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N,α-Diethylphenethylamine

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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
Identifiers
  • N-Ethyl-1-phenylbutan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H19N
Molar mass177.291 g·mol−1
3D model (JSmol)
  • C(C)NC(CC1=CC=CC=C1)CC
  • 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

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]

Adulterant in nutritional supplements

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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

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References

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  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. ^ a b 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. ^ a b "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
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