User:IllusionalFate/Phenethylamines

                           

                                      
                                          phenylethan-2-amine

beta-Phen[yl]ethylamine, or PEA, is a trace amine that acts as a neuromodulator in the human body. Many psychotropics have been derived from this compound by adding substituents to the side chain and/or aromatic ring. The following is a list of substituted phenethylamines.

File:Phenylethylamine-ifa.png

Phenylethylamine

Ethylamine Side Chain Substituents (N, α, β)

• Substituted amphetamines
• Substituted cathinones

#	Name	Chemical formula	Substituent	Duration
1	Phenelzine	C8H12N2	[N] R-NH2	1-3 weeks
2	Methylphenethylamine	C9H13N	[N] R-CH3	?
3	Amphetamine	C9H13N	[α] R-CH3	5-6 hours
4	Bemphetamine	C9H13N	[β] R-CH3	?
5	Cathinone	C9H11NO	[β] R=O	3-4 hours
6	PEP	C12H17N	[N-N'] R{-CH2-CH2-CH2-CH2-R'}	?
7	Methylphenidate	C14H19NO2	[N-α] R-CH2-CH2-CH2-CH2-R' [β] R-C(=O)-O-CH3	3-5 hours
8	Fencamfamine	C15H21N	[N] R-CH2-CH3 [α-β] R-CH(-CH2-)-CH2-CH2-(CH)-R'	?
9	Zylofuramine	C15H23N	[N] R-CH2-CH3 [α] R-CH{-CH2-CH2-CH2-O-}	?

• 
  1) N-aminophenethylamine
• 2) N-methylphenethylamine
  2) N-methylphenethylamine
• 3) α-Methylphenethylamine
  3) α-Methylphenethylamine
• 4) β-Methylphenethylamine
  4) β-Methylphenethylamine
• 5) Benzoylethanamine
  5) Benzoylethanamine
• 
  6) Phenylethylpyrrolidine
• 7) N,α-Butylene-β-methoxycarbonyl.. ..phenethylamine
  7) N,α-Butylene-β-methoxycarbonyl..
  ..phenethylamine
• 
  8) Phenylnorbornanethyl..
  ..amine
• 9) α-Tetrahydrofuranethyl.. ..phenethylamine
  9) α-Tetrahydrofuranethyl..
  ..phenethylamine

Substituted amphetamines

An amphetamine is a phenethylamine with a methyl group attached to the alpha carbon. The name is a shortened version of its chemical name, alpha-methylphenethylamine.

#	Name	Chemical formula	Substituent	Duration
1	Cathine / Phenylpropanolamine	C9H13NO	[β] R-OH
2	Methamphetamine	C10H15N	[N] R-CH3
3	Phentermine	C10H15N	[α] R-CH3
4	Alfetamine	C11H15N	[α] R-CH2-CH=CH2
5	Amfecloral	C11H12Cl3N	[N] R=CH-C-Cl3
6	Ephedrine / Pseudoephedrine	C10H15NO	[β] R-OH
7	Ethamphetamine	C11H17N	[N] R-CH2-CH3
8	Dimethylamphetamine	C11H17N	[N,N] R-CH3
9	Mephentermine	C11H17N	[N,α] R-CH3
10	Phenpentermine	C11H17N	[β,α] R-CH3
11	Fenproporex	C12H16N2	[N] R-CH2-CH2-C≡N
12	Selegiline	C13H17N	[N] R-CH2-C≡CH
13	Mefenorex	C12H18ClN	[N] R-CH2-CH2-CH2-Cl
14	Propylamphetamine	C12H19N	[N] R-CH2-CH2-CH3
15	Isopropylamphetamine	C12H19N	[N] R-CH(-CH3)-CH3
16	Furfenorex	C15H19NO	[N] R-CH3 [N'] R-CH2{-C-O-CH=CH-CH=}
17	Clobenzorex	C16H18ClN	[N] R-CH2{-C=CH-CH=CH-CH=C(-Cl)-}
18	Amphetaminil	C17H18N2	[N] R-CH(-C≡N){-C=CH-CH=CH-CH=CH-}
19	Benzphetamine	C17H21N	[N] R-CH3 [N'] R-CH2{-C=CH-CH=CH-CH=CH-}
20	Lisdexamfetamine	C15H25N3O	[N] R-C(=O)-CH(-NH2)-CH2-CH2-CH2-CH2-NH2
21	Fenethylline	C18H23N5O2	[N] R-CH2-CH2{-N-C(=)-C(=O)-N(-CH3)-C(=O)-N(-CH3)-(C)-N=CH-}
22	Fencamine	C19H25N5O2	[N] R-CH3 [N'] R-CH2-CH2{-N-C(=)-C(=O)-N(-CH3)-C(=O)-N(-CH3)-(C)-N=CH-}

