Phencyclidine (PCP) is believed to be the first arylcyclohexylamine with recognized anesthetic properties, but several arylcyclohexylamines were described before PCP in the scientific literature, beginning with PCA (1-phenylcyclohexan-1-amine) the synthesis of which was first published in 1907. PCP itself was discovered in 1926 but not researched by pharmaceutical industry until the 1950s. PCE was reported in 1953 and PCMo (4-(1-phenyl-cyclohexyl)-morpholine[1] see chart below for figure) in 1954, with PCMo described as a potent sedative.[2] Arylcyclohexylamine anesthetics were intensively investigated at Parke-Davis, beginning with the 1956 studies of PCP and later the related compound ketamine.[2] The 1970s saw the debut of these compounds, especially PCP and its analogues, as illicitly used recreational drugs due to their dissociativehallucinogenic and euphoriant effects. Since that time, the class has been expanded by scientific research into stimulant, analgesic, and neuroprotective agents, and also by clandestinechemists in search of novel recreational drugs.[3][4][5]
Structure
General structure of arylcyclohexylamines
An arylcyclohexylamine is composed of a cyclohexylamine unit with an arylmoiety attachment. The aryl group is positioned geminal to the amine. In the simplest cases, the aryl moiety is typically a phenyl ring, sometimes with additional substitution. The amine is usually not primary; secondary amines such as methylamine or ethylamine, or tertiary cycloalkylamines such as piperidine and pyrrolidine, are the most commonly encountered N-substituents.
Pharmacology
Arylcyclohexylamines varyingly possess NMDA receptor antagonistic,[6][7]dopamine reuptake inhibitory,[8] and μ-opioid receptoragonistic[9] properties. Additionally, σ receptor agonistic,[10]nACh receptor antagonistic,[11] and D2 receptor agonistic[12] actions have been reported for some of these agents. Antagonism of the NMDA receptor confers anesthetic, anticonvulsant, neuroprotective, and dissociative effects; blockade of the dopamine transporter mediates stimulant and euphoriant effects as well as psychosis in high amounts; and activation of the μ-opioid receptor causes analgesic and euphoriant effects. Stimulation of the σ and D2 receptors may also contribute to hallucinogenic and psychotomimetic effects.[12]
These are versatile agents with a wide range of possible pharmacological activities depending on the extent and range to which chemical modifications are implemented.[13][14][15][16][17][18][19][20][21] The various choice of substitutions that are made allows for "fine-tuning" of the pharmacological profile that results. As examples, BTCP is a selective dopamine reuptake inhibitor,[8] PCP is primarily an NMDA antagonist,[6] and BDPC is a potent μ-opioid agonist,[22] while PRE-084 is a selective sigma receptor agonist.[23] Thus, radically different pharmacology is possible through different structural combinations.
Notes on numbering
PCP itself is composed of three six-membered rings, which can each be substituted by a variety of groups. These are traditionally numbered in the older research as first the cyclohexyl ring, then the phenyl, and finally the piperidine ring, with the different rings represented by prime notation (') next to the number. For instance, 4-methyl-PCP, 4'-methyl-PCP and 4''-methyl-PCP are all known compounds, with similar activity but quite different potencies.
4-Methyl-PCP, 4'-Methyl-PCP and 4''-Methyl-PCP (left to right)
However, since the widespread sale of these compounds as grey-market designer drugs, nearly all such compounds that have come to prominence either have a bare cyclohexyl ring or a 2-ketocyclohexyl ring, while the piperidine is replaced by a variety of alkyl or cycloalkyl amines and most substitution has taken place on the phenyl ring. Consequently, it is common for widely used phenyl substituted analogues such as 3'-MeO-PCP and 3'-MeO-PCE to be referred to as 3-MeO-PCP and 3-MeO-PCE without the prime, even though this is technically incorrect and could lead to confusion.
