DOC

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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
5-hydroxytryptamine receptor 2A 69	Agonist 2,678		4.0 nM [Ki]
5-hydroxytryptamine receptor 2C 26	Agonist 2,678		3.54 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2,578

PubMed

Title	Date	PubMed
No data available in table

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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.