Substituted phenethylamines are a chemical class of drugs that are variable in their clinical use, side effects, pharmacology and substituents.

Chemical structures[edit | edit source]

Generalized structure of substituted phenethylamines

Note: α, β can be further divided into two substituents coming off the α and β positions, respectively. Usually the second substituent is trivial as it is hydrogen and is hence not mentioned, but if not they are mentioned under Rα and Rβ, respectively.



Anorectics[edit | edit source]

Traditional name R3 R4 Rα Rβ RN1 RN2
Amfepramone - - CH3 =O C2H5 C2H5
Benzfetamine - - (S)-CH3 - CH2-C6H5 -
Clobenzorex - - CH3 - CH2-C6H4-2-Cl -
Ethcathinone
[note 1]
- - CH3 =O C2H5 -
Fenfluramine CF3 - CH3 - C2H5 -
Fenproporex - - CH3 - CH2-CH2-C≡N -
Norfenfluramine CF3 - CH3 - - -
Phendimetrazine - - CH3 -O-CH2-CH2- CH3
Phentermine - - CH3, CH3 - - -
Sibutramine - Cl CH2-CH(CH3)2 -C3H6-[note 2] CH3 CH3

Empathogens/entactogens[edit | edit source]

Traditional name R3 R4 Rα RN1
MDMA -O-CH2-O- CH3 CH3
Tenamfetamine -O-CH2-O- CH3 -

Hormones and neurotransmitters[edit | edit source]

Traditional name R3 R4 Rβ RN1
3-methoxytyramine O-CH3 OH - -
Adrenaline OH OH OH CH3
Dopamine OH OH - -
N-methylphenethylamine - - - CH3
Noradrenaline OH OH OH -
m-octopamine OH - OH -
p-octopamine - OH OH -
m-tyramine OH - - -
p-tyramine - OH - -

Psychedelics[edit | edit source]

Street name R2 R3 R4 R5 R6 Rα RN1
2C-I O-CH3 - I O-CH3 - - -
25I-NBOMe O-CH3 - I O-CH3 - - CH2-C6H4-O-CH3
Bromo-DragonFLY -O-CH=CH- Br -O-CH=CH- CH3 -
DOI O-CH3 - I O-CH3 - CH3 -
Mescaline - O-CH3 O-CH3 O-CH3 - - -

Stimulants[edit | edit source]

Traditional name R4 Rβ Rα RN1
Amfetamine - - CH3 -
Cathine - (S)-OH (S)-CH3 -
Cathinone - =O (S)-CH3 -
Ephedrine - (R)-OH (S)-CH3 CH3
Lisdexamfetamine - - (S)-CH3 (S)-C(O)-CH2(NH2)-C4H8-NH2
Mephedrone CH3 =O CH3 CH3
Metamfetamine - - CH3 CH3
Methcathinone - =O CH3 CH3
Methylphenidate - COOCH3 -CH2-CH2-CH2-CH2-
Pemoline - =O -O-C(NH2)=
Pipradrol - -OH, -C6H5 -CH2-CH2-CH2-CH2-

Others[edit | edit source]

Traditional name R3 R4 Rα Rβ RN1 RN2
Bupropion Cl - CH3 =O C-(CH3)3 -
Desvenlafaxine - OH - C(OH)-CH2-CH2-CH2-CH2-CH2-
[note 3]
CH3 CH3
Salbutamol CH2-OH OH - OH C-(CH3)3 -
Venlafaxine - O-CH3
[note 4]
- C(OH)-CH2-CH2-CH2-CH2-CH2-
[note 5]
CH3 CH3

Notes[edit | edit source]

  1. This is the active metabolite of amfepramone
  2. Forming a cyclobutane with the β-carbon
  3. Cyclohexane with an alcohol group off the carbon that connects this group with the β-carbon
  4. Methoxy group
  5. Cyclohexane with an alcohol group off the carbon that connects this group with the β-carbon
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