• 1) β-Hydroxyamphetamine
  1) β-Hydroxyamphetamine
• 2) N-Methylamphetamine
  2) N-Methylamphetamine
• 3) α-Methylamphetamine
  3) α-Methylamphetamine
• 
  4) α-Allylamphetamine
• 
  5) N- Trichloroethyleneamphet..
  ..amine
• 
  6) β- hydroxymethamphetamine
• 7) N-Ethylamphetamine
  7) N-Ethylamphetamine
• 8) N, N-Dimethylamphetamine
  8) N, N-Dimethylamphetamine
• 9) N, α-Dimethylamphetamine
  9) N, α-Dimethylamphetamine
• 10) α, β-Dimethylamphetamine
  10) α, β-Dimethylamphetamine
• 11) N-Ethylnitrilamphetamine
  11) N-Ethylnitrilamphetamine
• 12) N- Propargylmethamphet.. ..amine
  12) N- Propargylmethamphet..
  ..amine
• 13) N- Chloropropylamphetamine
  13) N- Chloropropylamphetamine
• 14) N-Propylamphetamine
  14) N-Propylamphetamine
• 15) N-Isopropylamphetamine
  15) N-Isopropylamphetamine
• 16) N- Furfurylmethamphetamine
  16) N- Furfurylmethamphetamine
• 17) N- Chlorobenzylamphetamine
  17) N- Chlorobenzylamphetamine
• 
  18) N- Phenacetonitrilamphet..
  ..amine
• 19) N- Benzylmethamphetamine
  19) N- Benzylmethamphetamine
• 20) N- Diaminohexanoylamphet.. ..amine
  20) N- Diaminohexanoylamphet..
  ..amine
• 21) N-Ethyltheophyllinamphet.. ..amine
  21) N-Ethyltheophyllinamphet..
  ..amine
• 22) N- Ethyltheophyllinemetham.. ..phetamine
  22) N- Ethyltheophyllinemetham..
  ..phetamine

Phenyl Ring Substituents (2, 3, 4, 5, 6)

• Substituted amphetamines
• Substituted cathinones

#	Name	Chemical formula	Substituent	Duration
1	Tyramine
2	Dopamine
3	Octopamine
4	Oxidopamine
5	Norepinephrine
6	Phenylephrine
7	Epinephrine
8	Salbutamol

Substituted amphetamines

#	Name	Chemical formula	Substituent	Duration
1	2-FA
2	3-FA
3	4-BA
4	4-CA
5	4-FA
6	4-IA
7	Norpholedrine
8	3,4-DHA
9	4-FMA
10	Ortetamine
11	3-MA
12	4-MA
13	Norfenfluramine
14	Clortermine
15	Chlorphentermine
16	Levonordefrin
17	PMA
18	4-MTA
19	Pholedrine
20	5-APDB
21	Oxilofrin
22	4-MMA
23	Xylopropamine
24	Bromo-DragonFLY
25	NAP
26	Fludorex
27	4-ETA
28	MMA
29	PMMA
30	IAP
31	2,4-DMA
32	2,5-DMA
33	3,4-DMA
34	Fenfluramine
35	Tiflorex
36	PMEA
37	TMA
38	TMA-2
39	TMA-3
40	TMA-4
41	TMA-5
42	TMA-6
43	Aleph
44	Ganesha
45	Aleph-2
46	Amfepentorex
47	Aleph-6
48	Aleph-7
49	Aleph-4
50	Benfluorex

MDx

• Chemistry: The majority of substituted methylenedioxyphenethylamines contain a methylenedioxy functional group (R-O-CH₂-O-R') at the 3 and 4 positions of the phenyl ring.

• Psychological effects: Empathy, entactogenesis, euphoria, musical enhancement, psychedelia.

DOx

The DOx family, or para-substituted 2,5-Dimethoxyamphetamines, are the amphetamine versions of various 2-Cx compounds.

#	Name	Chemical formula	Substituent	Duration
1	DOB	C11H16BrNO2	[4] R-Br	18-30 hours
2	DOC	C11H16ClNO2	[4] R-Cl	~10 hours
3	DOF	C11H16FNO2	[4] R-F	?
4	DOI	C11H16INO2	[4] R-I	16-30 hours
5	DON	C11H16N2O4	[4] R-N+-O2-	?
6	DOM	C12H19NO2	[4] R-CH3	14-20 hours
7	DOE	C13H21NO2	[4] R-CH2-CH3	14-20 hours

• 1) 2,5-Dimethoxy-4-bromoamphetamine
  1) 2,5-Dimethoxy-4-bromoamphetamine
• 2) 2,5-Dimethoxy-4-chloroamphetamine
  2) 2,5-Dimethoxy-4-chloroamphetamine
• 
  3) 2,5-Dimethoxy-4-fluoroamphetamine
• 
  4) 2,5-Dimethoxy-4-iodoamphetamine
• 
  5) 2,5-Dimethoxy-4-nitroamphetamine
• 6) 2,5-Dimethoxy-4-methylamphetamine
  6) 2,5-Dimethoxy-4-methylamphetamine
• 7) 2,5-Dimethoxy-4-ethylamphetamine
  7) 2,5-Dimethoxy-4-ethylamphetamine