Other similar compounds exist where the base ring has been varied, or the amine chain replaced with other groups.[44] More cycloalkane ring sizes have been experimented with than just purely thinking in terms of the cyclohexylamine. The cyclopentyl homologue of PCP is active with around one-tenth the potency,[45] while the cycloheptyl and cyclooctyl derivatives are inactive, though some substituted arylcycloheptylamines retain activity.[46] The requisite cycloalkylketone is reacted with PhMgBr; 3° alcohol is then reacted with NaN3; azide then reduced with LAH. Then in the final step the piperidine ring is constructed with 1-5-dibromo-pentane.[47] Other compounds are known where the cyclohexyl base ring is replaced by rings such as norbornyl, adamantyl,[48] tetralin, oxane, thiane [49] or piperidine.[50]Conformationally constrained analogs have been prepared and researched by Morieti et al.[51]
^ abMorris H, Wallach J (2014). "From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs". Drug Testing and Analysis. 6 (7–8): 614–32. doi:10.1002/dta.1620. PMID24678061.
^Valter K, Arrizabalaga P (1998). Designer Drugs Directory. Elsevier. ISBN0-444-20525-X.
^Wallach J, Brandt SD (August 2018). "Phencyclidine-Based New Psychoactive Substances". New Psychoactive Substances. Handbook of Experimental Pharmacology. Vol. 252. pp. 261–303. doi:10.1007/164_2018_124. ISBN978-3-030-10560-0. PMID30105474.
^Wallach J, Brandt SD (2018). "1,2-Diarylethylamine- and Ketamine-Based New Psychoactive Substances". New Psychoactive Substances. Handbook of Experimental Pharmacology. Vol. 252. pp. 305–352. doi:10.1007/164_2018_148. ISBN978-3-030-10560-0. PMID30196446.
^ abcAhmadi A, Mahmoudi A (2005). "Synthesis and biological properties of 2-hydroxy-1-(1-phenyltetralyl)piperidine and some of its intermediates as derivatives of phencyclidine". Arzneimittel-Forschung. 55 (9): 528–32. doi:10.1055/s-0031-1296900. PMID16229117. S2CID29006399.
^ abAhmadi A, Khalili M, Hajikhani R, Naserbakht M (April 2011). "New morpholine analogues of phencyclidine: chemical synthesis and pain perception in rats". Pharmacology, Biochemistry, and Behavior. 98 (2): 227–33. doi:10.1016/j.pbb.2010.12.019. PMID21215770. S2CID24650035.
^ abChaudieu I, Vignon J, Chicheportiche M, Kamenka JM, Trouiller G, Chicheportiche R (March 1989). "Role of the aromatic group in the inhibition of phencyclidine binding and dopamine uptake by PCP analogs". Pharmacology, Biochemistry, and Behavior. 32 (3): 699–705. doi:10.1016/0091-3057(89)90020-8. PMID2544905. S2CID7672918.
^Itzhak Y, Simon EJ (August 1984). "A novel phencyclidine analog interacts selectively with mu opioid receptors". The Journal of Pharmacology and Experimental Therapeutics. 230 (2): 383–6. PMID6086884.
^ abHe XS, Raymon LP, Mattson MV, Eldefrawi ME, de Costa BR (April 1993). "Synthesis and biological evaluation of 1-[1-(2-benzo[b]thienyl)cyclohexyl]piperidine homologues at dopamine-uptake and phencyclidine- and sigma-binding sites". Journal of Medicinal Chemistry. 36 (9): 1188–93. doi:10.1021/jm00061a009. PMID8098066.
^ abSeeman P, Ko F, Tallerico T (September 2005). "Dopamine receptor contribution to the action of PCP, LSD and ketamine psychotomimetics". Molecular Psychiatry. 10 (9): 877–83. doi:10.1038/sj.mp.4001682. PMID15852061.
^al-Deeb OA (May 1996). "New analgesics derived from the phencyclidine analogue thienylcyclidine". Arzneimittel-Forschung. 46 (5): 505–8. PMID8737636.
^Ahmadi A, Khalili M, Hajikhani R, Hosseini H, Afshin N, Nahri-Niknafs B (March 2012). "Synthesis and study the analgesic effects of new analogues of ketamine on female wistar rats". Medicinal Chemistry. 8 (2): 246–51. doi:10.2174/157340612800493683. PMID22385170. S2CID42842315.
