4-methylaminorex

Structural formula
	(4 R , 5 S ) shape (top left), (4 S , 5 R ) shape (top right), (4 S , 5 S ) shape (bottom left) and (4 R , 5 R ) shape (bottom right)
General
Non-proprietary name	4-methylaminorex
other names	cis - trans - (±) -2-amino-4-methyl-5-phenyl [4 H ] oxazoline; cis - trans - (±) -4,5-dihydro-4-methyl-5-phenyloxazol-2-amine; (4 R , 5 S ) -2-Amino-4-methyl-5-phenyl [4 H ] oxazoline; (4 R , 5 S ) - 4,5-dihydro-4-methyl-5-phenyloxazol-2-amine; cis - (±) -2-amino-4-methyl-5-phenyl [4 H ] oxazoline; cis - (±) -4,5-dihydro-4-methyl-5-phenyloxazol-2-amine; Euphoria;
Molecular formula	C 10 H 12 N 2 O
External identifiers / databases
PubChem	92196
DrugBank	DB01447
Wikidata	Q230007
Drug information
Drug class	stimulant
properties
Molar mass	176.21 g mol −1
Melting point	Racemate from (4 R , 5 S ) form and (4 S , 5 R ) form: 154.5-156 ° C and 139-142 ° C
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
Toxicological data	17 mg kg −1 ( LD 50 , mouse , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

4-Methylaminorex (syn. Euphoria ) is a synthetic drug with an amphetamine- like effect.

history

The substance was developed as an appetite suppressant in the early 1960s and patented in 1964. In 1963 a strongly euphoric side effect was demonstrated. Therefore the substance was not marketed. It is traded illegally under the names Euphoria , U4Euh , Intellex , Verbosamin , Aminorex or Ice . The name ice comes from the appearance of the milky to clear crystals, some of which are sold as rocks or stones in large pieces. Also methamphetamine is called ice marketed illegally; therefore there may be confusion.

In 1986, attendees at a music event reported unpleasant sensations and aggression after taking Euphoria with LSD . As a result, the drug had a bad rap for a while. The substance is now relatively popular again, but not too widespread. In 1987, 4-methylaminorex was declared illegal in the United States . A few larger underground laboratories had primarily manufactured this drug. 4-Methylaminorex is also subject to the Narcotics Act (BtMG) in Germany and is illegal as a non-marketable narcotic.

Stereoisomers

4-Methylaminorex contains two stereogenic centers, so the following four stereoisomers exist:

(4 R , 5 S ) shape
(4 S , 5 R ) shape
(4 S , 5 S ) shape
(4 R , 5 R ) shape

It is known that the stereoisomers have different pharmacological effects.

The racemate (1: 1 mixture) from the (4 R , 5 S ) form and the enantiomeric (4 S , 5 R ) form is also called cis - (±) -4-methylaminorex.

How to use

Due to the low melting point , the crystals can be heated on aluminum foil and the vapors inhaled using a tube. Oral ingestion is less common, as the small amounts required are difficult to estimate without a laboratory scale. Also due to the low melting point, it is difficult to unobtrusively stretch the substance with other substances, as is common with cocaine and heroin .

effect

Psychological effect

Smoking around 10 mg creates well-being and a stimulating and stimulating effect for around 4–6 hours. Many users feel more intelligent and believe that they can solve problems better under the influence of the substance. Monotonous work processes should be easier and perceived as less stressful. As a performance drug, 4-methylaminorex is said to be more effective than amphetamine , because incorrect actions and confusion occur less often, depending on the dose. Higher doses from approx. 50 mg lead to euphoria at the expense of the ability to concentrate . Physical tiredness is eliminated; Sleep becomes impossible. Consumers feel the need to keep doing new things or to keep talking.

This condition can be maintained for several days by continued use. Sleeping pills are sometimes taken to counter the excruciating insomnia.

Physical effect

Common side effects are diarrhea, dry mouth, and bad breath and body odor. Physical habituation occurs quickly. With continued use, the consumer needs ever higher doses. This is reduced again after some time through abstinence.

