Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and U-47700: Difference between pages

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Rescuing 1 sources and tagging 0 as dead.) #IABot (v2.0.9.5) (Maxim Masiutin - 19348
 
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{{Short description|Opioid analgesic}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid [{{fullurl:AH-7921|oldid=476511013}} 476511013] of page [[AH-7921]] with values updated to verified values.}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 451554906
| verifiedrevid = 477235538
| IUPAC_name = 3,4-dichloro-N-[(1-dimethylamino)cyclohexylmethyl]benzamide
| IUPAC_name = 3,4-Dichloro-''N''-[(1''R'',2''R'')-2-(dimethylamino)cyclohexyl]-''N''-methylbenzamide
| image = AH-7921_structure.png
| image = U-47700 fixedstructure.svg
| width = 200
| image2 = U-47700.png

<!--Clinical data-->
<!--Clinical data-->
| tradename =
| tradename =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category =
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_AU = S9
| legal_CA =
| legal_BR = F1
| legal_UK =
| legal_CA = Schedule I
| legal_US =
| legal_DE = Anlage II
| legal_status =
| legal_UK = Class A
| legal_US = Schedule I
| routes_of_administration =
| legal_status = In general Unscheduled, Illegal in Finland, China and Sweden

| routes_of_administration =
<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| bioavailability =
| bioavailability =
| protein_bound =
| protein_bound =
| metabolism =
| metabolism =
| elimination_half-life =
| elimination_half-life =
| excretion =
| excretion =

<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref =
| CAS_number = <!-- blanked - oldvalue: 55154-30-8 -->
| CAS_number = 82657-23-6
| ATC_prefix = none
| ATC_prefix =
| ATC_suffix =
| ATC_suffix =
| PubChem = 187760
| PubChem = 13544016
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C22730
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 163208
| ChemSpiderID = 23113403
| synonyms = AH-7921
| ChEMBL = 277572
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6IY4WX208T


<!--Chemical data-->
<!--Chemical data-->
| C=16 | H=22 | Cl=2 | N=2 | O=1
| C=16 | H=22 | Cl=2 | N=2 | O=1
| molecular_weight = 329.265 g/mol
| molecular_weight =
| smiles = Clc1ccc(cc1Cl)C(=O)NCC2(N(C)C)CCCCC2
| smiles = ClC1=C(C=CC(=C1)C(=O)N(C)[C@@H]2CCCC[C@H]2N(C)C)Cl
| InChI = 1/C16H22Cl2N2O/c1-20(2)16(8-4-3-5-9-16)11-19-15(21)12-6-7-13(17)14(18)10-12/h6-7,10H,3-5,8-9,11H2,1-2H3,(H,19,21)
| StdInChI = 1S/C16H22Cl2N2O/c1-19(2)14-6-4-5-7-15(14)20(3)16(21)11-8-9-12(17)13(18)10-11/h8-10,14-15H,4-7H2,1-3H3/t14-,15-/m1/s1
| StdInChIKey = JGPNMZWFVRQNGU-HUUCEWRRSA-N
| InChIKey = JMZROFPPEXCTST-UHFFFAOYAO
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C16H22Cl2N2O/c1-20(2)16(8-4-3-5-9-16)11-19-15(21)12-6-7-13(17)14(18)10-12/h6-7,10H,3-5,8-9,11H2,1-2H3,(H,19,21)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JMZROFPPEXCTST-UHFFFAOYSA-N
}}
}}

