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Methylnaphthidate: Wikis

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HDMP-28
Systematic (IUPAC) name
methyl (2R)-2-naphthyl[(2R)-piperidin-2-yl]acetate
Identifiers
CAS number  ?
ATC code  ?
PubChem 9817261
Chemical data
Formula C 18H21NO2  
Mol. mass 283.365
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes  ?

HDMP-28 or methylnaphthidate is a piperidine based stimulant drug. It is 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

MMNPC&HDMP-28.png

Regarding HDMP-28, an important consideration is that most of the TMP analogs have SERT Ki values in the range >10,000.[2] Interestingly, HDMP-28 behaved as a triple reuptake inhibitor.

aEffect of (dl-threo) TMP and analogs on DA and 5HT Transporters.
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
p,m-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

References

  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. 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. 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. 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
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