Napthylaminopropane
File:Naphthylisopropylamine.svg | |
Systematic (IUPAC) name | |
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(±)-1-(2-naphthyl)propan-2-amine | |
Clinical data | |
Pregnancy category |
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Routes of administration | Oral |
Legal status | |
Legal status |
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Identifiers | |
CAS Number | 18085-03-5 |
ATC code | none |
PubChem | CID 10219723 |
ChemSpider | 8395215 |
Synonyms | 1-(2-naphthyl)-2-aminopropane; alpha-methylnapthylethylamine |
Chemical data | |
Formula | C13H15N |
Molar mass | 185.27 g/mol[[Script error: No such module "String".]] |
Script error: No such module "collapsible list". | |
Naphthylisopropylamine (PAL-287) is an experimental drug currently under investigation for the treatment of alcohol and stimulant addiction.[1]
Naphthylisopropylamine acts as a non-neurotoxic releasing agent of serotonin, norepinephrine, and dopamine, with EC50 values of 3.4 nM, 11.1 nM, and 12.6 nM, respectively.[2] It also has affinity for the 5-HT2A, 5-HT2B, and 5-HT2C receptors (EC50 values = 466 nM, 40 nM, and 2.3 nM, respectively),[1] and acts as a full agonist at 5-HT2B and as a partial agonist at 5-HT2C, while its affinity for 5-HT2A is probably too low to be significant.[1]
In animal studies, naphthylisopropylamine was shown to reduce cocaine self-administration, yet produced relatively weak stimulant effects when administered alone, being a lesser stimulant than d-amphetamine for comparison.[3][4][5] Further research is now being conducted in primates to see if it will be a useful substitute for treating drug addiction in humans as well.[6]
An important observation is that in behavioral studies, rodents would consistently self-administer selective norepinephrine and dopamine releasing agents such as d-amphetamine, yet compounds that also release serotonin like naphthylisopropylamine would not be self-administered.[3]
See also
- 5-APDB
- 6-APB
- 6-APDB
- 5-(2-Aminopropyl)indole
- Ethylenedioxymethamphetamine
- Indanylaminopropane
- Tetralinylaminopropane
- Naphyrone
References
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Phenethylamines | Psychedelics: 2C-B • 2C-B-FLY • 2C-C • 2C-D • 2C-E • 2C-G • 2C-I • 2C-N • 2C-P • 2C-SE • 2C-T • 2C-T-2 • 2C-T-4 • 2C-T-7 • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 2C-TFM • 2C-YN • Allylescaline • DESOXY • Escaline • Isoproscaline • Jimscaline • Macromerine • MEPEA • Mescaline • Metaescaline • Methallylescaline • Proscaline • Psi-2C-T-4 • TCB-2 Stimulants: 2-OH-PEA • β-Me-PEA • Hordenine • N-Me-PEA • Phenethylamine (PEA) Entactogens: Lophophine • MDPEA • MDMPEA Others: BOH • DMPEA |
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Amphetamines Phenylisopropylamines | Psychedelics: 3C-BZ • 3C-E • 3C-P • Aleph • Beatrice • Bromo-DragonFLY • D-Deprenyl • DMA • DMCPA • DMMDA • DOB • DOC • DOEF • DOET • DOI • DOM • DON • DOPR • DOTFM • Ganesha • MMDA • MMDA-2 • Psi-DOM • TMA • TeMA Stimulants: 4-MA • 4-MMA • 4-MTA • 5-IT • Alfetamine • Amfecloral • Amfepentorex • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Benfluorex • Benzphetamine • Cathine • Clobenzorex • Dimethylamphetamine • Ephedrine (EPH) • Ethylamphetamine • Fencamfamine • Fencamine • Fenethylline • Fenfluramine (Dexfenfluramine) • Fenproporex • Fludorex • Furfenorex • Isopropylamphetamine • Lefetamine • Mefenorex • Methamphetamine (Dextromethamphetamine, Levomethamphetamine) • Methoxyphenamine • MMA • Oxilofrine • Ortetamine • PBA • PCA • Phenpromethamine • PFA • PFMA • PIA • PMA • PMEA • PMMA • Phenylpropanolamine (PPA) • Prenylamine • Propylamphetamine • Pseudoephedrine (PSE) • Sibutramine • Tiflorex (Flutiorex) • Tranylcypromine • Xylopropamine • Zylofuramine Entactogens: 5-APDB • 6-APB • 6-APDB • IAP • MDA • MDEA • MDHMA (FLEA) • MDMA ("Ecstasy") • MDOH • MMDMA • NAP • TAP Others: Amiflamine • D-Deprenyl • L-Deprenyl (Selegiline) |
Phentermines | Stimulants: Chlorphentermine • Cloforex • Clortermine • Etolorex • Mephentermine • Pentorex (Phenpentermine) • Phentermine Entactogens: MDPH • MDMPH |
Cathinones | Stimulants: Amfepramone • Brephedrone • Buphedrone • Bupropion (Amfebutamone) • Cathinone (Propion) • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Ethcathinone (Ethylpropion) • Flephedrone • Methcathinone (Methylpropion) • Mephedrone • Methedrone Entactogens: Ethylone • Methylone |
Phenylisobutylamines | |
Phenylalkylpyrrolidines | |
Catecholamines (and relatives..) | 6-FNE • 6-OHDA • α-Me-DA • α-Me-TRA • Adrenochrome • Ciladopa • D-DOPA (Dextrodopa) • Dopamine • Epinephrine (Adrenaline) • Epinine • Fenclonine • Ibopamine • L-DOPA (Levodopa) • L-DOPS (Droxidopa) • L-Phenylalanine • L-Tyrosine • meta-Octopamine • meta-Tyramine • Metanephrine • Metirosine • Methyldopa • Nordefrin (Levonordefrin) • Norepinephrine (Noradrenaline) • Normetanephrine • para-Octopamine • para-Tyramine |
Miscellaneous | Amidephrine • Arbutamine • Cafedrine • Denopamine • Dobutamine • Dopexamine • Etafedrine • Ethylnorepinephrine • Etilefrine • Famprofazone • Gepefrine • Isoprenaline (Isoproterenol) • Isoetarine • Metaraminol • Metaterol • Methoxamine • Norfenefrine • Orciprenaline • Phenylephrine (Neosynephrine) • Phenoxybenzamine • Prenalterol • Pronethalol • Propranolol • Salbutamol (Albuterol; Levosalbutamol) • Synephrine (Oxedrine) • Theodrenaline • Xamoterol |
- ↑ 1.0 1.1 1.2 Rothman RB, Blough BE, Baumann MH (2007). "Dual dopamine/serotonin releasers as potential medications for stimulant and alcohol addictions". The AAPS Journal. 9 (1): E1–10. doi:10.1208/aapsj0901001. PMC 2751297 Freely accessible. PMID 17408232. CS1 maint: Multiple names: authors list (link)
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ 3.0 3.1 Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ MEHES G (1952). "[On the pharmacological effects of 1-(alpha-naphthyl)-, and 1-(beta-naphthyl)-2-aminopropane; a contribution on the problem of chemical structure and effect.]". Acta Physiologica Hungarica (in Undetermined). 3 (1): 137–151. PMID 13050439. CS1 maint: Unrecognized language (link)
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
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