U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C11H16ClNO2
Molecular Weight 229.703
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOC

SMILES

COC1=CC(CC(C)N)=C(OC)C=C1Cl

InChI

InChIKey=ACRITBNCBMTINK-UHFFFAOYSA-N
InChI=1S/C11H16ClNO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C11H16ClNO2
Molecular Weight 229.703
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

2,5-Dimethoxy-4-chloroamphetamine (DOC) is a substituted alpha-methylated phenethylamine, a psychedelic drug. It was presumably first synthesized by Alexander Shulgin. DOC acts as a selective -hydroxytryptamine (5-HT2) receptor 5-HT2A and 5-HT2c agonist.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P28223
Gene ID: 3356.0
Gene Symbol: HTR2A
Target Organism: Homo sapiens (Human)
4.0 nM [Ki]
Target ID: P28335
Gene ID: 3358.0
Gene Symbol: HTR2C
Target Organism: Homo sapiens (Human)
3.54 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
First case report of recreational use of 2,5-dimethoxy-4-chloroamphetamine confirmed by toxicological screening.
2008 Dec
Patents

Patents

Sample Use Guides

A fatal intoxication: dosage range of 1.5–3.0 mg with duration time of 12–24 h. At the highest ingested dose (2.4 mg)
Route of Administration: Oral
5-HT2A and 5-HT2C receptors HEK cells expressing the human 5-HT2A receptor (HEK-5-HT2A cells) or the human 5-HT2C receptor (HEK-5-HT2C cells) were used. In the 5-HT2A [3H]AA release assay, 2,5-Dimethoxy-4-chloroamphetamine (DOC) and 5-HT were agonists with similar efficacies while potencies differed significantly. DOC were very potent with EC50 values that did not differ from serotonin and LSD. In HEK-h5-HT2C cells, the phenethylamines were tested for their affinities for the [125I]DOI binding site and effects on 5-HT2C-mediated IP-1 turnover. In the [125I]DOI binding assay, there were significant differences in affinities DOC, serotonin and LSD had similar, low nanomolar, affinities.
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:22:30 GMT 2023
Edited
by admin
on Sat Dec 16 11:22:30 GMT 2023
Record UNII
8Y1C6K0PCA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DOC
Common Name English
4-CHLORO-2,5-DIMETHOXYAMPHETAMINE
Systematic Name English
J275.082A
Code English
4-CL-2,5-DMA
Common Name English
2,5-DIMETHOXY-4-CHLOROAMPHETAMINE
Systematic Name English
BENZENEETHANAMINE, 4-CHLORO-2,5-DIMETHOXY-.ALPHA.-METHYL-
Systematic Name English
Classification Tree Code System Code
WIKIPEDIA Designer-drugs-2,5-Dimethoxy-4-chloroamphetamine
Created by admin on Sat Dec 16 11:22:30 GMT 2023 , Edited by admin on Sat Dec 16 11:22:30 GMT 2023
WIKIPEDIA PiHKAL
Created by admin on Sat Dec 16 11:22:30 GMT 2023 , Edited by admin on Sat Dec 16 11:22:30 GMT 2023
Code System Code Type Description
FDA UNII
8Y1C6K0PCA
Created by admin on Sat Dec 16 11:22:30 GMT 2023 , Edited by admin on Sat Dec 16 11:22:30 GMT 2023
PRIMARY
EPA CompTox
DTXSID60894189
Created by admin on Sat Dec 16 11:22:30 GMT 2023 , Edited by admin on Sat Dec 16 11:22:30 GMT 2023
PRIMARY
CAS
123431-31-2
Created by admin on Sat Dec 16 11:22:30 GMT 2023 , Edited by admin on Sat Dec 16 11:22:30 GMT 2023
PRIMARY
SMS_ID
100000182707
Created by admin on Sat Dec 16 11:22:30 GMT 2023 , Edited by admin on Sat Dec 16 11:22:30 GMT 2023
PRIMARY
WIKIPEDIA
2,5-DIMETHOXY-4-CHLOROAMPHETAMINE
Created by admin on Sat Dec 16 11:22:30 GMT 2023 , Edited by admin on Sat Dec 16 11:22:30 GMT 2023
PRIMARY
PUBCHEM
542036
Created by admin on Sat Dec 16 11:22:30 GMT 2023 , Edited by admin on Sat Dec 16 11:22:30 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY