Chem 30B  Dr. R. Rinehart
Chapter 16:  Amines
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NEUROTRANSMITTERS, HORMONES, DRUGS, and ALKALOIDS

Common Name

“IUPAC” Name

Line Structure

Comments

glycine

aminoacetate

inhibitory neurotransmitter in spinal  tract; antagonized by strychnine and brucine. and yes, it’s one of the 20 common amino acids!

glutamate

2-amino
pentanedioate

neurotransmitter
many people are sensitive to MSG added to foods; it’s also one of the 20 common amino acids!

g-aminobutyric acid
GABA

3-aminobutanoate

neurotransmitter and antihypertensive drug

dopamine

2-(3,4-dihydroxy
phenyl) ethanamine

neurotransmitter involved in CNS control of muscle movement;  deficient in Parkinson’s disease

L-DOPA

L-3,4-dihydroxy
phenylalanine

biosynthetic precursor to dopamine, norepinephrine, epinephrine, and melanin. Used as a drug to treat Parkinson’s disease.

norepinephrine or
noradrenaline

1-(3,4-dihydroxyphenyl)
 –2-amino ethanol

postganglionic neurotransmitter in the sympathetic nervous system, also a CNS neurotransmitter. Also a hormone produced by the adrenal medulla, elevates blood glucose levels by stimulating  glycogen breakdown in the liver. Also stimulates fat breakdown in adipose tissue and affects heart rate.

epinephrine or
adrenaline

N-methyl-1-
(3,4-dihydroxyphenyl)
–2-amino ethanol

“fight or flight” hormone produced in adrenal medulla;  powerful cardiac stimulant, bronchodilator, peripheral vasoconstrictor

amphetamine

1-amino-2-phenyl
propane

sympathomimetic, CNS stimulant, depresses appetite; drug of abuse

methamphetamine

1-methylamino-2-phenyl propane

sympathomimetic, CNS stimulant, depresses appetite; major drug of abuse, closely linked to psychotic and violent behavior.

phenethylamine

1-amino-2-phenyl
ethane

it’s the “love drug” found in chocolate

mescaline

2-(3,4,5-trimethoxy
phenyl)ethanamine

hallucinogen; the active ingredient in peyote;

MMDA 
“Ecstasy”

5-methyl-3,4-
methylenedioxy
methamphetamine

highly problematic illegal hallucinogenic drug

serotonin

2-(5-hydroxy-3-
indolyl)-1-amino
ethane
5-hydroxytryptamine

neurotransmitter and hormone

melatonin

N-acetyl serotonin

hormone produced by pineal gland; affects sleep and other behavior.

psilocybin

4-hydroxytryptamine

hallucinogenic drug from “shrooms”

DMT

N,N-dimethyltryptamine

a fast- and short-acting hallucinogen and psychotogen used in the ‘60s

LSD-25

lysergic acid
N,N-diethylamide

serotonin antagonist and incredibly potent hallucinogen – as little as 125 mg causes profound hallucinations that last for many hours. Note the indole ring with an N two carbons away from the 3-position.

histamine

1-amino-2-
(5-imidazolyl)
ethane

produced by mast cells; powerful vasodilator; involved in allergic reactions

diphenhydramine
Benadryl^®

C₁₇H₂₁NO

antihistamine, used to treat allergies and motion sickness

acetazolamide
Diamox^®

xxx

inhibits renal carbonic anhydrase and acts as diuretic

thyroxine
T4

xxx

a thyroid hormone; stimulates metabolism

cocaine

local anesthetic and drug of serious abuse

caffeine

1,3,7-trimethyl xanthine

stimulant from coffee, tea, guarana, kola nuts, and other plants

theobromine

3,7-dimethyl xanthine

found in cacao, tea, and kola nuts; used as bronchodilator, diuretic, and cardiac stimulant

theophylline

1,3-dimethyl
xanthine

found in tea; has diuretic, bronchodilator, and cardiac stimulant activities

quinine

xxx

antimalarial from bark of cinchona tree

coniine

xxx

the poison in hemlock [remember Socrates?]

nicotine

xxx

from tobacco; claimed to be more addictive than heroin. partial antagonist to acetylcholine at neuromuscular junction [hence, the term “nicotinic” receptors]

acetylcholine

xxx

neurotransmitter  in CNS and peripherally  [parasympathetic, preganglionic sympathetic, and neuromuscular junction]

decamethonium

N,N,N,N’,N’,N’-
hexamethyl-1,10-
decanediaminium dibromide

skeletal muscle relaxant used in surgery

tubocurarine

[C₃₉H₄₆N₂O₅]²⁺

morphine

C₁₇H₁₉NO₃

powerful and addictive analgesic from the opium poppy

naloxone

C₁₉H₂₁NO₄

potent receptor-blocking antagonist of morphine and other opiates. Used in diagnosis and treatment of opiate overdose and addiction.

fentanyl

C₂₂H₂₈N₂O

synthetic narcotic analgesic with high addiction potential

methadone

C₂₁H₂₇NO

another synthetic and highly addictive narcotic. Used to “treat” heroin addicts, it leaves them addicted to it instead and causes physical damage to the body.

strychnine

C₂₁H₂₂N₂O₂

incredibly toxic alkaloid from Nux vomica – as little as 1 mg can be fatal

brucine

C₂₃H₂₆N₂O₄

about ⅓ as toxic as strychnine. In the movie The Mechanic, this is what the young apprentice hitman Jan-Michael Vincent used to kill his mentor Charles Bronson once he felt ready to take over the action.