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

Chemical structuresEdit

Substituted phenethylamines generalized structure

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.



AnorecticsEdit

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/entactogensEdit

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

Hormones and neurotransmittersEdit

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 - -

PsychedelicsEdit

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 - - -

StimulantsEdit

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-

OthersEdit

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

NotesEdit

  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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