Ортетамин

Description

Orthetamine is a substituted amphetamine, also known as 2-methylamphetamine. Chemically, it is the primary amine of the phenylethylamine series: α,2-dimethylbenzenethanamine, that is, an amphetamine with a methyl group in the ortho position of the benzene ring. The compound was obtained in the middle of the 20th century during the study of the dependence of pharmacological activity on the structure in the phenethylamine series and did not enter clinical practice. Commodity status: research reagent and reference compound.

Identification

• CAS No.: 5580-32-5 (in the list of synonyms also 35373-71-8)
• English name: Ortetamine
• Chemical formula: C10H15N
• Systematic name: α,2-dimethylbenzenethanamine
• Synonyms: 2-methylamphetamine, o,α-dimethylphenethylamine, DL-o,α-dimethylphenethylamine, (±)-o-methyl-α-methylphenylethylamine, orthetamine

Physico-chemical indicators

• Molecular weight: 149.237
• Exact weight: 149.23
• Density: 0.938 g/cm³
• Boiling point: 233.9 °C at 760 mm Hg. Art.
• Flash point: 100.1 °C
• Refractive index: 1.525
• PSA: 26
• XLogP3: 2.585

Structure and pharmacological profile

The molecule contains an asymmetric carbon atom at the amino group, therefore it exists in the form of two enantiomers; trade and reference designations with the prefixes DL- and (±) indicate a racemic mixture. The compound differs from amphetamine in the position of the methyl substituent: it is in the ortho position of the ring, while in the more studied 4-methylamphetamine it is in the para position.

According to the mechanism of action, the substance belongs to the amphetamine-type stimulants: it enhances the release of monoamines - dopamine, norepinephrine and serotonin - from presynaptic endings. Unlike clinically used amphetamines, orthetamine has remained a research tool and is used primarily as a reference in the study of amphetamine analogues and their effects on neurotransmitter dynamics in the central nervous system.

Scope of application

• reference compound in structure-activity studies in the series of substituted amphetamines
• reference sample in analytical and forensic chemical practice for the identification of phenethylamines
• reagent for neuropharmacological studies of monoamine release mechanisms

Safety Information

There is no GHS hazard classification, H, or P for this compound in the product data sheet. The handling procedure is determined by the supplier's safety data sheet. A flash point of 100.1 °C classifies the substance as a flammable liquid: keep away from sources of ignition and oxidizers. As a primary aromatic amine, the product can be absorbed through the skin, so durable gloves, safety glasses and working under a fume hood are required.

Legal status

The compound is an amphetamine derivative. The circulation of such substances is regulated by legislation on narcotic drugs and psychotropic substances and their precursors; The procedure for purchase, storage, accounting and use is specified in accordance with the current regulations of the country of application before placing an order.