ContaminantDB: dimethocaine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-06-03 11:13:54 UTC

Update Date

2016-11-09 01:22:59 UTC

Accession Number

CHEM043748

Identification

Common Name

dimethocaine

Class

Small Molecule

Description

Dimethocaine, also known as DMC or larocaine, is a compound with a stimulatory effect. This effect resembles that of cocaine, although dimethocaine appears to be less potent. Just like cocaine, dimethocaine is addictive due to its stimulation of the reward pathway in the brain. However, dimethocaine is a legal cocaine replacement in some countries and is even listed by the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) under the category “synthetic cocaine derivatives”. The structure of dimethocaine, being a 4-Aminobenzoic acid ester, resembles that of procaine. It is found as a white powder at room temperature.When a product sold online in the UK in June 2010, advertised as dimethocaine was tested, it was found to in fact be a mixture of caffeine and lidocaine, and the lack of any dopaminergic stimulant ingredient in such mixes may explain the limited recreational effects reported by many users. Other samples tested have however been shown to contain genuine dimethocaine, and one branded "bath salt" product containing primarily dimethocaine as the active ingredient, was noted to have been particularly subject to abuse by intravenous drug users in Ireland.

Contaminant Sources

STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Dimethocaine hydrochloride	MeSH
3-(Diethylamino)-2,2-dimethylpropyl 4-aminobenzoate	MeSH

Chemical Formula

C₁₆H₂₆N₂O₂

Average Molecular Mass

278.396 g/mol

Monoisotopic Mass

278.199 g/mol

CAS Registry Number

94-15-5

IUPAC Name

3-(diethylamino)-2,2-dimethylpropyl 4-aminobenzoate

Traditional Name

dimethocaine

SMILES

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

InChI Identifier

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

InChI Key

OWQIUQKMMPDHQQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Aminobenzoic acid or derivatives
Benzoate ester
Benzoyl
Aniline or substituted anilines
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Amine
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.53 g/L	ALOGPS
logP	3.19	ALOGPS
logP	2.91	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	10.06	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.56 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	83.92 m³·mol⁻¹	ChemAxon
Polarizability	32.37 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01r6-0690000000-50795ce1817ccd53b35d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0596-1930000000-6dd6d570bccc368f5148	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9600000000-a7c020dadd99be069bde	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2390000000-d23c6b51f9d4a5f54ed6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00mx-5930000000-9a81677fe4a292b252b7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-9200000000-6db5afe40f2097ae13f7	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Dimethocaine

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

7177

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

dimethocaine (CHEM043748)

Structure for CHEM043748: dimethocaine