Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C10H12N2O |
| Molecular Weight | 176.2151 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@H]1N=C(N)O[C@@H]1C2=CC=CC=C2
InChI
InChIKey=LJQBMYDFWFGESC-CBAPKCEASA-N
InChI=1S/C10H12N2O/c1-7-9(13-10(11)12-7)8-5-3-2-4-6-8/h2-7,9H,1H3,(H2,11,12)/t7-,9-/m0/s1
4-Methylaminorex is a stimulant drug, synthesized by McNeil Laboratories as an appetite suppressant. Its development was discontinued in favor of aminorex, which was withdrawn from the market when its use was linked with the development of fatal pulmonary hypertension. 4-Methylaminorex exists as four stereoisomers (±)-cis and (±)-trans. In neurochemical and behavioral studies trans-4S,5S-isomer was the most potent isomer followed by the equally effective cis-isomers, whereas trans-4R,5R-isomer was relatively ineffective. The racemic cis-4-methylaminorex has been reported to be the most frequently encountered form in illicit samples The drug is known under street names "U4Euh" or "Ice", is used a a stimulant and is classified as a schedule I substance. Neurochemical data suggest that behavioral effects of the isomers of 4-methylaminorex are related to drug-induced dopamine release.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Q01959 Gene ID: 6531.0 Gene Symbol: SLC6A3 Target Organism: Homo sapiens (Human) |
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Target ID: P31645 Gene ID: 6532.0 Gene Symbol: SLC6A4 Target Organism: Homo sapiens (Human) |
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Target ID: P23975 Gene ID: 6530.0 Gene Symbol: SLC6A2 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 2-AMINO-5-ARYL-2-OXAZOLINES. POTENT NEW ANORECTIC AGENTS. | 1963 May |
|
| Stimulus properties of a new designer drug: 4-methylaminorex ("U4Euh"). | 1990 Mar |
|
| Acute neurochemical and behavioral effects of stereoisomers of 4-methylaminorex in relation to brain drug concentrations. | 2002 Feb |
|
| Pharmacokinetics and tissue distribution of the stereoisomers of 4-methylaminorex in the rat. | 2004 Jun |
|
| Characterization of a novel and potentially lethal designer drug (±)-cis-para-methyl-4-methylaminorex (4,4'-DMAR, or 'Serotoni'). | 2014 Jul-Aug |
Patents
Sample Use Guides
4-Methylaminorex is a white crystalline (or powdered) substance which is most commonly insufflated (snorted) or taken orally but can also be smoked in either the freebase or hydrochloride salt forms.
Route of Administration:
Other
For release assays, 9 nM [3H]-1-methyl-4-phenylpyridinium ([3H]MPP+) was used as the radiolabeled substrate for dopamine transporters (DAT) and norepinephrine transporters (NET), while 5 nM [3H]5-HT was used as the radiolabeled substrate for 5-HT transporters (SERT). All buffers used in the release assay methods contained 1 µM reserpine to block vesicular uptake of substrates. The selectivity of release assays was optimized for a single transporter by including unlabeled blockers to prevent the uptake of [3H]MPP+ or [3H]5-HT by competing transporters. Rat synaptosomes were preloaded with the radiolabeled substrate in Krebs-phosphate buffer for 1 h (steady state). Release assays were initiated by adding 850 µl of preloaded synaptosomes to 150 µl of the test drug. The release was terminated by vacuum filtration and retained radioactivity was quantified by scintillation counting.
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DEA NO. |
1590
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SUBSTANCE RECORD
