HDMP-28
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|---|---|
| Systematic (IUPAC) name | |
| methyl (2R)-2-naphthyl[(2R)-piperidin-2-yl]acetate | |
| Clinical data | |
| Legal status | ? |
| Identifiers | |
| ATC code | ? |
| PubChem | CID 9817261 |
| ChemSpider | 7993011  |
| Chemical data | |
| Formula | C18H21NO2 |
| Mol. mass | 283.365 |
| SMILES
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| (what is this?) (verify) | |
HDMP-28 or methylnaphthidate is a piperidine based stimulant drug, closely related to methylphenidate, but with the phenyl ring replaced by naphthalene. It is a potent dopamine reuptake inhibitor, with several times the potency of methylphenidate and a short duration of action,[1] and is a structural isomer of another potent dopamine reuptake inhibitor, N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate.
HDMP-28 and CFT overlay
Most of the TMP analogs of HDMP-28 have SERT Ki values in the range >10,000 and so are selective for dopamine and noradrenaline reuptake, with little or no effect on serotonin. HDMP-28 also has high affinity to SERT, and so behaves as a triple reuptake inhibitor.[2]
| Ar | [3H]CFT DAT | [3H]DA Uptake | [3H]RTI-55 SERT | Inhibition by 10μM | D.R. | Potency |
|---|---|---|---|---|---|---|
| Ph | 83.9 | 224 | >>10,000 | 19.6 | 2.7 | 1.00 |
| p-F | 35.0 | 142 | >10,000 | 36.9 | 4.1 | 3.33 |
| m-Cl | 5.1 | 23.0 | >10,000 | 45.5 | 4.5 | 2.42 |
| p-Me | 33.0 | 126 | >10,000 | 45.0 | 3.8 | 0.74 |
| p-NH2 | 34.5 | 114 | >>10,000 | 7.9 | 3.3 | 2.18 |
| m,p-Cl2 | 5.3 (2.67)b | 7.0 | 1,064 (>10,000)b | 93.3 | 1.3 | 7.98 |
| β-Naphthyl | 33.9b 11.0c | 53.0c | 71.6b | nd | 4.8c | — |
| Cocaine | 160 | 404 | 401 | nd | 2.5 | 0.41 |
| aSchweri, et al. (2002);[3] bDavies, et al. (2004);[4] cDeutsch, et al. (2001).[5] | ||||||
D.R. = Discrimination Ratio = [3H]DA ÷ [3H]CFT.
A low D.R. = addictive, whereas a high D.R. = low propensity for self-administration.
See also
- Naphthylisopropylamine
- Naphyrone
- 2β-Propanoyl-3β-(2-naphthyl)-tropane (WF-23)
References
- ↑ Lile JA, Wang Z, Woolverton WL, France JE, Gregg TC, Davies HM, Nader MA. The reinforcing efficacy of psychostimulants in rhesus monkeys: the role of pharmacokinetics and pharmacodynamics. Journal of Pharmacology and Experimental Therapeutics. 2003 Oct;307(1):356-66. PMID 12954808
- ↑ Davies HM, Hopper DW, Hansen T, Liu Q, Childers SR. Synthesis of methylphenidate analogues and their binding affinities at dopamine and serotonin transport sites. Bioorg Med Chem Lett. 2004 Apr 5;14(7):1799-802. doi:10.1016/j.bmcl.2003.12.097 PMID 15026075
- ↑ Schweri MM, Deutsch HM, Massey AT, Holtzman SG. Biochemical and behavioral characterization of novel methylphenidate analogs. J Pharmacol Exp Ther. 2002 May;301(2):527-35. doi:10.1124/jpet.301.2.527 PMID 11961053
- ↑ Davies HM, Hopper DW, Hansen T, Liu Q, Childers SR. Synthesis of methylphenidate analogues and their binding affinities at dopamine and serotonin transport sites. Bioorg Med Chem Lett. 2004 Apr 5;14(7):1799-802. doi:10.1016/j.bmcl.2003.12.097 PMID 15026075
- ↑ Deutsch HM, Ye X, Shi Q, Liu Z, Schweri MM. Synthesis and pharmacology of site specific cocaine abuse treatment agents: a new synthetic methodology for methylphenidate analogs based on the Blaise reaction. Eur J Med Chem. 2001 Apr;36(4):303-11. PMID 11461755
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