HDMP-28

HDMP-28 or methylnaphthidate is a stimulant drug of the piperidine and naphthylaminopropane groups, closely related to methylphenidate (Ritalin), 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

HDMP-28

Legal status
Legal status	CA: Schedule III DE: NpSG (Industrial and scientific use only) UK: Class B
Identifiers
IUPAC name Methyl (naphthalen-2-yl)(piperidin-2-yl)acetate
CAS Number	231299-82-4 N 219915-69-2 (HCl)
PubChem CID	9817261
ChemSpider	7993011 N
UNII	T52Y9T2U0W
Chemical and physical data
Formula	C18H21NO2
Molar mass	283.371 g·mol−1
3D model (JSmol)	Interactive image Interactive image
SMILES 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 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
NY (what is this?)  (verify)

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
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