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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H12N2O
Molecular Weight 176.2155
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-METHYLAMINOREX, (4S,5R)-

SMILES

C[C@@]1([H])[C@@]([H])(c2ccccc2)OC(=N)N1

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 176.2155
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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 Its development was discontinued in favor of aminorex, which was withdrawn from the market when its use was linked with the development of fatal pulmonary hypertension. 4-Methylaminorex exists as four stereoisomers (±)-cis and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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q01959
Gene ID: 6531.0
Gene Symbol: SLC6A3
Target Organism: Homo sapiens (Human)
Target ID: P31645
Gene ID: 6532.0
Gene Symbol: SLC6A4
Target Organism: Homo sapiens (Human)
Target ID: P23975
Gene ID: 6530.0
Gene Symbol: SLC6A2
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
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

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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 08:55:51 UTC 2021
Edited
by admin
on Sat Jun 26 08:55:51 UTC 2021
Record UNII
J5G5N6R0TM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4-METHYLAMINOREX, (4S,5R)-
Common Name English
(4S,5R)-4-METHYLAMINOREX
Common Name English
2-OXAZOLAMINE, 4,5-DIHYDRO-4-METHYL-5-PHENYL-, (4S,5R)-
Systematic Name English
4-METHYLAMINOREX, (4S-CIS)-
Common Name English
Code System Code Type Description
FDA UNII
J5G5N6R0TM
Created by admin on Sat Jun 26 08:55:51 UTC 2021 , Edited by admin on Sat Jun 26 08:55:51 UTC 2021
PRIMARY
CAS
75493-87-7
Created by admin on Sat Jun 26 08:55:51 UTC 2021 , Edited by admin on Sat Jun 26 08:55:51 UTC 2021
PRIMARY
PUBCHEM
3058692
Created by admin on Sat Jun 26 08:55:51 UTC 2021 , Edited by admin on Sat Jun 26 08:55:51 UTC 2021
PRIMARY