'''U-47700''', also known as '''U4''', '''pink heroin''', '''pinky''', and '''pink''', is an [[opioid]] [[analgesic]] drug developed by a team at [[Upjohn]] in the 1970s<ref>{{cite web | url=https://patents.google.com/patent/US4098904 | title=Patent US4098904 - Analgesic N-(2-aminocycloaliphatic)benzamides | date=4 July 1978 | vauthors = Szmuszkovicz J }}</ref> which has around 7.5 times the potency of [[morphine]] in animal models.<ref>{{cite journal | vauthors = Cheney BV, Szmuszkovicz J, Lahti RA, Zichi DA | title = Factors affecting binding of trans-N-[2-(methylamino)cyclohexyl]benzamides at the primary morphine receptor | journal = Journal of Medicinal Chemistry | volume = 28 | issue = 12 | pages = 1853–1864 | date = December 1985 | pmid = 2999404 | doi = 10.1021/jm00150a017 }}</ref><ref>{{cite journal | vauthors = Harper NJ, Veitch GB, Wibberley DG | title = 1-(3,4-Dichlorobenzamidomethyl)cyclohexyldimethylamine and related compounds as potential analgesics | journal = Journal of Medicinal Chemistry | volume = 17 | issue = 11 | pages = 1188–1193 | date = November 1974 | pmid = 4416926 | doi = 10.1021/jm00257a012 }}</ref><ref>{{cite journal | vauthors = Szmuszkovicz J, Von Voigtlander PF | title = Benzeneacetamide amines: structurally novel non-m mu opioids | journal = Journal of Medicinal Chemistry | volume = 25 | issue = 10 | pages = 1125–1126 | date = October 1982 | pmid = 6128415 | doi = 10.1021/jm00352a005 }}</ref>
[[File:Sample of U-47700.png|thumb|Physical Sample of U-47700<ref>{{cite journal | vauthors = Alzghari SK, Fleming SW, Rambaran KA, Long JE, Burkhart S, An J, Furmaga J | title = U-47700: An Emerging Threat | journal = Cureus | volume = 9 | issue = 10 | pages = e1791 | date = October 2017 | pmid = 29282436 | pmc = 5741271 | doi = 10.7759/cureus.1791 | doi-access = free }}</ref>]]
U-47700 is a structural isomer of the earlier opioid [[AH-7921]]<ref>{{cite journal | vauthors = Brittain RT, Kellett DN, Neat ML, Stables R | title = Proceedings: Anti-nociceptive effects in N-substituted cyclohexylmethylbenzamides | journal = British Journal of Pharmacology | volume = 49 | issue = 1 | pages = 158P–159P | date = September 1973 | pmid = 4207044 | pmc = 1776456 | doi = 10.1111/j.1476-5381.1973.tb08279.x }}</ref> and the result of a great deal of work elucidating the [[quantitative structure–activity relationship]] of the scaffold. Upjohn looked for the key [[moiety (chemistry)|moieties]] which gave the greatest activity<ref>{{cite book| vauthors = Michalson ET, Szmuszkovicz J |title=Progress in Drug Research |chapter=Medicinal agents incorporating the 1,2-diamine functionality|journal=Progress in Drug Research. Fortschritte der Arzneimittelforschung. Progres des Recherches Pharmaceutiques |publisher=Birkhäuser Basel|volume=33|date=1989|isbn=9783034891462|pages=135–149|doi=10.1007/978-3-0348-9146-2_6|pmid=2687936}}</ref> and posted over a dozen patents on related compounds, each optimizing one moiety<ref>{{cite web | url=https://patents.google.com/patent/US3258489 | title=Patent US US3258489 - N-(1-aminocyclohexylmethyl)anilines and N-(1-nitrocyclohexylmethyl)anilines | date=28 June 1966 | vauthors = Mullins DD }}</ref><ref>{{cite web | url=https://patents.google.com/patent/US3975443 | title=Patent US3975443 - 1-(3,4-dichlorobenzamidomethyl)-cyclohexyldimethylamine | date=17 August 1976 | vauthors = Harper NJ, Veitch GB }}</ref><ref>{{cite web | url=https://patents.google.com/patent/US3499033 | title=Patent US3499033 - Ethers of α-phenyl-2-aminocycloalkanemethanols | date=3 March 1970 | vauthors = Szmuszkovicz J }}</ref><ref>{{cite web | url=https://patents.google.com/patent/US3510492 | title=Patent US3510492 - 2-anilino and 2-anilinomethyl cycloalkylamines | date=5 May 1970 | vauthors = Szmuszkovicz J }}</ref><ref>{{cite web | url=https://patents.google.com/patent/US3647804 | title=Patent US3647804 - Cycloalkanecarboxamides | date=7 March 1972 | vauthors = Rynbrandt RH, Skaletzky LL }}</ref><ref>{{cite web | url=https://patents.google.com/patent/US3825595 | title=Patent US3825595 - N-cyclopentyl-N-2-hydroxyalkyl-ring-substituted benzamides | date=23 July 1974 | vauthors = Roll W }}</ref><ref>{{cite web | url=https://patents.google.com/patent/US4049663 | title=Patent US4049663 - Ethylene diamine derivatives | date=20 September 1977 | vauthors = Harper NJ, Veitch GB }}</ref><ref>{{cite web | url=https://patents.google.com/patent/US4463013 | title=Patent US4463013 - Oxygen substituted amino-cyclohexyl-benzeneacetamides and -benzamides as water diuretic drugs | date=9 April 1982 | vauthors = Collins RJ, Kaplan LJ, Ludens JH, Von Voigtlander PF }}</ref> until they discovered that U-47700 was the most active.<ref>{{cite book| vauthors = Casy AF, Parfitt RT |title=Opioid Analgesics |chapter=Miscellaneous Groups of Analgesics|publisher=Springer US|date=1986|isbn=9781489905857|pages=385–403|doi=10.1007/978-1-4899-0585-7_11}}</ref>

