β-hydroxyamphetamine
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β-hydroxyamphetamine
Hydroxyamphetamine may refer to: * β-Hydroxyamphetamine (phenylisopropanolamine; two chiral centers and four possible stereoisomers) ** Phenylpropanolamine (racemic phenylpropanolamine; norephedrine; (1''R'',2''S''/1''S'',2''R'')-β-hydroxyamphetamine; (±)-phenylpropanolamine) *** (1R,2S)-Phenylpropanolamine, (1''R'',2''S'')-Phenylpropanolamine ((1''R'',2''S'')-β-hydroxyamphetamine) *** (1S,2R)-Phenylpropanolamine, (1''S'',2''R'')-Phenylpropanolamine ((1''S'',2''R'')-β-hydroxyamphetamine) ** Norpseudoephedrine (racemic norpseudoephedrine; (1''S'',2''S''/1''R'',2''R'')-β-hydroxyamphetamine; (±)-norpseudoephedrine) *** Cathine ((1''S'',2''S'')-β-hydroxyamphetamine; D-Norpseudoephedrine; (+)-norpseudoephedrine) *** L-Norpseudoephedrine, L-Norpseudoephedrine ((1''R'',2''R'')-β-hydroxyamphetamine; (−)-norpseudoephedrine) * Gepefrine (3-hydroxyamphetamine) * 4-Hydroxyamphetamine * N-Hydroxyamphetamine, ''N''-Hydroxyamphetamine See also

* Hydroxymethylamphetamine * Substitut ...
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Substituted β-hydroxyamphetamine
Substituted β-hydroxyamphetamines, or simply β-hydroxyamphetamines, also known as phenylisopropanolamines, phenylpropanolamines, norephedrines, or cathinols, are derivatives of β-hydroxyamphetamine with one or more chemical substituents. They are substituted phenethylamines, phenylethanolamines (β-hydroxyphenethylamines), and amphetamines (α-methylphenethylamines), and are closely related to but distinct from the substituted cathinones (β-ketoamphetamines). Examples of β-hydroxyamphetamines include the β-hydroxyamphetamine stereoisomers phenylpropanolamine and cathine and the stereospecific ''N''-methylated β-hydroxyamphetamine derivatives ephedrine and pseudoephedrine, among many others. In terms of pharmacological activity, the β-hydroxyamphetamines include indirectly acting norepinephrine and dopamine releasing agents and directly acting α- and β-adrenergic receptor agonists, among other actions. In contrast to their amphetamine counterparts, ephedrine and ...
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Phenylpropanolamine
Phenylpropanolamine (PPA), sold under many brand names, is a sympathomimetic agent used as a decongestant and appetite suppressant. It was once common in prescription and over-the-counter cough and cold preparations. The medication is taken orally. Side effects of phenylpropanolamine include increased heart rate and blood pressure. Rarely, PPA has been associated with hemorrhagic stroke. PPA acts as a norepinephrine releasing agent, indirectly activating adrenergic receptors. As such, it is an indirectly acting sympathomimetic. It was once thought to act as a sympathomimetic with additional direct agonist action on adrenergic receptors, but this proved wrong. Chemically, phenylpropanolamine is a substituted amphetamine and is closely related to ephedrine, pseudoephedrine, amphetamine, and cathinone. It is usually a racemic mixture of the (1''R'',2''S'')- and (1''S'',2''R'')-enantiomers of β-hydroxyamphetamine and is also known as ''dl''-norephedrine. Phenylpropanolami ...
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Hydroxymethylamphetamine
Hydroxymethylamphetamine, or hydroxymethamphetamine, also known as phenylpropanolmethylamine, may refer to: * β-Hydroxy-''N''-methylamphetamine (two chiral centers and four possible stereoisomers) ** Racephedrine (racemic ephedrine; (1''R'',2''S''/1''S'',2''R'')-ephedrine) *** (1''R'',2''S'')-Ephedrine (ephedrine) *** (1''S'',2''R'')-Ephedrine ** Racemic pseudoephedrine ((1''R'',2''R''/1''S'',2''S'')-pseudoephedrine) *** (1''S'',2''S'')-Pseudoephedrine (pseudoephedrine) *** (1''R'',2''R'')-Pseudoephedrine * Pholedrine (4-hydroxy-''N''-methylamphetamine) * ''N''-Hydroxymethamphetamine (''N''-hydroxy-''N''-methylamphetamine) See also * Hydroxyamphetamine * Substituted β-hydroxyamphetamine Substituted β-hydroxyamphetamines, or simply β-hydroxyamphetamines, also known as phenylisopropanolamines, phenylpropanolamines, norephedrines, or cathinols, are derivatives of β-hydroxyamphetamine with one or more chemical substituents. ... References External links Pheny ...