^Ahmadi A, Khalili M, Abbassi S, Javadi M, Mahmoudi A, Hajikhani R (2009). "Synthesis and study on analgesic effects of 1-[1-(4-methylphenyl) (cyclohexyl)] 4-piperidinol and 1-[1-(4-methoxyphenyl) (cyclohexyl)] 4-piperidinol as two new phencyclidine derivatives". Arzneimittel-Forschung. 59 (4): 202–6. doi:10.1055/s-0031-1296386. PMID19517897. S2CID5402425.
^Ahmadi A, Khalili M, Marami S, Ghadiri A, Nahri-Niknafs B (January 2014). "Synthesis and pain perception of new analogues of phencyclidine in NMRI male mice". Mini Reviews in Medicinal Chemistry. 14 (1): 64–71. doi:10.2174/1389557513666131119203551. PMID24251803.
^Ahmadi A, Solati J, Hajikhani R, Pakzad S (2011). "Synthesis and analgesic effects of new pyrrole derivatives of phencyclidine in mice". Arzneimittel-Forschung. 61 (5): 296–300. doi:10.1055/s-0031-1296202. PMID21755813. S2CID24287727.
^Ahmadi A, Khalili M, Mihandoust F, Barghi L (2010). "Synthesis and determination of acute and chronic pain activities of 1-[1-(3-methylphenyl) (tetralyl)]piperidine as a new derivative of phencyclidine via tail immersion and formalin tests". Arzneimittel-Forschung. 60 (1): 30–5. doi:10.1055/s-0031-1296245. PMID20184224. S2CID23966936.
^Hajikhani R, Ahmadi A, Naderi N, Yaghoobi K, Shirazizand Z, Rezaee NM, Niknafs BN (2012). "Effect of phencyclidine derivatives on anxiety-like behavior using an elevated-plus maze test in mice". Advances in Clinical and Experimental Medicine. 21 (3): 307–12. PMID23214193.
^Ahmadi A, Khalili M, Mirza B, Mohammadi-Diz M, Azami-Lorestani F, Ghaderi P, Nahri-Niknafs B (2017). "Synthesis and Antinociception Activities of Some Novel Derivatives of Phencyclidine with Substituted Aminobenzothiazoles". Mini Reviews in Medicinal Chemistry. 17 (1): 78–84. doi:10.2174/1389557516666160428112532. PMID27121715.
^Lednicer D, VonVoigtlander PF (October 1979). "4-(p-Bromophenyl)-4-(dimethylamino)-1-phenethylcyclohexanol, an extremely potent respresentative of a new analgesic series". Journal of Medicinal Chemistry. 22 (10): 1157–8. doi:10.1021/jm00196a001. PMID513062.
^ abcThurkauf A, de Costa B, Yamaguchi S, Mattson MV, Jacobson AE, Rice KC, Rogawski MA (May 1990). "Synthesis and anticonvulsant activity of 1-phenylcyclohexylamine analogues". Journal of Medicinal Chemistry. 33 (5): 1452–8. doi:10.1021/jm00167a027. PMID2329567.
^Sauer C, Peters FT, Staack RF, Fritschi G, Maurer HH (April 2008). "Metabolism and toxicological detection of a new designer drug, N-(1-phenylcyclohexyl)propanamine, in rat urine using gas chromatography-mass spectrometry". Journal of Chromatography A. 1186 (1–2): 380–90. doi:10.1016/j.chroma.2007.11.002. PMID18035363.
^Kalir A, Teomy S, Amir A, Fuchs P, Lee SA, Holsztynska EJ, et al. (October 1984). "N-allyl analogues of phencyclidine: chemical synthesis and pharmacological properties". Journal of Medicinal Chemistry. 27 (10): 1267–71. doi:10.1021/jm00376a006. PMID6481761.
^Sauer C, Peters FT, Schwaninger AE, Meyer MR, Maurer HH (February 2009). "Investigations on the cytochrome P450 (CYP) isoenzymes involved in the metabolism of the designer drugs N-(1-phenyl cyclohexyl)-2-ethoxyethanamine and N-(1-phenylcyclohexyl)-2-methoxyethanamine". Biochemical Pharmacology. 77 (3): 444–50. doi:10.1016/j.bcp.2008.10.024. PMID19022226.
