HDMP-28
Encyclopedia
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, and is a structural isomer of another potent dopamine reuptake inhibitor, N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate.
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.
D.R. = Discrimination Ratio = [3H]DA ÷ [3H]CFT.
A low D.R. = addictive, whereas a high D.R. = low propensity for self-administration.
Piperidine
Piperidine is an organic compound with the molecular formula 5NH. This heterocyclic amine consists of a six-membered ring containing five methylene units and one nitrogen atom...
based stimulant
Stimulant
Stimulants are psychoactive drugs which induce temporary improvements in either mental or physical function or both. Examples of these kinds of effects may include enhanced alertness, wakefulness, and locomotion, among others...
drug, closely related to methylphenidate
Methylphenidate
Methylphenidate is a psychostimulant drug approved for treatment of attention-deficit hyperactivity disorder, postural orthostatic tachycardia syndrome and narcolepsy. It may also be prescribed for off-label use in treatment-resistant cases of lethargy, depression, neural insult and obesity...
, but with the phenyl ring replaced by naphthalene
Naphthalene
Naphthalene is an organic compound with formula . It is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings...
. It is a potent dopamine reuptake inhibitor
Dopamine reuptake inhibitor
A dopamine reuptake inhibitor is a type of drug that acts as a reuptake inhibitor for the neurotransmitter dopamine by blocking the action of the dopamine transporter...
, with several times the potency of methylphenidate and a short duration of action, and is a structural isomer of another potent dopamine reuptake inhibitor, N,O-Dimethyl-4-(2-naphthyl)piperidine-3-carboxylate.
Most of the TMP analogs of HDMP-28 have SERT
Serotonin transporter
The serotonin transporter is a monoamine transporter protein.This protein is an integral membrane protein that transports the neurotransmitter serotonin from synaptic spaces into presynaptic neurons. This transport of serotonin by the SERT protein terminates the action of serotonin and recycles it...
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.
| Ar | [3H]CFT DAT | [3H]DA Uptake | [3H]RTI-55 SERT | Inhibition by 10μM | D.R. | Potency |
|---|---|---|---|---|---|---|
| Ph Methylphenidate Methylphenidate is a psychostimulant drug approved for treatment of attention-deficit hyperactivity disorder, postural orthostatic tachycardia syndrome and narcolepsy. It may also be prescribed for off-label use in treatment-resistant cases of lethargy, depression, neural insult and obesity... | 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 4-Methylmethylphenidate threo-4-Methylmethylphenidate is a stimulant drug related to methylphenidate. It is slightly less potent than methylphenidate and has relatively low efficacy at blocking dopamine reuptake despite its high binding affinity, which led to its investigation as a possible substitute drug for treatment... | 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 3,4-Dichloromethylphenidate threo-3,4-Dichloromethylphenidate is a stimulant drug related to methylphenidate. It is around 7x more potent than methylphenidate in animal studies, but has weaker reinforcing effects due to its slower onset of action. However, H. M... | 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 Cocaine Cocaine is a crystalline tropane alkaloid that is obtained from the leaves of the coca plant. The name comes from "coca" in addition to the alkaloid suffix -ine, forming cocaine. It is a stimulant of the central nervous system, an appetite suppressant, and a topical anesthetic... | 160 | 404 | 401 | nd | 2.5 | 0.41 |
| aSchweri, et al. (2002); bDavies, et al. (2004); cDeutsch, et al. (2001). | ||||||
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
- NaphthylisopropylamineNaphthylisopropylamineNaphthylisopropylamine is an experimental drug currently under investigation for the treatment of alcohol and stimulant addiction....
- Naphyrone
- 2β-Propanoyl-3β-(2-naphthyl)-tropane (WF-23)