant Norbinaltorphimine Noribogaine Pawhuskin A PF-4455242 RB-64 Quadazocine Taxifolin UPHIT Zyklophin

Agonists

3CS-nalmefene
6'-GNTI
8-CAC
18-MC
14-Methoxymetopon
β-Chlornaltrexamine
β-Funaltrexamine
Adrenorphin (metorphamide)
Akuammicine
Alazocine (SKF-10047)
Allomatrine
Apadoline
Asimadoline
BAM-12P
BAM-18P
BAM-22P
Big dynorphin
Bremazocine
BRL-52537
Butorphan
Butorphanol
BW373U86
Cebranopadol
Ciprefadol
CR665
Cyclazocine
Cyclorphan
Cyprenorphine
Desmetramadol (desmethyltramadol)
Diamorphine (heroin)
Diacetylnalorphine
Difelikefalin
Dihydroetorphine
Dihydromorphine
Dinalbuphine sebacate
Diprenorphine
Dynorphin A
Dynorphin B (rimorphin)
Eluxadoline
Enadoline
Eptazocine
Erinacine E
Ethylketazocine
Etorphine
Fedotozine
Fentanyl
Gemazocine
GR-89696
GR-103545
Hemorphin-4
Herkinorin
HS665
Hydromorphone
HZ-2
Ibogaine
ICI-199,441
ICI-204,448
Ketamine
Ketazocine
Laudanosine
Leumorphin (dynorphin B-29)
Levallorphan
Levomethorphan
Levorphanol
Lexanopadol
Lofentanil
LPK-26
Lufuradom
Matrine
MB-1C-OH
Menthol
Metazocine
Metkefamide
Mianserin
Mirtazapine
Morphine
Moxazocine
MR-2034
N-MPPP
Nalbuphine
NalBzOH
Nalfurafine
Nalmefene
Nalodeine (N-allylnorcodeine)
Nalorphine
Naltriben
Niravoline
Norbuprenorphine
Norbuprenorphine-3-glucuronide
Noribogaine
Norketamine
Oripavine
Oxilorphan
Oxycodone
Pentazocine
Pethidine (meperidine)
Phenazocine
Proxorphan
Racemethorphan
Racemorphan
RB-64
Salvinorin A (salvia)
Salvinorin B ethoxymethyl ether
Salvinorin B methoxymethyl ether
Samidorphan
Spiradoline (U-62,066)
TH-030418
Thienorphine
Tifluadom
Tricyclic antidepressants (e.g., amitriptyline, desipramine, imipramine, nortriptyline)
U-50488
U-54,494A
U-69,593
Xorphanol

Antagonists

Nociceptin
(NOP)

Agonists	(Arg14,Lys15)Nociceptin ((pF)Phe⁴)Nociceptin(1-13)NH₂ (Phe¹Ψ(CH₂-NH)Gly²)Nociceptin(1-13)NH₂ Ac-RYYRWK-NH₂ Ac-RYYRIK-NH₂ BU08070 Buprenorphine Cebranopadol Dihydroetorphine Etorphine JNJ-19385899 Levomethorphan Levorphanol Lexanopadol MCOPPB MT-7716 NNC 63-0532 Nociceptin (orphanin FQ) Nociceptin (1-11) Nociceptin (1-13)NH₂ Norbuprenorphine Racemethorphan Racemorphan Ro64-6198 Ro65-6570 SCH-221510 SCH-486757 SR-8993 SR-16435 Sunobinop (S-117957) TH-030418
Antagonists	(Nphe¹)Nociceptin(1-13)NH₂ AT-076 BAN-ORL-24 BTRX-246040 (LY-2940094) J-113,397 JTC-801 NalBzOH Nociceptin (1-7) Nocistatin SB-612,111 SR-16430 Thienorphine Trap-101 UFP-101

Agonists