HDMP-28

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HDMP-28
HDMP-28.png
Systematic (IUPAC) name
methyl 2-(naphthalen-2-yl)-2-(piperidin-2-yl)acetate
Clinical data
Legal status
Identifiers
CAS Number 219915-69-2 N (hydrochloride)
Template:CAS (Component)
PubChem CID: 9817261
ChemSpider 7993011 N
Chemical data
Formula C18H21NO2
Molecular mass 283.365
  • O=C(OC)[C@H](C1=CC2=C(C=C1)C=CC=C2)[C@]3([H])CCCCN3
  • 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
 NYesY (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.

File:Naphthyl.png
HDMP-28 and CFT overlay

MMNPC&HDMP-28.png

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
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.

Legality

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

See also

References

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  1. ↑ 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
  2. ↑ 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
  3. ↑ 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
  4. ↑ 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
  5. ↑ 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
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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