^Iorio MA, Tomassini L, Mattson MV, George C, Jacobson AE (August 1991). "Synthesis, stereochemistry, and biological activity of the 1-(1-phenyl-2-methylcyclohexyl)piperidines and the 1-(1-phenyl-4-methylcyclohexyl)piperidines. Absolute configuration of the potent trans-(-)-1-(1-phenyl-2-methylcyclohexyl)piperidine". Journal of Medicinal Chemistry. 34 (8): 2615–23. doi:10.1021/jm00112a041. PMID1875352.
^Ahmadi A, Mahmoudi A (2006). "Synthesis with improved yield and study on the analgesic effect of 2-methoxyphencyclidine". Arzneimittel-Forschung. 56 (5): 346–50. doi:10.1055/s-0031-1296732. PMID16821645. S2CID10370245.
^Ortiz DM, Custodio RJ, Abiero A, Botanas CJ, Sayson LV, Kim M, et al. (July 2021). "The dopaminergic alterations induced by 4-F-PCP and 4-Keto-PCP may enhance their drug-induced rewarding and reinforcing effects: Implications for abuse". Addiction Biology. 26 (4): e12981. doi:10.1111/adb.12981. PMID33135332. S2CID226234538.
^ abOgunbadeniyi AM, Adejare A (2002). "Syntheses of fluorinated phencyclidine analogs". Journal of Fluorine Chemistry. 114: 39–42. doi:10.1016/S0022-1139(01)00565-6.
^ abWallach J, De Paoli G, Adejare A, Brandt SD (2013). "Preparation and analytical characterization of 1-(1-phenylcyclohexyl)piperidine (PCP) and 1-(1-phenylcyclohexyl)pyrrolidine (PCPy) analogues". Drug Testing and Analysis. 6 (7–8): 633–50. doi:10.1002/dta.1468. PMID23554350.
^Sayson LV, Botanas CJ, Custodio RJ, Abiero A, Kim M, Lee HJ, et al. (July 2019). "The novel methoxetamine analogs N-ethylnorketamine hydrochloride (NENK), 2-MeO-N-ethylketamine hydrochloride (2-MeO-NEK), and 4-MeO-N-ethylketamine hydrochloride (4-MeO-NEK) elicit rapid antidepressant effects via activation of AMPA and 5-HT2 receptors". Psychopharmacology. 236 (7): 2201–2210. doi:10.1007/s00213-019-05219-x. PMID30891619. S2CID83463722.
^WO 2021134086, Kruegel AC, Sames D, Hashimoto K, "Arylcyclohexylamine derivatives and their use in the treatment of psychiatric disorders", published 1 July 2021, assigned to Gilgamesh Pharmaceuticals, Inc. and The Trustees Of Columbia University In The City Of New York.
^Harvey M, Sleigh J, Voss L, Pruijn F, Jose J, Gamage S, Denny W (2015). "Determination of the Hypnotic Potency in Rats of the Novel Ketamine Ester Analogue SN 35210". Pharmacology. 96 (5–6): 226–32. doi:10.1159/000439598. PMID26352278. S2CID36017002.
^Ahmadi A, Khalili M, Hajikhani R, Naserbakht M (2011). "Synthesis and determination of acute and chronic pain activities of 1-[1-(4-methylphenyl) (cyclohexyl)] morpholine as a new phencyclidine derivative in rats". Arzneimittel-Forschung. 61 (2): 92–7. doi:10.1055/s-0031-1296173. PMID21428243. S2CID8094521.
^Zarantonello P, Bettini E, Paio A, Simoncelli C, Terreni S, Cardullo F (April 2011). "Novel analogues of ketamine and phencyclidine as NMDA receptor antagonists". Bioorganic & Medicinal Chemistry Letters. 21 (7): 2059–63. doi:10.1016/j.bmcl.2011.02.009. PMID21334205.
