5-EAPB

5-EAPB
Clinical data
Other names	5-(2-(Ethylamino)propyl)benzofuran; 1-(Benzofuran-5-yl)-N-ethylpropan-2-amine
Routes of; administration	Oral
Drug class	Entactogen
ATC code	None;
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); CA: Schedule I; DE: NpSG (Industrial and scientific use only); UK: Class B;
Identifiers
	IUPAC name 1-(1-benzofuran-5-yl)-N-ethylpropan-2-amine;
CAS Number	1445566-01-7 ;
PubChem CID	102336590;
ChemSpider	32078888;
UNII	889D8VM2SL;
CompTox Dashboard (EPA)	DTXSID701010104 ;
Chemical and physical data
Formula	C13H17NO
Molar mass	203.285 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(NCC)CC1=CC(C=CO2)=C2C=C1;
	InChI InChI=1S/C13H17NO/c1-3-14-10(2)8-11-4-5-13-12(9-11)6-7-15-13/h4-7,9-10,14H,3,8H2,1-2H3; Key:ZBZDDOARNPAMSP-UHFFFAOYSA-N;

5-EAPB, also known as 5-(2-(ethylamino)propyl)benzofuran, is a potentially entactogenic amphetamine and benzofuran which is structurally related to 5-MAPB and 5-APB. It might be predicted to show similar effects to these drugs in humans, but the pharmacology of 5-EAPB remains unstudied as of 2020.

5-EAPB is similar in structure to compounds such as 5-APB which are claimed to be agonists of the 5-HT_2C receptor^[2] as well as a triple monoamine reuptake inhibitor, however 5-EAPB is not listed as an example in this patent, and it is not yet established to what extent the activity of 5-EAPB resembles that of 5-APB.

Toxicity

Three people in their 30s were hospitalised after each taking approximately 500 mg of 5-EAPB, one of whom later died in hospital, whilst attending Brownstock music festival in Essex, UK on August 31, 2013.^[3]

Interactions

Society and culture

Legal status

Singapore

5-EAPB is listed in the Fifth Schedule of the Misuse of Drugs Act (MDA) and therefore illegal in Singapore as of May 2015.^[4]

United Kingdom

In the UK, all benzofurans are considered Class B drugs^[5] and are therefore illegal.

References

^ Anvisa (24 July 2023). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 25 July 2023). Archived from the original on 27 August 2023. Retrieved 27 August 2023.
^ US patent 7045545, Briner K, Burkhart P, Burkholder P, Fisher MJ, Gritton WH, Kohlman DT, Liang SX, Miller SC, Mullaney JT, Xu YX, "Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists", published 19 January 2000, issued 2006-16-03, assigned to Eli Lilly and Co
^ Stretch E (1 September 2013). "Festivalgoer's death prompts drug warning". The Guardian.
^ "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived from the original on 15 July 2015. Retrieved 24 July 2015.
^ "Ban on NBOMe and benzofurans comes into force". Gov.uk. 10 June 2014.

External links

5-EAPB - Isomer Design

[1] Anvisa (24 July 2023). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 25 July 2023). Archived from the original on 27 August 2023. Retrieved 27 August 2023.

[2] US patent 7045545, Briner K, Burkhart P, Burkholder P, Fisher MJ, Gritton WH, Kohlman DT, Liang SX, Miller SC, Mullaney JT, Xu YX, "Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists", published 19 January 2000, issued 2006-16-03, assigned to Eli Lilly and Co

[3] Stretch E (1 September 2013). "Festivalgoer's death prompts drug warning". The Guardian.

[4] "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived from the original on 15 July 2015. Retrieved 24 July 2015.

[5] "Ban on NBOMe and benzofurans comes into force". Gov.uk. 10 June 2014.

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