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Napthylaminopropane
Systematic (IUPAC) name
(±)-1-(2-naphthyl)propan-2-amine
Identifiers
CAS number 18085-03-5
ATC code  ?
PubChem 10219723
Chemical data
Formula C 13H15N 
Mol. mass 185.27 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status Uncontrolled
Routes  ?

Naphthylaminopropane (NAP; PAL-287), also known as naphthylisopropylamine or alpha-methylnaphthylethylamine, is psychoactive drug currently under investigation for the treatment of alcohol and stimulant addiction.[1] It 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]

In animal studies, naphthylaminopropane was shown to reduce cocaine self-administration, yet produced relatively weak stimulant effects when administered alone, being a lesser stimulant than dextroamphetamine 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 agent such as amphetamine, yet compounds that also release serotonin like naphthylaminopropane would not be self-administered.[3]

A possible limitation of naphthylaminopropane is that it also has high affinity for the 5-HT2C receptor,[3] which is suggestive that it may have significant anorectic effects.[7] This would be counterproductive in concept in that many of those who are addicted to stimulants are already malnourished or underweight. On the other hand, napthylaminopropane could additionally or instead be developed for the treatment of certain eating disorders like obesity and compulsive overeating.

See also

References

  1. ^ 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. PMID 17408232.  
  2. ^ Wee S, Anderson KG, Baumann MH, Rothman RB, Blough BE, Woolverton WL (May 2005). "Relationship between the serotonergic activity and reinforcing effects of a series of amphetamine analogs". The Journal of Pharmacology and Experimental Therapeutics 313 (2): 848–54. doi:10.1124/jpet.104.080101. PMID 15677348. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=15677348.  
  3. ^ a b c Rothman RB, Blough BE, Woolverton WL, et al. (June 2005). "Development of a rationally designed, low abuse potential, biogenic amine releaser that suppresses cocaine self-administration". The Journal of Pharmacology and Experimental Therapeutics 313 (3): 1361–1369. doi:10.1124/jpet.104.082503. PMID 15761112.  
  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.]" (in Undetermined). Acta Physiologica Hungarica 3 (1): 137–151. PMID 13050439.  
  5. ^ Glennon RA, Young R, Hauck AE, McKenney JD (December 1984). "Structure-activity studies on amphetamine analogs using drug discrimination methodology". Pharmacology, Biochemistry, and Behavior 21 (6): 895–901. PMID 6522418.  
  6. ^ Negus SS, Mello NK, Blough BE, Baumann MH, Rothman RB (February 2007). "Monoamine releasers with varying selectivity for dopamine/norepinephrine versus serotonin release as candidate "agonist" medications for cocaine dependence: studies in assays of cocaine discrimination and cocaine self-administration in rhesus monkeys". The Journal of Pharmacology and Experimental Therapeutics 320 (2): 627–636. doi:10.1124/jpet.106.107383. PMID 17071819.  
  7. ^ Sargent PA, Sharpley AL, Williams C, Goodall EM, Cowen PJ (October 1997). "5-HT2C receptor activation decreases appetite and body weight in obese subjects". Psychopharmacology 133 (3): 309–12. PMID 9361339. http://link.springer.de/link/service/journals/00213/bibs/7133003/71330309.htm.  
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