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Ethylamphetamine
INN: Etilamfetamine

Clinical data
Routes of administration	Oral, sublingual, insufflated, inhaled (vaporized), intravenous, rectal
ATC code	A08AA06 (WHO)
Legal status
Legal status	BR: Class B1 (Psychoactive drugs) CA: Schedule I DE: Anlage II (Authorized trade only, not prescriptible) UK: Class C US: Schedule I
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal
Identifiers
IUPAC name N-Ethyl-1-phenyl-propan-2-amine
CAS Number	457-87-4
PubChem CID	9982
ChemSpider	9588
UNII	022YON1XMX
KEGG	D07114
ChEMBL	ChEMBL276443
CompTox Dashboard (EPA)	DTXSID10860359
ECHA InfoCard	100.230.711
Chemical and physical data
Formula	C11H17N
Molar mass	163.264 g·mol
3D model (JSmol)	Interactive image
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, also known as N-ethylamphetamine and formerly sold under the brand names Apetinil and Adiparthrol, is a stimulant drug of the amphetamine family. It was invented in the early 20th century and was subsequently used as an anorectic or appetite suppressant in the 1950s, 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.

Pharmacology

Ethylamphetamine is a potent dopamine releasing agent in vitro, with an EC₅₀Tooltip half-maximal effective concentration of 88.5 nM. This is about 10-fold lower than the EC₅₀ of amphetamine. The EC₅₀ values of ethylamphetamine for induction of norepinephrine and serotonin release were not reported. Ethylamphetamine can also be N-dealkylated into amphetamine (5–18% excreted in urine after 24 hours).

Chemistry

The molecular structure of ethylamphetamine is analogous to methamphetamine, with an ethyl group in place of the methyl group. It can also be considered a substituted amphetamine, with an ethyl group on the amphetamine backbone.

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, though it is of weaker potency. At equipotent dosage, ethylamphetamine is subjectively less euphorigenic.

See also

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

References

1. Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
2. Junet R (October 1956). "". Praxis. 45 (43): 986–8. PMID 13389142.
3. ^ Reith ME, Blough BE, Hong WC, Jones KT, Schmitt KC, Baumann MH, Partilla JS, Rothman RB, Katz JL (February 2015). "Behavioral, biological, and chemical perspectives on atypical agents targeting the dopamine transporter". Drug Alcohol Depend. 147: 1–19. doi:10.1016/j.drugalcdep.2014.12.005. PMC 4297708. PMID 25548026.
4. Beckett AH, Shenoy EV (October 1973). "The effect of N-alkyl chain length of stereochemistry on the absorption, metabolism and during excretion of N-alkylamphetamines in man". J Pharm Pharmacol. 25 (10): 793–799. doi:10.1111/j.2042-7158.1973.tb09943.x. PMID 4151673.

Notes

1. Amphetamine is a substituted phenethylamine with a methyl group at R position.
2. The ethyl group of ethylamphetamine is at R 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.

• Anorectics
• Norepinephrine-dopamine releasing agents
• Substituted amphetamines