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Details

Stereochemistry ACHIRAL
Molecular Formula C16H26N2O2.ClH
Molecular Weight 314.851
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIMETHOCAINE HYDROCHLORIDE

SMILES

Cl.CCN(CC)CC(C)(C)COC(=O)C1=CC=C(N)C=C1

InChI

InChIKey=WWTWKTDXBNHESE-UHFFFAOYSA-N
InChI=1S/C16H26N2O2.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula C16H26N2O2
Molecular Weight 278.3898
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
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: 6531.0
Gene Symbol: SLC6A3
Target Organism: Homo sapiens (Human)
1.2 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Subtle differences in the discriminative stimulus effects of cocaine and GBR-12909.
2001 Apr
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. 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
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 Dec 16 03:59:21 UTC 2023
Edited
by admin
on Sat Dec 16 03:59:21 UTC 2023
Record UNII
Z768GH360Q
Record Status Validated (UNII)
Record Version
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Name Type Language
DIMETHOCAINE HYDROCHLORIDE
MI  
Common Name English
LAROCAINE HYDROCHLORIDE
Common Name English
DIMETHOCAINE HYDROCHLORIDE [MI]
Common Name English
3-DIETHYLAMINO-2,2-DIMETHYLPROPYL P-AMINOBENZOATE HYDROCHLORIDE
Common Name English
1-PROPANOL, 3-(DIETHYLAMINO)-2,2-DIMETHYL-, 4-AMINOBENZOATE (ESTER), MONOHYDROCHLORIDE
Common Name English
DIETHYLAMINONEOPENTYL ALCOHOL HYDROCHLORIDE P-AMINOBENZOATE
Common Name English
DIMETHOCAINE HCL
Common Name English
1-PROPANOL, 3-(DIETHYLAMINO)-2,2-DIMETHYL-, 1-(4-AMINOBENZOATE), HYDROCHLORIDE (1:1)
Common Name English
1-AMINOBENZOYL-2,2-DIMETHYL-3-DIETHYLAMINOPROPANOL HYDROCHLORIDE
Systematic Name English
1-PROPANOL, 3-(DIETHYLAMINO)-2,2-DIMETHYL-, P-AMINOBENZOATE (ESTER), MONOHYDROCHLORIDE
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID70970620
Created by admin on Sat Dec 16 03:59:21 UTC 2023 , Edited by admin on Sat Dec 16 03:59:21 UTC 2023
PRIMARY
FDA UNII
Z768GH360Q
Created by admin on Sat Dec 16 03:59:21 UTC 2023 , Edited by admin on Sat Dec 16 03:59:21 UTC 2023
PRIMARY
CAS
553-63-9
Created by admin on Sat Dec 16 03:59:21 UTC 2023 , Edited by admin on Sat Dec 16 03:59:21 UTC 2023
PRIMARY
MERCK INDEX
m4512
Created by admin on Sat Dec 16 03:59:21 UTC 2023 , Edited by admin on Sat Dec 16 03:59:21 UTC 2023
PRIMARY Merck Index
PUBCHEM
120286
Created by admin on Sat Dec 16 03:59:21 UTC 2023 , Edited by admin on Sat Dec 16 03:59:21 UTC 2023
PRIMARY