Naphthylpropylaminopentane
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| Other names | 1-(2-Naphthyl)-2-propylaminopentane; NPAP; 2-Naphthyl-α,N-dipropylphenethylamine |
| Drug class | Monoaminergic activity enhancer |
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| Chemical and physical data | |
| Formula | C18H25N |
| Molar mass | 255.405 g·mol−1 |
| 3D model (JSmol) | |
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1-(2-Naphthyl)-2-propylaminopentane (NPAP), also known as 2-naphthyl-α,N-dipropylphenethylamine, is a monoaminergic activity enhancer (MAE) of the α-propylphenethylamine and naphthylaminopropane families related to phenylpropylaminopentane (PPAP).[1] It is the analogue of PPAP in which the phenyl ring has been replaced with a naphthalene ring.[1] MAEs are agents that enhance the action potential-mediated release of monoamine neurotransmitters.[2][3][4] NPAP is a MAE of norepinephrine and dopamine but not of serotonin.[1] Its potency is similar to that of PPAP.[1] As with PPAP, the (–)-enantiomer of NPAP is more potent as a MAE.[1] Like PPAP, it is inactive as a classical monoamine releasing agent.[1] NPAP was developed by József Knoll and colleagues and was first described in 2001.[1]
See also
[edit]- Methylenedioxyphenylpropylaminopentane (MPAP)
- Benzofuranylpropylaminopentane (BPAP)
- Indolylpropylaminopentane (IPAP)
- Naphthylaminopropane
- Ethylnaphthylaminopropane
- Naphyrone (naphthylpyrovalerone)
- Ethylnaphthidate (HDEP-28)
- Methylnaphthidate (HDMP-28)
References
[edit]- ^ a b c d e f g Yoneda F, Moto T, Sakae M, Ohde H, Knoll B, Miklya I, et al. (May 2001). "Structure-activity studies leading to (-)1-(benzofuran-2-yl)-2-propylaminopentane, ((-)BPAP), a highly potent, selective enhancer of the impulse propagation mediated release of catecholamines and serotonin in the brain". Bioorganic & Medicinal Chemistry. 9 (5): 1197–1212. doi:10.1016/s0968-0896(01)00002-5. PMID 11377178.
- ^ Shimazu S, Miklya I (May 2004). "Pharmacological studies with endogenous enhancer substances: beta-phenylethylamine, tryptamine, and their synthetic derivatives". Progress in Neuro-Psychopharmacology & Biological Psychiatry. 28 (3): 421–427. doi:10.1016/j.pnpbp.2003.11.016. PMID 15093948. S2CID 37564231.
- ^ Miklya I (November 2016). "The significance of selegiline/(-)-deprenyl after 50 years in research and therapy (1965-2015)". Molecular Psychiatry. 21 (11): 1499–1503. doi:10.1038/mp.2016.127. PMID 27480491. S2CID 205202709.
- ^ Knoll J (August 2003). "Enhancer regulation/endogenous and synthetic enhancer compounds: a neurochemical concept of the innate and acquired drives". Neurochemical Research. 28 (8): 1275–1297. doi:10.1023/a:1024224311289. PMID 12834268.