N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate
::concepts
{{#invoke:Infobox|infobox}}{{#invoke:TemplatePar
|check
|template=Template:Infobox_drug
|all= |opt= pronounce= ATC_prefix= ATC_suffix= ATC_supplemental= ATCvet= CAS_number_Ref= CAS_number= CAS_supplemental= ChEBI= ChEBI_Ref= ChEMBL_Ref= ChEMBL= ChemSpiderID= ChemSpiderID_Ref= ChemSpiderID= DailyMedID= data_page= DrugBank_Ref= DrugBank= Drugs.com= duration_of_action= IUPAC_name= IUPHAR_ligand= KEGG_Ref= KEGG= MedlinePlus= NIAID_ChemDB= PDB_ligand= PubChemSubstance= PubChem= StdInChIKey_Ref= StdInChIKey_comment= StdInChIKey= StdInChI_Ref= StdInChI_comment= StdInChI= UNII_Ref= UNII= Verifiedfields= Watchedfields= addiction_liability= alt2= altL= altR= alt= bioavailability= boiling_high= boiling_notes= boiling_point= captionLR= caption= charge= chemical_formula= chemical_formula_ref= chemical_formula_comment= class1= class2= class3= class4= component1= component2= component3= component4= density= dependency_liability= drug_name= elimination_half-life= excretion= InChI= InChIKey= image2= imageL= imageR= imagename= image= legal_AU= legal_CA= legal_DE= legal_EU= legal_NZ= legal_UK= legal_UN= legal_US= legal_AU_comment= legal_CA_comment= legal_DE_comment= legal_UK_comment= legal_NZ_comment= legal_US_comment= legal_UN_comment= legal_EU_comment= legal_status= licence_EU= licence_US= mab_type= melting_high= melting_notes= melting_point= metabolism= metabolites= molecular_weight= molecular_weight_round= molecular_weight_unit= molecular_weight_ref= molecular_weight_comment= onset= pregnancy_AU= pregnancy_US= pregnancy_AU_comment= pregnancy_US_comment= pregnancy_category= protein_bound= routes_of_administration= sec_combustion= SMILES= smiles= solubility= source= specific_rotation= synonyms= target= tradename= type= vaccine_type= verifiedrevid= width2= widthL= widthR= width= Ac=Ag=Al=Am=Ar=As=At=Au=B=Ba=Be=Bh=Bi=Bk=Br=C=Ca=Cd=Ce=Cf=Cl=Cm=Cn=Co=Cr=Cs=Cu=
Db=Ds=Dy=Er=Es=Eu=F=Fe=Fl=Fm=Fr=Ga=Gd=Ge=H=He=Hf=Hg=Ho=Hs=I=In=Ir=K=Kr=La=Li=Lr=Lu=Lv=
Md=Mg=Mn=Mo=Mt=N=Na=Nb=Nd=Ne=Ni=No=Np=O=Os=P=Pa=Pb=Pd=Pm=Po=Pr=Pt=Pu=Ra=Rb=Re=Rf=Rg=Rh=Rn=Ru=
S=Sb=Sc=Se=Sg=Si=Sm=Sn=Sr=Ta=Tb=Tc=Te=Th=Ti=Tl=Tm=U=Uuo=Uup=Uus=Uut=V=W=Xe=Y=Yb=Zn=Zr
|cat=Chemical articles with unknown parameter in Infobox drug
|format=0|preview=1|errNS=0
}}
N,O-Dimethyl-4β-(2-naphthyl)piperidine-3β-carboxylate (DMNPC) is a piperidine based stimulant drug which is synthesised from arecoline. It is similar to nocaine in chemical structure, and has two and a half times more activity than cocaine as a dopamine reuptake inhibitor. However it is also a potent serotonin reuptake inhibitor, with similar affinity to fluoxetine.<ref name="titleFurther SAR Studies of Piperidine-Based Analogues of Cocaine. 2. Potent Dopamine and Serotonin Reuptake Inhibitors">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> It is a structural isomer of another potent dopamine reuptake inhibitor, HDMP-28.
| Ki Affinity of Piperidine Based MAT Inhibitors | ||||||
| ∗∗ | X | N | 5HT | DA | NE | |
| SS | p-Vinyl | Me | 138 | 131 | 175 | |
| p-Ethyl | 255 | >1.7K | >1.1K | |||
| p-Allyl | 309 | 964 | >1K | |||
| p-Ethynyl | 175 | 187 | 364 | |||
| p-Phenyl | 62 | 173 | 203 | |||
| β-Naphthyl | 7.6 | 21 | 34 | |||
| 3R,4S | 42 | 947 | 241 | |||
| RR | 192 | 87 | 27 | |||
| 3S,4R | 12 | 271 | 38 | |||
| H2Cl | 3.5 | 90 | 30 | |||
| SS/RR | α-Naphthyl | Me | 101 | 304 | 281 | |
Clearly it is not just the SS enantiomer of the title compound that is an active MAT inhibitor.
