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 animals 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 namesN,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
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC12H19N
Molar mass177.291 g·mol−1
3D model (JSmol)
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 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

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.
  9. Warning issued over CRAZE sports supplement. New Zealand Herald, 13 November 2013
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