CSUMB  ESSP 311 
Dr. R. Rinehart


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

3,4,5-trimethoxy
benzaldehyde

 

 

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+

 

 

from curare root, used to poison blowgun darts by South American natives; anticholinergic;
causes skeletal muscle paralysis by blocking ACh receptors at neuromuscular junction. 
Has been used in surgery but has low margin of safety

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.
Blocks receptors for glycine, a spinal inhibitory neurotransmitter, leading to uncontrolled neural excitation, muscle contractions and death from convulsions. Despite this, has been used in pre-Viagra "male performance" medications.

brucine

C23H26N2O4

 

 

also from Nux vomica
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.

Both brucine and strychnine are chiral and have been use to resolve racemic mixtures of carboxylic acids.

 © Ronald W. Rinehart, 2002   Structures drawn with MDL IsisDraw®