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Details

Stereochemistry ACHIRAL
Molecular Formula C16H22Cl2N2O
Molecular Weight 329.265
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AH-7921

SMILES

CN(C)C2(CNC(=O)C1=CC=C(Cl)C(Cl)=C1)CCCCC2

InChI

InChIKey=JMZROFPPEXCTST-UHFFFAOYSA-N
InChI=1S/C16H22Cl2N2O/c1-20(2)16(8-4-3-5-9-16)11-19-15(21)12-6-7-13(17)14(18)10-12/h6-7,10H,3-5,8-9,11H2,1-2H3,(H,19,21)

HIDE SMILES / InChI

Description

AH-7921 (3,4-Dichloro-N-([1-(dimethylamino)cyclohexyl] methyl)benzamide) is an N-substituted cyclohexylmethylbenzamide classified as an opioid analgesic with high addictive liability. The compound acts as an agonist of μ-opioid receptors, although at high doses it can also stimulate κ-opioid receptors. In animal studies, AH-7921 produced typical morphine-like actions, i.e., antinociception, respiratory depression, sedation, miosis, inhibition of gut propulsion, and lowered body temperature, with a potency almost equipotent to that of morphine. There is limited information available on the routes of administration and the doses of AH-7921 used. The compound is taken orally, nasally, by smoking, and, less commonly, by intravenous injection. Minimal oral effective doses for complete pain suppression by AH 7921 are 1.25 and 13.8 mg/kg for canine and rhesus monkey, respectively.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Light dose is 5-10 mg, common dose is 10–25 mg and strong dose is over 25 mg.
Route of Administration: Oral
In Vitro Use Guide
For metabolic stability, 1 μmol/L AH-7921 was incubated with human liver microsome (HLM) for up to 1 h, for metabolite profiling, 10 μmol/L was incubated with pooled human hepatocytes for up to 3 h. Hepatocyte samples were analyzed by liquid chromatography quadrupole/time-of-flight high-resolution mass spectrometry. AH-7921 in vitro half-life was 13.5±0.4 min.