With daily consumption over a long period of time there is a risk of dangerous, sometimes fatal pulmonary hypertension .

Trivia

The drug, known as Euphoria in the film Interstate 60 , is used there as a means of power to keep workers in a city. It is questionable whether the fictitious drug is actually 4-methylaminorex.

The drug is discussed in the episode Aktion Egg Swap (2x15) of the Beverly Hills, 90210 series . Brandon Walsh is generally against drugs. His girlfriend Emily Valentine secretly mixes him Euphoria in a drink, which ultimately leads to the relationship.

literature

Ralph Parnefjord: The drug paperback . 3. Edition. Thieme , Stuttgart 2005, ISBN 978-3-13-118033-9 , p. 56-58 .

Web links

4-methylaminorex . In: Erowid . (English)

Individual evidence

^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 1039, ISBN 978-0-911910-00-1 .
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Entry on 4-Methylaminorex in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ ^a ^b ^c ^d This section follows the description in Parnefjord, Das Drogentaschenbuch , 3rd edition, Thieme Verlag 2005, pp. 56–58 , unless other sources are expressly stated
Jump up ↑ GI Poos, J. Carson, J. Rosenau, A. Roszkowski, N. Kelly, J. McGowir: 2-Amino-5-Aryl-2-Oxazolines: New Anorectic Agents . In: Journal of Medicinal Chemistry . tape 6 , 1963, pp. 266-272 .
↑ Patent US3161650 : 2-Amino-5-Aryloxazoline Products. Published on 1964 , inventor: G. Poos. ‌
↑ J. Yelnasky, R. Katz: Sympathomimetic Actions of cis-2-Amino-4-Methyl-5-Phenyl-2-Oxazoline . In: Journal of Pharmacology and Experimental Therapeutics . tape 140 , 1963, pp. 180 .
↑ Annex I (to Section 1, Paragraph 1), narcotics that are not marketable) .
^ RA Glennon and B. Misenheimer, Pharmacology and Biochemical Behavior 35 (1990) 517.
↑ Seán P. Gaine, Lewis J. Rubin, James J. Kmetzo, Harold I. Palevsky, Thomas A. Traill: Recreational Use of Aminorex and Pulmonary Hypertension . In: Chest . March 23, 1963, doi : 10.1378 / chest.118.5.1496 .

[MerckIndex-1] The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 1039, ISBN 978-0-911910-00-1 .

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[ChemIDplus-3] Entry on 4-Methylaminorex in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[Parnefjord-4] This section follows the description in Parnefjord, Das Drogentaschenbuch , 3rd edition, Thieme Verlag 2005, pp. 56–58 , unless other sources are expressly stated

[5] Jump up ↑ GI Poos, J. Carson, J. Rosenau, A. Roszkowski, N. Kelly, J. McGowir: 2-Amino-5-Aryl-2-Oxazolines: New Anorectic Agents . In: Journal of Medicinal Chemistry . tape 6 , 1963, pp. 266-272 .

[6] Patent US3161650 : 2-Amino-5-Aryloxazoline Products. Published on 1964 , inventor: G. Poos. ‌

[7] J. Yelnasky, R. Katz: Sympathomimetic Actions of cis-2-Amino-4-Methyl-5-Phenyl-2-Oxazoline . In: Journal of Pharmacology and Experimental Therapeutics . tape 140 , 1963, pp. 180 .

[8] Annex I (to Section 1, Paragraph 1), narcotics that are not marketable) .

[Glennon-9] RA Glennon and B. Misenheimer, Pharmacology and Biochemical Behavior 35 (1990) 517.

[10] Seán P. Gaine, Lewis J. Rubin, James J. Kmetzo, Harold I. Palevsky, Thomas A. Traill: Recreational Use of Aminorex and Pulmonary Hypertension . In: Chest . March 23, 1963, doi : 10.1378 / chest.118.5.1496 .