Phenethylamine

Phenethylamine (1-amino-2-phenylethane) is a monoamine compound that is widespread in nature, even found in chocolate, but as well as the human brain where it is discussed as a putative neuromodulator or neurotransmitter. Some consider phenethylamine to have psychoactive effects, however, it quickly metabolized by the enzyme MAO so that significant concentrations do not reach the brain. It is structurally related to the amino acids phenylalanine and tyrosine. Substitutions to the phenethylamine molecule give rise to a group of compounds collectively known as phenethylamines. The term amphetamines is used to refer to the subset of phenethylamines that can be derived from substitution to amphetamine (α-methylphenethylamine), while those that derive from tyrosine are called catecholamines. Phenethylamines are\nwidespread in nature as hormones, neurotransmitters and\nalkaloids. Examples of fundamental importance in the human\nnervous system are dopamine, epinephrine (adrenaline) and\nnorepinephrine (noradrenaline). Plant alkaloids related to phenethylamine include the psychedelic drug mescaline,\nand the stimulants ephedrine and cathinone. Many synthetic phenethylamines have\nbeen investigated for their psychoactive effects, which are\ngenerally stimulant, empathogenic and/or psychedelic in\nnature. The most commonly used synthetic phenethylamines are\namphetamine (speed, Benzedrine), methamphetamine (meth, ice) and MDMA (Ecstasy). A\nphenethylamine backbone can also be identified in the more complex\nstructure of LSD. Some of the more important phenethylamines\nare tabulated below according to their structure. For simplicity the stereochemistry of these compounds is not covered in the table. Hundreds of other synthetic phenethylamines are known. This is due in large part to the pioneering work of Alexander Shulgin, much of which is described in the book PiHKAL. {| border=1\n|+ Substituted phenethylamines, tabulated by structure\n! Short Name\n| α\n| β \n! R2\n! R3 \n! R4 \n! R5 \n! N1 \n! Full Name\n|-\n|tyramine || || || || || OH || || || 4-hydroxyphenethylamine \n|-\n|dopamine || || || || OH || OH || || || 3,4-dihydroxyphenethylamine \n|-\n|epinephrine || || OH|| || OH || OH || || CH₃|| β,3,4-trihydroxy-N-methylphenethylamine \n|-\n|norepinephrine || || OH|| || OH || OH || || || β,3,4-trihydroxyphenethylamine \n|-\n|salbutamol || || OH || || || OH || CH₂CH₂OH || C(CH₃)₃ || α¹[tert-butylamino)methyl]-4-hydroxy-m-xylene-α1,α3'-diol\n|-\n|amphetamine || CH₃ || || || || || || || α-methylphenethylamine \n|-\n|methamphetamine|| CH₃ || || || || || || CH₃ || N-methylamphetamine \n|-\n|ephedrine || CH₃ || OH || || || || || CH₃ || N-methyl-β-hydroxyamphetamine\n|-\n|cathine || CH₃ || OH || || || || || || β-hydroxyamphetamine\n|-\n|cathinone || CH₃ || =O || || || || || || β-ketoamphetamine\n|-\n|methcathinone || CH₃ || =O || || || || ||CH₃ || N-methyl-β-ketoamphetamine\n|-\n|bupropion || CH₃ || =O || || Cl || || ||C(CH₃)₃ || 3-chloro-N-tert-butyl-β-ketoamphetamine\n|-\n|fenfluramine|| CH₃ || || || CF₃ || || || CH₂CH₃ || 3-trifluoromethyl-N-ethylamphetamine \n|-\n|phentermine || CH₃,CH₃ || || || || || || || α,α-dimethylphenethylamine \n|-\n|mescaline || || || || OCH₃ || OCH₃ || OCH₃ || || 3,4,5-trimethoxyphenethylamine\n|-\n|MDA || CH₃ || || ||colspan=2| -O-CH₂-O- || || || 3,4-methylenedioxyamphetamine\n|-\n|MDMA || CH₃ || || ||colspan=2| -O-CH₂-O- || || CH₃ || 3,4-methylenedioxy-N-methylamphetamine\n|-\n|DOM || CH₃ || || OCH₃ || || CH₃ || OCH₃ || ||2,5-dimethoxy-4-methylamphetamine\n|-\n|DOB|| CH₃ || || OCH₃ || || Br || OCH₃ || ||2,5-dimethoxy-4-bromoamphetamine\n|-\n|2C-B|| || || OCH₃ || || Br || OCH₃ || ||2,5-dimethoxy-4-bromophenethylamine\n|-\n|2C-C|| || || OCH₃ || || Cl || OCH₃ || ||2,5-dimethoxy-4-chlorophenethylamine\n|-\n|2C-I|| || || OCH₃ || || I || OCH₃ || ||2,5-dimethoxy-4-iodophenethylamine\n|-\n|2C-D|| || || OCH₃ || || CH₃ || OCH₃ || ||2,5-dimethoxy-4-methylphenethylamine\n|-\n|2C-E|| || || OCH₃ || || CH₂CH₃ || OCH₃ || ||2,5-dimethoxy-4-ethylphenethylamine\n|-\n|2C-T-2|| || || OCH₃ || || SCH₂CH₃ || OCH₃ || ||2,5-dimethoxy-4-ethylthiophenethylamine\n|-\n|2C-T-7|| || || OCH₃ || || SCH₂CH₂CH₃ || OCH₃ || ||2,5-dimethoxy-4-propylthiophenethylamine\n|-\n|2C-T-21|| || || OCH₃ || || FSCH₂CH₂CH₃ || OCH₃ || ||2,5-dimethoxy-4-(2-fluoroethylthio)phenethylamine\n|}

See also

\n* catecholamines\n* PiHKAL\n* Alexander Shulgin

External links

\n* Book II of PiHKAL online\n* Review and summary of PiHKAL, including table of 300+ phenethylamines: ascii postscript\n* A Structural Tour of PiHKAL Category:Phenethylamines\n