U-47700 became the lead compound of selective kappa-opioid receptor ligands such as [[U-50488]], U-51754 (containing a [[pyrrolidine]] rather than a [[dimethylamine]] substituent) and [[U-69,593]], which share very similar structures.<ref>{{cite journal | vauthors = Szmuszkovicz J, Zhao S, Totleben MJ, Mizsak SA, Freeman JP |title=Phenanthridone Analogs of the Opiate Agonist U-47,700 in the ''trans''-1,2-Diaminocyclohexane Benzamide Series|journal=Heterocycles|volume=52|issue=1|pages=325–332|doi=10.3987/com-99-s27 |year=2000|doi-broken-date=31 January 2024 }}</ref><ref name="NIDA">{{cite journal | vauthors = Loew G, Lawson J, Toll L, Frenking G, Berzetei-Gurske I, Polgar W | title = Structure activity studies of two classes of beta-amino-amides: the search for kappa-selective opioids | journal = NIDA Research Monograph | volume = 90 | pages = 144–151 | date = 1988 | pmid = 2855852 | url = https://archives.drugabuse.gov/pdf/monographs/90.pdf }}</ref> Although not used medically, the selective kappa ligands are used in research.<ref>{{cite book |title=Progress in Drug Research|volume=52| vauthors = Szmuszkovicz J |chapter=U-50,488 and the к receptor: A personalized account covering the period 1973 to 1990|journal=Progress in Drug Research. Fortschritte der Arzneimittelforschung. Progres des Recherches Pharmaceutiques |publisher=Birkhäuser Basel|date=1999|isbn=9783034887304|doi=10.1007/978-3-0348-8730-4_4|pmid=10396128|pages=167–195}}</ref><ref>{{cite journal | vauthors = Tsibulnikov SY, Maslov LN, Mukhomedzyanov AV, Krylatov AV, Tsibulnikova MR, Lishmanov YB | title = Prospects of Using of κ-Opioid Receptor Agonists U-50,488 and ICI 199,441 for Improving Heart Resistance to Ischemia/Reperfusion | journal = Bulletin of Experimental Biology and Medicine | volume = 159 | issue = 6 | pages = 718–721 | date = October 2015 | pmid = 26519268 | doi = 10.1007/s10517-015-3057-8 | s2cid = 1046853 }}</ref>

==Pharmacology==
U-47700 is an agonist of the [[μ-opioid receptor]] (K<sub>i</sub> 11.1 ± 0.4 nM) and possesses significantly lower affinity for the [[κ-opioid receptor]] (K<sub>i</sub> 287 ± 24 nM) and [[δ-opioid receptor]] (K<sub>i</sub> 1220 ± 82 nM). U-47700 is approximately 10-fold more potent than morphine in rats, although the binding of U-47700 is 2-4 times weaker than morphine at all three opioid receptors.<ref>{{cite journal | vauthors = Truver MT, Smith CR, Garibay N, Kopajtic TA, Swortwood MJ, Baumann MH | title = Pharmacodynamics and pharmacokinetics of the novel synthetic opioid, U-47700, in male rats | journal = Neuropharmacology | volume = 177 | pages = 108195 | date = October 2020 | pmid = 32533977 | pmc = 7554234 | doi = 10.1016/j.neuropharm.2020.108195 | s2cid = 219559700 }}</ref>

