Sympathomimetic drug
Sympathomimetic drugs (also known as adrenergic drugs and adrenergic amines) are stimulant compounds which mimic the effects of
These drugs can act through several mechanisms, such as directly activating
of certain neurotransmitters, or stimulating production and release of catecholamines.Mechanisms of action
The mechanisms of sympathomimetic drugs can be direct-acting (direct interaction between drug and receptor), such as
Structure-activity relationship
A primary or secondary aliphatic amine separated by 2 carbons from a substituted benzene ring is minimally required for high agonist activity. The pKa of the amine is approximately 8.5-10.[2] The presence of hydroxy group in the benzene ring at 3rd and 4th position shows maximum alpha- and beta-adrenergic activity.[medical citation needed]
For maximum sympathomimetic activity, a drug must have:
- Amine group two carbons away from an aromatic group
- A hydroxyl group at the chiral beta position in the R-configuration
- Hydroxyl groups in the meta and para position of the aromatic ring to form a catechol which is essential for receptor binding
The structure can be modified to alter binding. If the amine is primary or secondary, it will have direct action, but if the amine is tertiary, it will have poor direct action. Also, if the amine has bulky substituents, then it will have greater beta adrenergic receptor activity, but if the substituent is not bulky, then it will favor the alpha adrenergic receptors.
Direct-acting
Adrenergic receptor agonists
Direct stimulation of the α- and β-
Dopaminergic agonists
Stimulation of the
Indirect-acting
Dopaminergic stimulants such as amphetamine, ephedrine, and propylhexedrine work by causing the release of dopamine and norepinephrine, along with (in some cases) blocking the reuptake of these neurotransmitters.
Abuse potential
Illegal drugs such as cocaine and MDMA also affect dopamine, serotonin, and norepinephrine.
Norepinephrine is synthesized by the body from the amino acid tyrosine,
Sympathomimetic drugs are sometimes involved in development of cerebral vasculitis and generalized polyarteritis nodosa like diseases involving immune-complex deposition. Known reports of such hypersensitivity reactions include the use of pseudoephedrine,[5] phenylpropanolamine,[6] methamphetamine[7] and other drugs at prescribed doses as well as at over-doses.
Comparison
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Examples
- amphetamine (Evekeo)
- benzphetamine (Didrex)
- benzylpiperazine (BZP)
- Catha edulis)
- Catha edulis, khat)
- cocaine (found in Erythroxylum coca, coca)
- ephedrine (found in Ephedra)
- lisdexamfetamine (Vyvanse)
- maprotiline (Ludiomil)
- MDMA (Ecstasy, Molly)
- methamphetamine (Meth, Crank, Desoxyn)
- methcathinone
- methylenedioxypyrovalerone (MDPV)
- methylphenidate (Ritalin)
- 4-methylaminorex
- Vicks Sinex)
- pemoline (Cylert)
- phenmetrazine (Preludin)
- propylhexedrine (Benzedrex)
- pseudoephedrine (Sudafed, SudoGest, also found in Ephedra species)
See also
References
- OCLC 1287761421.
If a drug causes effects similar to the activation of the sympathetic nervous system, it is called a sympathomimetic [...] A sympathomimetic agent increases heart rate, force of cardiac contraction and blood pressure.
- ^ Medicinal Chemistry of Adrenergics and Cholinergics Archived 2010-11-04 at the Wayback Machine
- ^ Campbell, Neil A.; Reece, Jane B. (2005). Biology (7th ed.). Pearson - Benjamin Cummings.
- ^ Patestas, Maria A.; Gartner, Leslie P. (2006). A Textbook of Neuroanatomy. Blackwell Publishing.
- ^ "Pseudoephedrine Disease Interactions". Drugs.com. Retrieved 2021-11-21.
- ISSN 0031-4005.
- ISSN 0361-803X.
External links
- Amines,+Sympathomimetic at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
