HDMP-28

HDMP-28 or methylnaphthidate is a piperidine based stimulant drug, closely related to methylphenidate, but with the benzene 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
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC18H21NO2
Molar mass283.365 g·mol−1
3D model (JSmol)
 NY (what is this?)  (verify)

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]

aEffect of (dl-threo) TMP and analogs on DA and 5HT Transporters.
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 10μM D.R. Potency
Ph83.9224>>10,00019.62.71.00
p-F35.0142>10,00036.94.13.33
m-Cl5.123.0>10,00045.54.52.42
p-Me33.0126>10,00045.03.80.74
p-NH234.5114>>10,0007.93.32.18
m,p-Cl25.3 (2.67)b7.01,064 (>10,000)b93.31.37.98
β-Naphthyl33.9b 11.0c53.0c71.6bnd4.8c
Cocaine160404401nd2.50.41
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.

Legality

HDMP-28 is illegal in Switzerland as of December 2015.[6]

See also

References

  1. Lile JA, Wang Z, Woolverton WL, France JE, Gregg TC, Davies HM, Nader MA (October 2003). "The reinforcing efficacy of psychostimulants in rhesus monkeys: the role of pharmacokinetics and pharmacodynamics". The Journal of Pharmacology and Experimental Therapeutics. 307 (1): 356–66. doi:10.1124/jpet.103.049825. PMID 12954808.
  2. Davies HM, Hopper DW, Hansen T, Liu Q, Childers SR (April 2004). "Synthesis of methylphenidate analogues and their binding affinities at dopamine and serotonin transport sites". Bioorganic & Medicinal Chemistry Letters. 14 (7): 1799–802. doi:10.1016/j.bmcl.2003.12.097. PMID 15026075.
  3. Schweri MM, Deutsch HM, Massey AT, Holtzman SG (May 2002). "Biochemical and behavioral characterization of novel methylphenidate analogs". The Journal of Pharmacology and Experimental Therapeutics. 301 (2): 527–35. doi:10.1124/jpet.301.2.527. PMID 11961053.
  4. Davies HM, Hopper DW, Hansen T, Liu Q, Childers SR (April 2004). "Synthesis of methylphenidate analogues and their binding affinities at dopamine and serotonin transport sites". Bioorganic & Medicinal Chemistry Letters. 14 (7): 1799–802. doi:10.1016/j.bmcl.2003.12.097. PMID 15026075.
  5. Deutsch HM, Ye X, Shi Q, Liu Z, Schweri MM (April 2001). "Synthesis and pharmacology of site specific cocaine abuse treatment agents: a new synthetic methodology for methylphenidate analogs based on the Blaise reaction". European Journal of Medicinal Chemistry. 36 (4): 303–11. PMID 11461755.
  6. "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien". Der Bundesrat.
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