The metabolism of U-47700 in humans involves mono- and didesmethylation followed by hydroxylation.<ref>{{cite journal | vauthors = Krotulski AJ, Mohr AL, Papsun DM, Logan BK | title = Metabolism of novel opioid agonists U-47700 and U-49900 using human liver microsomes with confirmation in authentic urine specimens from drug users | journal = Drug Testing and Analysis | volume = 10 | issue = 1 | pages = 127–136 | date = January 2018 | pmid = 28608586 | doi = 10.1002/dta.2228 | doi-access = free }}</ref> The desmethyl metabolites of U-47700 have negligible affinity for the opioid receptors and are not thought to contribute to the activity of U-47700.<ref>{{cite journal | vauthors = Nordmeier F, Cannaert A, Stove CP, Schmidt PH, Meyer MR, Schaefer N | title = Are the N-demethylated metabolites of U-47700 more active than their parent compound? In vitro μ-opioid receptor activation of N-desmethyl-U-47700 and N,N-bisdesmethyl-U-47700 | journal = Drug Testing and Analysis | volume = 14 | issue = 4 | pages = 713–717 | date = April 2022 | pmid = 34669261 | doi = 10.1002/dta.3182 | url = https://biblio.ugent.be/publication/8751266 | hdl = 1854/LU-8751266 | hdl-access = free }}</ref><ref>{{cite journal | vauthors = Truver MT, Smith CR, Garibay N, Kopajtic TA, Swortwood MJ, Baumann MH | title = Pharmacodynamics and pharmacokinetics of the novel synthetic opioid, U-47700, in male rats | journal = Neuropharmacology | volume = 177 | pages = 108195 | date = October 2020 | pmid = 32533977 | pmc = 7554234 | doi = 10.1016/j.neuropharm.2020.108195 | s2cid = 219559700 }}</ref>

== Side effects ==

U-47700 has never been studied in humans, but it would be expected to produce effects similar to those of other potent opioid agonists, including strong analgesia, sedation, euphoria, constipation, itching and respiratory depression which could be harmful or fatal.<ref>{{cite web | url=http://www.nbcdfw.com/news/local/New-Synthetic-Opioid-Surfaces-in-North-Texas-371528161.html | title=New Synthetic Opioid Surfaces in North Texas | publisher=NBCDFW | date=9 March 2016 | vauthors = Davis TL }}</ref><ref>{{cite journal | vauthors = Jones MJ, Hernandez BS, Janis GC, Stellpflug SJ | title = A case of U-47700 overdose with laboratory confirmation and metabolite identification | journal = Clinical Toxicology | volume = 55 | issue = 1 | pages = 55–59 | date = January 2017 | pmid = 27549165 | doi = 10.1080/15563650.2016.1209767 | s2cid = 27920117 }}</ref><ref>{{cite journal | vauthors = Domanski K, Kleinschmidt KC, Schulte JM, Fleming S, Frazee C, Menendez A, Tavakoli K | title = Two cases of intoxication with new synthetic opioid, U-47700 | journal = Clinical Toxicology | volume = 55 | issue = 1 | pages = 46–50 | date = January 2017 | pmid = 27432224 | doi = 10.1080/15563650.2016.1209763 | s2cid = 46228909 }}</ref><ref>{{cite journal | vauthors = Ruan X, Chiravuri S, Kaye AD | title = Comparing fatal cases involving U-47700 | journal = Forensic Science, Medicine, and Pathology | volume = 12 | issue = 3 | pages = 369–371 | date = September 2016 | pmid = 27421264 | doi = 10.1007/s12024-016-9795-8 | s2cid = 24201474 }}</ref><ref>{{cite journal | vauthors = Elliott SP, Brandt SD, Smith C | title = The first reported fatality associated with the synthetic opioid 3,4-dichloro-N-[2-(dimethylamino)cyclohexyl]-N-methylbenzamide (U-47700) and implications for forensic analysis | journal = Drug Testing and Analysis | volume = 8 | issue = 8 | pages = 875–879 | date = August 2016 | pmid = 27232154 | doi = 10.1002/dta.1984 | s2cid = 205762837 | url = https://researchonline.ljmu.ac.uk/id/eprint/3396/1/DTA-16-0092.R1.pdf }}</ref><ref>{{cite journal | vauthors = Armenian P, Olson A, Anaya A, Kurtz A, Ruegner R, Gerona RR | title = Fentanyl and a Novel Synthetic Opioid U-47700 Masquerading as Street "Norco" in Central California: A Case Report | journal = Annals of Emergency Medicine | volume = 69 | issue = 1 | pages = 87–90 | date = January 2017 | pmid = 27473610 | doi = 10.1016/j.annemergmed.2016.06.014 }}</ref><ref>{{cite journal | vauthors = Helander A, Bäckberg M | title = New Psychoactive Substances (NPS) - the Hydra monster of recreational drugs | journal = Clinical Toxicology | volume = 55 | issue = 1 | pages = 1–3 | date = January 2017 | pmid = 27549399 | doi = 10.1080/15563650.2016.1217003 | s2cid = 35645218 }}</ref><ref name=":0">{{cite journal | vauthors = Rambaran KA, Fleming SW, An J, Burkhart S, Furmaga J, Kleinschmidt KC, Spiekerman AM, Alzghari SK | display-authors = 6 | title = U-47700: A Clinical Review of the Literature | journal = The Journal of Emergency Medicine | volume = 53 | issue = 4 | pages = 509–519 | date = October 2017 | pmid = 28911989 | doi = 10.1016/j.jemermed.2017.05.034 }}</ref> Tachycardia was another side effect encountered with U-47700 use.<ref name=":0" /> Tolerance and dependence would be expected to develop.<ref>{{cite journal | vauthors = Kimergård A, Breindahl T, Hindersson P, Deluca P | title = Tampering of opioid analgesics: a serious challenge for public health? | journal = Addiction | volume = 111 | issue = 10 | pages = 1701–1702 | date = October 2016 | pmid = 27273814 | doi = 10.1111/add.13436 | doi-access = free }}</ref>

