| 词条 | Gacyclidine |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 443998605 | IUPAC_name = 1-[(1R,2S)-2-methyl-1-thiophen-2-ylcyclohexyl]piperidine | image = Gacyclidine.png | width = 150 | tradename = | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 68134-81-6 | ATC_prefix = none | PubChem = 176265 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 1742478 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 9290ND070R | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 153540 | smiles = C[C@@H](CCCC1)[C@@]1(N2CCCCC2)C3=CC=CS3 | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C16H25NS/c1-14-8-3-4-10-16(14,15-9-7-13-18-15)17-11-5-2-6-12-17/h7,9,13-14H,2-6,8,10-12H2,1H3/t14-,16+/m0/s1 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = DKFAAPPUYWQKKF-GOEBONIOSA-N | C=16 | H=25 | N=1 | S=1 | molecular_weight = 263.4414 g/mol }}Gacyclidine[1] (GK-11)[2] is a psychoactive drug which acts as a dissociative via functioning as a non-competitive NMDA receptor antagonist. It is closely related to phencyclidine (PCP), and specifically, is a derivative of tenocyclidine (TCP).[3][4] SynthesisThe condensation of 2-methylcyclohexanone (I) with 2-thienyllithium (II) or 2-thienylmagnesium bromide (III) gives cyclohexanol (IV) as a diastereomeric mixture, which was treated with sodium azide (NaN3) in trichloroacetic acid to yield the azide (V). The reduction of (V) with lithium aluminium hydride (LiAlH4) or Raney nickel in isopropanol affords the corresponding amine (VI), preferentially with the cis-configuration. Finally, this compound is condensed with 1,5-dibromopentane (VII) by means of potassium carbonate (K2CO3) in acetonitrile to provide the target compound as a diastereomeric mixture.[5] See also
References1. ^{{US patent reference | number = 6107495 | title = Thienylcyclohexane derivatives for thienylcyclohexyl synthesis | inventor = Jean-Bernard Cazaux, Michel Dafniet, Jean-Marc Kamenka, Eric Manginot}} {{General_anesthetics}}{{Hallucinogens}}{{Dopamine receptor modulators}}{{Ionotropic glutamate receptor modulators}}{{hallucinogen-stub}}2. ^{{cite journal | title = The search for TCP analogues binding to the low affinity PCP receptor sites in the rat cerebellum |author1=Jacques Hamon |author2=Florence Espaze |author3=Jacques Vignon |author4=Jean-Marc Kamenka | journal = Eur. J. Med. Chem. | volume = 34 | year = 1999 | pages = 125–135 | doi = 10.1016/S0223-5234(99)80046-4 | issue = 2}} 3. ^{{cite journal |vauthors=Hirbec H, Gaviria M, Vignon J | title = Gacyclidine: a new neuroprotective agent acting at the N-methyl-D-aspartate receptor | journal = CNS Drug Reviews | year = 2001 | volume = 7 | issue = 2 | pages = 172–98 | doi = 10.1111/j.1527-3458.2001.tb00194.x | pmid = 11474423}} 4. ^{{cite journal |vauthors=Hirbec H, Mausset AL, Kamenka JM, Privat A, Vignon J | title = Re-evaluation of phencyclidine low-affinity or "non-NMDA" binding sites | journal = J Neurosci Res | year = 2002 | volume = 68 | issue = 3 | pages = 305–314 | doi = 10.1002/jnr.10203 | pmid = 12111860}} 5. ^{{US patent reference | title = Pharmaceutical compositions for neuroprotection containing arylcyclohexylamines | number = 5179109 | inventor = Jean-Marc Kamenka et al | date = 1993}} 4 : Dissociative drugs|NMDA receptor antagonists|Thiophenes|Piperidines |
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