4-Benzylpiperidine
Chemical compound
- DE: The NpSG do not apply to this substance, because it is not a 2-Phenylethylamine derivative
- UK: Under Psychoactive Substances Act
- 4-(phenylmethyl)piperidine
- 31252-42-3 N
- 31738
- 29432 Y
- JDF1T4667S
- ChEMBL144129 Y
- DTXSID3067603
- Interactive image
- C1CNCCC1CC2=CC=CC=C2
InChI
- InChI=1S/C12H17N/c1-2-4-11(5-3-1)10-12-6-8-13-9-7-12/h1-5,12-13H,6-10H2 Y
- Key:ABGXADJDTPFFSZ-UHFFFAOYSA-N Y
4-Benzylpiperidine is a drug and research chemical used in scientific studies. It acts as a monoamine releasing agent with 20- to 48-fold selectivity for releasing dopamine versus serotonin. It is most efficacious as a releaser of norepinephrine, with an EC50 of 109 nM (DA), 41.4 nM (NE) and 5246 nM (5-HT).[1] It has a fast onset of action and a short duration.[1] It also functions as a monoamine oxidase inhibitor (MAOI) with preference for MAO-A.[2]
Synthesis
4-Cyanopyridine can be reacted with toluene to give 4-benzylpyridine.[3] Catalytic hydrogenation of the pyridine ring then completes the synthesis.[4]
Applications
- RMI-10608 [35623-04-2] Patent (Ex 2/3):[5] (Ex 3)[6] This analogue of haloperidol was discovered to have utility in treating both psychosis as well as preventing brain damage by virtue of its NMDA antagonist pharmacology.
See also
References
- ^ a b Negus SS, Baumann MH, Rothman RB, Mello NK, Blough BE (April 2009). "Selective suppression of cocaine- versus food-maintained responding by monoamine releasers in rhesus monkeys: benzylpiperazine, (+)phenmetrazine, and 4-benzylpiperidine". The Journal of Pharmacology and Experimental Therapeutics. 329 (1): 272–281. doi:10.1124/jpet.108.143701. PMC 2670586. PMID 19151247.
- ^ Arai Y, Hamamichi N, Kinemuchi H (October 1986). "Time-dependent inhibition of rat brain monoamine oxidase by an analogue of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), 4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridine". Neuroscience Letters. 70 (2): 255–260. doi:10.1016/0304-3940(86)90473-8. PMID 3490636. S2CID 30243106.
- ^ Hoshikawa T, Inoue M (2013). "Photoinduced direct 4-pyridination of C(sp3)–H Bonds". Chemical Science. 4 (8): 3118. doi:10.1039/c3sc51080h. ISSN 2041-6520.
- ^ Siegel S (2001). "Rhodium on alumina.". e-EROS Encyclopedia of Reagents for Organic Synthesis. New York: John Wiley & Sons. doi:10.1002/047084289X.rr003. ISBN 978-0-471-93623-7. OCLC 1031885332.
- ^ Rafael Foguet, et al. U.S. patent 5,395,841 (1995 to Ferrer Internacional SA).
- ^ Sui Xiong Cai, et al. WO1996002250 (Cocensys Inc, Acea Pharmaceuticals Inc).
- v
- t
- e
- 3-Fluoromethcathinone
- 3,4-DMMC
- 4-BMC
- 4-CMC
- 4-Methylbuphedrone
- 4-Methylcathinone
- 4-MEAP
- 4-Methylpentedrone
- Amfepramone
- Benzedrone
- Buphedrone
- Bupropion
- Butylone
- Cathinone
- Dimethylcathinone
- Ethcathinone
- Ethylone
- Flephedrone
- Hexedrone
- Isoethcathinone
- Mephedrone
- Methcathinone
- Methedrone
- Methylenedioxycathinone
- Methylone
- Mexedrone
- N-Ethylbuphedrone
- N-Ethylhexedrone
- Pentedrone
- Pentylone
- Phthalimidopropiophenone
- A-84,543
- A-366,833
- ABT-202
- ABT-418
- AR-R17779
- Altinicline
- Anabasine
- Arecoline
- Bradanicline
- Cotinine
- Cytisine
- Dianicline
- Epibatidine
- Epiboxidine
- GTS-21
- Ispronicline
- Nicotine
- PHA-543,613
- PNU-120,596
- PNU-282,987
- Pozanicline
- Rivanicline
- Sazetidine A
- SIB-1553A
- SSR-180,711
- TC-1698
- TC-1827
- TC-2216
- Tebanicline
- UB-165
- Varenicline
- WAY-317,538
- 1-(4-Methylphenyl)-2-aminobutane
- 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane
- 2-Fluoroamphetamine
- 2-Fluoromethamphetamine
- 2-OH-PEA
- 2-Phenyl-3-aminobutane
- 2,3-MDA
- 3-Fluoroamphetamine
- 3-Fluoroethamphetamine
- 3-Methoxyamphetamine
- 3-Methylamphetamine
- 4-Fluoroamphetamine
- 4-Fluoromethamphetamine
- 4-MA
- 4-MMA
- 4-MTA
- 6-FNE
- AL-1095
- Alfetamine
- a-Ethylphenethylamine
