(diff) ← Older revision | Latest revision (diff) | Newer revision → (diff)
Short description: Chemical compound
N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate |
Identifiers |
---|
methyl (3S,4S)- 1-methyl- 4-(2-naphthyl)piperidine- 3-carboxylate
|
CAS Number | |
---|
PubChem CID | |
---|
Chemical and physical data |
---|
Formula | C18H21NO2 |
---|
Molar mass | 283.371 g·mol−1 |
---|
3D model (JSmol) | |
---|
COC(=O)C1CN(C)CCC1c3ccc2ccccc2c3
|
(verify) |
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.[1]
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
|
|
The stereochemistry of DMNPC dramatically affects it's binding affinity with the SS enantiomer having the highest overall activity. The 3R,4S enantiomer demonstrates the highest selectivity for 5-HTT.
In animal studies, DMNPC exhibits similar potency as fluoxetine but with greater activity for DAT and NET. N-Demethylation of DMNPC has shown to produce a 3-fold increase in potency for 5-HTT.[1]
Synthesis
A racemic mixture of DMNPC can be synthesized from freebase arecoline in a grignard reaction with 2-naphthylmagnesium bromide. Further reactions and separation methods can be used to produce enantiomerically pure products.[1]
A substantially simpler method that ablates the carbomethoxy ester substituent has been demonstrated by D. Koch in Ex2: U.S. Patent 6,303,627
See also
References
- ↑ 1.0 1.1 1.2 "Further SAR Studies of Piperidine-Based Analogues of Cocaine. 2. Potent Dopamine and Serotonin Reuptake Inhibitors". Journal of Medicinal Chemistry 43 (6): 1215–22. March 2000. doi:10.1021/jm9905561. PMID 10737754.
|
---|
Adamantanes | |
---|
Adenosine antagonists | |
---|
Alkylamines | |
---|
Ampakines | |
---|
Arylcyclohexylamines | |
---|
Benzazepines | |
---|
Cholinergics | |
---|
Convulsants | |
---|
Eugeroics | |
---|
Oxazolines | |
---|
Phenethylamines |
- 1-(4-Methylphenyl)-2-aminobutane
- 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane
- 2-Fuoroamphetamine
- 2-Fuoromethamphetamine
- 2-OH-PEA
- 2-Phenyl-3-aminobutane
- 2,3-MDA
- 3-Fuoroamphetamine
- 3-Fluoroethamphetamine
- 3-Fluoromethcathinone
- 3-Methoxyamphetamine
- 3-Methylamphetamine
- 3,4-DMMC
- 4-BMC
- 4-CMC
- 4-Fluoroamphetamine
- 4-Fluoromethamphetamine
- 4-MA
- 4-Methylbuphedrone
- 4-Methylcathinone
- 4-MEAP
- 4-MMA
- 4-Methylpentedrone
- 4-MTA
- 6-FNE
- AL-1095
- Alfetamine
- a-Ethylphenethylamine
- Amfecloral
- Amfepentorex
- Amfepramone
- Amidephrine
- 2-Amino-1,2-dihydronaphthalene
- 2-Aminoindane
- 5-(2-Aminopropyl)indole
- 2-Aminotetralin
- Acridorex
- Amphetamine (Dextroamphetamine, Levoamphetamine)
- Amphetaminil
- Arbutamine
- β-Methylphenethylamine
- β-Phenylmethamphetamine
- Benfluorex
- Benzedrone
- Benzphetamine
- BDB
- BOH
- 3-Benzhydrylmorpholine
- BPAP
- Buphedrone
- Bupropion
- Butylone
- Camfetamine
- Cathine
- Cathinone
- Chlorphentermine
- Cilobamine
- Cinnamedrine
- Clenbuterol
- Clobenzorex
- Cloforex
- Clortermine
- Cypenamine
- D-Deprenyl
- Denopamine
- Dimethoxyamphetamine
- Dimethylamphetamine
- Dimethylcathinone
- Dobutamine
- DOPA (Dextrodopa, Levodopa)
- Dopamine
- Dopexamine
- Droxidopa
- EBDB
- Ephedrine
- Epinephrine
- Epinine
- Etafedrine
- Ethcathinone
- Ethylnorepinephrine
- Ethylone
- Etilamfetamine
- Etilefrine
- Famprofazone
- Fencamfamin
- Fencamine
- Fenethylline
- Fenfluramine (Dexfenfluramine, Levofenfluramine)
- Fenproporex
- Feprosidnine
- Flephedrone
- Fludorex
- Formetorex
- Furfenorex
- Gepefrine
- Hexapradol
- Hexedrone
- HMMA
- Hordenine
- 4-Hydroxyamphetamine
- 5-Iodo-2-aminoindane
- Ibopamine
- Indanylamphetamine
- Iofetamine
- Isoetarine
- Isoethcathinone
- Isoprenaline
- L-Deprenyl (Selegiline)
- Lefetamine
- Lisdexamfetamine
- Lophophine
- MBDB
- MDA (tenamfetamine)
- MDBU
- MDEA
- MDMA (midomafetamine)
- MDMPEA
- MDOH
- MDPR
- MDPEA
- Mefenorex
- Mephedrone
- Mephentermine
- Metanephrine
- Metaraminol
- Mesocarb
- Methamphetamine (Dextromethamphetamine, Levomethamphetamine)
- Methoxamine
- Methoxyphenamine
- MMA
- Methcathinone
- Methedrone
- Methoxyphenamine
- Methylenedioxycathinone
- Methylone
- Mexedrone
- MMDA
- MMDMA
- MMMA
- Morforex
- N,alpha-Diethylphenylethylamine
- N-Ethylbuphedrone
- N-Ethylhexedrone
- N,N-Dimethylphenethylamine
- Naphthylamphetamine
- Nisoxetine
- Norepinephrine
- Norfenefrine
- Norfenfluramine
- Normetanephrine
- L-Norpseudoephedrine
- Octopamine (drug)
- Orciprenaline
- Ortetamine
- Oxifentorex
- Oxilofrine
- PBA
- PCA
- PCMA
- PHA
- Pentorex
- Pentedrone
- Pentylone
- Phenatine
- Phenpromethamine
- Phentermine
- Phenylalanine
- Phenylephrine
- Phenylpropanolamine
- Pholedrine
- PIA
- PMA
- PMEA
- PMMA
- PPAP
- Phthalimidopropiophenone
- Prenylamine
- Propylamphetamine
- Pseudoephedrine
- Ropinirole
- Salbutamol (Levosalbutamol)
- Sibutramine
- Solriamfetol
- Synephrine
- Theodrenaline
- Tiflorex
- Tranylcypromine
- Tyramine
- Tyrosine
- Xylopropamine
- Zylofuramine
|
---|
Phenylmorpholines | |
---|
Piperazines | |
---|
Piperidines | |
---|
Pyrrolidines | |
---|
Racetams | |
---|
Tropanes | |
---|
Tryptamines | |
---|
Others | |
---|
|
| Original source: https://en.wikipedia.org/wiki/N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate. Read more |