4-METHYLAMINOREX, CIS-(±)-

Possibly Marketed Outside US

First approved in 2023

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 Search

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	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.unodc.org/pdf/convention_1971_en.pdf | https://www.ncbi.nlm.nih.gov/pubmed/1971111 | https://www.ncbi.nlm.nih.gov/pubmed/14742748 | https://www.ncbi.nlm.nih.gov/pubmed/11805204 | https://www.ncbi.nlm.nih.gov/pubmed/14185981

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 Its development was discontinued in favor of aminorex, which was withdrawn from the market when its use was linked with the development of fatal pulmonary hypertension. 4-Methylaminorex exists as four stereoisomers (±)-cis and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
Sodium-dependent dopamine transporter 42 Target ID: Q01959 Gene ID: 6531.0 Gene Symbol: SLC6A3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24841869	Substrate 661
Sodium-dependent serotonin transporter 40 Target ID: P31645 Gene ID: 6532.0 Gene Symbol: SLC6A4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24841869	Substrate 661
Sodium-dependent noradrenaline transporter 38 Target ID: P23975 Gene ID: 6530.0 Gene Symbol: SLC6A2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24841869	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14185981	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
2-AMINO-5-ARYL-2-OXAZOLINES. POTENT NEW ANORECTIC AGENTS.	1963 May	14185981
Stimulus properties of a new designer drug: 4-methylaminorex ("U4Euh").	1990 Mar	1971111
Acute neurochemical and behavioral effects of stereoisomers of 4-methylaminorex in relation to brain drug concentrations.	2002 Feb	11805204
Pharmacokinetics and tissue distribution of the stereoisomers of 4-methylaminorex in the rat.	2004 Jun	14742748
Characterization of a novel and potentially lethal designer drug (±)-cis-para-methyl-4-methylaminorex (4,4'-DMAR, or 'Serotoni').	2014 Jul-Aug	24841869

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: Other

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 `Sat Dec 16 08:28:28 GMT 2023` Edited by `admin` on `Sat Dec 16 08:28:28 GMT 2023`
Record UNII	2149QZM652
Record Status	`Validated (UNII)`
Record Version

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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