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| Formula | C18H21NO2 |
| Molar mass | 283.371 g·mol−1 |
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HDMP-28 ormethylnaphthidate is astimulantdrug of thepiperidine andnaphthylaminopropane groups, closely related tomethylphenidate (Ritalin), but with thebenzene ring replaced bynaphthalene. It is a potentdopamine reuptake inhibitor, with several times the potency of methylphenidate and a short duration of action,[1] and is astructural isomer of another potent dopamine reuptake inhibitor,N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate. It has been sold as adesigner drug since around 2015.[2]
Most of the TMP analogs of HDMP-28 haveSERT 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 has high affinity to SERT, and so behaves as atriple reuptake inhibitor.[3]
| Inhibition of specific analogs at displacing CFT from binding to DAT & RTI-55 from binding to SERT | ||||||
| Ar | [3H]CFT DAT | [3H]DA Uptake | [3H]RTI-55 SERT | Inhibition by 10 μM | 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);[4]bDavies, et al. (2004);[5]cDeutsch, et al. (2001).[6] | ||||||
D.R. is the discrimination ratio = [3H]DA ÷ [3H]CFT.
A low D.R. indicates more addictive, whereas a high D.R. indicates low propensity for self-administration.
HDMP-28 is illegal in Switzerland as of December 2015.[7]