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Details

Stereochemistry ACHIRAL
Molecular Formula C16H26N2O2.C7H6O3
Molecular Weight 416.5115
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIMETHOCAINE SALICYLATE

SMILES

CCN(CC)CC(C)(C)COC(=O)c1ccc(cc1)N.c1ccc(c(c1)C(=O)O)O

InChI

InChIKey=RPLNBZIUJOFRHU-UHFFFAOYSA-N
InChI=1S/C16H26N2O2.C7H6O3/c1-5-18(6-2)11-16(3,4)12-20-15(19)13-7-9-14(17)10-8-13;8-6-4-2-1-3-5(6)7(9)10/h7-10H,5-6,11-12,17H2,1-4H3;1-4,8H,(H,9,10)

HIDE SMILES / InChI

Molecular Formula C16H26N2O2
Molecular Weight 278.3905
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C7H6O3
Molecular Weight 138.121
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Curator's Comment:: # Hoffmann-La Roche Company

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q01959
Gene ID: 6531
Gene Symbol: SLC6A3
Target Organism: Homo sapiens (Human)
1.19999999999999996 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
PubMed

PubMed

TitleDatePubMed
Subtle differences in the discriminative stimulus effects of cocaine and GBR-12909.
2001 Apr
Role of the dopamine transporter and the sodium channel in the cocaine-like discriminative stimulus effects of local anesthetics in rats.
2001 Sep
In vivo comparison of the reinforcing and dopamine transporter effects of local anesthetics in rhesus monkeys.
2005 Dec 15
Dimethocaine, a synthetic cocaine derivative: studies on its in vitro metabolism catalyzed by P450s and NAT2.
2014 Feb 10
Contribution of human esterases to the metabolism of selected drugs of abuse.
2015 Jan 5
Patents

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.
Route of Administration: Intraperitoneal
In Vitro Use Guide
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 03:57:16 UTC 2021
Edited
by admin
on Sat Jun 26 03:57:16 UTC 2021
Record UNII
080UKX74TN
Record Status Validated (UNII)
Record Version
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Name Type Language
DIMETHOCAINE SALICYLATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C245
Created by admin on Sat Jun 26 03:57:16 UTC 2021 , Edited by admin on Sat Jun 26 03:57:16 UTC 2021
Code System Code Type Description
PUBCHEM
23616375
Created by admin on Sat Jun 26 03:57:16 UTC 2021 , Edited by admin on Sat Jun 26 03:57:16 UTC 2021
PRIMARY
FDA UNII
080UKX74TN
Created by admin on Sat Jun 26 03:57:16 UTC 2021 , Edited by admin on Sat Jun 26 03:57:16 UTC 2021
PRIMARY
NCI_THESAURUS
C98209
Created by admin on Sat Jun 26 03:57:16 UTC 2021 , Edited by admin on Sat Jun 26 03:57:16 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY
ACTIVE MOIETY