Description
Buy Oxilofrine Cas 365-26-4
Oxilofrine, sold under the brand names
Carnigen and
Suprifen among others, is a
sympathomimetic medication which has been used as an
antihypotensive agent and
cough suppressant.
[4][5][6] It is taken
by mouth.
[1]
Oxilofrine acts as a
norepinephrine releasing agent and hence is an indirectly acting sympathomimetic.
[7][6][8] It is a
substituted amphetamine and is closely related to
ephedrine (with oxilofrine also being known as 4-hydroxyephedrine).
[4][8]
Oxilofrine was first developed in the 1930s.
[9] It is mostly no longer marketed today.
[10]
Pharmacology
Pharmacodynamics
Oxilofrine is described as an
ephedrine-like indirectly acting
sympathomimetic and
antihypotensive agent.
[4][7][6] It acts as a
norepinephrine releasing agent and indirectly activates the
α- and
β-adrenergic receptors.
[6][8] The drug has
positive inotropic effects (increases
myocardial contractility).
[6]
As an
α-adrenergic receptor agonist, Oxilofrine activates the
Alpha-1 adrenergic receptor. Activation of said receptor causes
vasoconstriction, which is likely how it treats
cough. By that mechanism, secretion of mucus into the airway would be dampened, thus reducing the urge to cough.
[11] It's also postulated that Oxilofrine acts as a
sigma-1 receptor agonist, since it shares structural similarities to
dextromethorphan and
methamphetamine, two other
sigma-1 receptor agonists.
Chemistry
Oxilofrine, also known as 4,β-dihydroxy-
N-methyl-α-methylphenethylamine or as 4,β-dihydroxy-
N-methylamphetamine, is a
substituted phenethylamine and
amphetamine derivative.
[4][10] It is the
racemic 4-
hydroxylated analogue of
ephedrine ((1
R,2
S)-β-hydroxy-
N-methylamphetamine).
[4] It is also related to
pholedrine (4-hydroxy-
N-methylamphetamine).
[4]
The predicted
log P of oxilofrine ranges from -0.13 to 0.6.
[12][1][13] It is more
hydrophilic than ephedrine, which has an experimental log P of 1.13 and a predicted log P of 0.9 to 1.32.
[14][15][16]
History
Oxilofrine was originally developed in the 1930s as a
cardiac stimulant. Trade names included Suprifen (
Bayer) and, combined with an
adenosine-containing standardized organ extract, Carnigen (
Hoechst AG).
[9]
In combination with
normethadone, it was marketed as a
cough suppressant under the trade name Ticarda. As of 2021, this formulation was still manufactured in Canada by
Valeant and sold as Cophylac.
[17]
Several other sympathomimetics and
vasodilators were developed as chemical derivatives of oxilofrine, such as the
β2-adrenergic receptor agonists buphenine and
isoxsuprine.
[18][19]
Society and culture
Names
Oxilofrine is the
generic name of the drug and its
INNTooltip International Nonproprietary Name.
[4][7][10] It is also known by synonyms including
methylsynephrine,
oxyphedrine, and
hydroxyephedrine.
[4][10] Brand names of oxilofrine include
Carnigen,
Cophylac (with
normethadone),
Suprifen, and
Ticarda (also with normethadone), among others.
[4][10][9]
Availability
Oxilofrine has been marketed in
Austria,
Canada, and
Germany.
[4][10]
Use in exercise and sports
Oxilofrine is currently a
World Anti-Doping Agency (WADA) prohibited substance when used in competition.
[20] It has been found as an
adulterant in some dietary supplements.
[9][21] Even after receiving warning letters from the FDA,
[22] some sports and weight loss supplement companies continue to use oxilofrine as an undeclared ingredient in their products despite it being prohibited.
[23]
List of doping cases
Several
doping cases involving oxilofrine have been publicized, including:
- In 2009, Brazilian/American cyclist Flávia Oliveira was suspended for 2 years after taking a supplement known as "HyperDrive 3.0+" which contained methylsynephrine, a chemical equivalent of oxilofrine, among other substances.[24] Her sentence was eventually reduced to 18 months after an appeal as there was enough evidence that she had unknowingly consumed said substance as the old label did not list methylsynephrine.[25]
- On 18 September 2010, Vietnamese weightlifter Hoàng Anh Tuấn, silver medalist in 2008 Summer Olympics was handed a four-year ban, later reduced to two years, for testing positive with the substance. It was found out that the substance came from unlabeled drinks he consumed during his training in China.[26]
- On July 14, 2013, Jamaican runners Asafa Powell and Sherone Simpson tested positive for oxilofrine prior to the 2013 World Athletics Championships.[27] Powell, however, maintained that he did not take any banned supplements knowingly or willfully.[28] Powell voluntarily withdrew as a result of the test. On 10 April 2014, both athletes received an 18-month suspension from competing, which was set to expire in December that year.[29] However, after appealing to the Court of Arbitration for Sport (CAS), both athletes' suspensions were lifted on 14 July 2014.[30]
- On July 16, 2015, Red Sox pitching prospect Michael Kopech was suspended without pay for 50 games after testing positive for oxilofrine, which is a banned substance under the Minor League Drug Prevention and Treatment Program. Kopech denied knowingly taking the substance.[31]
- In October 2018, the WBO stripped boxer Billy Joe Saunders of its middleweight world title after he tested positive for oxilofrine, as a result of a drug test administered by the Voluntary Anti-Doping Association (VADA). In his defense, Saunders held that while the substance was proscribed by VADA it was not banned "out of competition" by UK Anti-Doping, or the British Boxing Board of Control, but this appeal was rejected.[32]
Other drugs
Oxilofrine is a known
metabolite of
para-methoxymethamphetamine (PMMA).
[6]
Oxilofrine (free base) | CAS# 365-26-4 (free base)
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Oxilofrine (free base) is a sympathomimetic used to treat hypotensive states, with cardiac stimulatory effects similar to those of ephedrine.
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