N,α-Diethylphenethylamine

N,α-Diethylphenethylamine (N,α-DEPEA, 2-ethylamino-1-phenylbutane, EAPB) is a close chemical analog of methamphetamine, which has been sold as a designer drug.^[1][2][3] It was originally patented by Knoll Pharma as one of several analogs for pharmaceutical applications. In animal models these analogs showed properties of cognitive enhancement and increased pain tolerance.^[4] Nevertheless, this class of compounds was never developed into a medicine. N,α-DEPEA has not been studied in humans, but experts such as Pieter Cohen of Harvard Medical School expect it to be less potent than methamphetamine, but greater than ephedrine.^[5]

N,α-Diethylphenethylamine

Clinical data
Other names	N,α-Diethylphenylethylamine N,α-Diethylbenzeneethanamine 2-Amino-N-ethyl-1-phenylbutane 2-Ethylamino-1-phenylbutane Ethyl(1-phenylbutan-2-yl)amine
Legal status
Legal status	CA: Schedule I DE: NpSG (Industrial and scientific use only) NZ: Class C UK: Class A
Identifiers
IUPAC name N-Ethyl-1-phenylbutan-2-amine
CAS Number	119486-07-6 29805-52-5 (HCl)
PubChem CID	14833603
ChemSpider	27101303
UNII	7V4PP58Q6T
CompTox Dashboard (EPA)	DTXSID501017073
Chemical and physical data
Formula	C12H19N
Molar mass	177.291 g·mol−1
3D model (JSmol)	Interactive image
SMILES C(C)NC(CC1=CC=CC=C1)CC
InChI InChI=1S/C12H19N/c1-3-12(13-4-2)10-11-8-6-5-7-9-11/h5-9,12-13H,3-4,10H2,1-2H3 Key:KHWYSUBVXWWBRB-UHFFFAOYSA-N

Adulterant in nutritional supplements

In January 2013, the South Korean authorities reported seizing a large quantity of the pure material, predicting it would soon be found on the market.^[6] Later in 2013, it was found as an adulterant in biologically significant amounts in the pre-workout supplements Craze (marketed by Driven Sports, Inc.) and Detonate (marketed by Gaspari Nutrition).^[4][7] It was falsely claimed to be Dendrobium extract.^[5][8][9]

See also

• Buphedrone
• Butylone
• EBDB
• Etilamfetamine
• Eutylone
• N-Ethylbuphedrone
• Phenylisobutylamine

References

1. Wójtowicz M, Jarek A, Chajewska K, Turek-Lepa E, Kwiatkowska D (November 2015). "Determination of designer doping agent--2-ethylamino-1-phenylbutane--in dietary supplements and excretion study following single oral supplement dose". Journal of Pharmaceutical and Biomedical Analysis. 115: 523–33. doi:10.1016/j.jpba.2015.07.025. PMID 26311473.
2. Uralets V, App M, Rana S, Morgan S, Ross W (March 2014). "Designer phenethylamines routinely found in human urine: 2-ethylamino-1-phenylbutane and 2-amino-1-phenylbutane". Journal of Analytical Toxicology. 38 (2): 106–9. doi:10.1093/jat/bkt121. PMID 24451085.
3. "2-Ethylamino-1-phenylbutane". Cayman Chemical. Retrieved 4 November 2015.
4. Lee J, Venhuis BJ, Heo S, Choi H, Seol I, Kim E (2013). "Identification and quantitation of N,α-diethylphenethylamine in preworkout supplements sold via the Internet". Forensic Toxicology. 32: 148–153. doi:10.1007/s11419-013-0205-6. S2CID 41372093.
5. "Craze manufacturer disputes NSF's discovery of drug tainting". Nutraingredients. October 17, 2013.
6. Lee J, Choe S, Choi H, Heo S, Kim E, Kim H, Bang E, Chung H (January 2013). "Identification of N-ethyl-α-ethylphenethylamine in crystalline powder seized for suspected drug trafficking: A research chemical or a new designer drug?". Forensic Toxicology. 31: 54–58. doi:10.1007/s11419-012-0158-1. S2CID 13523048.
7. "Popular sports supplements contain meth-like compound". USA Today. October 25, 2013.
8. Cohen PA, Travis JC, Venhuis BJ (2014). "A methamphetamine analog (N,α-diethyl-phenylethylamine) identified in a mainstream dietary supplement". Drug Testing and Analysis. 6 (7–8): 805–7. doi:10.1002/dta.1578. PMID 24124092. S2CID 42232885.
9. Warning issued over CRAZE sports supplement. New Zealand Herald, 13 November 2013