=== Deaths ===

Combined consumption of U-47700 with [[fentanyl]] and [[flubromazepam]] caused one fatality in Belgium and Germany, respectively.<ref>{{cite journal | vauthors = Coopman V, Blanckaert P, Van Parys G, Van Calenbergh S, Cordonnier J | title = A case of acute intoxication due to combined use of fentanyl and 3,4-dichloro-N-[2-(dimethylamino)cyclohexyl]-N-methylbenzamide (U-47700) | journal = Forensic Science International | volume = 266 | pages = 68–72 | date = September 2016 | pmid = 27235591 | doi = 10.1016/j.forsciint.2016.05.001 | hdl-access = free | hdl = 1854/LU-8509152 }}</ref><ref>{{cite web | url=http://deredactie.be/cm/vrtnieuws/binnenland/1.2558454 | title=Twee doden in België door overdosis met fentanylpleisters | publisher=Deredactie | date=29 January 2016 | language=nl}}</ref><ref>{{cite journal | vauthors = Koch K, Auwärter V, Hermanns-Clausen M, Wilde M, Neukamm MA | title = Mixed intoxication by the synthetic opioid U-47700 and the benzodiazepine flubromazepam with lethal outcome: Pharmacokinetic data | journal = Drug Testing and Analysis | volume = 10 | issue = 8 | pages = 1336–1341 | date = April 2018 | pmid = 29637722 | doi = 10.1002/dta.2391 }}</ref> One death was reported in Ireland,<ref>{{cite news | url=https://www.irishtimes.com/news/ireland/irish-news/young-people-playing-russian-roulette-with-drugs-warns-coroner-1.3436602 | title=Young people playing Russian roulette with drugs, warns coroner | newspaper=[[The Irish Times]] }}</ref> another one in Italy.<ref>{{Cite news|url=http://www.lastampa.it/2017/10/20/cronaca/ucciso-dalla-droga-comprata-online-KBh25kwHaRNLZiqfP76GvK/pagina.html|title=Torino, ucciso dalla droga comprata online: la prima vittima italiana dell'U47700|work=LaStampa.it|access-date=2017-10-20|language=it-IT}}</ref> 17 opioid overdoses and several deaths in the United States had initially been associated with U-47700 in April 2016,<ref>{{cite news| vauthors = Zalkind S |title=Synthetic opiate makers stay step ahead of US drug laws as overdose cases rise|url=https://www.theguardian.com/world/2016/apr/11/synthetic-opiates-drug-laws-w-18-fentanyl|newspaper=The Guardian|date=11 April 2016|issn=0261-3077}}</ref> as of September 2016 at least 15 fatalities were confirmed. By December 2017, at least 46 fatalities had been associated with the use of U-47700.<ref>{{cite news | url=http://bigstory.ap.org/article/c36bdfeac0a448d881c1fbddd18dab6a/new-synthetic-drug-u-47700-has-states-rushing-stop-spread | title=New synthetic drug U-47700 has states rushing to stop spread | date=6 June 2016 | agency=Associated Press | vauthors = Draper B }}</ref><ref>{{cite journal | vauthors = Schneir A, Metushi IG, Sloane C, Benaron DJ, Fitzgerald RL | title = Near death from a novel synthetic opioid labeled U-47700: emergence of a new opioid class | journal = Clinical Toxicology | volume = 55 | issue = 1 | pages = 51–54 | date = January 2017 | pmid = 27448790 | doi = 