| Stereochemistry | ACHIRAL |
| Molecular Formula | C16H26N2O2 |
| Molecular Weight | 278.3898 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCN(CC)CC(C)(C)COC(=O)C1=CC=C(N)C=C1
InChI
InChIKey=OWQIUQKMMPDHQQ-UHFFFAOYSA-N
InChI=1S/C16H26N2O2/c1-5-18(6-2)11-16(3,4)12-20-15(19)13-7-9-14(17)10-8-13/h7-10H,5-6,11-12,17H2,1-4H3
Dimethocaine (DMC, larocaine), a synthetic derivative of cocaine, is a widely distributed "legal high" consumed as a "new psychoactive substance" (NPS), originally was used in the 1930s as an anesthetic, primarily in dentistry, ophthalmology, and otolaryngology. This drug completely inhibits dopamine transporter and has had the potential for abuse. Dimethocaine is intended for forensic and research purposes.
Originator
Approval Year
PubMed
Patents
Sample Use Guides
in rhesus monkeys: When responding was stable, dimethocaine (0.030-1.7 mg/kg/ infusion) was substituted for the cocaine training dose. Dimethocaine administration produced higher response rates compared with that of procaine, and was a more potent reinforcer. Drug effects on behavior were related to DAT occupancy in monkey striatum during neuroimaging with positron emission tomography (PET). DAT occupancy was determined by displacement of 8-(2-[(18)F]fluroethyl)2beta-carbomethoxy-3beta-(4-chlorophenyl)nortropane (FECNT). DAT occupancy was between 66 and 82% and <10-41% for doses of dimethocaine and procaine that maintained maximum response rates, respectively.
Acute administration of dimethocaine (10-40 mg/kg, IP) significantly increased locomotor activity and time spent on the drug-paired side and reduced the relative number of entries and time spent on the open arms of the plus-maze in mice.
Route of Administration:
Intraperitoneal
Dimethocaine showed full displacement of [3H]2-beta-carbomethoxy-3-beta-(4-fluorophenyl)tropane 1.5-naphthalenedisulfonate (CFT) binding (0-30 microM tested) and full inhibition of dopamine uptake (0-100 microM tested). Dimethocaine was only slightly less potent than cocaine with an estimated Ki of 1.4 micorM and an IC50 value of 1.2 microM for [3H]CFT binding and dopamine uptake.
ACTIVE MOIETY
SALT/SOLVATE (PARENT)
