Etilamfetamine

Etilamfetamine

Systematic (IUPAC) name
N-ethyl-1-phenyl-propan-2-amine
Clinical data
Routes of administration	Oral, sublingual, insufflated, inhaled (vaporized), intravenous, rectal
Legal status
Legal status	CA: Schedule I DE: Anlage II (Prohibited) UK: Class C US: Schedule I
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal
Identifiers
CAS Number	457-87-4
ATC code	A08AA06 (WHO)
PubChem	CID 9982
ChemSpider	9588
KEGG	D07114
ChEMBL	CHEMBL276443
Chemical data
Formula	C11H17N
Molar mass	163.259 g/mol
SMILES N(C(Cc1ccccc1)C)CC
InChI InChI=1S/C11H17N/c1-3-12-10(2)9-11-7-5-4-6-8-11/h4-8,10,12H,3,9H2,1-2H3 Key:YAGBSNMZQKEFCO-UHFFFAOYSA-N
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Etilamfetamine (Apetinil, Adiparthrol), also known as N-ethylamphetamine, is a stimulant drug of the phenethylamine and amphetamine chemical classes. It was invented in the early 20th century and was subsequently used as an anorectic or appetite suppressant in the 1950s,^[1] but was not as commonly used as other amphetamines such as amphetamine, methamphetamine, and benzphetamine, and was largely discontinued once newer drugs such as phenmetrazine were introduced.

Chemistry

The molecular structure of ethylamphetamine is analogous to amphetamine's.^{[Note 1]} It is a substituted amphetamine, with an ethyl group on the amphetamine backbone.^{[Note 2][Note 3]}

Recreational use

Ethylamphetamine can be used as a recreational drug and, while its prevalence is less than amphetamine's, it is still encountered as a substance taken for recreational purposes.

Ethylamphetamine produces effects similar to amphetamine and methamphetamine, its potency being slightly greater than amphetamine's and lesser than methamphetamine's.^{[Note 4][Note 5]}

See also

• 3-Fluoroethamphetamine
• Dimethylamphetamine
• Fenfluramine
• Isopropylamphetamine
• Propylamphetamine

References

1. Junet, R. (1956). "Ethylamphetamine in the treatment of obesity". Praxis 45 (43): 986–988. PMID 13389142.

Notes

1. Amphetamine is a substituted phenethylamine with a methyl group at R^A position.
2. The ethyl group of ethylamphetamine is at R^N position, hence the name N-ethylamphetamine.
3. Ethylamphetamine is structurally similar to N-methylamphetamine (methamphetamine), the ethyl group being replaced in methamphetamine with a methyl group.
4. Ethylamphetamine's higher potency may make its risk of causing abuse, dependence and/or addiction greater compared to amphetamine.
5. A cohort of Australian users in the 1990s found single 40 mg doses of commercially produced racemic ethylamphetamine hydrochloride substantially less effective recreationally than 40 mg doses of either racemic amphetamine sulphate, d-methylamphetamine hydrochloride or racemic fenethylline hydrochloride.