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Norpseudoephedrine
Norpseudoephedrine may refer to: * Cathine (or D-norpseudoephedrine), the (+)-enantiomer and most widely known form of the compound * L-Norpseudoephedrine, the (-)-enantiomer of the compound * , the racemic mixture of the compound See also *Pseudoephedrine Pseudoephedrine, sold under the brand name Sudafed among others, is a sympathomimetic medication which is used as a decongestant to treat nasal congestion. It has also been used off-label for certain other indications, like treatment of lo ... {{Chemistry index Beta-Hydroxyamphetamines ...
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Cathine
Cathine, also known as -norpseudoephedrine or as (+)-norpseudoephedrine, is a psychoactive drug of the phenethylamine and amphetamine groups which acts as a stimulant. Along with cathinone, it is found naturally in ''Catha edulis'' (khat), and contributes to the overall effects of the plant. Cathine has approximately 7 to 10% of the potency of amphetamine. Pharmacology Like amphetamines, cathinone and ephedrine, cathine acts as a norepinephrine releasing agent (NRA). It also acts as a dopamine releasing agent (DRA). Chemistry Cathine is one of the four stereoisomers of phenylpropanolamine (PPA). Regulation The World Anti-Doping Agency's list of prohibited substances (used for the Olympic Games among other athletic events) bans cathine in concentrations of over 5 micrograms per milliliter in urine. Cathine is a Schedule III drug under the Convention on Psychotropic Substances. In the United States, it is classified as a Schedule IV controlled substance. In Australia, C ...
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L-Norpseudoephedrine
-Norpseudoephedrine, or (−)-norpseudoephedrine, is a psychostimulant drug of the amphetamine family. It is one of the four optical isomers of phenylpropanolamine, the other three being cathine ((+)-norpseudoephedrine), (−)-norephedrine, and (+)-norephedrine; as well as one of the two enantiomers of norpseudoephedrine (the other being cathine). Similarly to cathine, -norpseudoephedrine acts as a releasing agent of norepinephrine ( EC50 = 30 nM) and to a lesser extent of dopamine (EC50 = 294 nM). Due to the 10-fold difference in its potency for inducing the release of the two neurotransmitters however, -norpseudoephedrine could be called a modestly selective or preferential norepinephrine releasing agent, similarly to related compounds like ephedrine and pseudoephedrine. See also * Cathine * Phenylpropanolamine * Cathinone * Pseudoephedrine * Ephedrine Ephedrine is a central nervous system (CNS) stimulant and sympathomimetic agent that is often used to pre ...
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Gepefrine
Gepefrine, also known as 3-hydroxyamphetamine or α-methyl-''meta''-tyramine and sold under the brand names Pressionorm and Wintonin, is a sympathomimetic medication used as an antihypotensive agent which has been marketed in Germany. Pharmacology Gepefrine is described as a sympathomimetic and antihypotensive agent. Chemistry Gepefrine, also known as 3-hydroxy-α-methylphenethylamine or as 3-hydroxyamphetamine, is a substituted phenethylamine and amphetamine derivative. It is used pharmaceutically as the (''S'')-enantiomer and as the tartrate salt. Related compounds include ''meta''-tyramine (3-hydroxyphenethylamine), 4-hydroxyamphetamine (norpholedrine), 3,4-dihydroxyamphetamine (α-methyldopamine), and metaraminol ((1''R'',2''S'')-3,β-dihydroxyamphetamine), among others. History Gepefrine was synthesized by 1968 and was introduced for medical use in Germany by 1981. Society and culture Names ''Gepefrine'' is the generic name of the drug and its . Brand names of gepe ...
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