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| Routes of administration | oral,insufflation,rectal |
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| Metabolism | Primarily by theliver |
| Excretion | Predominantlyrenal |
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| Formula | C14H17Cl2NO2 |
| Molar mass | 302.20 g·mol−1 |
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3,4-dichloromethylphenidate (abbreviated as3,4-DCMP, and incorrectly as3,4-CTMP for the d,l-threo diastereomer) is a potentstimulant drug from thephenidate class closely related tomethylphenidate. It acts as a potentserotonin-norepinephrine-dopamine reuptake inhibitor with a long duration of action.[clarification needed] It has been sold online as adesigner drug.[1][2]
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.[citation needed]
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 serotonergic activity, the other two beingHDMP-28 &HDEP-28. The reason for the serotonergic 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 bicyclicindole ring system of serotonin. Examples of compounds with the same SAR modifications done to increase serotonergic activity includenaphthylaminopropane and3,4-dichloroamphetamine.[citation needed]
The 3,4-dichloro group also increases resistance tometabolism, which can be seen on the compound's greatly increased duration of action andbiological half-life[clarification needed]. 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[citation needed]. Examples of compounds with the same SAR modification done to increase affinity to DAT & NET includedichloropane andO-2390.[citation needed]
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.[2][3][4][5][6][7] However, H. M. Deutsch's discrimination ratio[clarification needed] implies it to be more reinforcing thancocaine.[5]
| Compound | DAT (Ki, nM) | DA uptake IC50 (nM) | SERT (Ki, nM) | 5HT uptake IC50 (nM) | NET (Ki, nM) | NE uptake IC50 (nM) | NET/DAT selectivity | NE/DA uptake selectivity |
|---|---|---|---|---|---|---|---|---|
| 3,4-CTMP | 1.4 ± 0.1 | 23 ± 3 | 1,600 ± 150 | 540 ± 110 | 14 ± 6 | 10 ± 1 | 10.0 | 0.43 |
| 3,4-CEMP1 | 90 ± 14 | 800 ± 110 | 2,500 ± 420 | 1,100 ± 90 | 4,200 ± 1,900 | 190 ± 50 | 46.7 | 0.24 |
| TMP2 | 110 ± 9 | 110 ± 9 | 65,000 ± 4,000 | 5,100 ± 7,000 | 660 ± 50 | 61 ± 14 | 6.0 | 0.77 |
| Cocaine | 500 ± 65 | 240 ± 15 | 340 ± 40 | 250 ± 40 | 500 ± 90 | 210 ± 30 | 1.0 | 0.88 |
As of October 2015 3,4-CTMP is a controlled substance in China.[8]
3,4-CTMP was banned in the UK as aTemporary Class Drug from April 2015 following its unapproved sale as adesigner drug.[9]
Sweden's public health agency suggested to classify 3,4-CTMP as hazardous substance on 10 November 2014.[10]