10.1080/15563650.2016.1209764 | s2cid = 25206275 | url = https://escholarship.org/uc/item/9ps608xb }}</ref><ref>{{cite journal | vauthors = Mohr AL, Friscia M, Papsun D, Kacinko SL, Buzby D, Logan BK | title = Analysis of Novel Synthetic Opioids U-47700, U-50488 and Furanyl Fentanyl by LC-MS/MS in Postmortem Casework | journal = Journal of Analytical Toxicology | volume = 40 | issue = 9 | pages = 709–717 | date = November 2016 | pmid = 27590036 | doi = 10.1093/jat/bkw086 | doi-access = free }}</ref><ref>{{Cite web|title=19 Recent Deaths Associated With Synthetic Opioids; State Officials Urge Awareness|work=NC Department of Health and Human Services|date=24 March 2016|url=https://www.ncdhhs.gov/news/press-releases/19-recent-deaths-associated-synthetic-opioids-state-officials-urge-awareness}}</ref><ref name="DEA">{{Cite web|title=Proposed Rule: Schedules of Controlled Substances: Temporary Placement of U-47700 Into Schedule I|author=Drug Enforcement Administration (DEA)|publisher=Federal Register|date=7 September 2016|url=https://www.federalregister.gov/documents/2016/09/07/2016-21477/schedules-of-controlled-substances-temporary-placement-of-u-47700-into-schedule-i}}</ref><ref>{{cite journal | vauthors = Krotulski AJ, Mohr AL, Papsun DM, Logan BK | title = Metabolism of novel opioid agonists U-47700 and U-49900 using human liver microsomes with confirmation in authentic urine specimens from drug users | journal = Drug Testing and Analysis | volume = 10 | issue = 1 | pages = 127–136 | date = January 2018 | pmid = 28608586 | doi = 10.1002/dta.2228 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Moody MT, Diaz S, Shah P, Papsun D, Logan BK | title = Analysis of fentanyl analogs and novel synthetic opioids in blood, serum/plasma, and urine in forensic casework | journal = Drug Testing and Analysis | volume = 10 | issue = 9 | pages = 1358–1367 | date = September 2018 | pmid = 29633785 | doi = 10.1002/dta.2393 | s2cid = 4758125 }}</ref>

U-47700 was found in combination with fentanyl during the autopsy of the American artist [[Prince (musician)|Prince]] in 2016.<ref>{{cite web|url=https://www.forbes.com/sites/davidkroll/2016/11/30/furanyl-fentanyl-joins-u-47700-as-the-second-illicit-opioid-dea-banned-in-november/|title=Furanyl Fentanyl Joins U-47,700 As The Second Illicit Opioid Banned By DEA In November|website=[[Forbes]]}}</ref>

===Detection in biological fluids===
U-47700 may be measured in serum, plasma, blood or urine to monitor for abuse, confirm a diagnosis of poisoning, or assist in a medicolegal death investigation. Serum or blood U-47700 concentrations are expected to be in a range of 10–250 μg/L in intoxicated patients and 100–1,500 μg/L in deceased victims of acute overdosage. The detection usually involves analysis by [[liquid chromatography-mass spectrometry]].<ref>Baselt, R. (2017) ''Disposition of Toxic Drugs and Chemicals in Man'', 11th edition, Biomedical Publications, Foster City, CA, pp. 2208.</ref>

