Napthylaminopropane

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Napthylaminopropane
File:Naphthylisopropylamine.svg
Systematic (IUPAC) name
(±)-1-(2-naphthyl)propan-2-amine
Clinical data
Pregnancy
category
  •  ?
Routes of
administration
Oral
Legal status
Legal status
  • Uncontrolled
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".]]
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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

References

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  1. 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 2751297Freely accessible. PMID 17408232. 
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  4. 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. 
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