^Lednicer D, VonVoigtlander PF, Emmert DE (April 1980). "4-Amino-4-arylcyclohexanones and their derivatives, a novel class of analgesics. 1. Modification of the aryl ring". Journal of Medicinal Chemistry. 23 (4): 424–30. doi:10.1021/jm00178a014. PMID7381841.
^Ahmadi A, Solati J, Hajikhani R, Onagh M, Javadi M (2010). "Synthesis and analgesic effects of 1-[1-(2-methylphenyl)(cyclohexyl)]-3-piperidinol as a new derivative of phencyclidine in mice". Arzneimittel-Forschung. 60 (8): 492–6. doi:10.1055/s-0031-1296317. PMID20863005. S2CID24803623.
^Itzhak Y, Kalir A, Weissman BA, Cohen S (May 1981). "New analgesic drugs derived from phencyclidine". Journal of Medicinal Chemistry. 24 (5): 496–9. doi:10.1021/jm00137a004. PMID7241506.
^Vignon J, Pinet V, Cerruti C, Kamenka JM, Chicheportiche R (April 1988). "[3H]N-[1-(2-benzo(b)thiophenyl)cyclohexyl]piperidine ([3H]BTCP): a new phencyclidine analog selective for the dopamine uptake complex". European Journal of Pharmacology. 148 (3): 427–36. doi:10.1016/0014-2999(88)90122-7. PMID3384005.
^Wallach JV. Structure activity relationship (SAR) studies of arylcycloalkylamines as N-methyl-D-aspartate receptor antagonists. PhD. Thesis, University of the Sciences in Philadelphia, 19 Dec 2014.
^Shulgin AT, Mac Lean DE (1976). "Illicit synthesis of phencyclidine (PCP) and several of its analogs". Clinical Toxicology. 9 (4): 553–60. doi:10.3109/15563657608988157. PMID975751.
^Sun S, Wallach J, Adejare A (2014). "Syntheses and N-methyl-D-aspartate receptor antagonist pharmacology of fluorinated arylcycloheptylamines". Medicinal Chemistry. 10 (8). Shariqah (United Arab Emirates): 843–52. doi:10.2174/1573406410666140428104444. PMID24773376.
^McQuinn RL, Cone EJ, Shannon HE, Su TP (December 1981). "Structure-activity relationships of the cycloalkyl ring of phencyclidine". Journal of Medicinal Chemistry. 24 (12): 1429–32. doi:10.1021/jm00144a011. PMID7310819.
^Eaton TA, Houk KN, Watkins SF, Fronczek FR (April 1983). "Geometries and conformational processes in phencyclidine and a rigid adamantyl analogue: variable-temperature NMR, X-ray crystallographic, and molecular mechanics studies". Journal of Medicinal Chemistry. 26 (4): 479–86. doi:10.1021/jm00358a005. PMID6834381.
^Moriarty RM, Enache LA, Zhao L, Gilardi R, Mattson MV, Prakash O (February 1998). "Rigid phencyclidine analogues. Binding to the phencyclidine and sigma 1 receptors". Journal of Medicinal Chemistry. 41 (4): 468–77. doi:10.1021/jm970059p. PMID9484497.
Further reading
Morris H, Wallach J (2014). "From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs". Drug Testing and Analysis. 6 (7–8): 614–32. doi:10.1002/dta.1620. PMID24678061.