- Amfecloral
- Amfepentorex
- 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
- Benzphetamine
- BDB
- BOH
- 3-Benzhydrylmorpholine
- BPAP
- Camfetamine
- Cathine
- Chlorphentermine
- Cilobamine
- Cinnamedrine
- Clenbuterol
- Clobenzorex
- Cloforex
- Clortermine
- Cypenamine
- D-Deprenyl
- Denopamine
- Dimethoxyamphetamine
- Dimethylamphetamine
- Dobutamine
- DOPA (Dextrodopa, Levodopa)
- Dopamine
- Dopexamine
- Droxidopa
- EBDB
- Ephedrine
- Epinephrine
- Epinine
- Etafedrine
- Ethylnorepinephrine
- Etilamfetamine
- Etilefrine
- Famprofazone
- Fencamfamin
- Fencamine
- Fenethylline
- Fenfluramine (Dexfenfluramine, Levofenfluramine)
- Fenproporex
- Feprosidnine
- Fludorex
- Formetorex
- Furfenorex
- Gepefrine
- Hexapradol
- HMMA
- Hordenine
- 4-Hydroxyamphetamine
- 5-Iodo-2-aminoindane
- Ibopamine
- Indanylamphetamine
- Iofetamine
- Isoetarine
- Isoprenaline
- L-Deprenyl (Selegiline)
- Lefetamine
- Lisdexamfetamine
- Lophophine
- MBDB
- MDA (tenamfetamine)
- MDBU
- MDEA
- MDMA (midomafetamine)
- MDMPEA
- MDOH
- MDPR
- MDPEA
- Mefenorex
- Mephentermine
- Metanephrine
- Metaraminol
- Mesocarb
- Methamphetamine (Dextromethamphetamine, Levomethamphetamine)
- Methoxamine
- Methoxyphenamine
- MMA
- Methoxyphenamine
- MMDA
- MMDMA
- MMMA
- Morforex
- N,alpha-Diethylphenylethylamine
- N,N-Dimethylphenethylamine
- Naphthylamphetamine
- Nisoxetine
- Norepinephrine
- Norfenefrine
- Norfenfluramine
- Normetanephrine
- L-Norpseudoephedrine
- Octopamine
- Orciprenaline
- Ortetamine
- Oxifentorex
- Oxilofrine
- PBA
- PCA
- PCMA
- PHA
- Pentorex
- Phenatine
- Phenpromethamine
- Phentermine
- Phenylalanine
- Phenylephrine
- Phenylpropanolamine
- Pholedrine
- PIA
- PMA
- PMEA
- PMMA
- PPAP
- Prenylamine
- Propylamphetamine
- Pseudoephedrine
- Ropinirole
- Salbutamol (Levosalbutamol)
- Sibutramine
- Solriamfetol
- Synephrine
- Theodrenaline
- Tiflorex
- Tranylcypromine
- Tyramine
- Tyrosine
- Xylopropamine
- Zylofuramine
- 1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine
- 2-Benzylpiperidine
- 2-Methyl-3-phenylpiperidine
- 3,4-Dichloromethylphenidate
- 4-Benzylpiperidine
- 4-Fluoromethylphenidate
- 4-Methylmethylphenidate
- Desoxypipradrol
- Difemetorex
- Diphenylpyraline
- Ethylnaphthidate
- Ethylphenidate
- Methylnaphthidate
- Isopropylphenidate
- JZ-IV-10
- Methylphenidate (Dexmethylphenidate)
- Nocaine
- Phacetoperane
- Pipradrol
- Propylphenidate
- Serdexmethylphenidate
- SCH-5472
- 4-fluorotropacocaine
- 4'-Fluorococaine
- Altropane (IACFT)
- Brasofensine
- CFT (WIN 35,428)
- β-CIT (RTI-55)
- Cocaethylene
- Cocaine
- Dichloropane (RTI-111)
- Difluoropine
- FE-β-CPPIT
- FP-β-CPPIT
- Ioflupane (123I)
- Norcocaine
- PIT
- PTT
- RTI-31
- RTI-32
- RTI-51
- RTI-112
- RTI-113
- RTI-120
- RTI-121 (IPCIT)
- RTI-126
- RTI-150
- RTI-177
- RTI-229
- RTI-336
- RTI-354
- RTI-371
- RTI-386
- Salicylmethylecgonine
- Tesofensine
- Troparil (β-CPT, WIN 35,065-2)
- Tropoxane
- WF-23
- WF-33
- 2-MDP
- 3,3-Diphenylcyclobutanamine
- Amfonelic acid
- Amineptine
- Amiphenazole
- Atipamezole
- Atomoxetine
- Bemegride
- Benzydamine
- BTQ
- BTS 74,398
- Centanafadine
- Ciclazindol
- Clofenciclan
- Cropropamide
- Crotetamide
- D-161
- Desipramine
- Diclofensine
- Dimethocaine
- Efaroxan
- Etamivan
- Fenisorex
- Fenpentadiol
- Gamfexine
- Gilutensin
- GSK1360707F
- GYKI-52895
- Hexacyclonate
- Idazoxan
- Indanorex
- Indatraline
- JNJ-7925476
- Lazabemide
- Leptacline
- Lomevactone
- LR-5182
- Mazindol
- Meclofenoxate
- Medifoxamine
- Mefexamide
- Methamnetamine
- Methastyridone
- Methiopropamine
- Naphthylaminopropane
- Nefopam
- Nikethamide
- Nomifensine
- O-2172
- Oxaprotiline
- PNU-99,194
- PRC200-SS
- Rasagiline
- Rauwolscine
- Rubidium chloride
- Setazindol
- Tametraline
- Tandamine
- Thiopropamine
- Thiothinone
- Trazium
- UH-232
- Yohimbine
This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it. |
- v
- t
- e