N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate sections
Intro Effect of N-demethylation See also References
| PREVIOUS: Intro | NEXT: Effect of N-demethylation |
| << | >> |
Category::rowspan Reuptake::cocaine Potent::similar Potent::dopamine Dopamine::title HDMP-::small
{{#invoke:Infobox|infobox}}{{#invoke:TemplatePar
|check
|template=Template:Infobox_drug
|all= |opt= pronounce= ATC_prefix= ATC_suffix= ATC_supplemental= ATCvet= CAS_number_Ref= CAS_number= CAS_supplemental= ChEBI= ChEBI_Ref= ChEMBL_Ref= ChEMBL= ChemSpiderID= ChemSpiderID_Ref= ChemSpiderID= DailyMedID= data_page= DrugBank_Ref= DrugBank= Drugs.com= duration_of_action= IUPAC_name= IUPHAR_ligand= KEGG_Ref= KEGG= MedlinePlus= NIAID_ChemDB= PDB_ligand= PubChemSubstance= PubChem= StdInChIKey_Ref= StdInChIKey_comment= StdInChIKey= StdInChI_Ref= StdInChI_comment= StdInChI= UNII_Ref= UNII= Verifiedfields= Watchedfields= addiction_liability= alt2= altL= altR= alt= bioavailability= boiling_high= boiling_notes= boiling_point= captionLR= caption= charge= chemical_formula= chemical_formula_ref= chemical_formula_comment= class1= class2= class3= class4= component1= component2= component3= component4= density= dependency_liability= drug_name= elimination_half-life= excretion= InChI= InChIKey= image2= imageL= imageR= imagename= image= legal_AU= legal_CA= legal_DE= legal_EU= legal_NZ= legal_UK= legal_UN= legal_US= legal_AU_comment= legal_CA_comment= legal_DE_comment= legal_UK_comment= legal_NZ_comment= legal_US_comment= legal_UN_comment= legal_EU_comment= legal_status= licence_EU= licence_US= mab_type= melting_high= melting_notes= melting_point= metabolism= metabolites= molecular_weight= molecular_weight_round= molecular_weight_unit= molecular_weight_ref= molecular_weight_comment= onset= pregnancy_AU= pregnancy_US= pregnancy_AU_comment= pregnancy_US_comment= pregnancy_category= protein_bound= routes_of_administration= sec_combustion= SMILES= smiles= solubility= source= specific_rotation= synonyms= target= tradename= type= vaccine_type= verifiedrevid= width2= widthL= widthR= width= Ac=Ag=Al=Am=Ar=As=At=Au=B=Ba=Be=Bh=Bi=Bk=Br=C=Ca=Cd=Ce=Cf=Cl=Cm=Cn=Co=Cr=Cs=Cu=
Db=Ds=Dy=Er=Es=Eu=F=Fe=Fl=Fm=Fr=Ga=Gd=Ge=H=He=Hf=Hg=Ho=Hs=I=In=Ir=K=Kr=La=Li=Lr=Lu=Lv=
Md=Mg=Mn=Mo=Mt=N=Na=Nb=Nd=Ne=Ni=No=Np=O=Os=P=Pa=Pb=Pd=Pm=Po=Pr=Pt=Pu=Ra=Rb=Re=Rf=Rg=Rh=Rn=Ru=
S=Sb=Sc=Se=Sg=Si=Sm=Sn=Sr=Ta=Tb=Tc=Te=Th=Ti=Tl=Tm=U=Uuo=Uup=Uus=Uut=V=W=Xe=Y=Yb=Zn=Zr
|cat=Chemical articles with unknown parameter in Infobox drug
|format=0|preview=1|errNS=0
}}
N,O-Dimethyl-4β-(2-naphthyl)piperidine-3β-carboxylate (DMNPC) is a piperidine based stimulant drug which is synthesised from arecoline. It is similar to nocaine in chemical structure, and has two and a half times more activity than cocaine as a dopamine reuptake inhibitor. However it is also a potent serotonin reuptake inhibitor, with similar affinity to fluoxetine.<ref name="titleFurther SAR Studies of Piperidine-Based Analogues of Cocaine. 2. Potent Dopamine and Serotonin Reuptake Inhibitors">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> It is a structural isomer of another potent dopamine reuptake inhibitor, HDMP-28.
| Ki Affinity of Piperidine Based MAT Inhibitors | ||||||
| ∗∗ | X | N | 5HT | DA | NE | |
| SS | p-Vinyl | Me | 138 | 131 | 175 | |
| p-Ethyl | 255 | >1.7K | >1.1K | |||
| p-Allyl | 309 | 964 | >1K | |||
| p-Ethynyl | 175 | 187 | 364 | |||
| p-Phenyl | 62 | 173 | 203 | |||
| β-Naphthyl | 7.6 | 21 | 34 | |||
| 3R,4S | 42 | 947 | 241 | |||
| RR | 192 | 87 | 27 | |||
| 3S,4R | 12 | 271 | 38 | |||
| H2Cl | 3.5 | 90 | 30 | |||
| SS/RR | α-Naphthyl | Me | 101 | 304 | 281 | |
Clearly it is not just the SS enantiomer of the title compound that is an active MAT inhibitor.
N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate sections
Intro Effect of N-demethylation See also References
| PREVIOUS: Intro | NEXT: Effect of N-demethylation |
| << | >> |