NE9 Stasiun MRT Boon Keng文庆地铁站பூன் கெங்Angkutan cepatPeron Stastiun MRT NE9 Boon KengLokasi900 Serangoon RoadSingapura 328260Koordinat1°19′10″N 103°51′42″E / 1.319483°N 103.861722°E / 1.319483; 103.861722Jalur Jalur Timur Laut Jumlah peronPulauJumlah jalur2LayananBis, TaxiKonstruksiJenis strukturBawah tanahTinggi peron2Akses difabelYesInformasi lainKode stasiunNE9SejarahDibuka20 Juni 2003Operasi layanan Stasiun s…
Riccardo Pick-Mangiagalli Riccardo Pick-Mangiagalli (Strakonice, 10 luglio 1882 – Milano, 8 luglio 1949) è stato un pianista e compositore boemo naturalizzato italiano. Indice 1 Biografia 2 Opere principali 2.1 Opere liriche e balletti 2.2 Altre opere 3 Bibliografia 4 Voci correlate 5 Altri progetti 6 Collegamenti esterni Biografia Libretto del 1919 dell'opera Il Carillon Magico. Nato in Boemia, ma in parte di origine italiana, ha studiato e vissuto nella penisola. Studiò al Conservatorio Gi…
This article includes a list of general references, but it lacks sufficient corresponding inline citations. Please help to improve this article by introducing more precise citations. (February 2024) (Learn how and when to remove this message) New York Fighter WingActive1942–1944CountryUnited StatesBranchUnited States Air ForceRoleFighterEngagementsWorld War IICommandersNotablecommandersBrig General Earle E. PartridgeMilitary unit The New York Fighter Wing is an inactive United States Air Force…
Public university in Portales, New Mexico, U.S. Eastern New Mexico UniversityFormer nameEastern New Mexico Junior College (1927–1940)Eastern New Mexico College (1940–1949)MottoExplore. Experience. Excel.[1]TypePublic universityEstablished1927; 97 years ago (1927)Academic affiliationsCONAHECChancellorJames N JohnstonAcademic staff156 full-time and 83 part-time (Fall 2023)[2]Students5,106 (3,833 undergraduate) (Fall 2023)[3]LocationPortales, New Mexico…
Cet article est une ébauche concernant Internet et le Groenland. Vous pouvez partager vos connaissances en l’améliorant (comment ?) selon les recommandations des projets correspondants. .gl Début 1994 Type Domaine national de premier niveau État Actif Registre TELE Greenland Parrainé par TELE Greenland Pays Groenland Restrictions Aucune Structure Les noms peuvent enregistrés directement au deuxième niveau Site Web http://www.nic.gl/ modifier .gl est le domaine de premier nive…
Questa voce sull'argomento anime e manga è solo un abbozzo. Contribuisci a migliorarla secondo le convenzioni di Wikipedia. Segui i suggerimenti del progetto di riferimento. Hyper Doll楽勝!ハイパードール(Rakushō! Haipā Dōru)Generefantascienza, commedia, azione MangaAutoreShimpei Itoh EditoreTokuma Shoten RivistaShōnen Captain Targetshōnen 1ª edizione1994 – 1997 Tankōbon5 (completa) OAVHyper Doll: Mew & Mica the Easy FighterRegiaMakoto Mori…
Not to be confused with Jewish hip hop. This article's lead section may be too short to adequately summarize the key points. Please consider expanding the lead to provide an accessible overview of all important aspects of the article. (June 2015) Israeli hip hop refers to hip hop and rap music in Israel. Israeli hip hop artists have mainly emerged from the populations of Mizrahi Jews, Ethiopian Jews, and Israeli-Arabs, though there have also been numerous artists from Israeli Ashkenazi Jews espe…
This article needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed.Find sources: Philip Rea, 2nd Baron Rea – news · newspapers · books · scholar · JSTOR (March 2020) (Learn how and when to remove this message) The Right HonourableThe Lord ReaPCPhilip ReaLeader of the Liberal Party in the House of LordsIn office1955–1967Preceded byThe Viscoun…
American economist (1921–2017) Kenneth ArrowArrow in 1996BornKenneth Joseph ArrowAugust 23, 1921New York City, U.S.DiedFebruary 21, 2017Palo Alto, California, U.S.Education City College of New York (BS) Columbia University (MS, PhD) Academic careerInstitutionStanford UniversityUniversity of ChicagoHarvard UniversityField Microeconomics General equilibrium theory Social choice theory School ortraditionNeoclassical economicsDoctoraladvisorHarold HotellingDoctoralstudents David F. Bradford M…
