Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Metaphit: Difference between pages

| verifiedrevid = 461743085

| ImageFile = Metaphit.svg

| PIN = 1-[1-(3-Isothiocyanatophenyl)cyclohexyl]piperidine

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 96316-00-6

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = NFS3HJC8WD

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 41541

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| SMILES = S=C=N\c1cccc(c1)C3(N2CCCCC2)CCCCC3

| InChI = 1/C18H24N2S/c21-15-19-17-9-7-8-16(14-17)18(10-3-1-4-11-18)20-12-5-2-6-13-20/h7-9,14H,1-6,10-13H2

| InChIKey = FGSGBQAQSPSRJK-UHFFFAOYAE

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|Section2={{Chembox Properties

| Formula = C₁₈H₂₄N₂S

| MolarMass = 300.462

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

[[Image:Metaphit methanesulfonate.png|right|thumb|250 px|Metaphit as a [[methanesulfonate]] salt]]

'''Metaphit''' ('''1-[1-(3-Isothiocyanato)phenyl]cyclohexylpiperidine''') is a research chemical that acts as an acylator of [[NMDA receptor antagonist|NMDARAn]], [[Sigma receptor|sigma]] and [[Dopamine transporter|DAT]] binding sites in the [[Central nervous system|CNS]]. It is the ''m''-isothiocyanate derivative of [[phencyclidine]] (PCP) and binds irreversibly (forming a [[covalent bond]]) to the PCP binding site on the NMDA receptor complex.<ref>{{cite journal |pages=318–22 |doi=10.1016/0014-5793(85)80284-2 |title=A specific acylating agent for the [³H]phencyclidine receptors in rat brain |year=1985 |last1=Rafferty |first1=Michael F. |last2=Mattson |first2=Mariena |last3=Jacobson |first3=Arthur E. |last4=Rice |first4=Kenner C. |journal=FEBS Letters |volume=181 |issue=2 |pmid=2982662|doi-access=free }}</ref> However, later studies suggest the functionality of metaphit is mediated by sites not involved in PCP-induced passive avoidance deficit, and not related to the NMDA receptor complex.<ref>{{cite journal |pages=231–3 |doi=10.1016/0091-3057(91)90618-C |title=Metaphit fails to antagonize PCP-induced passive avoidance deficit |year=1991 |last1=Danysz |first1=Wojciech |journal=Pharmacology Biochemistry and Behavior |volume=38 |pmid=1826788 |issue=1}}</ref> Metaphit was also shown to prevent d-amphetamine induced hyperactivity, while significantly depleting dopamine content in the nucleus accumbens.<ref>{{cite journal |pages=267–74 |doi=10.1016/0014-2999(87)90283-4 |title=Metaphit, a proposed phencyclidine (PCP) antagonist, prevents PCP-induced locomotor behavior through mechanisms unrelated to specific blockade of PCP receptors |year=1987 |last1=French |first1=Edward D. |last2=Jacobson |first2=Arthur E. |last3=Rice |first3=Kenner C. |journal=European Journal of Pharmacology |volume=140 |issue=3 |pmid=2820762}}</ref> Metaphit was the first acylating ligand used to study the [[cocaine]] receptor.<ref>{{cite journal |first1=F. Ivy |last1=Carroll |first2=Anita H. |last2=Lewin |first3=John W. |last3=Boja |first4=Michael J. |last4=Kuharf |pages=969–81 |doi=10.1021/jm00084a001 |title=Cocaine receptor: Biochemical characterization and structure-activity relationships of cocaine analogs at the dopamine transporter |year=1992 |journal=Journal of Medicinal Chemistry |volume=35 |issue=6 |pmid=1552510}}</ref> It is a structural isomer of the similar research compound [[fourphit]], as it and metaphit both are isothiocyanate substituted derivatives of an analogous scaffold shared with PCP.<ref>{{cite journal | pmid = 1602399 | volume=261 | title=Fourphit: a selective probe for the methylphenidate binding site on the dopamine transporter | journal=J Pharmacol Exp Ther | pages=936-42 | last1 = Schweri | first1 = MM | last2 = Thurkauf | first2 = A | last3 = Mattson | first3 = MV | last4 = Rice | first4 = KC}}</ref>

==References==

{{Reflist|2}}

{{Navboxes

| title = [[Pharmacodynamics]]

| titlestyle = background:#ccccff

| list1 =

{{Monoamine reuptake inhibitors}}

{{Ionotropic glutamate receptor modulators}}

{{Sigma receptor modulators}}

}}

[[Category:Arylcyclohexylamines]]

[[Category:Dopamine reuptake inhibitors]]

[[Category:Dissociative drugs]]

[[Category:NMDA receptor antagonists]]

[[Category:1-Piperidinyl compounds]]

[[Category:Sigma agonists]]

[[Category:Irreversible antagonists]]

[[Category:Irreversible agonists]]

[[Category:Isothiocyanates]]

{{Pharma-stub}}