HDMP-28
Legal status
Legal status
Identifiers
  • Methyl (naphthalen-2-yl)(piperidin-2-yl)acetate
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC18H21NO2
Molar mass283.365 g·mol−1
3D model (JSmol)
  • O=C(OC)[C@H](C1=CC2=C(C=C1)C=CC=C2)[C@]3([H])CCCCN3

  • O=C(OC)[C@H](c2cc1ccccc1cc2)[C@@H]3NCCCC3
  • InChI=1S/C18H21NO2/c1-21-18(20)17(16-8-4-5-11-19-16)15-10-9-13-6-2-3-7-14(13)12-15/h2-3,6-7,9-10,12,16-17,19H,4-5,8,11H2,1H3/t16-,17-/m1/s1 ☒N
  • Key:DNRNSIJBSCBESJ-IAGOWNOFSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

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. It has been sold as a designer drug since around 2015.[2]

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 has high affinity to SERT, and so behaves as a triple reuptake inhibitor.[3]

aEffect of (dl-threo) TMP and analogs on DA and 5-HT 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 10 μM 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);[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.

Legality

HDMP-28 is illegal in Switzerland as of December 2015.[7]

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. S2CID 5654856.
  2. ↑ Carlier J, Giorgetti R, Varì MR, Pirani F, Ricci G, Busardò FP. Use of cognitive enhancers: methylphenidate and analogs. Eur Rev Med Pharmacol Sci. 2019 Jan;23(1):3-15. doi:10.26355/eurrev_201901_16741 PMID 30657540
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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.
  6. ↑ 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. doi:10.1016/s0223-5234(01)01230-2. PMID 11461755.
  7. ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien". Der Bundesrat.
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