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

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
Structure of 4-METHYLAMINOREX, CIS-(+/-)-

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

HIDE SMILES / InChI

Molecular Formula C10H12N2O
Molecular Weight 176.2151
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 Its development was discontinued in favor of aminorex, which was withdrawn from the market when its use was linked with the development of fatal pulmonary hypertension. 4-Methylaminorex exists as four stereoisomers (±)-cis and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

Approval Year

PubMed

PubMed

TitleDatePubMed
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

Patents

Sample Use Guides

In Vivo Use Guide
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: oral; nasal
In Vitro Use Guide
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.
Substance Class Chemical
Created
by admin
on Tue Oct 22 08:12:13 UTC 2019
Edited
by admin
on Tue Oct 22 08:12:13 UTC 2019
Record UNII
2149QZM652
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4-METHYLAMINOREX, CIS-(+/-)-
Common Name English
ICE
Common Name English
MCN-822
Code English
U4EUH
Common Name English
2-OXAZOLINE, 2-AMINO-4-METHYL-5-PHENYL-, CIS-(+/-)-
Systematic Name English
4-METHYLAMINOREX (CIS ISOMER)
Common Name English
(+/-)-CIS-2-AMINO-4-METHYL-5-PHENYL-2-OXAZOLINE
Systematic Name English
4-METHYLAMINOREX (+/-)-CIS-FORM [MI]
Common Name English
2-OXAZOLAMINE, 4,5-DIHYDRO-4-METHYL-5-PHENYL-, (4R,5S)-REL-
Systematic Name English
(+/-)-CIS-4-METHYLAMINOREX
Common Name English
(+/-)-CIS-MCN-822
Code English
2-OXAZOLAMINE, 4,5-DIHYDRO-4-METHYL-5-PHENYL-, CIS-(+/-)-
Systematic Name English
EU4EA
Common Name English
MCN-422
Code English
Classification Tree Code System Code
DEA NO. 1590
Created by admin on Tue Oct 22 08:12:13 UTC 2019 , Edited by admin on Tue Oct 22 08:12:13 UTC 2019
Code System Code Type Description
PUBCHEM
3058692
Created by admin on Tue Oct 22 08:12:13 UTC 2019 , Edited by admin on Tue Oct 22 08:12:13 UTC 2019
PRIMARY
EPA CompTox
29493-77-4
Created by admin on Tue Oct 22 08:12:13 UTC 2019 , Edited by admin on Tue Oct 22 08:12:13 UTC 2019
PRIMARY
CAS
29493-77-4
Created by admin on Tue Oct 22 08:12:13 UTC 2019 , Edited by admin on Tue Oct 22 08:12:13 UTC 2019
PRIMARY