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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H19NO2
Molecular Weight 233.3062
Optical Activity ( + )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ORG-37684 Free Base

SMILES

COC1=C(O[C@H]2CCNC2)C3=C(CCC3)C=C1

InChI

InChIKey=QDJAYXYEXHVXJV-NSHDSACASA-N
InChI=1S/C14H19NO2/c1-16-13-6-5-10-3-2-4-12(10)14(13)17-11-7-8-15-9-11/h5-6,11,15H,2-4,7-9H2,1H3/t11-/m0/s1

HIDE SMILES / InChI

Description

ORG 37684 is a selective full agonist of 5-hydroxytryptamine receptor 5-HT2 family with a high selectivity for 5-HT2C in comparison with 5-HT2B and 5-HT2A receptors. It was studied for treatment of depression, but that investigations were discontinued. On animal studies ORG 37684 possessed hypophagic effect, which was exclusively mediated by activation of 5-HT2C receptors. Thus, this compound can be further investigated in using for weight loss.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
7.11 null [pEC50]
8.17 null [pEC50]
7.96 null [pEC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
in rats: 1.84 mg/kg
Route of Administration: Intraperitoneal
In Vitro Use Guide
To examine the effect of receptor density on agonist efficacy, three agonists of differential efficacies were examined for GTPγ35S binding; a full agonist, Org37684, a partial agonist, quipazine, and a weak partial agonist LSD. Enhancement of GTPγ35S binding by Org37684 (10 μM) ranged from 93 to 101% as normalized to that of 5-HT (10 μM), quipazine from 52 to 67%, and LSD from 23 to 29% in these cell lines, with no appreciable dependence on receptor density.