== Society and culture ==
Common street names for U-47700 include pinky, pink, and U4.<ref name="Pinky Pubchem">{{cite web |title=Pinky |url=https://pubchem.ncbi.nlm.nih.gov/compound/Pinky |website=pubchem.ncbi.nlm.nih.gov |publisher=National Library of Medicine |access-date=16 July 2020 |language=en}}</ref>

=== Legal status ===

Following its sale as a [[designer drug]], U-47700 was made illegal in Sweden on January 26, 2016.<ref>{{cite web | url=https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2015/november/31-nya-amnen-kan-klassas-som-narkotika-eller-halsofarlig-vara/ | title=31 nya ämnen kan klassas som narkotika eller hälsofarlig vara | publisher=Folkhälsomyndigheten | language=sv | date=November 2015}}</ref>

U-47700 was emergency scheduled in Ohio on May 3, 2016, by [[executive order]] of Governor [[John Kasich]].<ref>{{cite web | url=http://governor.ohio.gov/Portals/0/pdf/executiveOrders/Executive%20Order%202016-01K.pdf | title=Executive Order 2016-01K | publisher=Governor of Ohio | date=May 3, 2016 | vauthors = Kasich JR }}</ref>

U-47700 was emergency scheduled in Florida on September 27, 2016, by an emergency rule of Florida Attorney General Pam Bondi.<ref>{{Cite web|url=http://www.myfloridalegal.com/newsrel.nsf/newsreleases/65BA140203BABF4A8525803B006709D3|title=News Release - Attorney General Bondi Outlaws Deadly Synthetic Drug|website=www.myfloridalegal.com|access-date=2016-09-27}}</ref>

Responding to a perceived threat to public health and safety, the U.S. Drug Enforcement Administration has placed U-47700 into Schedule I of the Controlled Substances Act, effective November 14, 2016.<ref>{{cite web |url=https://www.dea.gov/divisions/hq/2016/hq111016.shtml |title=46 confirmed deaths linked to dangerous opioid in '15 and '16 spark emergency action |publisher=DEA |date=November 11, 2016 |author=DEA Public Affairs |access-date=November 11, 2016 |archive-date=June 4, 2018 |archive-url=https://web.archive.org/web/20180604075957/https://www.dea.gov/divisions/hq/2016/hq111016.shtml |url-status=dead }}</ref> In April 2018, U-47700 was placed into Schedule I indefinitely.<ref>{{cite web|title=Schedules of Controlled Substances: Placement of Butyryl Fentanyl and U-47700 Into Schedule I|url=https://www.federalregister.gov/documents/2018/04/20/2018-08280/schedules-of-controlled-substances-placement-of-butyryl-fentanyl-and-u-47700-into-schedule-i|date=20 April 2018|website=Federal Register}}</ref>

U-47700 was placed into Schedule 1 of South Dakota's Controlled Substance Schedule. It was signed by Governor [[Dennis Daugaard|Daugaard]] on February 9, 2017.<ref>{{cite web|url=http://sdlegislature.gov/docs/legsession/2017/Bills/HB1041P.pdf|title=House Bill No. 1041|publisher=Governor Dauggard of South Dakota|author=South Dakota Legislature}}</ref>

=== In popular culture ===
'''''U-47700''''' is the title of a 2021 [[Netherlands|Dutch]] [[Science fiction|sci-fi]] [[short film]] by director [[Erasmo de la Parra]].<ref>{{Citation |title=Filmaffinity U-47700 (S) (2021) |url=https://www.filmaffinity.com/us/film335227.html |language=en |access-date=2022-05-16}}</ref> In the film, the characters are addicted to a new drug containing the substance U-47700.

== See also ==
* [[Metonitazene]]
* [[Spiradoline]]
* [[U-69,593]]
* [[U-77891]]
* [[U-50488]]
* [[3,4-MDO-U-47700]]
* [[Utopioid (drug class)|Utopioid]]

== References ==
{{Reflist|32em}}

{{Opioid receptor modulators}}

[[Category:Synthetic opioids]]
[[Category:Benzamides]]
[[Category:Mu-opioid receptor agonists]]
[[Category:Dimethylamino compounds]]
[[Category:Chlorobenzene derivatives]]
[[Category:Designer drugs]]