HDMP-28
- CA: Schedule III
- DE: NpSG (Industrial and scientific use only)
- UK: Class B
- Methyl (naphthalen-2-yl)(piperidin-2-yl)acetate
- 231299-82-4 N
219915-69-2 (HCl)
- 9817261
- 7993011 N
- T52Y9T2U0W
- Interactive image
- Interactive image
- 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
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]
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]
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 |
---|---|---|---|---|---|---|
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);[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
- 3-Bromomethylphenidate
- 3,4-Dichloromethylphenidate
- BMAPN
- Ethylphenidate
- HDEP-28
- Naphthylisopropylamine
- Naphyrone
- 2β-Propanoyl-3β-(2-naphthyl)-tropane (WF-23)
- Isopropylphenidate
- Propylphenidate
References
- ^ Lile JA, Wang Z, Woolverton WL, France JE, Gregg TC, Davies HM, et al. (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.
- ^ Carlier J, Giorgetti R, Varì MR, Pirani F, Ricci G, Busardò FP (January 2019). "Use of cognitive enhancers: methylphenidate and analogs". European Review for Medical and Pharmacological Sciences. 23 (1): 3–15. doi:10.26355/eurrev_201901_16741. PMID 30657540.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien". Der Bundesrat.
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