HDMP-28

HDMP-28
Systematic (IUPAC) name
methyl (2R)-2-naphthyl[(2R)-piperidin-2-yl]acetate
Clinical data
Pregnancy cat.  ?
Legal status  ?
Identifiers
ATC code  ?
PubChem CID 9817261
Chemical data
Formula C18H21NO2 
Mol. mass 283.365
SMILES eMolecules & PubChem
 YesY(what is this?)  (verify)

HDMP-28 or methylnaphthidate is a piperidine based stimulant drug, 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

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.
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.

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. 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



Wikimedia Foundation. 2010.

Look at other dictionaries:

  • HDMP — high dose methylprednisolone …   Medical dictionary

  • HDMP — • high dose methylprednisolone …   Dictionary of medical acronyms & abbreviations

  • Hang Dara Democratic Movement Party — The Hang Dara Democratic Movement Party (HDMP) is a Cambodian political party whose leader was Hang Dara. It was created in May 2002. Political ideologiesHere the HDMP believes in a variety of ideologies. With the right wing it believes in… …   Wikipedia

  • N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate — Systematic (IUPAC) name methyl (3S,4S) 1 methyl 4 (2 naphthyl)piperidine 3 carboxylate Clinical data Pr …   Wikipedia

  • HD media player — or HDD media player (HDMP) is a generic term used for a category of consumer product that combines a hard drive (HD) enclosure with hardware and software for playing audio, video and photos through a home entertainment system. It can be used… …   Wikipedia

  • List of cocaine analogues — Cocaine with it s numerical substitution positions. This is a list of cocaine analogues. A cocaine analogue retains 3β benzoyloxy or similar functionality unlike phenyltropanes. Cocaine analogues proper consist of the nine following classes of… …   Wikipedia

  • (-)-Methyl-1-methyl-4β-(2-naphthyl)piperidine-3β-carboxylate — Drugbox IUPAC name = methyl (3S,4S) 1 methyl 4 naphthalen 2 ylpiperidine 3 carboxylate width= 220 CAS number= ATC prefix= ATC suffix= PubChem= 10684403 DrugBank= C=18 | H=21 | N=1 | O=2 molecular weight = 283.364 smiles =… …   Wikipedia

  • Skelettszintigrafie — In der Medizin ist die Skelettszintigrafie, auch Knochenszintigrafie, (engl: Bone Scan) eine nuklearmedizinische Untersuchung (Szintigrafie), die zum Nachweis von Knochen Anteilen mit erhöhtem Knochenstoffwechsel dient. Solche Areale („Herde“)… …   Deutsch Wikipedia


Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”

We are using cookies for the best presentation of our site. Continuing to use this site, you agree with this.