Phenylisobutylamine

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Phenylisobutylamine
Clinical data
Other namesα-Ethylphenethylamine; α-Ethylphenylethylamine; Butanphenamine; B; AEPEA
Routes of
administration		Oral
Drug classNorepinephrine–dopamine releasing agent; Stimulant
ATC code
  • none
Legal status
Legal status
  • CA: Schedule I
  • DE: NpSG (Industrial and scientific use only)
  • UK:
    Class A
  • US:
    Schedule II (isomer of Methamphetamine)
Identifiers
  • 1-phenylbutan-2-amine
JSmol)
SMILES
  • CCC(CC1=CC=CC=C1)N
  • InChI=1S/C10H15N/c1-2-10(11)8-9-6-4-3-5-7-9/h3-7,10H,2,8,11H2,1H3
  • Key:IOLQWLOHKZENDW-UHFFFAOYSA-N

Phenylisobutylamine, also known as α-ethylphenethylamine (AEPEA) or as butanphenamine (B), is a

alpha position of the side chain with an ethyl group
.

Phenylisobutylamine acts as a

reinforcing effects in animals.[1][2][3] It shows much lower potency and a greater preference for induction of norepinephrine release compared to dextroamphetamine.[1]

"Phenylisobutylamine" is in fact a chemical misnomer because isobutylamine itself contains a branched chain. The correct name after this style for this class of compound would be "phenylsecbutylamine".

Derivatives

A number of notable

derivatives
of phenylisobutylamine are known, including the following:

Additional derivatives with longer α

MBDP, pentylone, MDPV, and hexedrone, as well as others, like mexedrone
.

Whereas MDMA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA), MBDB appears to be a highly selective serotonin–norepinephrine releasing agent (SNRA) and with significant preference for induction of serotonin release over norepinephrine release.[4][5][6][7]

The phenylisobutylamine counterparts of psychedelic phenethylamines and amphetamines, for instance MBDB (the α-ethyl homologue of

α-methyltryptamine (αMT).[10][4] In the case of Ariadne specifically, it may be due to reduced efficacy in activating the serotonin 5-HT2A receptor.[8]

See also

References

  1. ^
    PMID 33082158
    .
  2. ^
    PMID 36190536
    .
  3. ^
    S2CID 19069907
    .
  4. ^
    PMID 32909493
    .
  5. ^
    PMID 20575841
    .
  6. PMID 8400010
    .
  7. PMID 17223101
    .
  8. ^
    PMID 36521179
    .
  9. ^ Clark MR, Shaw HE, Fantegrossi WE (March 2024). Poster 21: In vivo characterization of MBDB and its enantiomers in C57BL/6 and autism-like BTBR T+Itpr3tf/J mice (PDF). 16th Annual Behavior, Biology, and Chemistry: Translational Research in Substance Use Disorders, San Antonio, Texas, Embassy Landmark, 22-24 March 2024.
  10. PMID 38093842
    .
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