3,4-dichloromethylphenidate (abbreviated as 3,4-DCMP, and incorrectly as 3,4-CTMP for the d,l-threo diastereomer) is a potent
stimulant
Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition, ...
drug from the
phenidate
This is a list of methylphenidate (MPH or MPD) Analog (chemistry), analogues, or Phenidates. The most well known compound from this family, methylphenidate, is widely prescribed around the world for the treatment of attention deficit hyperactivit ...
class closely related to
methylphenidate
Methylphenidate, sold under the brand names Ritalin ( ) and Concerta ( ) among others, is a central nervous system (CNS) stimulant used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. It may be taken Oral adm ...
. It acts as a potent
serotonin-norepinephrine-dopamine reuptake inhibitor with a long duration of action. It has been sold online as a
designer drug
A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. ...
.
Chemistry
3,4-DCMP is the 3,4-dichlorinated analogue of methylphenidate. The 3,4-dichlorination is a common modification done to most monoamine reuptake inhibitors.
Pharmacology
Pharmacodynamics
The result of the 3,4-dichlorination on 3,4-DCMP is a higher selectivity for the serotonin transporter and serotonin uptake inhibition. Serotonergic activity among phenidates is very rare, and 3,4-DCMP is one of only three compounds from this class with appreciable serotoninergic activity, the other two being
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, wit ...
&
HDEP-28
HDEP-28 or ethylnaphthidate is a stimulant drug of the piperidine and substituted naphthylaminopropane, naphthylaminopropane groups, closely related to ethylphenidate, but with the benzene ring replaced by naphthalene. It is even more closely re ...
. The reason for the serotoninergic activity of all three compounds is a bulky aryl ring system (in the case of the aforementioned compounds, a 2-naphthalene ring), which mimics the bicyclic
indole
Indole is an organic compound with the formula . Indole is classified as an aromatic heterocycle. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. Indoles are derivatives of indole ...
ring system of serotonin. Examples of compounds with the same SAR modifictions done to increase serotoninergic activity include
naphthylaminopropane
Naphthylaminopropane (NAP; code name PAL-287), also known as naphthylisopropylamine (NIPA), is an experimental drug of the amphetamine and naphthylaminopropane families that was under investigation for the treatment of alcohol and stimulant ad ...
and
3,4-dichloroamphetamine.
The 3,4-dichloro group also increases resistance to metabolism, which can be seen on the compound's greatly increased duration of action and biological half-life. Furthermore, it also results in a greatly increased affinity for both the dopamine and noradrenaline transporters, because the 3,4-dichloro group more closely mimics the 3,4-dihydroxy group found on dopamine and adrenaline. Examples of compounds with the same SAR modification done to increase affinity to DAT & NET include dichloropane and
O-2390
O-2390 (3,4-Dichloro-alpha-PVP, DCPVP) is a recreational designer drug from the substituted cathinone family, which acts as a potent inhibitor of dopamine and noradrenaline reuptake ''in vitro'', with weaker but still significant inhibition of se ...
.
3,4-CTMP, the d,l-threo diastereomer of 3,4-DCMP, is approximately seven times more potent than methylphenidate in animal studies, but has weaker reinforcing effects due to its slower onset of action.
However, H. M. Deutsch's discrimination ratio implies it to be more reinforcing than
cocaine
Cocaine is a tropane alkaloid and central nervous system stimulant, derived primarily from the leaves of two South American coca plants, ''Erythroxylum coca'' and ''Erythroxylum novogranatense, E. novogranatense'', which are cultivated a ...
.
*
1 This is an abbreviation of the d,l-erythro diastereomer of 3,4-DCMP.
*
2 This is an abbreviation of d,l-threomethylphenidate, more widely known by its brand name ''Ritalin''.
Legality
As of October 2015 3,4-CTMP is a controlled substance in China.
3,4-CTMP was banned in the UK as a
Temporary Class Drug
A temporary class drug is a relatively new status for controlled drugs, which has been adopted in some jurisdictions, notably New Zealand and the United Kingdom, to attempt to bring newly synthesised designer drugs under legal control. The contro ...
from April 2015 following its unapproved sale as a
designer drug
A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. ...
.
Sweden's public health agency suggested to classify 3,4-CTMP as hazardous substance on 10 November 2014.
See also
*
3-Bromomethylphenidate
3-Bromomethylphenidate (3-Br-MPH) is a compound from the phenidate family, which has reportedly been sold as a designer drug. It showed the most potent binding to the dopamine transporter of a series of ring-substituted methylphenidate derivative ...
*
4-Methylmethylphenidate
''threo''-4-Methylmethylphenidate (4-MeTMP) 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 le ...
*
Cilobamine
Cilobamine is a drug which acts as a norepinephrine-dopamine reuptake inhibitor (NDRI) and has stimulant and antidepressant effects.
It can clearly be seen that the structure is based on dichloroisoprenaline that has been fused onto the bicycl ...
*
Dichloropane
Dichloropane ((−)-2β-Carbomethoxy-3β-(3,4-dichlorophenyl)tropane, RTI-111, O-401) is a stimulant of the phenyltropane class that acts as a serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI) with IC50 values of 3.13, 18, and ...
*
HDEP-28
HDEP-28 or ethylnaphthidate is a stimulant drug of the piperidine and substituted naphthylaminopropane, naphthylaminopropane groups, closely related to ethylphenidate, but with the benzene ring replaced by naphthalene. It is even more closely re ...
*
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, wit ...
*
Isopropylphenidate
Isopropylphenidate (also known as IPH and IPPD) is a piperidine based stimulant drug, closely related to methylphenidate, but with the methyl ester replaced by an isopropyl ester. It has similar effects to methylphenidate but with a longer durat ...
*
LR-5182
LR-5182 is a stimulant drug which acts as a norepinephrine–dopamine reuptake inhibitor, structurally related to the better known drug fencamfamine. It was developed by the pharmaceutical company Eli Lilly and Company, Eli Lilly in the 1970s, an ...
*
O-2390
O-2390 (3,4-Dichloro-alpha-PVP, DCPVP) is a recreational designer drug from the substituted cathinone family, which acts as a potent inhibitor of dopamine and noradrenaline reuptake ''in vitro'', with weaker but still significant inhibition of se ...
*
Propylphenidate
Propylphenidate (also known as PPH) is a piperidine based stimulant drug, closely related to methylphenidate, but with the methyl ester replaced by a propyl ester. It was banned in the UK as a Temporary Class Drug from April 2015 following its u ...
References
{{DEFAULTSORT:Dichloromethylphenidate, 3,4-
Stimulants
Designer drugs
2-Piperidinyl compounds
Chloroarenes
Methyl esters