Ethylamphetamine
INN: Etilamfetamine

Clinical data
Trade names	Apetinil; Adiparthrol
Other names	Etilamfetamine; Ethylamphetamine;N-Ethylamphetamine; PAL-99; PAL99
Routes of administration	Oral,sublingual,insufflated, inhaled (vaporized),intravenous,rectal
ATC code	A08AA06 (WHO)
Legal status
Legal status	BR: Class B1 (Psychoactive drugs)[1] CA: Schedule I DE: Anlage II (Authorized trade only, not prescriptible) UK: Class C US: Schedule I
Pharmacokinetic data
Metabolism	Hepatic (N-dealkylation, others)[2]
Metabolites	Amphetamine[2]
Excretion	Urine (5–18% asamphetamine)[2]
Identifiers
IUPAC name N-Ethyl-1-phenyl-propan-2-amine
CAS Number	457-87-4 Y
PubChemCID	9982
ChemSpider	9588 Y
UNII	022YON1XMX
KEGG	D07114 Y
ChEMBL	ChEMBL276443 Y
CompTox Dashboard(EPA)	DTXSID10860359
ECHA InfoCard	100.230.711
Chemical and physical data
Formula	C11H17N
Molar mass	163.264 g·mol−1
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 Y Key:YAGBSNMZQKEFCO-UHFFFAOYSA-N Y
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Etilamfetamine, also known asN-ethylamphetamine and formerly sold under the brand namesApetinil andAdiparthrol, is astimulant drug of theamphetamine family. It was invented in the early 20th century and was subsequently used as ananorectic orappetite suppressant in the 1950s,^[3] but was not as commonly used as other amphetamines such asamphetamine,methamphetamine, andbenzphetamine, and was largely discontinued once newer drugs such asphenmetrazine were introduced.

Ethylamphetamine is apotentdopamine releasing agent (DRA)in vitro, with anEC₅₀Tooltip half-maximal effective concentration of 88.5 nM.^[4] This is about 10-fold lower than theEC₅₀ ofdextroamphetamine.^[4] TheEC₅₀ values of ethylamphetamine for induction ofnorepinephrine andserotonin release were not reported.^[4] However, theEC₅₀ values of itsdextrorotatoryenantiomer dextroethylamphetamine have been reported and were 44.1 nM, 28.8 nM, and 333 nM for norepinephrine, dopamine, and serotonin, respectively.^[5][6] Hence, dextroethylamphetamine acts as anorepinephrine–dopamine releasing agent (NDRA) with weak effects on serotonin.^[5][6]

In terms ofstructure–activity relationships, the potency of amphetamines asdopamine releasing agents andreuptake inhibitors decreases with increasingN-alkylchain length.^[4] That is, the order of potency ofN-alkylated amphetamines is as follows:amphetamine >methamphetamine > ethylamphetamine >propylamphetamine >butylamphetamine.^[4] Propylamphetamine is a weak dopamine reuptake inhibitor rather than releaser, whereas butylamphetamine is completely inactive as a dopamine releaser or reuptake inhibitor.^[4] The same relationship, formonoamine release andreuptake inhibition generally, has been shown with4-methylamphetamine and itsN-alkylated derivatives like4-methylmethamphetamine and so forth.^[7][8]

Ethylamphetamine is inactive as an agonist of the mouse and humantrace amine-associated receptor 1 (TAAR1), whereas findings in the case of the rat TAAR1 are conflicting.^[17][18] In one study, its K_i was 2,500 nM and itsEC₅₀Tooltip half-maximal effective concentration (E_maxTooltip maximal efficacy) was 880 nM (62%) at the rat TAAR1 (i.e., it was apartial agonist), whereas its K_i and/orEC₅₀ values at the mouse and human TAAR1 were >10,000 nM.[17] In another study however, ethylamphetamine showed very little capacity to activate the rat TAAR1.^[17]

Ethylamphetamine can beN-dealkylated intoamphetamine (5–18%excreted inurine after 24 hours).^[2] As such, amphetamine may contribute to its effectsin vivo.^[2]

Themolecular structure of ethylamphetamine isanalogous tomethamphetamine, with anethyl group in place of themethyl group.^{[Note 1]} It can also be considered asubstituted amphetamine, with an ethyl group on the amphetamine backbone.^{[Note 2][Note 3]}

Analogues of ethylamphetamine include amphetamine, methamphetamine,propylamphetamine,isopropylamphetamine,butylamphetamine,fenfluramine (3-trifluoromethyl-N-ethylamphetamine),dimethylamphetamine, and3-fluoroethamphetamine (3-fluoro-N-ethylamphetamine), among others.

Ethylamphetamine can be used as arecreational 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 lowerpotency.^{[citation needed]}

• Anorectics
• Designer prodrugs
• Norepinephrine-dopamine releasing agents
• Stimulants
• Substituted amphetamines
• TAAR1 agonists

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