Australian telecommunications company Not to be confused with Japanese telecommunications company au (mobile phone company) or Telstar. Telstra Group LimitedTelstra Corporate Centre in MelbourneTrade nameTelstraFormerly List Australian Telecommunications Commission (1979–1989) Australian Telecommunications Corporation (1989–1991) Australian and Overseas Telecommunications Corporation (1991–1993) Telstra Corporation Limited (1993–2023) Company typePublicTraded asASX: TLSS&P/ASX 2…
American drama TV series The Haunting of Bly ManorGenre Gothic romance[1] Drama Supernatural Horror Created byMike FlanaganBased onThe work of Henry JamesStarring Victoria Pedretti Oliver Jackson-Cohen Amelia Eve T'Nia Miller Rahul Kohli Tahirah Sharif Amelie Bea Smith Benjamin Evan Ainsworth Henry Thomas ComposerThe Newton BrothersCountry of originUnited StatesOriginal languageEnglishNo. of episodes9ProductionExecutive producers Darryl Frank Justin Falvey Trevor Macy Mike Flanagan Diane…
Penampakan fisik natrium bikarbonat. Struktur kimia natrium bikarbonat. Natrium bikarbonat atau soda kue (bahasa Inggris: baking soda) adalah senyawa kimia dengan rumus NaHCO3. Dalam penyebutannya kerap disingkat menjadi bicnat atau bicarb. Senyawa ini termasuk kelompok garam dan telah digunakan sejak lama (abad 19).[1] Senyawa ini merupakan kristal yang sering terdapat dalam bentuk serbuk. Natrium bikarbonat larut dalam air. Senyawa ini digunakan dalam roti atau kue karena bereaksi …
Colm Meaney Colm J. Meaney (bahasa Irlandia: Colm Ó Maonaigh; lahir 30 Mei 1953) merupakan seorang aktor berkebangsaan Irlandia yang menjadi terkenal saat bermain di Miles O'Brien di Star Trek: The Next Generation dan Star Trek: Deep Space Nine. Dia dilahirkan di Dublin. Dia berkarier di dunia film sejak tahun 1987. Filmografi Film Tahun Judul Peran Catatan 1981 Nailed Seorang Protestan muda 1987 Omega Syndrome Sean 1987 Dead The Dead Mr. Bergin 1990 Die Hard 2 Pilot 1990 Dick Tracy Cop at Tess…
لمعانٍ أخرى، طالع إرث (توضيح). الإرث (وقد يرادفه الميراث فهو تركة الميت) هي عادة توريث ممتلكات أو ألقاب أو ديون أو مسؤوليات عند وفاة أحد الأشخاص. وهي من العادات الأساسية في المجتمعات. وقوانين الميراث يختلف من مجتمع إلى آخر وما بين الأديان وكما أنه تطور عبر الأزمان ، مما ي…
Metro station in Chengdu, China Guanghua Park光华公园General informationLocationWenjiang District, Chengdu, SichuanChinaOperated byChengdu Metro LimitedLine(s) Line 4Platforms2 (1 island platform)HistoryOpened2 June 2017Services Preceding station Chengdu Metro Following station Nanxun Avenuetowards Wansheng Line 4 Yongquantowards Xihe Guanghua Park (Chinese: 光华公园) is a station on Line 4 of the Chengdu Metro in China.[1][2] Station layo…
President Woodrow Wilson directed U.S. foreign policy from 1913 to 1921 The history of U.S. foreign policy from 1913–1933 covers the foreign policy of the United States during World War I and much of the Interwar period. The administrations of Presidents Woodrow Wilson, Warren G. Harding, Calvin Coolidge, and Herbert Hoover successively handled U.S. foreign policy during this period. Wilson initially sought to remain neutral in World War I, but in 1917 he led the United States into the war on …
Маяцкая дача Основная информация Площадь18 га Дата основания14 октября 1975 Расположение 48°56′45″ с. ш. 37°32′58″ в. д.HGЯO Страна Украина Маяцкая дача Медиафайлы на Викискладе Маяцкая дача — ботанический памятник природы общегосударственного значения. Нах…
Men's social and athletic club in San Francisco, California, US This article is about the men's social and athletic club. For the boxing club, see San Francisco Athletic Club. This article needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed.Find sources: San Francisco Italian Athletic Club – news · newspapers · books · scholar · JSTOR (Octob…
-Hydroxynorketamine_Formula_V1.svg)
-4-Ph-4-OH-piperidine_structure.png)
